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50-00-0

Basic Information
CAS No.: 50-00-0
Name: Formaldehyde
Molecular Structure:
Molecular Structure of 50-00-0 (Formaldehyde)
Formula: CH2O
Molecular Weight: 30.026
Synonyms: FM 282;Fannoform;Floguard 1015;Fordor;Formaldehyde-12C;Formalin;Formalin LM;Formalin Taisei;Formalith;Formic aldehyde;Lysoform;Methaldehyde;Methanal;Methyl aldehyde;Methylene oxide;Morbicid;NSC 298885;Optilyse;Oxomethane;Oxymethylene;Paraform;Superlysoform;Fyde;Formol;Super Absorbent Polymer;Formaldehyde solution;TH3159 Additive Package for Diesel Engine Oil;Larrea tridentata (DC.) Cov. Extract;BFV;F-gen;Sodium Citrate;
EINECS: 200-001-8
Density: 1.09 g/mL at 25 °C
Melting Point: -15 °C
Boiling Point: 97 °C
Flash Point: 133 °F
Solubility: soluble in water
Appearance: Clear liquid
Hazard Symbols: ToxicT
Risk Codes: 23/24/25-34-40-43-39/23/24/25
Safety: 36/37-51-45-36/37/39-26
Transport Information: UN 1198 3/PG 3
PSA: 17.07000
LogP: 0.45100
Synthetic route
67-56-1

methanol

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%
1011-50-3

2-quinolin-2-yl-ethanol

A

91-63-4

2-methylquinoline

B

50-00-0

formaldehyd

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

phenylethane 1,2-diol

62820-00-2

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

A

50-00-0

formaldehyd

B

4714-62-9

4-cyano-N-methylaniline

C

100-52-7

benzaldehyde

D

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%
29166-01-6

2-(2-deuterioxyethyl)quinoline

A

50-00-0

formaldehyd

B

2-(monodeuteriomethyl)quinoline

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

sarcosine

A

50-00-0

formaldehyd

B

124-38-9

carbon dioxide

C

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
52316-59-3

N-chloro-sarcosine

A

50-00-0

formaldehyd

B

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;
41065-20-7

benzenesulfinyl-benzoyloxy-methane

A

50-00-0

formaldehyd

B

882-33-7

diphenyldisulfane

Conditions
ConditionsYield
With potassium hydroxide In methanolA 100%
B 61%
26492-31-9

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

A

50-00-0

formaldehyd

B

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%
85437-83-8

C6H16NO4P

A

50-00-0

formaldehyd

B

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%
85437-82-7

((bis(dimethylamino)phosphinyl)oxy)dimethylamine

A

50-00-0

formaldehyd

B

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%
180985-69-7

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

A

50-00-0

formaldehyd

B

115975-92-3

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

Conditions
ConditionsYield
In 1,3,5-trimethyl-benzene Heating;A n/a
B 100%
78402-17-2

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

chromium (III) ion

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+)

chromium (III) ion

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%
115-10-6

Dimethyl ether

A

50-00-0

formaldehyd

B

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%
34557-54-5

methane

10024-97-2

dinitrogen monoxide

A

67-56-1

methanol

B

50-00-0

formaldehyd

C

124-38-9

carbon dioxide

D

201230-82-2

carbon monoxide

E

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
89946-44-1

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

A

50-00-0

formaldehyd

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%
75-91-2

tert.-butylhydroperoxide

30931-67-0

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

A

67-56-1

methanol

B

50-00-0

formaldehyd

C

C18H18N4O6S4(1+)*2H3N

D

67-64-1

acetone

E

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%
99-97-8

Dimethyl-p-toluidine

A

50-00-0

formaldehyd

B

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.
1002-16-0

amyl nitrate

A

50-00-0

formaldehyd

B

71-41-0

pentan-1-ol

C

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
70458-96-7

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

A

50-00-0

formaldehyd

B

7664-41-7

ammonia

C

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%
779-52-2

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

A

2591-86-8

N-Formylpiperidine

B

50-00-0

formaldehyd

C

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%
76513-61-6

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

A

50-00-0

formaldehyd

B

74-85-1

ethene

C

420-56-4

trimethylsilyl fluoride

D

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%
67-56-1

methanol

A

50-00-0

formaldehyd

B

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;
14745-84-7

2-(N,N-dimethylaminomethyl)pyrrole

A

50-00-0

formaldehyd

B

62-75-9

N-Nitrosodimethylamine

C

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℃;
67-56-1

methanol

(4-methoxyphenoxy)methyl 2-iodobenzoate

A

93-58-3

benzoic acid methyl ester

B

50-00-0

formaldehyd

C

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%
110-91-8

morpholine

563-70-2

bromonitromethane

A

59-89-2

N-nitrosomorpholine

B

50-00-0

formaldehyd

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

lithium 2-nitropropane

1483-73-4

diphenyliodonium bromide

A

50-00-0

formaldehyd

B

591-50-4

iodobenzene

C

92-52-4

biphenyl

D

3964-18-9

2,3-dimethyl-2,3-dinitrobutane

E

3457-58-7

2-nitro-2-phenylpropane

F

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%
3958-63-2

lithium 2-nitropropane

1483-73-4

diphenyliodonium bromide

A

50-00-0

formaldehyd

B

591-50-4

iodobenzene

C

3457-58-7

2-nitro-2-phenylpropane

D

71-43-2

benzene

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

N,N-dimethyl-aniline

A

50-00-0

formaldehyd

B

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

50-00-0

formaldehyd

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

piperidine

123-56-8

Succinimide

50-00-0

formaldehyd

13314-95-9

N-piperidinomethyl-succinimide

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

morpholine

123-56-8

Succinimide

50-00-0

formaldehyd

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%
110-91-8

morpholine

50-00-0

formaldehyd

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%
451-40-1

phenyl benzyl ketone

50-00-0

formaldehyd

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%
120-72-9

indole

50-00-0

formaldehyd

700-06-1

indole-3-carbinol

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

pyrrole

50-00-0

formaldehyd

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%
50-00-0

formaldehyd

867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

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%
50-00-0

formaldehyd

299-42-3

ephedrine

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%
50-00-0

formaldehyd

299-42-3

ephedrine

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%
50-00-0

formaldehyd

108-80-5

cyanuric acid

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%
50-00-0

formaldehyd

141-43-5

ethanolamine

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
50-00-0

formaldehyd

141-43-5

ethanolamine

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;
50-00-0

formaldehyd

103-90-2

4-acetaminophenol

109-89-7

diethylamine

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%
50-00-0

formaldehyd

109-89-7

diethylamine

536-74-3

phenylacetylene

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%
50-00-0

formaldehyd

62-53-3

aniline

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%
50-00-0

formaldehyd

66-22-8

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%
50-00-0

formaldehyd

51-79-6

urethane

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
50-00-0

formaldehyd

75-08-1

ethanethiol

15909-30-5

(ethylthio)methanol

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

formaldehyd

105-53-3

diethyl 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%
50-00-0

formaldehyd

73-22-3

L-Tryptophan

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%
79-16-3

N-methyl-acetamide

50-00-0

formaldehyd

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;
1809-19-4

dibutyl hydrogen phosphite

50-00-0

formaldehyd

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%
50-00-0

formaldehyd

177698-19-0

Beta-pinene

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%
50-00-0

formaldehyd

917-92-0

2,2-dimethyl-3-butyne

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%
50-00-0

formaldehyd

56-41-7

L-alanin

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%
50-00-0

formaldehyd

61-90-5

L-leucine

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%
50-00-0

formaldehyd

629-05-0

n-octyne

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%
50-00-0

formaldehyd

95-93-2

1,2,4,5-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%
50-00-0

formaldehyd

60656-87-3

benzyloxyacetoaldehyde

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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History

 Formaldehyde was first reported by the Russian chemist Aleksandr Butlerov (1828-1886), but it was conclusively identified by August Wilhelm von Hofmann.

Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 2A IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 (1987),p. 211.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 29 (1982),p. 345.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 29 (1982),p. 345.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory. EPA Extremely Hazardous Substances List.

Standards and Recommendations

OSHA PEL: TWA 0.75 ppm; STEL 2 ppm
ACGIH TLV: CL 0.3 ppm (sensitizer); Suspected Human Carcinogen
DFG MAK: 0.5 ppm (0.6 mg/m3); Confirmed Animal Carcinogen with Unknown Relevance to Humans
NIOSH REL: (Formaldehyde) Limit to lowest feasible level
DOT Classification:  9; Label: None (UN 2209); DOT Class: 3; Label: Flammable Liquid (UN 1198)

Analytical Methods

For occupational chemical analysis use OSHA: #ID-102 or NIOSH: Formaldehyde (Oxazolidine), 2502; (Chromotropic Acid), 3500.

Specification

Formaldehyde (CAS NO.50-00-0) is the simplest aldehyde, ans it exists in water as the hydrate H2C(OH)2. Aqueous solutions of formaldehyde are referred to as formalin. Formaldehyde(50-00-0) is an intermediate in the oxidation (or combustion) of methane as well as other carbon compounds, e.g. forest fires, in automobile exhaust, and in tobacco smoke. In the pure form, Formaldehyde in the pure form is a gas with a boiling point of -21°C but is unstable and readily trimerizes to trioxane or polymerizes to paraformaldehyde. Formaldehyde is stable only in water solution, commonly 37 to 56% formaldehyde by weight and often with methanol (3 to15%) present as a stabilizer.

Physical properties about Formaldehyde are: (1)ACD/LogP: 0.35; (2)ACD/LogD (pH 5.5): 0.35; (3)ACD/LogD (pH 7.4): 0.35; (4)ACD/BCF (pH 5.5): 1.09; (5)ACD/BCF (pH 7.4): 1.09; (6)ACD/KOC (pH 5.5): 36.93; (7)ACD/KOC (pH 7.4): 36.93; (8)#H bond acceptors: 1; (9)Index of Refraction: 1.235; (10)Molar Refractivity: 6.536 cm3; (11)Molar Volume: 43.84 cm3; (12)Polarizability: 2.591 10-24cm3; (13)Surface Tension: 12.6099996566772 dyne/cm; (14)Density: 0.685 g/cm3; (15)Flash Point: -75.062 °C; (16)Enthalpy of Vaporization: 22.308 kJ/mol; (17)Boiling Point: -19.501 °C at 760 mmHg; (18)Vapour Pressure: 3463.82006835938 mmHg at 25°C

Preparation of Formaldehyde: Formaldehyde is produced solely from methanol by using a silver catalyst or a metal oxide catalyst. Either process can be air oxidation or simple dehydrogenation.
2CH3OH + O2 → 2HCH=O + 2H2O
CH3OH → HCH=O + H2
Those two reactions occur simultaneously in commercial units in a balanced autothermal reaction because the oxidative reaction furnishes the heat to cause the dehydrogenation to take place. In the process, fresh and recycle methanol are vaporized, superheated, and passed into the methanol-air mixer. Atmospheric air is purified, compressed, and preheated to 54 °C in a finned heat exchanger. The products leave the converter (a water-jacketed vessel containing the catalyst) at 620 °C and at 34 to 69 kPa absolute. About 65 percent of the methanol is converted per pass. Temperatures are on the order of 450 to 900 °C and there is a short contact time of 0.01 second. The reactor effluent contains about 25% formaldehyde, which is absorbed with the excess methanol and piped to the make tank. The latter feeds the methanol column for separation of recycle methanol overhead, the bottom stream containing the formaldehyde and a few percent methanol. The water intake adjusts the formaldehyde(50-00-0) to 37% strength (marketed as formalin). The catalyst is easily poisoned so stainless-steel equipment must be used to protect the catalyst from metal contamination.

Uses of Formaldehyde: Formaldehyde is a common building block for the synthesis of more complex compounds and materials. As a disinfectant and biocide: as it kills most bacteria and fungi (including their spores), an aqueous solution of formaldehyde can be useful as a disinfectant . It is also used as a preservative in vaccines. In photography: Formaldehyde can be used in low concentrations for process C-41 (color negative film) stabilizer in the final wash step. Tissue fixative and embalming agent: Formaldehyde solutions are used as a fixative for microscopy and histology. Formaldehyde-based solutions are also used in embalming to disinfect and temporarily preserve human and animal remains.

When you are using this chemical, please be cautious about it as the following:
Wear suitable protective clothing and gloves;
Use only in well-ventilated areas;
In case of accident or if you feel unwell, seek medical advice immediately (show label where possible);
Wear suitable protective clothing, gloves and eye/face protection;

You can still convert the following datas into molecular structure:
(1)InChI=1S/CH2O/c1-2/h1H2;
(2)InChIKey=WSFSSNUMVMOOMR-UHFFFAOYSA-N;
(3)SmilesC=O


The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LCLo inhalation 400mg/m3/2H (400mg/m3)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 69, 1982.
cat LDLo intravenous 30mg/kg (30mg/kg) BLOOD: OTHER CHANGES Acta Pharmacologica et Toxicologica. Vol. 8, Pg. 275, 1952.
 
dog LDLo intravenous 70mg/kg (70mg/kg)   International Polymer Science and Technology. Vol. 3, Pg. 93, 1976.
dog LDLo subcutaneous 350mg/kg (350mg/kg)   International Polymer Science and Technology. Vol. 3, Pg. 93, 1976.
frog LDLo parenteral 800ug/kg (.8mg/kg)   International Polymer Science and Technology. Vol. 3, Pg. 93, 1976.
guinea pig LD50 oral 260mg/kg (260mg/kg)   Journal of Industrial Hygiene and Toxicology. Vol. 23, Pg. 259, 1941.
human TCLo inhalation 17mg/m3/30M (17mg/m3) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
JAMA, Journal of the American Medical Association. Vol. 165, Pg. 1908, 1957.
 
man LDLo unreported 477mg/kg (477mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
man TCLo inhalation 300ug/m3 (.3mg/m3) BEHAVIORAL: AGGRESSION

SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 12(7), Pg. 20, 1968.
man TDLo oral 643mg/kg (643mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY OBSTRUCTION

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH
Japanese Journal of Toxicology. Vol. 4, Pg. 261, 1991.
man TDLo oral 646mg/kg (646mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH

GASTROINTESTINAL: GASTRITIS
Japanese Journal of Toxicology. Vol. 4, Pg. 261, 1991.
mouse LC50 inhalation 454gm/m3/4H (454000mg/m3)   Current Toxicology. Vol. 1, Pg. 47, 1993.
mouse LD50 oral 42mg/kg (42mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
National Technical Information Service. Vol. AD-A125-539,
mouse LD50 subcutaneous 300mg/kg (300mg/kg) LUNGS, THORAX, OR RESPIRATION: BRONCHIOLAR CONSTRICTION

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA
Acta Pharmacologica et Toxicologica. Vol. 6, Pg. 299, 1950.
mouse LDLo intraperitoneal 16mg/kg (16mg/kg)   Toxicology and Applied Pharmacology. Vol. 23, Pg. 288, 1972.
 
rabbit LD50 skin 270uL/kg (.27mL/kg)   Union Carbide Data Sheet. Vol. 4/21/1967,
rabbit LDLo intravenous 48mg/kg (48mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 213, 1955.
 
rabbit LDLo subcutaneous 240mg/kg (240mg/kg)   JAMA, Journal of the American Medical Association. Vol. 62, Pg. 984, 1914.
rat LC50 inhalation 203mg/m3 (203mg/m3) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 18(2), Pg. 55, 1974.
rat LD50 intravenous 87mg/kg (87mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 221, Pg. 166, 1954.
 
rat LD50 oral 100mg/kg (100mg/kg)   Food and Chemical Toxicology. Vol. 26, Pg. 447, 1988.
 
rat LD50 subcutaneous 420mg/kg (420mg/kg) LUNGS, THORAX, OR RESPIRATION: BRONCHIOLAR CONSTRICTION

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA
Acta Pharmacologica et Toxicologica. Vol. 6, Pg. 299, 1950.
women LDLo oral 1mL/kg (1mL/kg) GASTROINTESTINAL: ALTERATION IN GASTRIC SECRETION

CARDIAC: OTHER CHANGES

BEHAVIORAL: COMA
Intensive Care Medicine. Vol. 23, Pg. 708, 1997.
women LDLo oral 108mg/kg (108mg/kg)   "Practical Toxicology of Plastics," Lefaux, R., Cleveland, OH, Chemical Rubber Co., 1968Vol. -, Pg. 328, 1968.