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50-00-0 Usage

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].

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.

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.

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.]

Uses

Disinfectant.

Chemical Properties

Formaldehyde,HeHO, also known as methanol,formol,and methylene oxide,is a colorless gas at room temperature, In solution with water,it is a colorless poisonous liquid with a pungent odor. 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,

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.

Health Hazard

The probable oral lethal dose for humans is 0.5-5 g/kg, or between 1 ounce and 1 pint for a 150 pound person. Acute -- below 1 ppm, odor perceptible to most. 2-3 ppm, mild tingling of eyes. 4-5 ppm, increased discomfort, mild lacrimation. 10 ppm, profuse lacrimation; can be withstood only for few minutes. 10-20 ppm, breathing difficult, cough, severe burning of nose and throat. 50-100 ppm, acute irritation of respiratory tract, very serious injury likely. Skin -- primary irritation from strong solutions, gas. Delayed -- sensitization dermatitis. Suspected carcinogen. Effects in women include menstrual disorders and secondary sterility. Solutions splashed in eyes have caused injuries ranging from severe, permanent corneal opacification and loss of vision to minor discomfort. In people sensitized to formaldehyde, late asthmatic reactions may be provoked by brief exposures at approximately 3 ppm.

Air & Water Reactions

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

Definition

ChEBI: The simplest aldehyde.

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.

Trade name

DYNOFORM®; FANNOFORM®; FORMALITH®; FORMOL®; FYDE®; HERCULES 37 M6-8®; HOCH®; IVALON®; KARSAN®; LYSOFORM®; MAGNIFLOC 156C FLOCCULANT®; MORBICID®; STERIFORM®; SUPERLYSOFORM®
InChI:InChI=1/CH2O/c1-2/h1H2

50-00-0 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price 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
Supelco (47083-U)  Formaldehydesolution  stabilized with methanol, ~37 wt. % in H2O, analytical standard 50-00-0 47083-U 368.55CNY Detail
Alfa Aesar (A16163)  Formaldehyde, 37% w/w aq. soln., stab. with 7-8% methanol    50-00-0 2500ml 409.0CNY 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 100ml 207.0CNY 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 (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 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 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 500ml 306.0CNY Detail
TCI America (F0622)  Formaldehyde Solution (37%) (stabilized with Methanol)   50-00-0 300mL 130.00CNY 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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