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Source

Formaldehyde naturally occurs in jimsonweed, pears, black currant, horsemint, sago cycas seeds (1,640 to 2,200 ppm), oats, beets, and wild bergamot (Duke, 1992). Formaldehyde was formed when acetaldehyde in the presence of oxygen was subjected to continuous irradiation (λ >2200 ?) at room temperature (Johnston and Heicklen, 1964). 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 formaldehyde were 1,165 mg/kg of pine burned, 759 mg/kg of oak burned, and 599 mg/kg of eucalyptus burned. Gas-phase tailpipe emission rates from California Phase II reformulated gasoline-powered automobiles with and without catalytic converters were 8.69 and 884 mg/km, respectively (Schauer et al., 2002).

History

Formaldehyde is a by-product of combustion of organic compounds, metabolism, and other natural processes. Formaldehyde results from wood combustion and elevated atmospheric concentrations can result from forest fires, as well as from urban pollution sources such as transportation. Formaldehyde has been identified as a significant indoor air pollutant. Building materials such as particleboard, plywood, and paneling are major sources of formaldehyde because they incorporate formaldehyde resins as bonding adhesives. Other sources of formaldehyde in the home are carpets, upholstery, drapes, tobacco smoke, and indoor combustion products. Formaldehyde may be emitted from building materials for several years after installation. In the two decades of the 1960s and 1970s, a half million homes in the United States used urea formaldehyde foam insulation, but health complaints led to its elimination as an insulator in the early 1980s. People react differently to formaldehyde exposure, but it is estimated that between 10% and 20% of the population will experience some reaction at concentrations as low as 0.2 parts per million. Formaldehyde irritates the eyes, nose, and throats, producing coughing, sneezing, runny nose, and burning eyes. More severe reactions result in insomnia, headaches, rashes, and breathing difficulties. Some states have established indoor air quality standards ranging from 0.05 to 0.5 ppm.

Description

Formaldehyde is a colorless, flammable gas with a distinctive pungent odor. It is the simplest aldehyde, which is a class of organic compounds with the carbonyl group bonded to at least one hydrogen atom. Formaldehyde was described by August Wilhelm von Hoff mann (1818–1892) in 1867 after the Russian Aleksandr Butlerov (1828–1886) had inadvertently synthesized it in 1857. Formaldehyde readily dissolves in water to produce a solution called formalin, which is commonly marketed as a 37% solution.

Production Methods

The industrial preparation of formaldehyde has occurred since the late 1800s and involvesthe catalytic oxidation of methanol: 2CH3OH(g) + O2(g) → 2CH2O(g).the oxidationtakes place at temperatures between 400°C and 700°C in the presence of metal catalysts. Metalsinclude silver, copper, molybdenum, platinum, and alloys of these metals. Formaldehyde iscommonly used as an aqueous solution called formalin. Commercial formalin solutions varybetween 37% and 50% formaldehyde. When formalin is prepared, it must be heated anda methanol must be added to prevent polymerization; the final formalin solution containsbetween 5% and 15% alcohol.

Fire Hazard

Toxic vapors such as carbon dioxide and carbon monoxide are generated during combustion. Explosion hazard: when aqueous formaldehyde solutions are heated above their flash points, a potential for explosion hazard exists. High formaldehyde concentration or methanol content lowers flash point. Reacts with nitrogen oxides at about 180; the reaction becomes explosive. Also reacts violently with perchloric acid-aniline, performic acid, nitromethane, magnesium carbonate, and hydrogen peroxide. When heated, irritant formaldehyde gas evolved from solution. The main products of decomposition are carbon monoxide and hydrogen. Metals such as platinum, copper, chromia, and alumina also catalyze the formation of methanol, methylformate, formic acid, carbon dioxide, and methane. Reacts with peroxide, nitrogen oxide, and performic acid causing explosions. Can react with hydrogen chloride or other inorganic chlorides to form bis-chloromethylether (BCME), a known carcinogen. Very reactive, combines readily with many substances, 40% solution is powerful reducing agent. Incompatible with amines, azo compounds, dithiocarbamates, alkali and alkaline earth metals, nitrides, nitro compounds, unsaturated aliphatics and sulfides, organic peroxides, oxidizing agents, and reducing agents. Aqueous solutions are unstable. Commercial formaldehyde-alcohol solutions are stable. Gas is stable in absence of water. Avoid oxidizing and alkaline materials. Hazardous polymerization may occur. Compound will polymerize with active organic materials such as phenol. Will polymerize violently in the presence of caustics and nitrides; (amines) exothermic reaction, (Azo compound) exothermic reaction giving off nitrogen gas, (caustics) heat generation and violent polymerization, (dithiocarbamates) formation of flammable gases and toxic fumes, formation of carbon disulfide may result, (alkali and alkaline earth metals) heat generation and formation of a flammable hydrogen gas.

Physical properties

Formaldehyde is a clear, colorless liquid with a pungent, suffocating odor. Burning taste. Experimentally determined odor threshold concentrations of 1.0 ppmv and 0.50 ppmv were reported by Leonardos et al. (1969) and Nagata and Takeuchi (1990), respectively. Also,formalin is an aqueous solution that is 37% formaldehyde by weight; inhibited solutions (added to prevent polymeri zation) usually contain 6 12% methyl alcohol. Formaldehyde is used in the manufacture of plastics and resins by reaction with phenols,urea, and melamine. It is used as a preservative,a disinfectant, and as a chemical intermediate.

Incompatibilities

Pure formaldehyde may polymerize unless properly inhibited (usually with methanol). May form explosive mixture with air. Incompatible with strong acids; amines, strong oxidizers; alkaline materials; nitrogen dioxide; performic acid; phenols, urea. Reaction with hydrochloric acid forms bis-chloromethyl ether, a carcino gen. Formalin is incompatible with strong oxidizers, alkalis, acids, phenols, urea, oxides, isocyanates, caustics, anhydrides.

Chemical Properties

Formaldehyde is colorless gas with a very distinct, pungent odor. It is highly soluble in water and in a variety of organic solvents. It has the potential to react explosively with peroxides and nitrogen oxide. Formalin, the aqueous form of formaldehyde, is a colorless liquid with a very distinct, pungent odor. It is incompatible and may react with strong oxidizers, alkalis,and acids. The liquid has a variable molecular weight, which is dependent on the specific aqueous formulation.

storage

work with formaldehyde should be conducted in a fume hood to prevent exposure by inhalation, and splash goggles and impermeable gloves should be worn at all times to prevent eye and skin contact. Formaldehyde should be used only in areas free of ignition sources. Containers of formaldehyde should be stored in secondary containers in areas separate from oxidizers and bases.

Definition

Formalin: a colourless solution of methanal (formaldehyde) in waterwith methanol as a stabilizer; r.d.1.075–1.085. When kept at temperaturesbelow 25°C a white polymer ofmethanal separates out. It is used asa disinfectant and preservative forbiological specimens.

Potential Exposure

Formaldehyde has found wide indus trial usage as a fungicide, germicide; and in disinfectants and embalming fluids. It is also used in the manufacture of artificial silk and textiles, latex, phenol, urea, thiourea and melamine resins; dyes, and inks; cellulose esters and other organic molecules; mirrors, and explosives. It is also used in the paper, photographic, and furniture industries. It is an intermediate in drug manufacture and is a pesticide intermediate.

General Description

Formaldehyde, also called formic aldehyde or methyl aldehyde, has extensive application. For instance, it is used as a tissue preservative or organic chemical reagent. Thus, formaldehyde is very common to the chemical industry. In fact, formaldehyde is an important chemical used widely by industry to manufacture building materials and numerous household products. It is also a by-product of combustion and certain other natural processes. It is present in substantial concentrations both indoors and outdoors. Formaldehyde is well known as a preservative in medical laboratories, as an embalming fluid, and as a steriliser. Its primary use is in the production of resins and as a chemical intermediate. Urea–formaldehyde (uf) and phenol–formaldehyde (pf) resins are used in foam insulations, as adhesives in the production of particle board and plywood, and in the treating of textiles. Sources of formaldehyde in the home include building materials, smoking, household products, and the use of unvented, fuel-burning appliances, like gas stoves or kerosene space heaters. Formaldehyde, by itself or in combination with other chemicals, serves a number of purposes in manufactured products. Formaldehyde itself is a colourless gas, but it is more commonly purchased and used in aqueous solution (called formalin solution), with a maximum concentration of 40%. Formalin solutions often contain some amount of methanol as well. Both formaldehyde gas and solutions have a characteristic pungent, unpleasant odour.

Hazard

Moderate fire risk. Explosive limits in air 7– 73%. Toxic by inhalation, strong irritant, a carcinogen. (Solution) Avoid breathing vapor and avoid skin contact. Confirmed carcinogen.

Uses

Formaldehyde is used in the manufactureof phenolic resins, cellulose esters, artificialsilk, dyes, explosives, and organic chemicals.Other uses are as a germicide, fungicide, anddisinfectant; in tanning, adhesives, waterproofingfabrics, and for tonic and chromeprinting in photography; and for treating skindiseases in animals. In vitro neutralizationof scorpion venom toxicity by formaldehydehas been reported (Venkateswarlu et al.1988).Formaldehyde constitutes about 50% ofall aldehydes present in the air. It is oneof the toxic effluent gases emitted fromburning wood and synthetic polymeric substancessuch as polyethylene, nylon 6, andpolyurethane foams. Firefighters have a greaterrisk to its exposure. Incapacitation fromthe toxic effluent gases is reported to occurmore rapidly from the combustion of syntheticpolymers than from that of naturalcellulose materials.Formaldehyde is directly emitted into theair from vehicles. It is released in traceamounts from pressed wood products suchas particleboard and plywood paneling, fromold “sick” buildings, and from cotton andcotton–polyester fabrics with selected crosslinkfinishes. Formation of formaldehyde hasbeen observed in some frozen gadoid fishdue to enzymic decomposition of the additivetrimethylamine oxide (Rehbein 1985).Its concentration can build up during frozenstorage of fish (Leblanc and Leblanc 1988;Reece 1985). It occurs in the upper atmosphere,cloud, and fog; it also forms inphotochemical smog processes.

Waste Disposal

Return refillable compressed gas cylinders to supplier. Incineration in solution of combus tible solvent. Consult with environmental regulatory agen cies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, trans portation, treatment, and waste disposal.

Environmental Fate

Biological. Biodegradation products reported include formic acid and ethanol, each of which can further degrade to carbon dioxide (Verschueren, 1983).Photolytic. Major products reported from the photooxidation of formaldehyde with nitrogen oxides are carbon monoxide, carbon dioxide and hydrogen peroxide (Altshuller, 1983). In synthetic air, photolysis of formaldehyde gave hydrochloric acid andIrradiation of gaseous formaldehyde containing an excess of nitrogen dioxide over chlorine yielded ozone, carbon monoxide, nitrogen pentoxide, nitryl chloride, nitric acid and hydrochloric acid. Peroxynitric acid was the major photolysis product when chloChemical/Physical. Oxidizes in air to formic acid (Hartley and Kidd, 1987). Trioxymethylene may precipitate under cold temperatures (Sax, 1984). Polymerizes easily (Windholz et al., 1983). Anticipated products from the reaction of formaldehyde with ozone orhydroxyl radicals in air are carbon monoxide and carbon dioxide (Cupitt, 1980). Major products reported from the photooxidation of formaldehyde with nitrogen oxides are carbon monoxide, carbon dioxide and hydrogen peroxide (Altshuller, 1983).Reacts with hydrochloric acid in moist air forming bis(chloromethyl)ether. This compound may also form from an acidic solution containing chloride ion and formaldehyde (Frankel et al., 1974). In an aqueous solution at 25°C, nearly all the formaldehyde add

Chemical Reactivity

Reactivity with Water No reaction; Reactivity with Common Materials: No reactions; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

Uses

More than half of the commercial formaldehyde produced is used to manufacture phenolic,urea, and melamine formaldehyde resins. Polyacetyl resins use another 5–10% of formaldehyde,and approximately 80% of formaldehyde goes into the resins and plastics industry.Phenolic-formaldehyde resins were the first synthetic plastics to be produced. The first plasticwas called Bakelite.Formaldehyde has traditionally been used as a preservative in biology and medical laboratoriesand in embalming fluid. Embalming fluids typically contain 5–15% formaldehyde, a significant percentage of alcohol, and other additives to perform certain functions, for example,bleaches and coloring to preserve skin color. Formaldehyde has been used to preserve deadbodies since 1900 and has several qualities that make it the preferred preservative. Foremostamong these is its low cost, but it also has several biochemical advantages: it kills germs andmicroorganisms, destroys decomposition enzymes, retards decomposition of proteins, andhardens body tissues.

Uses

Formaldehyde is used as the preservative; disinfectant; antiseptic; in embalming solutions; in the manufacture of phenolic resins, artificial silk, cellulose esters, dyes, urea, thiourea, melamine res ins, organic chemicals, glass mirrors and explosives; used in improving fastness of dyes on fabrics; in tanning and preserving hides; in mordanting and waterproofing fabrics; as a germicide and fungicide for vegetables and other plants; in destroying flies and other insects; in preserving and coagulating rubber latex; prevent mildewand spelt in wheat and rot in oats; used to ren der casein, albumin, and gelatin insoluble; in chemical analysis; as a tissue fixative; as a component of particle board and plywood; in the manufacture of pentaerythritol, hexamethylenetetramine and lkbutanediol; used in ceiling and wall insulation; in res ins used to wrinkle-proof fabrics; in photography for hardening gelatin plates and papers, for toning gelatin-chloride papers and for chrome printing and developing; intermediate in drug manufacture; pesticide intermediate; in the production of urea, phenolic melamine and acetale resins; in textile products; as an astringent, disinfectant, and preservative in cosmetics, metal-working fluids, shampoos, etc.; antiperspirant in cosmetics; anticracking agent in dental plastics; in anhidrotics; chipboard production; in cleaning products, disinfectants and deodorizers, dry-cleaning materials, and glues; in mineral-wool production, paints and coatings, paper industry, phenolic resins and urea plastics; in adhesives and footwear, photographic paper and solutions, polishes, printing materials, tanning agents, wart remedies, embalming solutions, fertilizers, wood composites, and insulation.

Uses

Formaldehyde (methyl aldehyde, methylene oxide) is a ubiquitous compound found endogenously in the body and environment. It is a colorless, flammable gas with a distinct, pungent odor and is most commonly available in aqueous solutions under the name formalin (37% formaldehyde in water). Formaldehyde has been used as a disinfectant, an embalming agent, and in industry as a precursor in the fabrication of complex compounds. Since scientific research has identified links between formaldehyde and adverse health effects, precautions and protections must be considered during use.

Safety Profile

Confirmed carcinogen with experimental carcinogenic, tumorigenic, and teratogenic data. Human poison by ingestion. Experimental poison by ingestion, skin contact, inhalation, intravenous, intraperitoneal, and subcutaneous routes. Human systemic effects by inhalation: lachqmation, olfactory changes, aggression, and pulmonary changes. Experimental reproductive effects. Human mutation data reported. A human skin and eye irritant. If swallowed it causes violent vomiting and darrhea that can lead to collapse. Frequent or prolonged exposure can cause hypersensitivity leading to contact dermatitis, possibly of an eczematoid nature. An air concentration of 20 ppm is quickly irritating to eyes. A common air contaminant. Flammable liquid when exposed to heat or flame; can react vigorously with oxidizers. A moderate explosion hazard when exposed to heat or flame. The gas is a more dangerous fire hazard than the vapor. Should formaldehyde be involved in a fire, irritating gaseous formaldehyde may be evolved. When aqueous formaldehyde solutions are heated above their flash points, a potential for an explosion hazard exists. High formaldehyde concentration or methanol content lowers the flash point. Reacts with sodum hydroxide to yield formic acid and hydrogen. Reacts with NOx at about 180'; the reaction becomes explosive. Also reacts violently with perchloric acid + anhe, performic acid, nitromethane, magnesium carbonate, H2O2. Moderately dangerous because of irritating vapor that may exist in toxic concentrations locally if storage tank is ruptured. To fight fire, stop flow of gas (for pure form); alcohol foam for 37% methanol-free form. When heated to decomposition it emits acrid smoke and fumes. See also ALDEHYDES.

Air & Water Reactions

The solution gives up formaldehyde vapors readily. These vapors are flammable over a wide vapor-air concentration range. Water soluble.

Purification Methods

It commonly contains added MeOH. Add KOH solution (1 mole KOH: 100 moles HCHO) to ~37% by weight aqueous formaldehyde solution (formalin), or evaporate to dryness, to give paraformaldehyde polymer which, after washing with water, is dried in a vacuum desiccator over P2O5 or H2SO4. Formaldehyde is regenerated by heating the paraformaldehyde to 120o under vacuum, or by decomposing it with barium peroxide. The monomer, a colourless flammable gas, is passed through a glass-wool filter cooled to -48o in a CaCl2/ice mixture to remove particles of polymer, then dried by passage over P2O5 and either condensed in a bulb immersed in liquid nitrogen or absorbed in ice-cold conductivity water. The gas or aqueous solutions have pungent suffocating odours, are LACHRYMATORY and suspected carcinogens, handle carefully. Formalin is a disinfectant and a preservative of dead animal and plant tissues. [Beilstein 1 IV 3017.]

Trade name

DYNOFORM?; FANNOFORM?; FORMALITH?; FORMOL?; FYDE?; HERCULES 37 M6-8?; HOCH?; IVALON?; KARSAN?; LYSOFORM?; MAGNIFLOC 156C FLOCCULANT?; MORBICID?; STERIFORM?; SUPERLYSOFORM?

Carcinogenicity

Formaldehyde is known to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in humans and supporting data on mechanisms of carcinogenesis. Formaldehyde was first listed in the Second Annual Report on Carcinogens in 1981 as reasonably anticipated to be a human carcinogen based on sufficient evidence from studies in experimental animals. Since that time, additional cancer studies in humans have been published, and the listing status was changed to known to be a human carcinogen in the Twelfth Report on Carcinogens (2011).

Agricultural Uses

Microbiocide, Fungicide, Bactericide; Soil sterilent: Registered for use in the U.S. Not approved for use in EU countries. Formaldehyde has found wide industrial usage as a fungicide, germicide and in disinfectants. It is used most often in an aqueous solution stabilized with methanol (formalin). It is also a pesticide intermediate.

Contact allergens

Sources and uses of formaldehyde are numerous. Exposed people are mainly health workers, cleaners, painters, met alworkers, but also photographers (color developers) and carbonless copy paper users. Formaldehyde can induce contact urticaria. Formaldehyde may be the cause of sen sitization to formaldehyde releasers: benzylhemiformal, bromonitrodioxane, bromonitropropanediol (?), chloroal lylhexaminium chloride or Quaternium-15, diazolidinylu rea, dimethylol urea, dimethyloldimethylhydantoin or DMDM hydantoin, hexamethylenetetramine or methe namine, imidazolidinylurea, monomethyloldimethylhy dantoin or MDM hydantoin, N-methylolchloracetamide, paraformaldehyde and trihydroxyethylhexahydrotriazine or Grotan BK. Formaldehyde is used for the synthesis of many resins. Some of them, such as formaldehyde-urea and melamine formaldehyde resins, can be used in textiles and second arily release free formaldehyde (see Chap. 40). Other resins, such as p-tert-butylphenol formalde hyde resin or tosylamine formaldehyde resin, do not release formaldehyde.

Chemical Properties

Formaldehyde is an important chemical widely used by industry to manufacture building materials and numerous household products. It is also a by-product of combustion and certain other natural processes. It is present in substantial concentrations both indoors and outdoors. Formaldehyde is well known as a preservative in medical laboratories, as an embalming fl uid, and as a sterilizer. Its primary use is in the production of resins and as a chemical intermediate. Urea formaldehyde (uf) and phenol formaldehyde (pf) resins are used in foam insulations, as adhesives in the production of particle board and plywood, and in the treating of textiles. Sources of formaldehyde in the home include building materials, smoking, household products, and the use of unvented, fuel-burning appliances, like gas stoves or kerosene space heaters. Formaldehyde, by itself or in combination with other chemicals, serves a number of purposes in manufactured products. It has been reported that the use and production of formaldehyde in 1998 was about 11.3 billion pounds and the international production crossed over 46 billion pounds in 2004.

Health Hazard

Formaldehyde is moderately toxic by skin contact and inhalation. Exposure to formaldehyde gas can cause irritation of the eyes and respiratory tract, coughing, dry throat, tightening of the chest, headache, a sensation of pressure in the head, and palpitations of the heart. Exposure to 0.1 to 5 ppm causes irritation of the eyes, nose, and throat; above 10 ppm severe lacrimation occurs, burning in the nose and throat is experienced, and breathing becomes difficult. Acute exposure to concentrations above 25 ppm can cause serious injury, including fatal pulmonary edema. Formaldehyde has low acute toxicity via the oral route. Ingestion can cause irritation of the mouth, throat, and stomach, nausea, vomiting, convulsions, and coma. An oral dose of 30 to 100 mL of 37% formalin can be fatal in humans. Formalin solutions can cause severe eye burns and loss of vision. Eye contact may lead to delayed effects that are not appreciably eased by eye washing.Formaldehyde is regulated by OSHA as a carcinogen (Standard 1910.1048) and is listed in IARC Group 2A ("probable human carcinogen"). This substance is classified as a "select carcinogen" under the criteria of the OSHA Laboratory Standard. Prolonged or repeated exposure to formaldehyde can cause dermatitis and sensitization of the skin and respiratory tract. Following skin contact, a symptom free period may occur in sensitized individuals. Subsequent exposures can then lead to itching, redness, and the formation of blisters

Flammability and Explosibility

Formaldehyde gas is extremely flammable; formalin solution is a combustible liquid (NFPA rating = 2 for 37% formaldehyde (15% methanol), NFPA rating = 4 for 37% formaldehyde (methanol free)). Toxic vapors may be given off in a fire. Carbon dioxide or dry chemical extinguishers should be used to fight formaldehyde fires.

Shipping

UN1198 Formaldehyde solutions, flammable, Hazard Class: 3; Labels: 3-Flammable liquid, 8-Corrosive material. Cylinders must be transported in a secure upright position, in a well-ventilated truck. Protect cylinder and labels from physical damage. The owner of the compressed gas cylinder is the only entity allowed by federal law (49CFR) to transport and refill them. It is a violation of transportation regulations to refill compressed gas cylinders without the express written permission of the owner. UN2209 Formaldehyde solutions, with not<25% formal dehyde, Hazard class: 8; Labels: 8-Corrosive material. UN3077 For solids containing varying amounts of formal dehyde : UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.

Reactivity Profile

FORMALDEHYDE, SOLUTION, reacts violently with strong oxidizing agents (hydrogen peroxide, performic acid, perchloric acid in the presence of aniline, potassium permanganate, nitromethane). Reacts with bases (sodium hydroxide, potassium hydroxide, ammonia), and with nitrogen dioxide (explosive reaction around 180°C). Reacts with hydrochloric acid to form highly toxic bis(chloromethyl) ether. Polymerization reaction with phenol may develop sudden destructive pressure [Bretherick, 5th ed., 1995, p.168].
InChI:InChI=1/CH2O/c1-2/h1H2

50-00-0 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (F0622)  Formaldehyde Solution (37%) (stabilized with Methanol)   50-00-0 300mL 130.00CNY Detail
Alfa Aesar (33314)  Formaldehyde, 37% in aq. soln., ACS, 36.5-38.0%, stab. with 10-15% methanol    50-00-0 500ml 306.0CNY Detail
Alfa Aesar (33314)  Formaldehyde, 37% in aq. soln., ACS, 36.5-38.0%, stab. with 10-15% methanol    50-00-0 1L 491.0CNY Detail
Alfa Aesar (33314)  Formaldehyde, 37% in aq. soln., ACS, 36.5-38.0%, stab. with 10-15% methanol    50-00-0 4L 1166.0CNY Detail
Alfa Aesar (33314)  Formaldehyde, 37% in aq. soln., ACS, 36.5-38.0%, stab. with 10-15% methanol    50-00-0 *4x1L 1730.0CNY Detail
Alfa Aesar (33314)  Formaldehyde, 37% in aq. soln., ACS, 36.5-38.0%, stab. with 10-15% methanol    50-00-0 *4x4L 3232.0CNY Detail
Alfa Aesar (A16163)  Formaldehyde, 37% w/w aq. soln., stab. with 7-8% methanol    50-00-0 100ml 207.0CNY Detail
Alfa Aesar (A16163)  Formaldehyde, 37% w/w aq. soln., stab. with 7-8% methanol    50-00-0 500ml 244.0CNY Detail
Alfa Aesar (A16163)  Formaldehyde, 37% w/w aq. soln., stab. with 7-8% methanol    50-00-0 2500ml 409.0CNY Detail
Supelco (47083-U)  Formaldehydesolution  stabilized with methanol, ~37 wt. % in H2O, analytical standard 50-00-0 47083-U 368.55CNY Detail
Sigma-Aldrich (15513)  Formaldehydesolution  meets analytical specification of Ph.?Eur., BP, 35 wt. %, contains 10% methanol as stabilizer 50-00-0 15513-1L-R 391.95CNY Detail

50-00-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Formaldehyde

1.2 Other means of identification

Product number -
Other names superlysoform

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Formaldehyde is used predominantly as a chemical intermediate. It also has minor uses in agriculture, as an analytical reagent, in concrete and plaster additives, cosmetics, disinfectants, fumigants, photography, and wood preservation. One of the most common uses of formaldehyde in the U.S is manufacturing urea-formaldehyde resins, used in particleboard products. Formaldehyde (as urea formaldehyde foam) was extensively used as an insulating material until 1982 when it was banned by the U.S. Consumer Product Safety Commission.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:50-00-0 SDS

50-00-0Synthetic route

methanol
67-56-1

methanol

formaldehyd
50-00-0

formaldehyd

Conditions
ConditionsYield
With PQQTME; calcium perchlorate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile Oxidation;100%
at 370℃; under 760.051 Torr; for 1h; Reagent/catalyst; Temperature; Inert atmosphere; Flow reactor;100%
With sulfuric acid Electrochemical reaction;100%
2-quinolin-2-yl-ethanol
1011-50-3

2-quinolin-2-yl-ethanol

A

2-methylquinoline
91-63-4

2-methylquinoline

B

formaldehyd
50-00-0

formaldehyd

Conditions
ConditionsYield
In benzene Ambient temperature; Irradiation;A 100%
B 100%
phenylethane 1,2-diol
93-56-1

phenylethane 1,2-diol

4-cyano-N,N-dimethylaniline-N-oxide
62820-00-2

4-cyano-N,N-dimethylaniline-N-oxide

A

formaldehyd
50-00-0

formaldehyd

B

4-cyano-N-methylaniline
4714-62-9

4-cyano-N-methylaniline

C

benzaldehyde
100-52-7

benzaldehyde

D

4-cyano-N,N-dimethylaniline
1197-19-9

4-cyano-N,N-dimethylaniline

Conditions
ConditionsYield
With chloro(5,10,15,20-tetraphenylporphyrinato)chromium(III) In acetonitrile for 0.666667h; Rate constant; Ambient temperature; Irradiation; oxygen transfer was investigated, different irradiation time;A n/a
B n/a
C 100%
D 100%
2-(2-deuterioxyethyl)quinoline
29166-01-6

2-(2-deuterioxyethyl)quinoline

A

formaldehyd
50-00-0

formaldehyd

B

2-(monodeuteriomethyl)quinoline

2-(monodeuteriomethyl)quinoline

Conditions
ConditionsYield
In benzene Ambient temperature; Irradiation;A 100%
B 100%
sarcosine
107-97-1

sarcosine

A

formaldehyd
50-00-0

formaldehyd

B

carbon dioxide
124-38-9

carbon dioxide

C

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; sodium perchlorate; chlorine at 24.9℃; Mechanism; Rate constant; Equilibrium constant; multistep reaction: 1.) water, 298 deg K, 2.) water, 298 deg K; reactions under var. conditions;A 100%
B n/a
C n/a
N-chloro-sarcosine
52316-59-3

N-chloro-sarcosine

A

formaldehyd
50-00-0

formaldehyd

B

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
In water at 24.9℃; Rate constant; Mechanism; Thermodynamic data; Irradiation; I=0.5 mol-1 L-1; various pH; ΔH(excit.), ΔS(excit.);A 100%
B n/a
With water In 1,4-dioxane at 25℃;
With water In 1,4-dioxane at 25℃; Kinetics; Mechanism;
benzenesulfinyl-benzoyloxy-methane
41065-20-7

benzenesulfinyl-benzoyloxy-methane

A

formaldehyd
50-00-0

formaldehyd

B

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
With potassium hydroxide In methanolA 100%
B 61%
p-nitro-N,N-dimethylaniline-N-oxide
26492-31-9

p-nitro-N,N-dimethylaniline-N-oxide

A

formaldehyd
50-00-0

formaldehyd

B

N,N-Dimethyl-4-nitroaniline
100-23-2

N,N-Dimethyl-4-nitroaniline

Conditions
ConditionsYield
With 1H-imidazole; meso-tetraphenylporphyrin iron(III) chloride; DMA-OCH3 In chloroform at 25℃; for 0.5h;A n/a
B 100%
C6H16NO4P
85437-83-8

C6H16NO4P

A

formaldehyd
50-00-0

formaldehyd

B

trans-nitrosomethane dimer
2717-67-1, 17606-84-7, 37765-15-4

trans-nitrosomethane dimer

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid for 2h;A n/a
B 100%
((bis(dimethylamino)phosphinyl)oxy)dimethylamine
85437-82-7

((bis(dimethylamino)phosphinyl)oxy)dimethylamine

A

formaldehyd
50-00-0

formaldehyd

B

trans-nitrosomethane dimer
2717-67-1, 17606-84-7, 37765-15-4

trans-nitrosomethane dimer

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid for 2h;A n/a
B 100%
With 3-chloro-benzenecarboperoxoic acid for 2h;A n/a
B 100%
1-(3,4-Dihydro-benzo[c][1,2]oxazin-1-yl)-2-methyl-propan-1-one
180985-69-7

1-(3,4-Dihydro-benzo[c][1,2]oxazin-1-yl)-2-methyl-propan-1-one

A

formaldehyd
50-00-0

formaldehyd

B

2-isopropyl-4H-3,1-benzoxazine
115975-92-3

2-isopropyl-4H-3,1-benzoxazine

Conditions
ConditionsYield
In 1,3,5-trimethyl-benzene Heating;A n/a
B 100%
(H2O)5Cr(CH2OCH3)(2+)
78402-17-2

(H2O)5Cr(CH2OCH3)(2+)

chromium (III) ion

chromium (III) ion

formaldehyd
50-00-0

formaldehyd

Conditions
ConditionsYield
With water; mercury ion In water Kinetics; byproducts: MeOH, H(1+); excess of Hg(2+) soln. (mol. ratio of Hg(2+)/Cr-compd. 2:1) added to soln. of Cr-compd. at 24.8°C under N2 by controlled ionic strength;Co(NH3)5F has no effect; not sepd., detected by UV;100%
(H2O)5CrCH2OH(2+)

(H2O)5CrCH2OH(2+)

chromium (III) ion

chromium (III) ion

formaldehyd
50-00-0

formaldehyd

Conditions
ConditionsYield
With mercury ion In methanol; water Kinetics; byproducts: H(1+); excess of Hg(2+) soln. (mol. ratio of Hg(2+)/Cr-compd. 2:1) added to soln. of Cr-compd. in 1 M aq. MeOH at 24.8°C under N2 by controlledionic strength; Co(NH3)5F and typ of alcohols has no effect; not sepd., detected by UV;100%
Dimethyl ether
115-10-6

Dimethyl ether

A

formaldehyd
50-00-0

formaldehyd

B

Methyl formate
107-31-3

Methyl formate

Conditions
ConditionsYield
With nitrogen; oxygen at 239.84℃; Conversion of starting material;A 99.7%
B 0.3%
With nitrogen; oxygen at 239.84℃; Conversion of starting material;A 98.8%
B 1.2%
With nitrogen; oxygen at 239.84℃; Conversion of starting material;A 98.6%
B 1.4%
methane
34557-54-5

methane

dinitrogen monoxide
10024-97-2

dinitrogen monoxide

A

methanol
67-56-1

methanol

B

formaldehyd
50-00-0

formaldehyd

C

carbon dioxide
124-38-9

carbon dioxide

D

carbon monoxide
201230-82-2

carbon monoxide

E

nitrogen
7727-37-9

nitrogen

Conditions
ConditionsYield
In neat (no solvent) Kinetics; Oxidation of CH4 by N2O in presence of catalyst (773 K): deposited Cu(2+) on carbon;;A 0.2%
B 0.3%
C 99.5%
D 0%
E n/a
In neat (no solvent) Kinetics; byproducts: C2H5OH (small quantity); oxidation of CH4 by N2O in presence of catalyst (773 K): deposited Ti(4+) on carbon;;A 13.8%
B 0%
C 86.2%
D 0%
E n/a
In neat (no solvent) Kinetics; Oxidation of CH4 by N2O in presence of catalyst (773 K): deposited Co(2+) on carbon;;A 0%
B 0%
C 75%
D 25%
E n/a
6,10b-dimethyl-4a,10b-dihydro-3H-naphtho<2,1-e><1,2,4>trioxine
89946-44-1

6,10b-dimethyl-4a,10b-dihydro-3H-naphtho<2,1-e><1,2,4>trioxine

A

formaldehyd
50-00-0

formaldehyd

(1S,2R)-1,4-Dimethyl-1,2-dihydro-naphthalene-1,2-diol
114390-56-6

(1S,2R)-1,4-Dimethyl-1,2-dihydro-naphthalene-1,2-diol

Conditions
ConditionsYield
With acetic acid; zinc at 16℃; for 0.25h;A n/a
B 99%
tert.-butylhydroperoxide
75-91-2

tert.-butylhydroperoxide

2,2'-azinobis-(3-ethyl-2,3-dihydrobenzothiazole-6-sulphonate) diammonium salt
30931-67-0

2,2'-azinobis-(3-ethyl-2,3-dihydrobenzothiazole-6-sulphonate) diammonium salt

A

methanol
67-56-1

methanol

B

formaldehyd
50-00-0

formaldehyd

C

C18H18N4O6S4(1+)*2H3N

C18H18N4O6S4(1+)*2H3N

D

acetone
67-64-1

acetone

E

tert-butyl alcohol
75-65-0

tert-butyl alcohol

Conditions
ConditionsYield
Fe(III)T4MPyP In water at 30℃; Rate constant; Kinetics; Mechanism; the catalyst Fe(III)T4MPyP is 5,10,15,20-tetra(N-methyl-4-pyridyl)-porphyrinatoiron(III) pentachloride; pH 9.2; investigation of the dependence of velocity constant on ionic strength, pH and t-butyl hydroperoxide concentration;A 3%
B n/a
C 72%
D 4%
E 98%
Dimethyl-p-toluidine
99-97-8

Dimethyl-p-toluidine

A

formaldehyd
50-00-0

formaldehyd

B

N-methyl-p-toluidine
623-08-5

N-methyl-p-toluidine

Conditions
ConditionsYield
With {Ru(IV)O(2,2`-bipyridine)(PEt3)}(ClO4)2 In acetonitrile at 21℃; Rate constant; Kinetics; Thermodynamic data; other Ru(IV) complex catalyst, ΔH(excit), ΔS(excit) determined;A n/a
B 98%
With iron 5,10,15,20-tetrakis(2,4,6-trimethylphenyl)porphyrin; 3-chloro-benzenecarboperoxoic acid; 3-chlorobenzoate In dichloromethane at -50.1℃; Rate constant; also horseradish peroxidase and H2O2 as reagents; kinetic isotope effect; var. temp. and solvents;
With dihydrogen peroxide; sodium tartrate; 5,10,15,20-Ph4-21H,23H-porphine-p,p',p'',p'''-(SO4)4*FeCl3 In water; acetonitrile at 25℃; pH=4; oxidative N-demethylation;A n/a
B 10 % Chromat.
amyl nitrate
1002-16-0

amyl nitrate

A

formaldehyd
50-00-0

formaldehyd

B

pentan-1-ol
71-41-0

pentan-1-ol

C

n-butane
106-97-8

n-butane

D

NO2

NO2

Conditions
ConditionsYield
In tetralin at 154℃; Mechanism; Kinetics; Ea, log A, ΔH(activation), volume of activation; other solvents, other temperatures;A n/a
B 98%
C 2%
D n/a
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid
70458-96-7

1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

A

formaldehyd
50-00-0

formaldehyd

B

ammonia
7664-41-7

ammonia

C

6-fluoro-7-amino-1-ethyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
75001-63-7

6-fluoro-7-amino-1-ethyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Conditions
ConditionsYield
With potassium permanganate; cetyltrimethylammonim bromide; acetic acid In water; acetonitrile at 24.84℃; Kinetics; Catalytic behavior; Mechanism; Thermodynamic data; Activation energy; Temperature; Concentration; Solvent; UV-irradiation;A n/a
B n/a
C 98%
1-phenyl-2-piperidin-1-yl-ethanone
779-52-2

1-phenyl-2-piperidin-1-yl-ethanone

A

N-Formylpiperidine
2591-86-8

N-Formylpiperidine

B

formaldehyd
50-00-0

formaldehyd

C

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With dihydrogen peroxide In ethanolA 14%
B n/a
C 96%
With dihydrogen peroxide In ethanolA 14%
B n/a
C 94%
[2-(2-[1,3]Dithian-2-yl-1-methyl-ethoxymethoxy)-ethyl]-trimethyl-silane
76513-61-6

[2-(2-[1,3]Dithian-2-yl-1-methyl-ethoxymethoxy)-ethyl]-trimethyl-silane

A

formaldehyd
50-00-0

formaldehyd

B

ethene
74-85-1

ethene

C

trimethylsilyl fluoride
420-56-4

trimethylsilyl fluoride

D

2-(2-hydroxypropyl-1')-1,3-dithiane
14950-49-3

2-(2-hydroxypropyl-1')-1,3-dithiane

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In N,N,N,N,N,N-hexamethylphosphoric triamide at 45℃; for 5h;A n/a
B n/a
C n/a
D 96%
methanol
67-56-1

methanol

A

formaldehyd
50-00-0

formaldehyd

B

Dimethyl ether
115-10-6

Dimethyl ether

Conditions
ConditionsYield
molybdenum(VI) oxide In gas at 290 - 350℃; under 750.06 Torr; Thermodynamic data; Product distribution; structure sensitive oxidation with orthorhomb. or microcrystalline MoO3, further temperatures, activation energy EA;A 95%
B 5%
With oxygen; aluminophosphate zeolite at 300℃; Product distribution; temperature, without oxygen, effect of catalysts;
With oxygen; vanadia at 300 - 600℃; Product distribution; further catalysts;
2-(N,N-dimethylaminomethyl)pyrrole
14745-84-7

2-(N,N-dimethylaminomethyl)pyrrole

A

formaldehyd
50-00-0

formaldehyd

B

N-Nitrosodimethylamine
62-75-9

N-Nitrosodimethylamine

C

maleimidemonooxime
74230-05-0

maleimidemonooxime

Conditions
ConditionsYield
With sodium nitrite In water at 25℃; for 0.05h; Product distribution; Mechanism; variation of amount of reagent and reaction period;A n/a
B 95%
C n/a
With sodium nitrite In water; acetic acid at 25℃; for 0.05h;A n/a
B 95%
C n/a
With sodium nitrite In water; acetic acid at 25℃;
methanol
67-56-1

methanol

(4-methoxyphenoxy)methyl 2-iodobenzoate

(4-methoxyphenoxy)methyl 2-iodobenzoate

A

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

B

formaldehyd
50-00-0

formaldehyd

C

4-methoxy-phenol
150-76-5

4-methoxy-phenol

Conditions
ConditionsYield
With potassium carbonate at 40℃; for 1.5h; Schlenk technique;A 95%
B n/a
C 90%
morpholine
110-91-8

morpholine

bromonitromethane
563-70-2

bromonitromethane

A

N-nitrosomorpholine
59-89-2

N-nitrosomorpholine

B

formaldehyd
50-00-0

formaldehyd

Conditions
ConditionsYield
In acetonitrile at 70℃; for 168h;A 94%
B n/a
lithium 2-nitropropane
3958-63-2

lithium 2-nitropropane

diphenyliodonium bromide
1483-73-4

diphenyliodonium bromide

A

formaldehyd
50-00-0

formaldehyd

B

iodobenzene
591-50-4

iodobenzene

C

biphenyl
92-52-4

biphenyl

D

2,3-dimethyl-2,3-dinitrobutane
3964-18-9

2,3-dimethyl-2,3-dinitrobutane

E

2-nitro-2-phenylpropane
3457-58-7

2-nitro-2-phenylpropane

F

benzene
71-43-2

benzene

Conditions
ConditionsYield
In methanol at 30℃; for 48h; Mechanism; Product distribution; other diaryliodonium bromides, other times, effect of light and oxygen;A 38%
B 94%
C 5%
D 5%
E 41%
F 43%
lithium 2-nitropropane
3958-63-2

lithium 2-nitropropane

diphenyliodonium bromide
1483-73-4

diphenyliodonium bromide

A

formaldehyd
50-00-0

formaldehyd

B

iodobenzene
591-50-4

iodobenzene

C

2-nitro-2-phenylpropane
3457-58-7

2-nitro-2-phenylpropane

D

benzene
71-43-2

benzene

Conditions
ConditionsYield
In methanol at 30℃; for 48h; Further byproducts given;A 38%
B 94%
C 41%
D 43%
N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

A

formaldehyd
50-00-0

formaldehyd

B

N-methylaniline
100-61-8

N-methylaniline

Conditions
ConditionsYield
With {Ru(IV)O(2,2`-bipyridine)(PPh3)}(ClO4)2 In acetonitrile at 21℃; Rate constant; Kinetics; Thermodynamic data; other Ru(IV) complex catalyst, ΔH(excit), ΔS(excit) determined;A n/a
B 94%
With dihydrogen peroxide; FePp In ethanol at 38℃; for 0.166667h; Product distribution; borate buffer, pH 9; further educts;
With phosphate buffer; dihydrogen peroxide; cytochrome c at 30℃; Equilibrium constant; Rate constant; also in the presence of phosphate bilayer;
C17H30B2O2

C17H30B2O2

formaldehyd
50-00-0

formaldehyd

Conditions
ConditionsYield
In water-d2 for 0.5h;94%
piperidine
110-89-4

piperidine

Succinimide
123-56-8

Succinimide

formaldehyd
50-00-0

formaldehyd

N-piperidinomethyl-succinimide
13314-95-9

N-piperidinomethyl-succinimide

Conditions
ConditionsYield
With aluminum oxide In water for 0.2h; Condensation; microwave irradiation;100%
With ethanol; water
morpholine
110-91-8

morpholine

Succinimide
123-56-8

Succinimide

formaldehyd
50-00-0

formaldehyd

N-[{morpholin-1-yl}-methyl]-pyrrolidine-2,5-dione
13314-97-1

N-[{morpholin-1-yl}-methyl]-pyrrolidine-2,5-dione

Conditions
ConditionsYield
With aluminum oxide In water for 0.2h; Condensation; microwave irradiation;100%
In ethanol at 60℃; for 2h;88%
morpholine
110-91-8

morpholine

formaldehyd
50-00-0

formaldehyd

4-methyl-morpholine
109-02-4

4-methyl-morpholine

Conditions
ConditionsYield
With oxalic acid at 100 - 120℃; Eschweiler-Clarke methylation;100%
With hydrogen In methanol at 100℃; under 9750.98 Torr; for 3h; Autoclave;97%
With acetic acid at 30℃; for 2h;96%
phenyl benzyl ketone
451-40-1

phenyl benzyl ketone

formaldehyd
50-00-0

formaldehyd

1,2-diphenylprop-2-en-1-one
4452-11-3

1,2-diphenylprop-2-en-1-one

Conditions
ConditionsYield
With piperidine; acetic acid In methanol Inert atmosphere; Reflux;100%
With trifluoroacetic acid; diisopropylamine 2,2,2-trifluoroacetic acid salt In tetrahydrofuran for 2h; Reflux;88%
With piperidine; acetic acid In methanol; water for 6h; Reflux;88%
indole
120-72-9

indole

formaldehyd
50-00-0

formaldehyd

indole-3-carbinol
700-06-1

indole-3-carbinol

Conditions
ConditionsYield
With sodium methylate for 8h; Heating;100%
With methanol; sodium hydrogencarbonate
With sodium methylate
pyrrole
109-97-7

pyrrole

formaldehyd
50-00-0

formaldehyd

(1H-pyrrole-2,5-diyl)dimethanol
6249-04-3

(1H-pyrrole-2,5-diyl)dimethanol

Conditions
ConditionsYield
With potassium carbonate In water at 5℃; for 168h;100%
With sodium hydroxide for 3h; Ambient temperature;46.4%
With potassium carbonate In water at 5℃; for 168h; Inert atmosphere; Sealed flask; Darkness;32%
formaldehyd
50-00-0

formaldehyd

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

ethyl 2-diethoxyphosphinoylacrylate
20345-61-3

ethyl 2-diethoxyphosphinoylacrylate

Conditions
ConditionsYield
Stage #1: formaldehyd; diethoxyphosphoryl-acetic acid ethyl ester With piperidine In methanol at 80℃; for 36h;
Stage #2: With toluene-4-sulfonic acid In toluene for 16h; Dean-Stark; Reflux;
100%
Stage #1: formaldehyd With piperidine In methanol for 0.5h; Heating;
Stage #2: diethoxyphosphoryl-acetic acid ethyl ester In methanol for 70h; Heating;
73%
piperidine In methanol Heating;60%
formaldehyd
50-00-0

formaldehyd

ephedrine
299-42-3

ephedrine

(-)-N-methylephedrine
552-79-4

(-)-N-methylephedrine

Conditions
ConditionsYield
With HCOOH (98percent) In water for 18h; Heating;100%
With formic acid at 80℃; for 0.0666667h; Microwave irradiation; Neat (no solvent);90%
With formic acid at 65℃; for 6h;89%
formaldehyd
50-00-0

formaldehyd

ephedrine
299-42-3

ephedrine

(4S,5R)-3,4-dimethyl-5-phenyl-1,3-oxazolidine
123618-06-4

(4S,5R)-3,4-dimethyl-5-phenyl-1,3-oxazolidine

Conditions
ConditionsYield
for 1h; Ambient temperature;100%
With potassium carbonate In benzene for 6h; Heating;93%
With sodium sulfate; potassium hydroxide In methanol for 6h; Reflux;85%
formaldehyd
50-00-0

formaldehyd

cyanuric acid
108-80-5

cyanuric acid

1,3,5-tri(hydroxymethyl)-1,3,5-triaza-2,4,6-cyclohexanetrione
10471-40-6

1,3,5-tri(hydroxymethyl)-1,3,5-triaza-2,4,6-cyclohexanetrione

Conditions
ConditionsYield
In water100%
In pyridine; water for 15h; Ambient temperature;90%
formaldehyd
50-00-0

formaldehyd

ethanolamine
141-43-5

ethanolamine

1,3,5-tris(2-hydroxyethyl)-1,3,5-triazacyclohexane
4719-04-4

1,3,5-tris(2-hydroxyethyl)-1,3,5-triazacyclohexane

Conditions
ConditionsYield
In methanol at 20℃; for 16h;100%
In methanol for 48h;86%
With water
In ethanol Cyclization;
at 50 - 80℃; for 1h;92 g
formaldehyd
50-00-0

formaldehyd

ethanolamine
141-43-5

ethanolamine

N-(hydroxyethyl)aminomethanesulfonic acid
88788-08-3

N-(hydroxyethyl)aminomethanesulfonic acid

Conditions
ConditionsYield
Stage #1: formaldehyd; ethanolamine In water at 10℃; for 24h;
Stage #2: With sulfur dioxide In water at 20℃; pH=<= 1.0;
100%
With water und anschliessende Saettigung mit SO2;
formaldehyd
50-00-0

formaldehyd

4-acetaminophenol
103-90-2

4-acetaminophenol

diethylamine
109-89-7

diethylamine

N-{3-[(diethylamino)methyl]-4-hydroxyphenyl}acetamide
121-78-8

N-{3-[(diethylamino)methyl]-4-hydroxyphenyl}acetamide

Conditions
ConditionsYield
In ethanol at 80℃; for 1.5h; Microwave irradiation;100%
In ethanol for 12h; Heating;80%
In ethanol at 80℃; for 1h; Microwave irradiation;77%
formaldehyd
50-00-0

formaldehyd

diethylamine
109-89-7

diethylamine

phenylacetylene
536-74-3

phenylacetylene

diethyl-(3-phenyl-prop-2-ynyl)-amine
22396-72-1

diethyl-(3-phenyl-prop-2-ynyl)-amine

Conditions
ConditionsYield
With copper dichloride at 80℃; under 150.015 Torr; for 3h; Mannich reaction;100%
With silver nitrate at 105℃; for 0.133333h; microwave irradiation;99%
copper(l) iodide In water; dimethyl sulfoxide at 30℃; for 10h;98%
formaldehyd
50-00-0

formaldehyd

aniline
62-53-3

aniline

1,3,5-triphenylhexahydro-1,3,5-triazine
91-78-1

1,3,5-triphenylhexahydro-1,3,5-triazine

Conditions
ConditionsYield
In toluene at 120℃; for 0.5h;100%
With triethylamine In ethanol; water at 25℃; for 0.25h; Mannich Aminomethylation; Sonication; Irradiation;98%
With PEG-400 for 0.0833333h; Catalytic behavior;95%
formaldehyd
50-00-0

formaldehyd

uracil
66-22-8

uracil

5-hydroxymethyl uracil
4433-40-3

5-hydroxymethyl uracil

Conditions
ConditionsYield
With potassium hydroxide In water at 50 - 52℃; for 68h;100%
With potassium hydroxide for 0.05h; microwave irradiation;98%
With potassium hydroxide In water at 0 - 55℃; for 36h;98%
formaldehyd
50-00-0

formaldehyd

urethane
51-79-6

urethane

ethyl N-(hydroxymethyl)carbamate
5027-16-7

ethyl N-(hydroxymethyl)carbamate

Conditions
ConditionsYield
With potassium carbonate In benzene at 70 - 75℃; for 3.5h;100%
With barium dihydroxide In water for 40h; Ambient temperature;38%
With barium dihydroxide
formaldehyd
50-00-0

formaldehyd

ethanethiol
75-08-1

ethanethiol

(ethylthio)methanol
15909-30-5

(ethylthio)methanol

Conditions
ConditionsYield
With sodium hydroxide; water at 25 - 40℃; for 1h; Addition;100%
With water
for 2h; Ambient temperature;
formaldehyd
50-00-0

formaldehyd

diethyl malonate
105-53-3

diethyl malonate

diethyl bis(hydroxymethyl)malonate
20605-01-0

diethyl bis(hydroxymethyl)malonate

Conditions
ConditionsYield
With potassium carbonate In water at 20℃;100%
With triethylamine In tetrahydrofuran; 1,4-dioxane; water a) from 4 deg C to 6 deg C, 20 min, b) RT, 40 min;96%
With hydrogenchloride; sodium carbonate In water at 15 - 20℃; under 100 Torr; pH=6-7; Large scale;90%
formaldehyd
50-00-0

formaldehyd

L-Tryptophan
73-22-3

L-Tryptophan

3-carboxy-1,2,3,4-tetrahydro-2-carboline
42438-90-4

3-carboxy-1,2,3,4-tetrahydro-2-carboline

Conditions
ConditionsYield
With sulfuric acid Pictet-Spengler condensation;100%
With sulfuric acid In water Pictet-Spengler condensation;100%
With sulfuric acid under 750.075 Torr; Pictet-Spengler cyclization; Inert atmosphere;100%
N-methyl-acetamide
79-16-3

N-methyl-acetamide

formaldehyd
50-00-0

formaldehyd

N-methyl-N-chloromethylacetamide
4270-65-9

N-methyl-N-chloromethylacetamide

Conditions
ConditionsYield
With chloro-trimethyl-silane for 2h; Heating;100%
With chloro-trimethyl-silane for 1h; Heating;64%
(i), (ii) PCl5, dioxane; Multistep reaction;
dibutyl hydrogen phosphite
1809-19-4

dibutyl hydrogen phosphite

formaldehyd
50-00-0

formaldehyd

dibutyl (hydroxymethyl)phosphonate
24630-66-8

dibutyl (hydroxymethyl)phosphonate

Conditions
ConditionsYield
With potassium carbonate In cyclohexane at 20℃; for 48h; Inert atmosphere;100%
triethylamine In toluene at 60℃; for 3h;89.1%
With triethylamine at 90℃; for 16h; Inert atmosphere;76.3%
formaldehyd
50-00-0

formaldehyd

Beta-pinene
177698-19-0

Beta-pinene

nopol
128-50-7

nopol

Conditions
ConditionsYield
With iron(III) phosphate In acetonitrile at 80℃; for 4h; Prins condensation;100%
With mesoporous SnSBA-15(5) In toluene at 89.84℃; for 6h; Prins reaction;96.7%
at 150℃;61%
formaldehyd
50-00-0

formaldehyd

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

4,4-dimethylpent-2-yn-1-ol
52323-98-5

4,4-dimethylpent-2-yn-1-ol

Conditions
ConditionsYield
Stage #1: 3,3-Dimethylbut-1-yne With n-butyllithium In tetrahydrofuran at 0 - 20℃;
Stage #2: formaldehyd In tetrahydrofuran at 20 - 65℃; for 17h;
Stage #3: With water In ethyl acetate
100%
Stage #1: 3,3-Dimethylbut-1-yne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h;
Stage #2: formaldehyd In tetrahydrofuran; hexane at -78 - 20℃; for 1h;
98%
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78 - 20℃; for 2h;97%
formaldehyd
50-00-0

formaldehyd

L-alanin
56-41-7

L-alanin

N,N-dimethyl-L-alanine
2812-31-9

N,N-dimethyl-L-alanine

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 20h;100%
With 10 mol% palladium on carbon; hydrogen In water at 20℃; under 760.051 Torr; for 36.5h; Reflux;99%
With sodium dihydrogenphosphate; zinc at 30℃; for 20h;92%
formaldehyd
50-00-0

formaldehyd

L-leucine
61-90-5

L-leucine

(S)-2-dimethylamino-4-methyl-pentanoic acid
2439-37-4

(S)-2-dimethylamino-4-methyl-pentanoic acid

Conditions
ConditionsYield
With sodium cyanoborohydride; acetic acid In water; acetonitrile at 22℃; for 1h; pH=Ca.7; Inert atmosphere;100%
With sodium dihydrogenphosphate; zinc at 30℃; for 20h;95%
With sodium tetrahydroborate In 2,2,2-trifluoroethanol for 48h; Reflux;88%
formaldehyd
50-00-0

formaldehyd

n-octyne
629-05-0

n-octyne

2-nonyn-1-ol
5921-73-3

2-nonyn-1-ol

Conditions
ConditionsYield
Stage #1: n-octyne With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 1h; Inert atmosphere;
Stage #2: formaldehyd In tetrahydrofuran; hexane at -78 - 20℃; for 16h; Inert atmosphere;
100%
Stage #1: n-octyne With n-butyllithium In diethyl ether; hexane at -78℃; for 0.5h;
Stage #2: formaldehyd In diethyl ether; hexane at 20℃;
98%
Stage #1: n-octyne With n-butyllithium In diethyl ether; hexane at -78℃; Inert atmosphere;
Stage #2: formaldehyd In diethyl ether; hexane at -78 - 20℃; for 14.5h; Inert atmosphere;
88%
formaldehyd
50-00-0

formaldehyd

1,2,4,5-tetramethylbenzene
95-93-2

1,2,4,5-tetramethylbenzene

1,4-bis(chloromethyl)-2,3,5,6-tetramethylbenzene
3022-16-0

1,4-bis(chloromethyl)-2,3,5,6-tetramethylbenzene

Conditions
ConditionsYield
Stage #1: formaldehyd; 1,2,4,5-tetramethylbenzene With hydrogenchloride; sodium chloride In water at 120℃; for 5h;
Stage #2: With zinc(II) chloride In water for 24h; Reflux;
100%
With hydrogenchloride; sodium chloride In water at 120℃; for 31h;91%
With hydrogenchloride; zinc(II) chloride at 90℃; for 9h;26%
formaldehyd
50-00-0

formaldehyd

benzyloxyacetoaldehyde
60656-87-3

benzyloxyacetoaldehyde

2-(benzyloxy)acrylaldehyde
62222-04-2

2-(benzyloxy)acrylaldehyde

Conditions
ConditionsYield
With pyrrolidine In dichloromethane; water at 45℃; for 1h;100%
With L-proline In water; N,N-dimethyl-formamide at 50℃; for 8h;99%
With pyrrolidine; propionic acid In water; isopropyl alcohol at 45℃; for 4h;98%
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