108-95-2

Basic information

• Product Name: Phenol
• Synonyms: Carbolic Acid;Benzenol;Phenylic Acid;Hydroxybenzene;Phenic acid;Monohydroxybenzene;Monophenol;Oxybenzene;Phenyl alcohol;Phenyl hydrate;Phenyl hydroxide;Phenylic alcohol
• CAS NO: 108-95-2
• Molecular Formula: C₆H₆O
• Molecular Weight: 94.11124
• EINECS: 203-632-7
• Mol File: 108-95-2.mol
• Article Data: 3165

Chemical Properties

• Melting Point: 40-42℃
• Boiling Point: 181.8 °C at 760 mmHg
• Flash Point: 72.5 °C
• Appearance: transparent crystalline solid
• Density: 1.07 g/cm³
• Vapor Density: 3.24 (vs air)
• Vapor Pressure: 0.09 psi ( 55 °C)
• Refractive Index: 1.5418
• Storage Temp.: 2-8°C
• Solubility: H2O: 50?mg/mL at?20?°C, clear, colorless
• PKA: 9.89(at 20℃)
• Water Solubility: 8 g/100 mL
• Merck: 14,7241
• BRN: 969616
• CAS DataBase Reference: Phenol(CAS DataBase Reference)
• NIST Chemistry Reference: Phenol(108-95-2)
• EPA Substance Registry System: Phenol(108-95-2)

Safety Data

• Hazard Codes: T:Toxic;;
• Statements: R23/24/25:; R34:; R40:; R48/20/21/22:; R68:
• Safety Statements: S28A:; S36/37:; S45:
• RIDADR: UN 2821 6.1/PG 2
• WGK Germany: 2
• RTECS: SJ3325000
• F: 8-23
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 108-95-2(Hazardous Substances Data)

Usage

Chemical Properties

Phenol is the simplest member of a class of organic compounds possessing a hydroxyl group attached to a benzene ring or to a more complex aromatic ring system.Also known as carbolic acid or monohydroxybenzene, phenol is a colorless to white crystalline material of sweet odor, having the composition C6H5OH, obtained from the distillation of coal tar and as a by-product of coke ovens.Phenol has broad biocidal properties, and dilute aqueous solutions have long been used as an antiseptic. At higher concentrations, it causes severe skin burns; it is a violent systemic poison. It is a valuable chemical raw material for the production of plastics, dyes, pharmaceuticals, syntans, and other products.Phenol melts at about 43°C and boils at 183°C. The pure grades have melting point of 39°C, 39.5°C, and 40°C. The technical grades contain 82%-84% and 90%-92% phenol. The crystallization point is given as 40.41°C. The specific gravity is 1.066. It dissolves in most organic solvents. By melting the crystals and adding water, liquid phenol is produced, which remains liquid at ordinary temperatures. Phenol has the unusual property of penetrating living tissues and forming a valuable antiseptic. It is also used industrially in cutting oils and compounds and in tanneries. The value of other disinfectants and antiseptics is usually measured by comparison with phenol.

Uses

Phenol is an important organic chemical raw material, widely used in the production of phenolic resin and bisphenol A, in which bisphenol A is important raw material for polycarbonate, epoxy resin, polysulfone resin and other plastics. In some cases the phenol is used to produce iso-octylphenol, isononylphenol, or isododecylphenol through addition reaction with long-chain olefins such as diisobutylene, tripropylene, tetra-polypropylene and the like, which are used in production of nonionic surfactants. In addition, it can also be used as an important raw material for caprolactam, adipic acid, dyes, medicines, pesticides and plastic additives and rubber auxiliaries.

Production

Coal tar was once the main source of phenol, and was extracted from sodium hydroxide solution. In earlier time, people use sulfonation method to produce phenol: react sodium benzene sulfonate with sodium hydroxide to generate the sodium salt of phenol, and then treat it with acid to obtain phenol. In recent years, hydrolyzing chlorobenzene or oxidizing cumene has become the major production method. The by-product acetone in latter method is also an important industrial raw material, so oxidizing cumene is more economic industrially thus widely applied. Cumene method: This method generates cumene from propylene and benzene in the presence of aluminum trichloride. It oxidizes to cumene hydroperoxide and then decomposes with cation exchange resin to give phenol and acetone. For each ton of phenol produced, 0.62 tons of acetone can be produced. Sulfonation method: se sulfuric acid to sulfonate benzene to generate benzene sulfonic acid, neutralize it with sodium sulfite, and then undergo acidification and vacuum distillation in caustic soda solution. Hydrogen benzene hydrolysis method: hydrogen benzene is hydrolyzed in caustic soda solution with high temperature and high pressure to generate phenol sodium, which is then neutralized to give phenol.

Toxicity

Phenol is highly corrosive and toxic. It mainly affects the central nervous system. The oral lethal dose for adults is 1 g. It can be irritating, numbing or necrotizing to the skin. It is toxic to skin contact, swallowing or inhalation of phenol. Misuse of a small amount of phenol can cause nausea, vomiting, shock, coma and even death in case of respiratory failure. Very few amounts are used as a preservative, so that adverse reactions are rarely found. Due to its high toxicity, it has been replaced by more effective and less toxic phenolic derivatives.

Description

Phenol is a stable chemical substance and appear as colourless/white crystals with a characteristic, distinct aromatic/acrid odour. It is reactive and incompatible with strong oxidising agents, strong bases, strong acids, alkalis, and calcium hypochlorite. Phenol is flammable and may discolour in light. Phenol is used in the manufacture or production of explosives, fertiliser, coke, illuminating gas, lampblack, paints, paint removers, rubber, perfumes, asbestos goods, wood preservatives, synthetic resins, textiles, drugs, and pharmaceutical preparations. It is also extensively used as a disinfectant in the petroleum, leather, paper, soap, toy, tanning, dye, and agricultural industries.

Chemical Properties

Phenol, C6H5OH, also known as carbolic acid and phenylic acid, is a white poisonous crystalline solid that melts at 43 °C (110 OF) and boils at 182°C (360 OF). Phenol has a sharp burning taste,a distinctive odor, and it irritates tissue. It is toxic not only by ingestion or inhalation, but also by skin absorption. Phenol is soluble in water,alcohol,and ether. It is used in the production of resins,germicides,weedkillers,pharmaceuticals, and as a solvent in the refining of lubricating oils.

Chemical Properties

Phenol has a strong odor that is sickeningly sweet and irritating. Phenol has powerful disinfectant and sanitizing qualities. It has been used as a topical anesthetic and antiseptic preservative, reagent and chemical reactant. Its use for direct addition to food is limited to a role as a flavoring ingredient in a few foods at a maximum level below 10 ppm.

Physical properties

Phenol is a colorless or white crystalline solid that is slightly soluble in water. Phenol is the simplest of the large group of organic chemicals known as phenols, which consist of compounds where a carbon in the phenyl aromatic group (C6H5) is directly bonded to hydroxyl, OH.

Occurrence

It is reported found in over 150 natural products including apricot, sour cherry, black currant, bilberry, cranberry, other berries, grapes, guava fruit, peach, pineapple, asparagus, onion, cooked potato, tomato, cinnamon bark, cassia leaf, ginger, pennyroyal oil, many cheeses, butter, milk, milk powder, boiled egg, fish and fish oil, cooked and cured meats, beer, wheaten bread, crisp bread, cognac, rose wine, cocoa, coffee, tea, whiskies, roasted filbert, roasted peanut, soybean, pecans, honey, avocado, Arctic bramble, passion fruit, beans, mushrooms, burley tobacco, cooked beef and chicken, fermented soy sauce, trassi, roasted almonds, sesame seed, fenugreek, mango, tamarind, Brazil nut, rice, rhubarb, licorice, buckwheat, watercress, malt, wort, dried bonito, loquat, myrtle berry, rosemary, Tahiti and Bourbon vanilla, endive, shrimp, crab, crayfish, clam, squid, truffle and Chinese quince.

History

Phenol’s first prominent use was by Joseph Lister (1827–1912) as an antiseptic. Throughout human history,infection often resulted in death,even when the wound could be surgically treated.A broken bone piercing the skin, which today is a painful but not life-threatening injury,historically resulted in infection and possible amputation or death. Lister was inspired by Louis Pasteur’s (1822–1895) germ theory of disease,and he began to use antiseptic methods during routine surgery during the 1860s.

Uses

The predominant use of phenol today is for phenolic resins.it is a powerful bactericide,phenol can be found in numerous consumer products includingmouthwashes,antiseptic ointments,throat lozenges,air fresheners,eardrops,and lipbalms.Phenol continues to be a primary chemical used to make thermoset resins.These resinsare made by combining phenol with aldehydes such as formaldehyde.More than 4 billionpounds of phenolic resins are used annually in the United States.Phenolic resins findtheir widest use in the construction industry.They are used as binding agents and fillers inwood products such as plywood,particleboard,furniture, and paneling.Phenolic resins areimpregnated into paper,which,after hardening,produces sheets that can be glued togetherto form laminates for use in wall paneling and countertops.Decking in boats and docksare made from phenolic resin composites.Phenolic resins are used as sealing agents andfor insulation. Because phenolic resins have high heat resistance and are good insulators,they are used in cookware handles.Because they are also good electrical insulators,they areused in electrical switches,wall plates, and for various other electrical applications.In theautomotive industry,phenolic resins are used for parts such as drive pulleys,water pumphousings, brakes,and body parts.In addition to the construction industry,phenol has many other applications.It isused in pharmaceuticals,in herbicides and pesticides,and as a germicide in paints.It can beused to produce caprolactam,which is the monomer used in the production of nylon 6.Another important industrial compound produced from phenol is bisphenol A,which ismade from phenol and acetone.Bisphenol A is used in the manufacture of polycarbonateresins.Polycarbonate resins are manufactured into structural parts used in the manufactureof various products such as automobile parts,electrical products,and consumer appliances.Items such as compact discs, reading glasses,sunglasses,and water bottles are made frompolycarbonates.

Uses

Phenol is used in the manufacture of variousphenolic resins; as an intermediate in the production of many dyes and pharmaceuticals;as a disinfectant for toilets, floors, and drains;as a topical antiseptic; and as a reagentin chemical analysis. It has been detectedin cigarette smoke and automobile exhaust.Smoke emitted from a burning mosquito coil(a mosquito repellent) has been found to con-tain submicron particles coated with phenoland other substances; a lengthy exposure canbe hazardous to health (Liu et al. 1987).

Uses

phenol is frequently used for medical chemical face peels. It may trap free radicals and can act as a preservative. Phenol, however, is an extremely caustic chemical with a toxicity potential. It is considered undesirable for use in cosmetics. even at low concentrations, it frequently causes skin irritation, swelling, and rashes.

Definition

ChEBI: An organic hydroxy compound that consists of benzene bearing a single hydroxy substituent. The parent of the class of phenols.

Production Methods

Historically, phenol was produced by the distillation of coal tar. Today, phenol is prepared by one of several synthetic methods, such as the fusion of sodium benzenesulfonate with sodium hydroxide followed by acidification; the hydrolysis of chlorobenzene by dilute sodium hydroxide at high temperature and pressure to give sodium phenate, which on acidification liberates phenol (Dow process); or the catalytic vapor-phase reaction of steam and chlorobenzene at 500°C (Raschig process).

Definition

1. (carbolic acid, hydroxybenzene, C6H5OH) A white crystalline solid used to make a variety of other organic compounds. 2. A type of organic compound in which at least one hydroxyl group is bound directly to one of the carbon atoms of an aromatic ring. Phenols do not show the behavior typical of alcohols. In particular they are more acidic because of the electron-withdrawing effect of the aromatic ring. The preparation of phenol itself is by fusing the sodium salt of the sulfonic acid with sodium hydroxide: C6H5SO2.ONa + 2NaOH → C6H5ONa + Na2SO3 + H2O The phenol is then liberated by sulfuric acid: 2C6H5ONa + H2SO4 → 2C6H5OH + Na2SO4 Reactions of phenol include: 1. Replacement of the hydroxyl group with a chlorine atom using phosphorus(V) chloride. 2. Reaction with acyl halides to form esters of carboxylic acids. 3. Reaction with haloalkanes under alkaline conditions to give mixed alkyl–aryl ethers. In addition phenol can undergo further substitution on the benzene ring. The hydroxyl group directs other substituents into the 2- and 4-positions.

Production Methods

Phenol was prepared before World War I through the distillation of coal tar. The firstsynthetic process involved the sulfonation of benzene followed by desulfonation with abase.The most common current method of phenol production is from the cumene hydroperoxiderearrangement process.In this process,benzene reacts with propylene to produce cumene.Cumene is oxidized to cumene hydroperoxide.When cumene hydroperoxide is treated withdilute sulfuric acid,it rearranges and splits into phenol and acetone. Because the reactants areinexpensive and the process is simple,the acidic oxidation of cumene is used to produce morethan 95% of the world’s supply of phenol.

Preparation

Phenol is formed in dry distillation of wood, peat and coal; coal tar is one of the commercial sources of phenol and its homologues.

Indications

Phenol in dilute solution (0.5% to 2%) decreases itch by anesthetizing the cutaneous nerve endings. Phenol should never be used on pregnant women or infants younger than 6 months of age.

World Health Organization (WHO)

Phenol became widely used as an antiseptic following demonstration of its germicidal activity in 1867. It is an intensely corrosive substance and percutaneous absorption can produce serious systemic toxicity. It has been withdrawn from pharmaceutical preparations by at least one national regulatory authority. However, it is still used widely in concentrations of the order of 1.4% in proprietary preparations for the relief of soreness of the mouth and throat.

Aroma threshold values

Detection: 5.5 ppm. Aroma characteristics at 1.0%: medicinal, creosote, smoky, spicy, phenolic, leatherlike with notes of fried meat and coffee.

Taste threshold values

Taste characteristics at 3 ppm: spicy, phenolic, tobacco, musty, woody, medicinal, smoky, tarlike and slightly spicy clovelike.

Synthesis Reference(s)

Journal of the American Chemical Society, 107, p. 2153, 1985 DOI: 10.1021/ja00293a054Synthetic Communications, 19, p. 453, 1989 DOI: 10.1080/00397918908050686

General Description

A solid melting at 110°F. Colorless if pure, otherwise pink or red. Flash point 175°F. Density 9.9 lb / gal. Vapors are heavier than air Corrosive to the skin (turning skin white) but because of its anesthetic quality numbs rather than burn. Lethal amounts can be absorbed through the skin. Used to make plastics and adhesives.

Air & Water Reactions

Decomposes slowly in air. Mixtures of 9-10% phenol in air are explosive. Soluble in water

Reactivity Profile

PHENOL is a weak acid. Reacts exothermically with bases. Reacts with strong oxidizing agents. Emits acrid smoke and irritating fumes when heated to decomposition. Undergoes, in the presence of aluminum chloride, potentially explosive reactions with nitromethane, butadiene, formaldehyde, peroxodisulfuric acid, peroxosulfuric acid, and sodium nitrite . Reacts violently with sodium nitrate in the presence of trifluoroacetic acid [Bretherick, 5th ed., 1995, p. 770]. May corrode lead, aluminum and its alloys, certain plastics, and rubber. Phenol may explode in contact with peroxodisulfuric acid (Dns, J. Ber., 1910, 43, 1880; Z. Anorg. Chem., 1911, 73, 1911.) or peroxomonosulfuric acid. (Sidgwick, 1950, 939)

Health Hazard

Phenol and its vapors are corrosive to the eyes, skin, and respiratory tract. The corrosive effect on skin and mucous membranes is due to a protein-degenerating effect. Repeated or prolonged skin contact with phenol may cause dermatitis, and potentially second and third-degree burns. Inhalation of phenol vapor may cause lung edema. Phenol may adversely effect the central nervous system and heart. Long-term, or repeated exposure, to phenol may have harmful effects on the liver and kidneys.While there is no evidence that phenol causes cancer in humans it is readily absorbed through the skin; systemic poisoning can occur in addition to the local caustic burns. Resorptive poisoning by a large quantity of phenol can occur even with only a small area of skin, rapidly leading to paralysis of the central nervous system and a severe drop in body temperature. Phenol is also a reproductive toxin causing increased risk of abortion and low birth weight indicating retarded development in utero.Chemical burns from skin exposures can be decontaminated by washing with polyethylene glycol or isopropyl alcohol; flushing with copious amounts of water will help to remediate the burn. Removal of contaminated clothing is required, as well as immediate hospital treatment for large splashes.https://ehs.ucsc.edu/lab-safety-manual/specialty-chemicals/phenol.html

Fire Hazard

Flammable vapors when heated. Runoff from fire control water may give off poisonous gases and cause pollution. Mixtures of 9-10% phenol in air are explosive. Avoid aluminum chloride/nitrobenzene mixture, peroxodisulfuric acid, peroxomonosulfuric acid and strong oxidizing agents. Decomposes slowly on air contact. Avoid contact with strong oxidizing agents.

Flammability and Explosibility

Phenol is a combustible solid (NFPA rating = 2). When heated, phenol produces flammable vapors that are explosive at concentrations of 3 to 10% in air. Carbon dioxide or dry chemical extinguishers should be used to fight phenol fires.

Pharmaceutical Applications

Phenol is used mainly as an antimicrobial preservative in parenteral pharmaceutical products. It has also been used in topical pharmaceutical formulations and cosmetics; Phenol is widely used as an antiseptic, disinfectant, and therapeutic agent, although it should not be used to preserve preparations that are to be freeze-dried.

Industrial uses

Phenol is the simplest member of a class oforganic compounds possessing a hydroxylgroup attached to a benzene ring or to a morecomplex aromatic ring system. Also known as carbolic acid or monohydroxybenzene,phenol is a colorless to whitecrystalline material of sweet odor, having thecomposition C6H5OH, obtained from the distillationof coal tar and as a by-product ofcoke ovens. Phenol has broad biocidal properties, anddilute aqueous solutions have long been usedas an antiseptic. At higher concentrations itcauses severe skin burns; it is a violent systemicpoison. It is a valuable chemical raw materialfor the production of plastics, dyes, pharmaceuticals,syntans, and other products.Phenol is one of the most versatile industrialorganic chemicals. It is the starting point formany diverse products used in the home andindustry. A partial list includes nylon, epoxyresins, surface active agents, synthetic detergents,plasticizers, antioxidants, lube oil additives,phenolic resins (with formaldehyde, furfural,and so on), cyclohexanol, adipic acid,polyurethanes, aspirin, dyes, wood preservatives,herbicides, drugs, fungicides, gasolineadditives, inhibitors, explosives, and pesticides.

Biochem/physiol Actions

Phenol?has the ability to denature protein, hence can lead to denervation. At lower concentration, it can serve as a local anaesthetic and can also act as a neurolytic agent in higher concentration. It is also linked with tissue damage at higher concentrations.

Safety

Phenol is highly corrosive and toxic, the main effects being on the central nervous system. The lethal human oral dose is estimated to be 1 g for an adult. Phenol is absorbed from the gastrointestinal tract, skin, and mucous membranes, and is metabolized to phenylglucuronide and phenyl sulfate, which are excreted in the urine. Although there are a number of reports describing the toxic effects of phenol, these largely concern instances of accidental poisoning or adverse reactions during its use as a therapeutic agent.Adverse reactions associated with phenol used as a preservative are less likely owing to the smaller quantities that are used; however, it has been suggested that the body burden of phenol should not exceed 50 mg in a 10-hour period.This amount could be exceeded following administration of large volumes of phenolpreserved medicines. LD50 (mouse, IV): 0.11 g/kg LD50 (mouse, oral): 0.3 g/kg LD50 (rabbit, skin): 0.85 g/kg LD50 (rat, skin): 0.67 g/kg LD50 (rat, oral): 0.32 g/kg LD50 (rat, SC): 0.46 g/kg

Potential Exposure

Phenol is used as a pharmaceutical, in the production of fertilizer; coke, illuminating gas; lampblack, paints, paint removers; rubber, asbestos goods; wood preservatives; synthetic resins; textiles, drugs, pharmaceutical preparations; perfumes, bakelite, and other plastics (phenolformaldehyde resins); polymer intermediates (caprolactam, bisphenol-A and adipic acid). Phenol also finds wide use as a disinfectant and veterinary drug.

Carcinogenicity

Phenol had been investigated for carcinogenicity in animals by the oral and dermal routes. IARC and IRIS determined that animal human evidence for carcinogenicity was inadequate.

Source

Detected in distilled water-soluble fractions of 87 octane unleaded gasoline (1.53 mg/L), 94 octane unleaded gasoline (0.19 mg/L), Gasohol (0.33 mg/L), No. 2 fuel oil (0.09 mg/L), jet fuel A (0.09 mg/L), diesel fuel (0.07 mg/L), and military jet fuel JP-4 (0.22 mg/L) (Potter, 1996). Phenol was also detected in 80% of 65 gasoline (unleaded regular and premium) samples (62 from Switzerland, 3 from Boston, MA). At 25 °C, phenol concentrations ranged from 63 to 130,000 μg/L in gasoline and from 150 to 1,500 μg/L in water-soluble fractions. Average concentrations were 26 mg/L in gasoline and 6.1 mg/L in water-soluble fractions (Schmidt et al., 2002). Thomas and Delfino (1991) equilibrated contaminant-free groundwater collected from Gainesville, FL with individual fractions of three individual petroleum products at 24–25 °C for 24 h. The aqueous phase was analyzed for organic compounds via U.S. EPA approved test method 625. Average phenol concentrations reported in water-soluble fractions of unleaded gasoline, kerosene, and diesel fuel were 20, 8, and 19 μg/L, respectively. A high-temperature coal tar contained phenol at an average concentration of 0.61 wt % (McNeil, 1983). Phenol occurs naturally in many plants including blueberries (10 to 60 ppb), marjoram (1,431– 8,204 ppm), sweetflag, safflower buds (40 ppb), mud plantain, capillary wormwood, asparagus shoots, tea leaves, petitgrain, cinnamon, cassia, licorice, witch hazel, Japanese privet, St. John’s wort, European pennyroyal, tomatoes, white mulberries, tobacco leaves, benneseed, sesame seeds, tamarind, white sandlewood, patchouli leaves, rue, slash pine, bayberries, Scotch pine, and tarragon (Duke, 1992). A liquid swine manure sample collected from a waste storage basin contained phenol at a concentration of 22.0 mg/L (Zahn et al., 1997). Schauer et al. (2001) measured organic compound emission rates for volatile organic compounds, gas-phase semi-volatile organic compounds, and particle phase organic compounds from the residential (fireplace) combustion of pine, oak, and eucalyptus. The gas-phase emission rates of phenol were 525 mg/kg of pine burned, 300 mg/kg of oak burned, and 434 mg/kg of eucalyptus burned. Releases toxic and noxious fumes when heated at temperatures greater than its boiling point. Drinking water standard: No MCLGs or MCLs have been proposed, however, a DWEL of 20 mg/L was recommended (U.S. EPA, 2000).

Environmental fate

Biological. Under methanogenic conditions, inocula from a municipal sewage treatment plant digester degraded phenol to carbon dioxide and methane (Young and Rivera, 1985). Chloroperoxidase, a fungal enzyme isolated from Caldariomyces fumago, reacted with phenol forming 2- and 4-chlorophenol, the latter in a 25% yield (Wannstedt et al., 1990). In activated sludge, 41.4% mineralized to carbon dioxide after 5 d (Freitag et al., 1985). When phenol was statically incubated in the dark at 25 °C with yeast extract and settled domestic wastewater inoculum, significant biodegradation with rapid adaptation was observed. At concentrations of 5 and 10 mg/L, 96 and 97% biodegradation, respectively, were observed after 7 d (Tabak et al., 1981). Phenol is rapidly degraded in aerobically incubated soil but is much slower under anaerobic conditions (Baker and Mayfield, 1980). Soil. Loehr and Matthews (1992) studied the degradation of phenol in different soils under aerobic conditions. In a slightly basic sandy loam (3.25% organic matter) and in acidic clay soil (<1.0% organic matter), the resultant degradation half-lives were 4.1 and 23 d, respectively. Soil sorption distribution coefficients (Kd) were determined from centrifuge column tests using kaolinite as the absorbent (Celorie et al., 1989). Values for Kd ranged from 0.010 to 0.054 L/g. Surface Water. Vaishnav and Babeu (1987) reported a half-life of 11 d in river waters and 3 d in harbor waters. Groundwater. Nielsen et al. (1996) studied the degradation of phenol in a shallow, glaciofluvial, unconfined sandy aquifer in Jutland, Denmark. As part of the in situ microcosm study, a cylinder that was open at the bottom and screened at the top was installed through a cased borehole approximately 5 m below grade. Five liters of water was aerated with atmospheric air to ensure aerobic conditions were maintained. Groundwater was analyzed weekly for approximately 3 months to determine phenol concentrations with time. The experimentally determined first-order biodegradation rate constant and corresponding half-life were 0.5/d and 33.4 h, respectively. Vaishnav and Babeu (1987) reported a biodegradation rate constant of 0.035/d and a half-life of 20 d in groundwater. Photolytic. Absorbs UV light at a maximum wavelength of 269 nm (Dohnal and Fenclová, 1995). In an aqueous, oxygenated solution exposed to artificial light (λ = 234 nm), phenol was photolyzed to hydroquinone, catechol, 2,2 -, 2,4 - and 4,4 -dihydroxybiphenyl (Callahan et al., 1979). When an aqueous solution containing potassium nitrate (10 mM) and phenol (1 mM) was irradiated with UV light (λ = 290–350 nm) up to a conversion of 10%, the following products formed: hydroxyhydroquinone, hydroquinone, resorcinol, hydroxybenzoquinone, benzoquinone, catechol, nitrosophenol, 4-nitrocatechol, nitrohydroquinone, 2- and 4-nitrophenol. Catechnol and hydroquinone were the major and minor products, respectively (Niessen et al., 1988). Titanium dioxide suspended in an aqueous solution and irradiated with UV light (λ = 365 nm) converted phenol to carbon dioxide at a significant rate (Matthews, 1986). Chemical/Physical. In an environmental chamber, nitrogen trioxide (10,000 ppb) reacted quickly with phenol (concentration 200 ppb to 1.4 ppm) to form phenoxy radicals and nitric acid (Carter et al., 1981). The phenoxy radicals may react with oxygen and nitrogen dioxide to form quinones and nitrohydroxy derivatives, respectively (Nielsen et al., 1983).

storage

When exposed to air and light, phenol turns a red or brown color, the color being influenced by the presence of metallic impurities. Oxidizing agents also hasten the color change. Aqueous solutions of phenol are stable. Oily solutions for injection may be sterilized in hermetically sealed containers by dry heat. The bulk material should be stored in a well-closed, light-resistant container at a temperature not exceeding 15°C.

Shipping

UN1671 Phenol, solid, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN2312 Molten phenol, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN2821 Phenol solutions, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Purification Methods

Steam is passed through a boiling solution containing 1mole of phenol and 1.5-2.0moles of NaOH in 5L of H2O until all non-acidic material has distilled. The residue is cooled, acidified with 20% (v/v) H2SO4, and the phenol is separated, dried with CaSO4 and fractionally distilled under reduced pressure. It is then fractionally crystallised several times from its melt [Andon et al. J Chem Soc 5246 1960]. Purification via the benzoate has been used by Berliner, Berliner and Nelidow [J Am Chem Soc 76 507 1954]. The benzoate,(m 70o, b 314o/760mm), is crystallised from 95% EtOH, then hydrolysed to the free phenol by refluxing with two equivalents of KOH in aqueous EtOH until the solution becomes homogeneous. It is acidified with HCl and extracted with diethyl ether. The ether layer is freed from benzoic acid by thorough extraction with aqueous NaHCO3, and, after drying and removing the ether, the phenol is distilled. Phenol has also been crystallised from a 75% w/w solution in water by cooling to 11o and seeding with a crystal of the hydrate. The crystals are centrifuged off, rinsed with cold water (0-2o), saturated with phenol, and dried. It can be crystallised from pet ether [Berasconi & Paschalis J Am Chem Soc 108 2969 1986]. Draper and Pollard [Science 109 448 1949] added 12% water, 0.1% aluminium (can also use zinc) and 0.05% NaHCO3 to phenol, and distilled it at atmospheric pressure until the azeotrope was removed, The phenol was then distilled at 25mm. Phenol has also been dried by distillation from the *benzene solution to remove the water/*benzene azeotrope and the excess *benzene, followed by distillation of the phenol at reduced pressure under nitrogen. Processes such as this are probably adequate for analytical grade phenol which has as its main impurity water. Phenol has also been crystallised from pet ether/*benzene or pet ether (b 40-60o). The purified material is stored in a vacuum desiccator over P2O5 or CaSO4. [Beilstein 6 IV 531.]

Incompatibilities

Phenol, available in solid or liquid form, is colorless to light pink and has a sweet aromatic odor. It is stable under normal conditions of storage and use. The liquid and vapor are combustible. Phenol is incompatible with strong oxidizing agents, calcium hypochlorite, halogens, halogenated compounds, aluminum chloride, and nitrobenzene. Hot phenol can attack aluminum, lead, magnesium and zinc. It can react exothermally with peroxymonosulfuric acid, sodium nitrate, 1,3-butadiene and boron trifluoride diethyl ether. When phenol is heated to decomposition (ca. 715 °C), decomposition products include carbon monoxide and carbon dioxide.https://www.cdc.gov/niosh/npg/npgd0493.htmlhttp://www51.honeywell.com/sm/common/documents/Public_Risk_Summary_-_GPS0075_Phenol_Dec_2012.pdf

Waste Disposal

Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. Incineration.

Precautions

Acute poisoning of phenol by ingestion, inhalation or skin contact may lead to death. Phenol is readily absorbed through the skin. It is highly toxic by inhalation. It is corrosive and causes burns and severe irritation effects. During use and handling of phenol, occupational workers should be very careful. Workers should use protective clothing, rubber boots, and goggles to protect the eyes from vapors and spillage.

Regulatory Status

Included in the FDA Inactive Ingredients Database (injections). Included in medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.

InChI:InChI=1/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H

Synthetic route

2-Iodophenol (533-58-4) → phenol (108-95-2)

Conditions	Yield
With potassium tert-butylate; N,N-dimethyl-formamide at 35℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation;	100%
With tris-(trimethylsilyl)silane In acetonitrile for 24h; Schlenk technique; Inert atmosphere; Irradiation;	98%
With aluminium trichloride In dichloromethane; ethanethiol for 0.15h; Mechanism; Ambient temperature; var. other halogenated phenols;	86.7%
With potassium phosphate; palladium diacetate; hydrazine hydrate In dimethyl sulfoxide; N,N-dimethyl-formamide at 20℃; for 8h; Green chemistry;	68%

phenyltrimethylsilyl ether (1529-17-5) → phenol (108-95-2)

Conditions	Yield
montmorillonite K-10 for 0.0166667h; Product distribution; Further Variations:; Catalysts; Solid phase reaction; desilylation; microwave irradiation;	100%
With bismuth(lll) trifluoromethanesulfonate In methanol at 20℃; for 0.0333333h;	98%
With methanol; 1,3-disulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.0666667h; Green chemistry;	98%

phenyl propionate (637-27-4) → ethene (74-85-1) + pentan-3-one (96-22-0) + phenol (108-95-2)

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine at 54℃; for 20h; Product distribution; Rate constant; Thermodynamic data; other solvents, reagents, reagents ratio, time, temperature; activation energy, ΔH<*>, ΔS<*>;	A 100% B n/a C 100%

4-phenylbutyl acetate (7492-40-2) → 4-phenyl-butan-1-ol (3360-41-6) + phenol (108-95-2)

Conditions	Yield
With phosphate buffer; Phenyl acetate In diethyl ether for 2.75h; Ambient temperature; pig liver acetone powder;	A 5% B 100%

phenyl-α-chloroethyl-carbonate (50972-20-8) + ammonium thiocyanate → phenyl 1-thiocyanoethylcarbonate (109548-52-9) + phenol (108-95-2)

Conditions	Yield
In formamide for 72h; Ambient temperature;	A 100% B 35%

thiophenol (108-98-5) → thallium thiophenoxide (57340-80-4) + phenol (108-95-2)

Conditions	Yield
With thallous phenoxide In diethyl ether for 24h;	A 100% B 94%

methoxybenzene (100-66-3) → phenol (108-95-2)

Conditions	Yield
With aluminium(III) iodide; tetra-(n-butyl)ammonium iodide In cyclohexane for 0.3h; Heating;	100%
With water; hydrogen bromide; Aliquat 336 at 105℃; for 5h; Catalytic behavior;	96%
With monochloroborane dimethyl sulfide complex In benzene Heating;	95%

4-chloro-phenol (106-48-9) → phenol (108-95-2)

Conditions	Yield
With hydrogen; sodium hydroxide In water under 760.051 Torr; for 0.833333h; Kinetics; Reagent/catalyst; Solvent; Green chemistry;	100%
With hydrogen; sodium hydroxide In water at 20℃; for 2h; Kinetics; Catalytic behavior; Solvent; Reagent/catalyst;	99.1%
With hydrogen; sodium hydroxide In water at 25℃; under 760.051 Torr; for 2h; Reagent/catalyst; Solvent;	99.9%

7,7,8,8-Tetramethyl-3-methylene-5-phenoxy-1,4,6,9-tetraoxa-5λ5-phospha-spiro[4.4]nonan-2-one (105930-58-3) → 2-hydroxy-4,4,5,5-tetramethyl<1,3,2>dioxaphospholane-2-oxide (13882-05-8) + 2-oxo-propionic acid (127-17-3) + phenol (108-95-2)

Conditions	Yield
With water In acetone at 20℃; for 24h;	A 100% B n/a C n/a

Phenyl acetate (122-79-2) → phenol (108-95-2)

Conditions	Yield
With HZSM-5(30) In water for 7h; Product distribution; Heating; var. catalysts; other acetylated alcohols;	100%
silica gel; toluene-4-sulfonic acid In water; toluene at 80℃; for 6h;	100%
With sodium hydrogen telluride; acetic acid In ethanol for 0.5h; Heating;	100%

acetic acid phenethyl ester (103-45-7) → 2-phenylethanol (60-12-8) + phenol (108-95-2)

Conditions	Yield
With phosphate buffer; Phenyl acetate In diethyl ether for 2.75h; Ambient temperature; pig liver acetone powder;	A 18% B 100%

3-phenylpropyl acetate (122-72-5) → 3-Phenyl-1-propanol (122-97-4) + phenol (108-95-2)

Conditions	Yield
With phosphate buffer; Phenyl acetate In diethyl ether for 2.75h; Ambient temperature; pig liver acetone powder;	A 9% B 100%

phenyl formate (1864-94-4) → phenol (108-95-2)

Conditions	Yield
With perchloric acid In diethyl ether; water at 20℃; for 0.166667h;	100%
With samarium diiodide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 0.0833333h; Etherification;	99.3%
With sodium hydroxide In water at 20℃;	91%

O-methoxymethylphenol (824-91-9) → phenol (108-95-2)

Conditions	Yield
H6P2W18O62; silica gel In tetrahydrofuran; methanol at 65℃; for 0.916667h; Product distribution; Further Variations:; Catalysts;	100%
With bismuth(III) chloride In water; acetonitrile at 50℃; for 1h; Reagent/catalyst; Solvent; Temperature;	95%
sodium hydrogen sulfate; silica gel In dichloromethane at 20℃; for 1.5h;	94%

bis(1,5-cyclooctadiene)nickel (0) (1295-35-8) + tetrakis(triphenylphosphine)nickel(0) (15133-82-1) → nickel(II) propionate + (triphenylphosphine)3(CO)nickelk (15376-83-7) + ethene (74-85-1) + phenol (108-95-2)

Conditions	Yield
With triphenylphosphine In neat (no solvent) (N2 or Ar or vac.), EtCOOPh added to Ni(cod)2 and Ni(PPh3)4, mixture stirred at 54°C for 20 h; GLC;	A 73% B n/a C 100% D 91%

bis(1,5-cyclooctadiene)nickel (0) (1295-35-8) + phenyl propionate (637-27-4) → (triphenylphosphine)3(CO)nickelk (15376-83-7) + ethene (74-85-1) + phenol (108-95-2)

Conditions	Yield
With triphenylphosphine In neat (no solvent) Kinetics; byproducts: diethyl ketone, 1,3-cyclooctadiene, 1,4-cyclooctadiene; further byproducts: 1,5-cyclooctadiene, bicyclooctene-1, bicyclooctene-2, (N2 or Ar or vac.), EtCOOPh added to Ni(cod)2 and PPh3 (PPh3/Ni = 10), mixture stirred at 54°C for 21 h; gas chromy., volatile removed in vac., recrystd. from THF-hexane;	A 80% B 100% C 100%
With triphenylphosphine In neat (no solvent) Kinetics; byproducts: diethyl ketone, 1,3-cyclooctadiene, 1,4-cyclooctadiene; further byproducts: 1,5-cyclooctadiene, bicyclooctene-1, bicyclooctene-2, (N2 or Ar or vac.), EtCOOPh added to Ni(cod)2 and PPh3 (PPh3/Ni = 4),mixture stirred at 54°C for 20 h; gas chromy., volatile removed in vac., recrystd. from THF-hexane;	A 60% B 100% C 100%
With triphenylphosphine In neat (no solvent) Kinetics; byproducts: diethyl ketone, 1,3-cyclooctadiene, 1,4-cyclooctadiene; further byproducts: 1,5-cyclooctadiene, bicyclooctene-1, bicyclooctene-2, (N2 or Ar or vac.), EtCOOPh added to Ni(cod)2 and PPh3 (PPh3/Ni = 3),mixture stirred at 54°C for 20 h; gas chromy., volatile removed in vac., recrystd. from THF-hexane;	A 60% B 90% C 90%
With triphenylphosphine In neat (no solvent) Kinetics; byproducts: diethyl ketone, 1,3-cyclooctadiene, 1,4-cyclooctadiene; further byproducts: 1,5-cyclooctadiene, bicyclooctene-1, bicyclooctene-2, (N2 or Ar or vac.), EtCOOPh added to Ni(cod)2 and PPh3 (PPh3/Ni = 2),mixture stirred at 54°C for 12 h; gas chromy., volatile removed in vac., recrystd. from THF-hexane;	A 30% B 60% C 60%
With triphenylphosphine In neat (no solvent) Kinetics; byproducts: diethyl ketone, 1,3-cyclooctadiene, 1,4-cyclooctadiene; further byproducts: 1,5-cyclooctadiene, bicyclooctene-1, bicyclooctene-2, (N2 or Ar or vac.), EtCOOPh added to Ni(cod)2 and PPh3 (PPh3/Ni = 1),mixture stirred at 54°C for 12 h; gas chromy., volatile removed in vac., recrystd. from THF-hexane;	A n/a B 40% C 50%

bis(1,5-cyclooctadiene)nickel (0) (1295-35-8) + phenyl propionate (637-27-4) + Tri(p-tolyl)phosphine (1038-95-5) → ethene (74-85-1) + Ni(CO)(P(C6H4CH3)3)3 (74887-07-3) + phenol (108-95-2)

Conditions	Yield
In further solvent(s) Kinetics; (N2 or Ar or vac.), EtCOOPh added to Ni(cod)2 and P(C6H4CH3)3 (P(Ph-CH3)3/Ni = 3) in acetophenone, mixture stirred at 65°C for 50 h;	A 80% B 85% C 100%

cyclopropanecarboxylic acid phenyl ester (5296-56-0) → phenol (108-95-2)

Conditions	Yield
With aluminum (III) chloride; diphenyl diselenide; zinc In acetonitrile at 70℃; for 19.25h;	100%

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6) → phenol (108-95-2)

Conditions	Yield
With urea hydrogen peroxide adduct In methanol at 27 - 29℃; for 0.25h; Green chemistry; chemoselective reaction;	100%
With dihydrogen peroxide; 1-butyl-3-methylimidazolium chloride In water at 20℃; for 0.5h; Green chemistry;	97%
With water; 3-chloro-benzenecarboperoxoic acid In ethanol at 20℃; for 6h;	96%

potassium phenyltrifluoborate → phenol (108-95-2)

Conditions	Yield
With urea hydrogen peroxide adduct In methanol at 27 - 29℃; for 0.25h; Green chemistry; chemoselective reaction;	100%
With Oxone; water In acetone at 20℃; for 0.0333333h;	96%
With LACTIC ACID; dihydrogen peroxide In water at 20℃; for 0.166667h; Green chemistry;	89%

phenylboronic acid (98-80-6) → phenol (108-95-2)

Conditions	Yield
With C5H11N*Cu(2+)*2NO3(1-); water at 30℃; for 2h;	100%
With water at 60℃; for 5h; Green chemistry;	100%
With water; oxygen; sodium sulfite at 50℃; for 1h; Temperature; Green chemistry;	100%

phenyl 3,3-dimethylacrylate (54897-52-8) → phenol (108-95-2)

Conditions	Yield
With perchloric acid In acetonitrile at 20℃; for 1.25h; photo-Fries rearrangement; Inert atmosphere; Irradiation;	100%

phenyl methanesulfonate (16156-59-5) → phenol (108-95-2)

Conditions	Yield
With sodium phosphate In aq. phosphate buffer; water; dimethyl sulfoxide at 25℃; for 0.333333h; pH=7.5; Enzymatic reaction;	100%

2-hydroxyphenyl boronic acid (89466-08-0) → phenol (108-95-2)

Conditions	Yield
In dimethylsulfoxide-d6 at 120℃; for 2h; Suzuki Coupling; Inert atmosphere;	100%
In dimethyl sulfoxide at 120℃; for 4h; Solvent; Temperature;	100%
In dimethyl sulfoxide at 120℃; for 4h; Solvent; Temperature; Time; Reagent/catalyst;	95%
With N-methyliminodiacetic acid In dimethyl sulfoxide; toluene at 120℃; for 12h; Inert atmosphere; Molecular sieve;
With 3-methyl-5H-1,4,2-dioxazol-5-one; Cp*Rh(OAc)2*H2O In tetrahydrofuran at 20℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube;

C8H11BO → phenol (108-95-2)

Conditions	Yield
With water In dimethyl sulfoxide at 120℃; for 24h; Time; Reagent/catalyst;	100%
In dimethyl sulfoxide at 120℃; for 12h;	96%
Multi-step reaction with 2 steps 1: dimethyl sulfoxide; toluene / 12 h / Molecular sieve; Reflux; Dean-Stark 2: dimethyl sulfoxide / 240 h / 120 °C View Scheme

2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (269409-97-4) → phenol (108-95-2)

Conditions	Yield
In dimethyl sulfoxide at 120℃; for 24h;	100%
In dimethyl sulfoxide at 120℃; for 24h;	96%

(p-hydroxyphenyl)boronic acid (71597-85-8) → phenol (108-95-2)

Conditions	Yield
With acetic acid In 1,4-dioxane at 100℃; Reagent/catalyst; Solvent; Enzymatic reaction;	100%
In formic acid at 60℃; for 2h;	82%
With acetic acid at 130℃; for 1h; Reagent/catalyst; Temperature; Green chemistry;	81%
With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In toluene at 70℃; for 1.5h; Temperature; Microwave irradiation; Green chemistry;	65%

1-phenoxyhexane (1132-66-7) → phenol (108-95-2)

Conditions	Yield
With boron tribromide In dichloromethane	100%

(benzyloxy)benzene (946-80-5) → toluene (108-88-3) + cyclohexanol (108-93-0) + phenol (108-95-2)

Conditions	Yield
With Ni0.85Rh0.15; hydrogen In water at 95℃; under 760.051 Torr; for 16h; Reagent/catalyst;	A 100% B 5% C 79%
With isopropyl alcohol at 150℃; under 7500.75 Torr; for 48h; Inert atmosphere; Autoclave;	A 100% B 12.2% C 87.5%
With isopropyl alcohol at 150℃; under 7500.75 Torr; for 3h; Catalytic behavior; Temperature; Inert atmosphere; Autoclave;	A 100% B 73.1% C 22.4%
With Ru0.6Ni0.4; hydrogen In water at 95℃; under 760.051 Torr; for 16h; Reagent/catalyst;	A 98% B 61% C 6%
With hydrogen In n-heptane at 140℃; under 750.075 Torr; for 6h; Catalytic behavior;	A 34 %Chromat. B 12 %Chromat. C 22 %Chromat.

3,4-dihydro-2H-pyran (110-87-2) + phenol (108-95-2) → 2-phenoxytetrahydropyran (4203-50-3)

Conditions	Yield
With cerium(III) chloride; sodium iodide at 25℃; for 26h;	100%
With poly-p-styryl-acetonyltriphenylphosphonium bromide In dichloromethane at 20℃; for 3h;	99%
With zirconium(IV) chloride In dichloromethane for 1h;	99%

2-bromo-pyridine (109-04-6) + phenol (108-95-2) → 2-phenoxypyridine (4783-68-0)

Conditions	Yield
With copper; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 0.166667h; Ullmann Condensation; Microwave irradiation; Inert atmosphere;	100%
With 1,1,1,5,5,5-hexafluoroacetylacetone; copper(II) ferrite; caesium carbonate In 1-methyl-pyrrolidin-2-one at 135℃; for 24h; Ullmann Condensation; Inert atmosphere; Schlenk technique;	99%
With 2-acetonylpyridine; caesium carbonate; copper(I) bromide In dimethyl sulfoxide at 90℃; for 15h; Inert atmosphere; chemoselective reaction;	98%

styrene oxide (96-09-3) + phenol (108-95-2) → AB_0000810 (53574-80-4)

Conditions	Yield
With erbium(III) triflate In diethyl ether at 25℃; for 24h;	100%
With BiCl6(3-)*2C4H10N2*ClH*3H(1+)*H2O In neat (no solvent) at 20℃; for 0.166667h;	90%
With toluene-4-sulfonic acid; toluene Trennung von (+-)-1-Phenoxy-1-phenyl-aethanol-(2) und (+-)-2-Phenoxy-1-phenyl-aethanol-(1) ueber die 2-Carboxy-benzoyl-Derivate;
In benzene
Stage #1: phenol With sodium hydroxide In water at 80℃; for 0.166667h; Stage #2: styrene oxide In water at 100℃; for 3h; Reagent/catalyst;	15.0 g

4-chloro-3-nitropyridine (13091-23-1) + phenol (108-95-2) → 3-nitro-4-phenoxypyridine (132038-21-2)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃;	100%
With sodium hydride In tetrahydrofuran at 20℃;	99%
With potassium carbonate In N,N-dimethyl-formamide at 80℃;	97%

chloroformic acid ethyl ester (541-41-3) + phenol (108-95-2) → ethyl phenyl carbonate (3878-46-4)

Conditions	Yield
With pyridine In toluene at 220℃; for 24h;	100%
With pyridine	97%
With pyridine In toluene at 20 - 100℃; for 1h;	65.2%

acetic anhydride (108-24-7) + phenol (108-95-2) → Phenyl acetate (122-79-2)

Conditions	Yield
With pyridine; aluminum oxide at 103 - 105℃; for 2h; microwave irradiation;	100%
With 2,6-di-tert-butyl-pyridine; sodium tetracarbonyl cobaltate In acetonitrile for 12h;	100%
With SBA-15-Ph-Pr-SO3H at 20℃; for 0.25h;	100%

benzoyl chloride (98-88-4) + phenol (108-95-2) → benzoic acid phenyl ester (93-99-2)

Conditions	Yield
With tetrabutyl-ammonium chloride; sodium hydroxide In dichloromethane; water at 0℃; for 0.0833333h;	100%
zinc(II) chloride In toluene	99%
With sodium hydride In tetrahydrofuran at 20℃; for 1h;	98%

phenyl isocyanate (103-71-9) + phenol (108-95-2) → phenyl N-phenylcarbamate (4930-03-4)

Conditions	Yield
at 20℃; for 2h;	100%
With cesium fluoride	93.1%
With triethylamine In acetonitrile for 24.5h; Esterification;	89%

methanesulfonyl chloride (124-63-0) + phenol (108-95-2) → phenyl methanesulfonate (16156-59-5)

Conditions	Yield
With triethylamine In benzene at 10℃; Kinetics; Mechanism; Thermodynamic data; Various temperatures, various concentrations. E(act.), ΔS(act.);	100%
With triethylamine In dichloromethane at -15℃; for 1h; Green chemistry;	100%
With triethylamine In ethyl acetate at 0 - 20℃; for 0.166667h; Green chemistry;	97%

methyl ethynyl ketone (1423-60-5) + phenol (108-95-2) → (E)-4-phenoxybut-3-en-2-one (72024-02-3)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In dichloromethane at 20℃; for 12h; Inert atmosphere;	100%
With dmap In dichloromethane at 20℃; for 3h; Inert atmosphere;	99%
dmap In dichloromethane at 20℃; for 2h;	81%
With diethyl ether; triethylamine

4-Fluoronitrobenzene (350-46-9) + phenol (108-95-2) → 4-nitrophenyl phenyl ether (620-88-2)

Conditions	Yield
With cesium fluoride/clinoptilolite In dimethyl sulfoxide at 110℃; for 0.15h; Reagent/catalyst; Solvent; Temperature; Ullmann Condensation;	100%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 17h;	100%
With potassium fluoride on basic alumina; 18-crown-6 ether In acetonitrile for 1h; Heating;	98%

p-toluenesulfonyl chloride + phenol (108-95-2) → toluene-4-sulfonic acid phenyl ester (640-60-8)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 2h; Green chemistry;	100%
With potassium carbonate for 0.05h; microwave irradiation;	99%
With sodium carbonate In water at 20℃; for 3h; Catalytic behavior; Reagent/catalyst;	99%

butanone (78-93-3) + phenol (108-95-2) → Bisphenol B (77-40-7)

Conditions	Yield
With hydrogenchloride at 15 - 20℃; for 3h;	100%
With hydrogenchloride

isopentanoyl chloride (108-12-3) + phenol (108-95-2) → phenyl 3-methylbutanoate (15806-38-9)

Conditions	Yield
With tetrabutyl-ammonium chloride; sodium hydroxide In dichloromethane; water at 0℃; for 0.0833333h;	100%

epichlorohydrin (106-89-8) + phenol (108-95-2) → Phenyl glycidyl ether (122-60-1)

Conditions	Yield
Stage #1: phenol With sodium hydroxide In water at 25℃; for 0.666667h; Stage #2: epichlorohydrin In water at 30 - 35℃; for 16h;	100%
With n-Bu4NOSO2OCH2CHOHCH3; potassium carbonate at 75 - 80℃; for 1.5h;	91%
With n-BuNOSO2OCH2CHOHCH3; potassium carbonate at 75 - 80℃; for 1.5h; other aryl alcohols, var. phase transfer catalysts, var. reaction time;	91%

methyl iodide (74-88-4) + phenol (108-95-2) → methoxybenzene (100-66-3)

Conditions	Yield
With potassium hydroxide; acyclic polyethylene oxides In dichloromethane; water for 0.5h;	100%
With aluminum oxide; potassium fluoride In N,N-dimethyl-formamide for 1h; Product distribution; Ambient temperature; other phenols and alcohols, other alkylating agents, other reagents and solvents, var. time;	100%
With potassium hydroxide; Aliquat 336 at 20℃; for 5h;	99%

Isopropyl isocyanate (1795-48-8) + phenol (108-95-2) → phenyl N-isopropylcarbamate (17614-10-7)

Conditions	Yield
With triethylamine In dichloromethane at 23℃; for 2h; Inert atmosphere;	100%
With dmap In tetrahydrofuran at 60℃; for 24h;	94%
With dmap In tetrahydrofuran Heating;	94%
With aluminium trichloride

phenylacetic acid (103-82-2) + phenol (108-95-2) → phenyl phenylacetate (722-01-0)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	100%
Stage #1: phenylacetic acid With phosphoric acid; trifluoroacetic anhydride In acetonitrile at 25℃; for 0.5h; Stage #2: phenol In acetonitrile at 25℃; for 20h;	93%
Stage #1: phenylacetic acid With (E)-ethyl 2-cyano-2-(2-nitrophenylsulfonyloxyimino)acetate; N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; Stage #2: phenol In dichloromethane at 25℃;	87%

prenyl bromide (870-63-3) + phenol (108-95-2) → phenyl prenyl ether (14309-15-0)

Conditions	Yield
at 170℃;	100%
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 1h; Williamson Ether Synthesis; Darkness; Inert atmosphere;	97%
With sodium hydroxide In N-methyl-acetamide; water	75%

tertiary butyl chloride (507-20-0) + phenol (108-95-2) → para-tert-butylphenol (98-54-4)

Conditions	Yield
With ethylaluminum dichloride bis(2-chloroethyl) ether complex In hexane; Cyclohexane-d12 at 25℃; for 2.5h; Catalytic behavior; Friedel-Crafts Alkylation; Glovebox; Inert atmosphere; regioselective reaction;	100%
bei Siedetemperatur;
at 75℃; unter Druck;

phenol (108-95-2) → triphenyl phosphite (101-02-0)

Conditions	Yield
With Hexamethylphosphorous triamide In toluene at 130℃; for 8h; Schlenk technique; Sealed tube; Inert atmosphere; regioselective reaction;	100%
With phosphorus trichloride at 35 - 160℃; under 7.50075 Torr; for 6h; Temperature; Flow reactor; Inert atmosphere;	94%
With 1H-imidazole; carbon disulfide; Hexamethylphosphorous triamide In benzene at 20 - 25℃; for 24h;	86%

phenol (108-95-2) → 4-bromo-phenol (106-41-2)

Conditions	Yield
With benzyltriphenylphosphonium peroxodisulfate; potassium bromide In acetonitrile for 4.5h; Heating;	100%
With sulfuric acid; C20H22Br2N2O5V; dihydrogen peroxide In methanol; water at 20℃; for 1.33333h; Catalytic behavior;	100%
With oxygen; sodium bromide In dibutyl ether at 45℃; under 760.051 Torr; for 5h; Schlenk technique;	99%

phenol (108-95-2) → (4-hydroxyphenyl)tellurium trichloride (42368-15-0)

Conditions	Yield
With tellurium tetrachloride In tetrachloromethane for 3h; Substitution; Heating;	100%
With tetrachloromethane; tellurium tetrachloride
With tellurium tetrachloride

phenol (108-95-2) → potassium phenolate (100-67-4)

Conditions	Yield
With potassium hydride In tetrahydrofuran at 70℃; Inert atmosphere;	100%
With potassium hydroxide In water at 24℃; for 0.5h;	98%
With potassium hydroxide In water for 0.25h;	98%

phenol (108-95-2) → benzene-1,2-diol (120-80-9)

Conditions	Yield
With dihydrogen peroxide; MgAlZr0.1-HT In Petroleum ether at 79.9℃; for 8h;	100%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In methanol; chloroform at -25℃; for 0.333333h;	97%
With tert.-butylhydroperoxide In water; acetonitrile at 70℃; for 6h; Catalytic behavior; Temperature; Solvent;	89%

phenol (108-95-2) → p-benzoquinone (106-51-4)

Conditions	Yield
With CuCl2 In acetonitrile	100%
With [CuII2(μ-OH)(1,2-bis(2-(bis(2-pyridylmethyl)aminomethyl)-6-pyridyl)ethane)](ClO4)3 ; dihydrogen peroxide; triethylamine In water; acetonitrile at 50℃; for 10h; Catalytic behavior; Inert atmosphere;	99%
With manganese(IV) oxide; sulfuric acid; aniline at 10℃; for 1.5h;	95%

phenol (108-95-2) → cyclohexanol (108-93-0)

Conditions	Yield
With hydrogen; tetra(n-butyl)ammonium hydrogensulfate; rhodium colloidal catalyst In water at 36℃; under 180018 Torr; for 62h; pH=7.5; Catalytic hydrogenation;	100%
In methanol; water	100%
With hydrogen In water at 70℃; under 7500.75 Torr; for 0.25h;	100%

4-nitro-aniline (100-01-6) + phenol (108-95-2) → 4-(4'-hydroxyphenylazo)nitrobenzene (1435-60-5, 81944-71-0)

Conditions	Yield
Stage #1: 4-nitro-aniline With hydrogenchloride; sodium nitrite In water at 2℃; for 1.5h; Stage #2: phenol With sodium hydroxide In water at 2 - 20℃; for 4h;	100%
Stage #1: 4-nitro-aniline With carboxyl- and nitrite- functionalized graphene quantum dots at 20℃; for 0.0833333h; Stage #2: phenol In water at 20℃; for 0.166667h;	96%
Stage #1: 4-nitro-aniline With hydrogenchloride In water; acetone at 0℃; Inert atmosphere; Stage #2: With sodium nitrite In water; acetone at 0℃; for 1h; Inert atmosphere; Stage #3: phenol With sodium carbonate; sodium hydroxide In water; acetone at 0 - 20℃; for 3h; Inert atmosphere;	92%

1,1,3,3-tetramethyldisilazane (15933-59-2) + phenol (108-95-2) → dimethylphenoxysilane (18246-19-0)

Conditions	Yield
	100%
With dimethylmonochlorosilane; triethylamine for 1h; temp.: below 40 deg C;	57%
With dimethylmonochlorosilane Heating;
at 20 - 160℃; for 2h; Inert atmosphere;

3-Phenylpropionic acid (501-52-0) + phenol (108-95-2) → phenyl 3-phenylpropanoate (726-26-1)

Conditions	Yield
With dmap; trimethylsilylethoxyacetylene; mercury(II) oxide In 1,2-dichloro-ethane at 40℃; for 0.5h;	100%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	100%
With dmap; di-2-thienyl carbonate In dichloromethane at 20℃; for 2h;	95%

Upstream product

• 65996-92-1 COAL TAR 
• 34123-59-6 Isoproturon 
• 515-42-4 Benzenesulfonic acid sodium salt 
• 65996-83-0 Phenol crude 
• 65997-17-3 Fiber Glass Wool 
• 8032-32-4 PETROLEUM ETHER 
• 68476-85-7 Liquefied petroleum ges 
• 98-82-8 CUMENE 
• 7757-83-7 Sodium sulfite 
• 80-15-9 Cumyl hydroperoxide 
• 99-88-7 4-Isopropylaniline 

Downstream Products

• 1836-75-5 NITROFEN 
• 491-37-2 4-Chromanone 
• 26967-76-0 Tri(4-isopropylphenyl) phosphate 
• 603-50-9 Bisacodyl 
• 64257-84-7 Fenpropathrin 
• 112665-43-7 Seratrodast 
• 131-52-2 Sodium pentachlorophenolate 
• 4430-25-5 Tetrabromophenol Blue 
• 732-26-3 2,4,6-Tri-tert-butylphenol 
• 6303-58-8 4-Phenoxybutanoic acid 
• 31570-04-4 Tris(2,4-ditert-butylphenyl) phosphite 
• 84-62-8 DIPHENYL PHTHALATE 
• 7170-38-9 3-Phenoxypropionic acid 
• 92-83-1 Xanthene 
• 78628-28-1 Roxatidine acetate 
• 940-31-8 2-Phenoxypropionic acid 
• 501-98-4 4-Hydroxycinnamic acid 
• 620-88-2 4-NITROPHENYL PHENYL ETHER 
• 94-74-6 2-Methyl-4-chlorophenoxyacetic acid 
• 3253-39-2 BISPHENOL A DIMETHACRYLATE 
• 156150-40-2 SODIUM PHENOLATE TRIHYDRATE 
• 6358-57-2 Acid Red 111 
• 184901-84-6 DL-4-HYDROXYMANDELIC ACID MONOHYDRATE 
• 3586-12-7 3-PHENOXYANILINE 
• 88-06-2 2,4,6-Trichlorophenol 
• 99902-72-4 6-PHENOXYNICOTINONITRILE 
• 25085-50-1 ALKYLPHENOL DISULFIDE 
• 2082-79-3 Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate 
• 5335-29-5 3-CHLORO-4-PHENOXYANILINE 
• 2589-71-1 4-Hydroxyvalerophenone 
• 5031-78-7 4'-Phenoxyacetophenone 

Recommend Products

• 60523-66-2  2-(2,3,4,6-tetra-О-acetyl-β-d-glucopyranosyloxy)benzyl bromide 
• 108-95-2  phenol 
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• 2896-13-1  phenyl-(penta-O-acetyl-α-D-gluco-[2]heptulopyranoside) 
• 112047-90-2  Hexa-O-acetyl-α-D-gluco-[2]heptulopyranose 
• 2896-13-1  phenyl-(penta-O-acetyl-α-D-manno-[2]heptulopyranoside) 
• 66904-33-4  Hexa-O-acetyl-α-D-manno-[2]heptulopyranose 
• 120498-97-7  phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside 
• 10022-13-6  1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose 
• 75-21-8  oxirane 
• 50-00-0  formaldehyd 
• 122-99-6  2-Phenoxyethanol 
• 139-02-6  sodium phenoxide 
• 104-68-7  2-(2-phenoxyethoxy)ethanol