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Basic Information
CAS No.: 108-95-2
Name: Phenol
Article Data: 3165
Molecular Structure:
Molecular Structure of 108-95-2 (Phenol)
Formula: C6H6O
Molecular Weight: 94.113
Synonyms: Carbolic Acid;Benzenol;Phenylic Acid;Hydroxybenzene;Phenic acid;Monohydroxybenzene;Monophenol;Oxybenzene;Phenyl alcohol;Phenyl hydrate;Phenyl hydroxide;Phenylic alcohol;
EINECS: 203-632-7
Density: 1.07 g/cm3
Melting Point: 40-42 °C(lit.)
Boiling Point: 181.8 °C at 760 mmHg
Flash Point: 72.5 °C
Solubility: 8 g/100 mL in water
Appearance: transparent crystalline solid
Hazard Symbols: ToxicT,CorrosiveC,FlammableF,HarmfulXn
Risk Codes: 23/24/25-34-48/20/21/22-68-40-39/23/24/25-11-36-20/21/22-24/25
Safety: 26-36/37/39-45-36/37-28A-28-24/25-1/2-36-16
Transport Information: UN 1671 6.1/PG 2
PSA: 20.23000
LogP: 1.39220
Synthetic route
533-58-4

2-Iodophenol

108-95-2

phenol

Conditions
ConditionsYield
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%
1529-17-5

phenyltrimethylsilyl ether

108-95-2

phenol

Conditions
ConditionsYield
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%
637-27-4

phenyl propionate

A

74-85-1

ethene

B

96-22-0

pentan-3-one

C

108-95-2

phenol

Conditions
ConditionsYield
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%
7492-40-2

4-phenylbutyl acetate

A

3360-41-6

4-phenyl-butan-1-ol

B

108-95-2

phenol

Conditions
ConditionsYield
With phosphate buffer; Phenyl acetate In diethyl ether for 2.75h; Ambient temperature; pig liver acetone powder;A 5%
B 100%
50972-20-8

phenyl-α-chloroethyl-carbonate

ammonium thiocyanate

A

109548-52-9

phenyl 1-thiocyanoethylcarbonate

B

108-95-2

phenol

Conditions
ConditionsYield
In formamide for 72h; Ambient temperature;A 100%
B 35%
108-98-5

thiophenol

A

57340-80-4

thallium thiophenoxide

B

108-95-2

phenol

Conditions
ConditionsYield
With thallous phenoxide In diethyl ether for 24h;A 100%
B 94%
100-66-3

methoxybenzene

108-95-2

phenol

Conditions
ConditionsYield
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%
106-48-9

4-chloro-phenol

108-95-2

phenol

Conditions
ConditionsYield
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%
105930-58-3

7,7,8,8-Tetramethyl-3-methylene-5-phenoxy-1,4,6,9-tetraoxa-5λ5-phospha-spiro[4.4]nonan-2-one

A

13882-05-8

2-hydroxy-4,4,5,5-tetramethyl<1,3,2>dioxaphospholane-2-oxide

B

127-17-3

2-oxo-propionic acid

C

108-95-2

phenol

Conditions
ConditionsYield
With water In acetone at 20℃; for 24h;A 100%
B n/a
C n/a
122-79-2

Phenyl acetate

108-95-2

phenol

Conditions
ConditionsYield
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%
Raw Materials
108-86-1
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Consensus Reports

NCI Carcinogenesis Bioassay (oral); No Evidence: mouse, rat NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-203 ,1980. . EPA Extremely Hazardous Substances List. Community Right-To-Know List. Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Standards and Recommendations

OSHA PEL: TWA 5 ppm (skin)
ACGIH TLV: TWA 5 ppm (skin); BEI: 250 mg(total phenol)/g creatinine in urine at end of shift; Not Classifiable as a Human Carcinogen
DFG MAK: Confirmed Animal Carcinogen with Unknown Relevance to Humans; BAT: 300 mg/L at end of shift
NIOSH REL: (Phenol) TWA 20 mg/m3; CL 60 mg/m3/15M
DOT Classification:  6.1; Label: Poison

Analytical Methods

For occupational chemical analysis use OSHA: #32 or NIOSH: Phenol, 3502; Phenol and p-Cresol in Urine, 8305.

Specification

The Phenol, monohydroxy derivative of benzene, is an organic compound with the chemical formula C6H5OH. It has the EINECS register number 203-632-7 and CAS register number 108-95-2. Phenol is appreciably soluble in water, with about 8.3 g dissolving in 100 mL (0.88 M). In addition, Phenol is a colourless crystals with a characteristic odour. It is stable which should be protected from strong oxidizing agents, strong bases, strong acids, alkalies and calcium hypochlorite. Phenol is flammable which may discolour in light. 

Physical properties about Phenol are: (1)ACD/LogP: 1.54; (2)ACD/LogD (pH 5.5): 1.54; (3)ACD/LogD (pH 7.4): 1.54; (4)ACD/BCF (pH 5.5): 8.72; (5)ACD/BCF (pH 7.4): 8.69; (6)ACD/KOC (pH 5.5): 164.00; (7)ACD/KOC (pH 7.4): 163.44; (8)#H bond acceptors: 1; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Index of Refraction: 1.553; (12)Molar Refractivity: 28.134 cm3; (13)Molar Volume: 87.863 cm3; (14)Polarizability: 11.153 10-24cm3; (15)Surface Tension: 40.9669990539551 dyne/cm; (16)Density: 1.071 g/cm3; (17)Flash Point: 72.475 °C; (18)Enthalpy of Vaporization: 43.524 kJ/mol; (19)Boiling Point: 181.839 °C at 760 mmHg; (20)Vapour Pressure: 0.614000022411346 mmHg at 25°C

Preparation of Phenol: Phenol has been made, over the years, by a variety of processes. Historically, an important method was the sulfonation of benzene followed by desulfonation with caustic soda:

C6H6 + H2SO4 → C6H5SO3H + H2O
C6H5SO3H + 2 NaOH → C6H5OH + Na2SO4

The above route to Phenol has no longer used. The principal process in use is the peroxidation of cumene (iso-propylbenzene) at 130 °C in the presence of air and a catalyst followed by decomposition of the peroxide at 55 to 65 °C in the presence of sulfuric acid. In the cumene process, cumene is oxidized to form cumene hydroperoxide that is then concentrated and cleaved to produce phenol and acetone. By-products of the oxidation reaction are acetophenone and dimethyl benzyl alcohol, which is dehydrated in the cleavage reaction to produce alpha-methylstyrene.

C6H6 + CH2=CH-CH3 → C6H5CH(CH3)2
C6H5CH(CH3)2 + O2 → C6H5C(CH3)2OOH
C6H5C(CH3)2OOH [H2SO4]→ C6H5OH + CH3COCH3

The toluene-benzoic acid process of preparation of Phenol involves three chemical reactions: (l) oxidation of toluene to form benzoic acid, (2) oxidation of benzoic acid to form phenyl benzoate, (3) hydrolysis of phenyl benzoate to form phenol.

2 C6H5CH3 + 3 O2 → 2 C3H5CO2H + 2 H2O
4 C6H5CO2H + O2 → 2 C6H5CO2C6H5 + 2 H2O + 2 CO2
C6H5CO2C6H5 + 2 OH- → 2 C6H5OH + CO2

Uses of  Phenol: Phenol was widely used as an antiseptic, especially as Carbolic soap. Phenol is also used in the preparation of cosmetics including sunscreens, hair dyes, and skin lightening preparations. The major uses of Phenol involve its conversion to plastics or related materials. Condensation with acetone gives bisphenol-A. Phenol is also used as an oral anesthetic/analgesic, commonly used to temporarily treat pharyngitis. Phenol is also a versatile precursor to a large collection of drugs, most notably aspirin but also many herbicides and pharmaceuticals. Phenol is one of the chemicals for embalming bodies for study because of its ability to preserve tissues for extended periods of time.

When you are using Phenol, please be cautious about it. Phenol is toxic, harmful, corrosive and highly flammable. There will be a danger of serious damage to health by prolonged exposure through inhalation, and in contact with skin and if swallowed. In addition, Phenol is toxic by inhalation, in contact with skin and if swallowed. What's more, there is a danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact Phenol, you should wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, you can seek medical advice immediately (show label where possible). Meanwhile, you must avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC=C(C=C1)O
(2)InChI: InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H
(3)InChIKey: ISWSIDIOOBJBQZ-UHFFFAOYSA-N

Toxicity of Phenol:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo oral 80mg/kg (80mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1319, 1935.
cat LDLo subcutaneous 80mg/kg (80mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 80, Pg. 233, 1944.
cat LDLo unreported 250mg/kg (250mg/kg)   Revue Medicale de la Suisse Romande. Vol. 15, Pg. 561, 1895.
dog LDLo oral 500mg/kg (500mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1319, 1935.
dog LDLo unreported 200mg/kg (200mg/kg)   Revue Medicale de la Suisse Romande. Vol. 15, Pg. 561, 1895.
frog LDLo parenteral 290mg/kg (290mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: OTHER CHANGES
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 166, Pg. 437, 1932.
frog LDLo subcutaneous 75mg/kg (75mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1319, 1935.
frog LDLo subcutaneous 290mg/kg (290mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 1, Pg. 228, 1955.
guinea pig LDLo intraperitoneal 300mg/kg (300mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 1, Pg. 228, 1955.
guinea pig LDLo subcutaneous 450mg/kg (450mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 1, Pg. 228, 1955.
human LDLo oral 140mg/kg (140mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

SKIN AND APPENDAGES (SKIN): SWEATING: OTHER
"Practical Toxicology of Plastics," Lefaux, R., Cleveland, OH, Chemical Rubber Co., 1968Vol. -, Pg. 329, 1968.
human LDLo oral 14gm/kg (14000mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 463, 1969.
infant LDLo oral 10mg/kg (10mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 463, 1969.
mammal (species unspecified) LD50 oral 500mg/kg (500mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 32(10), Pg. 25, 1988.
man TDLo unreported 5714ug/kg (5.714mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION Veterinary and Human Toxicology. Vol. 41, Pg. 151, 1999.
mouse LC50 inhalation 177mg/m3 (177mg/m3)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 41(6), Pg. 103, 1976.
mouse LD50 intraperitoneal 180mg/kg (180mg/kg)   Pharmacologist. Vol. 10, Pg. 172, 1968.
mouse LD50 intravenous 112mg/kg (112mg/kg) BEHAVIORAL: TREMOR Quarterly Journal of Pharmacy & Pharmacology. Vol. 12, Pg. 212, 1939.
mouse LD50 oral 270mg/kg (270mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 38(8), Pg. 6, 1973.
mouse LD50 subcutaneous 344mg/kg (344mg/kg)   Industrial Health. Vol. 5, Pg. 143, 1967.
rabbit LD50 skin 630mg/kg (630mg/kg)   Union Carbide Data Sheet. Vol. 1/6/1966,
rabbit LDLo intraperitoneal 620mg/kg (620mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 80, Pg. 233, 1944.
rabbit LDLo intravenous 180mg/kg (180mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 80, Pg. 233, 1944.
rabbit LDLo oral 420mg/kg (420mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 80, Pg. 233, 1944.
rabbit LDLo subcutaneous 620mg/kg (620mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 80, Pg. 233, 1944.
rabbit LDLo unreported 150mg/kg (150mg/kg)   Revue Medicale de la Suisse Romande. Vol. 15, Pg. 561, 1895.
rat LC50 inhalation 316mg/m3 (316mg/m3)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 41(6), Pg. 103, 1976.
rat LD50 intraperitoneal 127mg/kg (127mg/kg)   Food and Chemical Toxicology. Vol. 22, Pg. 665, 1984.
rat LD50 oral 317mg/kg (317mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Proceedings of the Society for Experimental Biology and Medicine. Vol. 32, Pg. 592, 1935.
rat LD50 skin 669mg/kg (669mg/kg) BEHAVIORAL: TREMOR

KIDNEY, URETER, AND BLADDER: HEMATURIA

SKIN AND APPENDAGES (SKIN): CUTANEOUS SENSITIZATION (EXPERIMENTAL): AFTER TOPICAL EXPOSURE
British Journal of Industrial Medicine. Vol. 27, Pg. 155, 1970.
rat LD50 subcutaneous 460mg/kg (460mg/kg)   Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 10, Pg. 1, 1963.