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74-89-5

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Basic Information
CAS No.: 74-89-5
Name: Methanamine
Molecular Structure:
Molecular Structure of 74-89-5 (Methanamine)
Formula: CH5N
Molecular Weight: 31.06
Synonyms: Methylamine(8CI);Aminomethane;Carbinamine;Monomethylamine;Methylamine;
EINECS: 200-820-0
Density: 0.70 g/cm3
Melting Point: -93 °C
Boiling Point: -6.5 °C
Flash Point: 61°F
Solubility: Soluble in water, ethanol and ether
Appearance: colourless gas
Hazard Symbols: HighlyF+, HarmfulXn, CorrosiveC, FlammableF, ToxicT
Risk Codes: 12-20-37/38-41-34-20/22-11-39/23/24/25-36/37/38-23/24/25
Safety: 7-16-26-36/37-45-29-36/37/39-3/7-3-39-33
Transport Information: UN 1061
PSA: 26.02000
LogP: 0.27520
Synthetic route
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;
60-35-5

acetamide

79483-05-9

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole

A

111869-87-5

ethylbis(dimethyl(2-penten-2-yl)silyloxy)borane

B

74-89-5

methylamine

Conditions
ConditionsYield
In 1,2,5-trimethyl-benzene dropwise addn. of acetamide to boron compd. soln., 160°C, 3.5h; heating (reflux), 10h; evapn.; all under Ar; distn.; elem. anal.;A 100%
B 98%
75-52-5

nitromethane

74-89-5

methylamine

Conditions
ConditionsYield
With borane-ammonia complex In methanol; water at 20℃; for 0.0833333h;99%
With ammonia borane; Pd/MIL-101 In methanol; water at 20℃; for 0.025h;99%
With sodium tetrahydroborate In methanol; water at 20℃; for 0.0666667h; Sealed tube; Green chemistry;99%
110-89-4

piperidine

110-68-9

N-n-butyl-N-methylamine

A

4945-48-6

1-butyl-piperidine

B

74-89-5

methylamine

Conditions
ConditionsYield
palladium at 160℃; for 5h;A 98%
B n/a
110-89-4

piperidine

103-67-3

benzyl-methyl-amine

A

2905-56-8

N-Benzylpiperidine

B

74-89-5

methylamine

Conditions
ConditionsYield
palladium at 130℃; for 10h;A 97%
B n/a

1-methyl-2-methylamino-4-imino-6-(2,3-dimethylguanidino)-1,4-dihydro-1,3,5-triazine

A

6726-47-2

1-methyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione

B

3324-71-8

N,N'-dimethyl-guanidine

C

74-89-5

methylamine

Conditions
ConditionsYield
With hydrogenchloride for 10h; Heating;A 15%
B 96%
C 4%
96-31-1

N,N'-Dimethylurea

18522-92-4

sodium p-toluenesulfonamide

A

13909-69-8

N-Methyl-N'-toluene-p-sulfonylurea

B

74-89-5

methylamine

Conditions
ConditionsYield
at 160℃; for 3h; Product distribution; Rate constant; Equilibrium constant; Other temperature, other time, other ratio of reactants, activation energy, ΔH, ΔS;;A 95.5%
B n/a
at 160℃; for 3h;A 95.5%
B n/a
107-15-3

ethylenediamine

103-67-3

benzyl-methyl-amine

A

74-89-5

methylamine

B

4152-09-4

N-benzylethylenediamine

Conditions
ConditionsYield
palladium at 120℃; for 10h;A n/a
B 95%
13325-10-5

4-Aminobutanol

79483-05-9

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole

A

129363-73-1

4,5-diethyl-2,2,3-trimethyl-6-oxa-1-azonia-2-sila-5-boratabicyclo{5.3.0}dec-3-ene

B

129363-50-4

4,5-diethyl-2,2,3-trimethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclodecene

C

74-89-5

methylamine

Conditions
ConditionsYield
In neat (no solvent) addn. of boron compd. to equimolar amt. of aminoalkanol, room temp.; driving out CH3NH2 in a stream of Ar, 20-80°C, 4h;; distn. (vac.); elem. anal.; monocyclic : bicyclic isomer = 95:5;A n/a
B n/a
C 95%
79878-19-6

6-methyl-8-nitro-1,6-naphthyridin-5(6H)-one

A

90004-07-2

8-methylpyrido<2,3-d>pyridazin-5-one

B

74-89-5

methylamine

C

NH3

NH3

Conditions
ConditionsYield
With hydrazine hydrate at 130 - 140℃; for 5h;A 94%
B n/a
C n/a
79483-05-9

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole

141-43-5

ethanolamine

A

129363-47-9

4,5-diethyl-2,2,3-trimethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclooctene

B

74-89-5

methylamine

Conditions
ConditionsYield
In 1,2,5-trimethyl-benzene heating under Ar, 40-70°C, 4h;A 93%
B 93%
In neat (no solvent) addn. of boron compd. to equimolar amt. of aminoalkanol, room temp.; driving out CH3NH2 in a stream of Ar, 20°C, 24h;; distn. (vac.); elem. anal.;A 82%
B 87%
5856-63-3

(2R)-2-aminobutan-1-ol

79483-05-9

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole

A

129444-01-5

(R)-4,5,7-triethyl-2,2,3-trimethyl-6-oxa-1-azonia-2-sila-5-boratabicyclo{3.3.0}oct-3-ene

B

129444-00-4

(R)-4,5,7-triethyl-2,2,3-trimethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclooctene

C

74-89-5

methylamine

Conditions
ConditionsYield
In neat (no solvent) addn. of boron compd. to equimolar amt. of aminoalkanol, room temp.; driving out CH3NH2 in a stream of Ar, 20-25°C, 18h; distn. (vac.); elem. anal.; monocyclic : bicyclic isomer = 95:5;A n/a
B n/a
C 91%
123-75-1

pyrrolidine

103-67-3

benzyl-methyl-amine

A

4383-25-9

N-benzylcyclohexylamine

B

2211-66-7

N-phenyl(methylidene)cyclohexanamine

C

74-89-5

methylamine

Conditions
ConditionsYield
palladium at 120℃; for 10h;A 10%
B 90%
C n/a
96-20-8, 13054-87-0

2-aminobutanol

79483-05-9

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole

A

129363-71-9

4,5,7-triethyl-2,2,3-trimethyl-6-oxa-1-azonia-2-sila-5-boratabicyclo{3.3.0}oct-3-ene

B

129363-48-0

4,5,7-triethyl-2,2,3-trimethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclooctene

C

74-89-5

methylamine

Conditions
ConditionsYield
In neat (no solvent) addn. of boron compd. to equimolar amt. of aminoalkanol, room temp.; driving out CH3NH2 in a stream of Ar, 20-25°C, 22h; distn. (vac.); elem. anal.; monocyclic: bicyclic isomer = 95:5;A n/a
B n/a
C 89%
160745-23-3

N-methylisoephedrine

A

52500-61-5

2-hydroxy-1-phenylpropylamine

B

50-00-0

formaldehyd

C

100-52-7

benzaldehyde

D

75-07-0

acetaldehyde

E

124-40-3

dimethyl amine

F

74-89-5

methylamine

Conditions
ConditionsYield
With water at 25℃; Product distribution; Mechanism; anodic oxidation, carbonate buffer, pH 10; effect of substituents investigated with different types of β-alkanolamines;A 1.3%
B 28%
C 82%
D 88%
E 38%
F 33%
79483-05-9

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole

591-27-5

m-Hydroxyaniline

A

129390-09-6

C30H48B2N2O2Si2

B

74-89-5

methylamine

Conditions
ConditionsYield
In 1,2,5-trimethyl-benzene at 125-150°C, 26h under Ar; evapn.; elem. anal.;A n/a
B 88%
3913-67-5

N-methylalanine

A

124-38-9

carbon dioxide

B

75-07-0

acetaldehyde

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 n/a
B 87%
C n/a
299-42-3

2-methylamino-1-phenylpropanol

A

50-00-0

formaldehyd

B

100-52-7

benzaldehyde

C

75-07-0

acetaldehyde

D

65-85-0

benzoic acid

E

74-89-5

methylamine

Conditions
ConditionsYield
Mechanism; Product distribution; anodic oxidation;A 12%
B 65%
C 68%
D 12%
E 87%
81620-70-4

4,5-diethyl-2,5-dihydro-3-isopropenyl-1,2,2-trimethyl-1,2,5-azasilaborole

141-43-5

ethanolamine

A

129363-59-3

4,5-diethyl-3-isopropenyl-2,2-dimethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclooctene

B

129363-70-8

4,5-diethyl-3-isopropenyl-2,2-dimethyl-6-oxa-1-azonia-2-sila-5-boratabicyclo{3.3.0}oct-3-ene

C

74-89-5

methylamine

Conditions
ConditionsYield
In neat (no solvent) addn. of boron compd. to equimolar amt. of aminoalkanol, room temp.; driving out CH3NH2 in a stream of Ar, 20-25°C, 22h;; distn. (vac.); standing at room temp.; crystn. of bicyclic isomer; elem. anal.;A 57%
B n/a
C 87%
79483-05-9

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole

156-87-6

propan-1-ol-3-amine

A

129363-72-0

4,5-diethyl-2,2,3-trimethyl-6-oxa-1-azonia-2-sila-5-boratabicyclo{4.3.0}non-3-ene

B

129363-49-1

4,5-Diethyl-2,2,3-trimethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclononene

C

74-89-5

methylamine

Conditions
ConditionsYield
In neat (no solvent) addn. of boron compd. to equimolar amt. of aminoalkanol, room temp.; driving out CH3NH2 in a stream of Ar, 20-80°C, 24h;; distn. (vac.); elem. anal.; monocyclic : bicyclic isomer = 95:5;A n/a
B n/a
C 87%
90-82-4

pseudoephedrine

79483-05-9

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole

A

129363-65-1

(4S,5S)-2-Ethyl-4-methyl-5-phenyl-1,3,2-oxazaborolan

B

129363-66-2

{(1S,2S)-2-[Dimethyl-((E)-1-methyl-but-1-enyl)-silanyloxy]-1-methyl-2-phenyl-ethyl}-methyl-amine

C

129443-99-8

(7S,8S)-4,5-Diethyl-2,2,3,6,7-pentamethyl-8-phenyl-1-oxa-6-aza-2-sila-5-bora-3-cycloocten

D

74-89-5

methylamine

Conditions
ConditionsYield
In 1,2,5-trimethyl-benzene dropwise addn. of boron compd. to aminoalkanol soln. under Ar, 0.5h; heating to 140-150°C, 12h; evapn.; distn. (vac.); elem. anal.;A n/a
B n/a
C 75%
D 86%
60-35-5

acetamide

74-89-5

methylamine

Conditions
ConditionsYield
With sodium hydroxide; benzyltrimethylazanium tribroman-2-uide In water at 70℃; for 2h;85%
With potassium hydroxide; bromine ueber mehrere Stufen;
With potassium hydroxide; bromine
With water; bromine; calcium carbonate ueber mehrere Stufen;
With sodium hydroxide; sodium bromite In water at 70℃; for 0.5h; Yield given;
103-67-3

benzyl-methyl-amine

A

102-05-6

N-methyldibenzylamine

B

74-89-5

methylamine

Conditions
ConditionsYield
palladium at 120℃; for 20h;A 85%
B n/a
108-01-0

2-(N,N-dimethylamino)ethanol

79483-05-9

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole

A

129363-54-8

(E)-3-<<2-(Dimethylamino)ethoxy>ethylboryl>-2-<<2-(dimethylamino)ethoxy>dimethylsilyl>-2-penten

B

74-89-5

methylamine

Conditions
ConditionsYield
In neat (no solvent) stirring under Ar, 0-20°C, 1-2h; heating to a maximum of 140°C, 10h; distn. (vac.); elem. anal.;A 82%
B 76%
109-83-1

(2-hydroxyethyl)(methyl)amine

79483-05-9

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole

A

129363-52-6

4,5-diethyl-2,2,3,6-tetramethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclooctene

B

74-89-5

methylamine

Conditions
ConditionsYield
In neat (no solvent) dropwise addn. of boron compd. to aminoalkanol, 10 min; stirring in a stream of Ar, 20°C, 24h;; distn. (vac.); elem. anal.;A 81%
B 82%
854457-30-0

trimethyl-borane; compound with methylamine

A

593-90-8

trimethylborane

B

74-89-5

methylamine

Conditions
ConditionsYield
at 130.0°C, 77.4 Torr equilibrium;A 81.95%
B 81.95%
at 130.0°C, 77.4 Torr equilibrium;A 81.95%
B 81.95%
at 85.4°C, 52.5 Torr equilibrium;A 38.86%
B 38.86%
at 85.4°C, 52.5 Torr equilibrium;A 38.86%
B 38.86%
299-42-3

L(-)-ephedrine hemihydrate

79483-05-9

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole

A

129363-53-7

(7S,8R)-4,5-diethyl-2,2,3,6,7-pentamethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclooctene

B

74-89-5

methylamine

Conditions
ConditionsYield
In neat (no solvent) dropwise addn. of boron compd. to aminoalkanol under Ar, 5 min; heating to 110-150°C, 8.5h;; distn. (vac.); elem. anal.;A 73%
B 80.5%
110-68-9

N-n-butyl-N-methylamine

103-67-3

benzyl-methyl-amine

A

31844-65-2

N-Butyl-N-methylbenzenemethanamine

B

74-89-5

methylamine

Conditions
ConditionsYield
palladium at 120℃; for 10h;A 80%
B n/a
123-56-8

Succinimide

74-89-5

methylamine

3025-97-6

N-methyl-succinic diamide

Conditions
ConditionsYield
at 20℃; under 600.048 - 750.06 Torr; Addition; soid-gas reaction; ring cleavage;100%
With water
In water for 1h; Ambient temperature;
487-89-8

Indole-3-carboxaldehyde

74-89-5

methylamine

22980-06-9

3-(N-methylformimidoyl)-1H-indole

Conditions
ConditionsYield
With magnesium sulfate In methanol; dichloromethane for 7h; Heating;100%
With water
In water 1.) 40 - 45 deg C, 15 min, 2.) room temp., 4 h; Yield given;
87-41-2

2-benzofuran-1(3H)-one

74-89-5

methylamine

5342-91-6

2-methylisoindolin-1-one

Conditions
ConditionsYield
In water at 220℃; under 114000 Torr; for 4h;100%
With ethanol at 220℃;
In 5,5-dimethyl-1,3-cyclohexadiene
136918-14-4

phthalimide

74-89-5

methylamine

19532-98-0

N1,N2-dimethylphthalamide

Conditions
ConditionsYield
at -20℃; under 75.006 Torr; Addition; solid-gas reaction; ring cleavage;100%
In ethanol55%
81-84-5

1,8-Naphthalic anhydride

74-89-5

methylamine

2382-08-3

N-methylnaphthalimide

Conditions
ConditionsYield
In ethanol; water at 20℃; for 72h; Inert atmosphere;100%
In water for 72h; Reflux;100%
In water100%
4295-06-1

4-chloro-2-methylquinoline

74-89-5

methylamine

21875-68-3

N,2-dimethylquinolin-4-amine

Conditions
ConditionsYield
In ethanol at 120℃; for 7h; Sealed tube; Microwave irradiation;100%
With ethanol at 120℃;
With phenol at 190℃;
104-87-0

4-methyl-benzaldehyde

74-89-5

methylamine

17972-13-3, 29086-13-3, 53699-34-6

p-methylbenzylidene-methylamine

Conditions
ConditionsYield
at 20℃; for 12h;100%
In methanol; dichloromethane for 18h; Molecular sieve;86%
2004-06-0

6-Chloropurine riboside

74-89-5

methylamine

1867-73-8

N6-methyladenosine

Conditions
ConditionsYield
With triethylamine In ethanol for 4h; Reflux;100%
In ethanol; water Sealed tube; Reflux;94%
In ethanol; water at 100℃; for 72h; Sealed tube;54%
100-52-7

benzaldehyde

74-89-5

methylamine

622-29-7

N-Benzylidenemethylamine

Conditions
ConditionsYield
at 20℃; for 12h;100%
In water for 1h; Ambient temperature;95%
at 20℃; for 15h;95%
123-08-0

4-hydroxy-benzaldehyde

74-89-5

methylamine

5766-74-5

4-(Methylimino-methyl)-phenol

Conditions
ConditionsYield
at 0℃; under 187.515 Torr; Solid phase reaction; gas-solid reaction;100%
at 20℃; for 12h;100%
With ethanol; water at 40℃;
123-11-5

4-methoxy-benzaldehyde

74-89-5

methylamine

13114-23-3

4-methoxybenzyl-N-methylimine

Conditions
ConditionsYield
In ethanol; water at 40℃; for 2h;100%
In ethanol at 0 - 40℃;90%
In water for 10h; Ambient temperature;80%
90-02-8

salicylaldehyde

74-89-5

methylamine

3117-65-5

2-(methyliminomethyl)phenol

Conditions
ConditionsYield
In ethanol at 20℃; for 8h;100%
In ethanol at 20℃; for 8h;100%
With molecular sieve In ethanol; water for 0.5h;96%
1605-65-8

N,N,N',N'-Tetramethylphosphorodiamidic chloride

74-89-5

methylamine

10159-46-3

Pentamethylphosphoramide

Conditions
ConditionsYield
at 20℃; for 48h;100%
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane at 0℃; for 1h;83%
64%
120-14-9

3,4-dimethoxy-benzaldehyde

74-89-5

methylamine

17972-14-4

N-(3,4-dimethoxybenzylidene)methanamine

Conditions
ConditionsYield
With 4 A molecular sieve In toluene at 0℃;100%
With benzene
In methanol at 40℃; for 5h;
In ethanol at 50℃;
In benzene for 2h; Reflux;
100-83-4

meta-hydroxybenzaldehyde

74-89-5

methylamine

7221-33-2

3-(Methylimino-methyl)-phenol

Conditions
ConditionsYield
In ethanol at 0 - 5℃; for 2h;100%
at 20℃; for 12h;100%
With benzene zuletzt unter Abdestillieren des gebildeten Wassers;
556-61-6

methyl thioisocyanate

74-89-5

methylamine

534-13-4

N,N-dimethylthiourea

Conditions
ConditionsYield
at 0℃; under 375.03 Torr; Addition; solid-gas reaction;100%
292638-85-8

acrylic acid methyl ester

74-89-5

methylamine

24549-12-0

methyl 3-(methylamino)propanoate

Conditions
ConditionsYield
In diethyl ether at 4℃; Addition;100%
With C12H18NO3S(1+)*HO4S(1-) at 25℃; for 0.0833333h; Ionic liquid; Neat (no solvent); chemoselective reaction;99%
In ethanol at -10℃;86%
98-86-2

acetophenone

74-89-5

methylamine

6907-71-7

N-(1-phenylethylidene)methanamine

Conditions
ConditionsYield
In ethanol at 20℃; for 48h; Molecular sieve; Inert atmosphere;100%
In ethanol at 20℃; for 48h; Molecular sieve; Inert atmosphere;100%
With triethylamine In ethanol for 1h; Molecular sieve;97%
591-31-1

3-methoxy-benzaldehyde

74-89-5

methylamine

16928-30-6

N-(3-methoxybenzylidene)methanamine

Conditions
ConditionsYield
at 20℃; for 12h;100%
In ethanol at 0 - 40℃;90%
In water for 10h; Ambient temperature;86%
135-02-4

ortho-anisaldehyde

74-89-5

methylamine

1125-90-2

1-(2-methoxyphenyl)-N-methylmethanimine

Conditions
ConditionsYield
In ethanol at 0 - 40℃;100%
In water for 10h; Ambient temperature;80%
With water
100-10-7

4-dimethylamino-benzaldehyde

74-89-5

methylamine

877-79-2

4-(dimethylamino)-N-methylbenzylimine

Conditions
ConditionsYield
at 20℃; under 750.06 Torr; Solid phase reaction; gas-solid reaction;100%
at 20℃; for 12h;100%
With benzene
1493-27-2

ortho-nitrofluorobenzene

74-89-5

methylamine

612-28-2

2-nitro-N-methylaniline

Conditions
ConditionsYield
In ethanol; water Reflux;100%
In methanol; water Heating;98%
In water at 20℃; for 2h; Inert atmosphere;93%
97-00-7

1-chloro-2,4-dinitro-benzene

74-89-5

methylamine

2044-88-4

N-methyl-2,4-dinitroaniline

Conditions
ConditionsYield
In ethanol at 20℃; for 15h;100%
In ethanol; water at 20℃; for 1h;100%
In ethanol at 0 - 20℃; for 15h;95%
551-06-4

1-isothiocyanatonaphthalene

74-89-5

methylamine

2740-98-9

1-methyl-3-naphthalene-1-yl-thiourea

Conditions
ConditionsYield
at 20℃; under 750.06 Torr; Addition; solid-gas reaction;100%
With ethanol
2131-61-5

p-nitrophenyl isothiocyanate

74-89-5

methylamine

16361-69-6

1-(4-nitrophenyl)-3-methyl-thiourea

Conditions
ConditionsYield
at 20℃; under 750.06 Torr; Addition; solid-gas reaction;100%
74-89-5

methylamine

135-19-3

β-naphthol

2216-67-3

2-N-methylaminonaphthalene

Conditions
ConditionsYield
With ammonium chloride In ethanol at 200℃; for 20h;100%
With water at 200 - 220℃; unter Druck;
With sodium hydrogensulfite In water Bucherer reaction; Autoclave;
74-89-5

methylamine

28188-41-2

3-(bromomethyl)benzonitrile

90389-96-1

3-((methylamino)methyl)benzonitrile

Conditions
ConditionsYield
In THjfF (tetrahydrofuran) at 20℃; for 3h; Inert atmosphere;100%
In tetrahydrofuran at 20℃; for 24h;96%
In water at 0 - 20℃; for 3.16h;82%
74-89-5

methylamine

1985-12-2

4-Bromophenyl isothiocyanate

61449-55-6

1-(4-bromophenyl)-3-methyl-thiourea

Conditions
ConditionsYield
at 20℃; under 750.06 Torr; Addition; solid-gas reaction;100%
With ethanol
74-89-5

methylamine

86-51-1

2,3-dimethyoxybenzaldehyde

722495-95-6

(2,3-dimethoxy-benzylidene)-methyl-amine

Conditions
ConditionsYield
at 20℃; for 12h;100%
In ethanol at 0 - 40℃;90%
With benzene zuletzt unter Erwaermen und Entfernen des gebildeten Wassers;
In benzene for 2h; Reflux;
In ethanol; water
74-89-5

methylamine

49845-33-2

2,4-Dichloro-5-nitropyrimidine

89283-49-8

2-chloro-4-(methylamino)-5-nitropyrimidine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; methanol at -78 - 20℃; for 3h;100%
With N-ethyl-N,N-diisopropylamine In dichloromethane at -60℃; for 1h;85%
With N-ethyl-N,N-diisopropylamine In ethanol; dichloromethane at 0℃; for 0.5h;85.4%
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    New supplier

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History

Methylamine(74-89-5) was first prepared by Wurtz by the hydrolysis of methylisocyanate and related compounds.

Consensus Reports

Reported in EPA TSCA Inventory.

Standards and Recommendations

OSHA PEL: TWA 10 ppm
ACGIH TLV: TWA 5 ppm; STEL 15 ppm
DFG MAK: 10 ppm (13 mg/m3)
DOT Classification:  2.3; Label: Poison Gas, Flammable Gas (UN 1061); DOT Class: 3; Label: Flammable Liquid, Corrosive (UN 1235)

Analytical Methods

For occupational chemical analysis use OSHA: #40.

Specification

The IUPAC name of this chemical is methanamine. With the CAS registry number 74-89-5, it is also named as Aminomethane. The product's categories are Refrigerants; Alkylamines; Biochemistry; Monofunctional & alpha,omega-Bifunctional Alkanes; Monofunctional Alkanes; Reagents for Oligosaccharide Synthesis. It is colourless gas which is soluble in water, ethanol and ether. In addition, it is the simplest primary amine. It is sold as a solution in methanol, ethanol, THF, and water, or as the anhydrous gas in pressurized metal containers. It is flammable by fire and heat. When heated to decomposition it emits toxic fumes of NOx. So the storage environment should be ventilate, low-temperature and dry.

The other characteristics of Methylamine can be summarized as: 
(1)ACD/LogP: -0.66; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -3.76; (4)ACD/LogD (pH 7.4): -3.54; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 1; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.34; (13)Molar Refractivity: 10.21 cm3; (14)Molar Volume: 48.7 cm3; (15)Polarizability: 4.05×10-24 cm3; (16)Surface Tension: 18.4 dyne/cm; (17)Enthalpy of Vaporization: 25.6 kJ/mol; (18)Vapour Pressure: 3970 mmHg at 25°C; (19)Exact Mass: 31.042199; (20)MonoIsotopic Mass: 31.042199; (21)Topological Polar Surface Area: 26; (22)Heavy Atom Count: 2; (23)Complexity: 2.

Preparation of Methylamine:
It can be obtained by many methods. For example: it is produced by the reaction of ammonia with methanol in the presence of a silicoaluminate catalyst. Dimethylamine and trimethylamine are coproduced. CH3OH + NH3 → CH3NH2 + H2
2CH3OH+NH3→(CH3)2NH+2H2O
3CH3OH+NH3→(CH3)3N+3H2O

Uses of Methylamine: 
It is widely used in manufacturing of pharmaceuticals, pesticides, explosives, dyes, photographic developer, vulcanization accelerators, surfactants, preservatives, etc. And it is a good nucleophile as it is highly basic and unhindered, though, as an amine it is considered a weak base. Its use in organic chemistry is pervasive. Liquid methylamine can be used as a solvent analogous to liquid ammonia. Methylamine can also be used for scavenging H2S from hydrocarbon in refining applications. Furthermore, it is used as a building block for the synthesis of many other commercially available compounds.

When you are using Methylamine, please be cautious about it as the following:
It is extremely flammable and can cause burns, so people should keep it away from sources of ignition. And it is not only toxic by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. So it must not empty into drains. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 

People can use the following data to convert to the molecule structure.
1. SMILES:NC
2. InChI:InChI=1/CH5N/c1-2/h2H2,1H3 
3. InChIKey:BAVYZALUXZFZLV-UHFFFAOYAN

The following are the toxicity data of Methylamine:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LDLo subcutaneous 200mg/kg (200mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
mammal (species unspecified) LC50 inhalation 2400mg/m3 (2400mg/m3)   Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Substances. For English translation, see TNICS*. Vol. 14, Pg. 80, 1975.
mouse LC50 inhalation 2400mg/m3/2H (2400mg/m3)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 81, 1982.
mouse LDLo subcutaneous 2500mg/kg (2500mg/kg)   "Merck Index; an Encyclopedia of Chemicals, Drugs, and Biologicals", 11th ed., Rahway, NJ 07065, Merck & Co., Inc. 1989Vol. 11, Pg. 949, 1989.
rat LC50 inhalation 448ppm/2.5H (448ppm) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

SKIN AND APPENDAGES (SKIN): "DERMATITIS, IRRITATIVE: AFTER SYSTEMIC EXPOSURE"
Journal of Environmental Biology. Vol. 13, Pg. 273, 1992.
rat LD50 oral 100mg/kg (100mg/kg)   Inhalation Toxicology. Vol. 2, Pg. 29, 1990.
rat LDLo subcutaneous 200mg/kg (200mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.