Product Name

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  • Name

    Methylamine

  • EINECS 200-820-0
  • CAS No. 74-89-5
  • Article Data911
  • CAS DataBase
  • Density 0.70 g/cm3
  • Solubility Soluble in water, ethanol and ether
  • Melting Point -93 °C
  • Formula CH5N
  • Boiling Point -6.5 °C
  • Molecular Weight 31.0574
  • Flash Point 61°F
  • Transport Information UN 1061
  • Appearance colourless gas
  • Safety 7-16-26-36/37-45-29-36/37/39-3/7-3-39-33
  • Risk Codes 12-20-37/38-41-34-20/22-11-39/23/24/25-36/37/38-23/24/25
  • Molecular Structure Molecular Structure of 74-89-5 (Methylamine)
  • Hazard Symbols HighlyF+, HarmfulXn, CorrosiveC, FlammableF, ToxicT
  • Synonyms Methylamine(8CI);Aminomethane;Carbinamine;Monomethylamine;Methylamine;
  • PSA 26.02000
  • LogP 0.27520

Synthetic route

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;
acetamide
60-35-5

acetamide

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
79483-05-9

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

A

ethylbis(dimethyl(2-penten-2-yl)silyloxy)borane
111869-87-5

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

B

methylamine
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%
nitromethane
75-52-5

nitromethane

methylamine
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%
piperidine
110-89-4

piperidine

N-n-butyl-N-methylamine
110-68-9

N-n-butyl-N-methylamine

A

1-butyl-piperidine
4945-48-6

1-butyl-piperidine

B

methylamine
74-89-5

methylamine

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

piperidine

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

A

N-Benzylpiperidine
2905-56-8

N-Benzylpiperidine

B

methylamine
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

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

A

1-methyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione
6726-47-2

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

B

N,N'-dimethyl-guanidine
3324-71-8

N,N'-dimethyl-guanidine

C

methylamine
74-89-5

methylamine

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

N,N'-Dimethylurea

sodium p-toluenesulfonamide
18522-92-4

sodium p-toluenesulfonamide

A

N-Methyl-N'-toluene-p-sulfonylurea
13909-69-8

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

B

methylamine
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
ethylenediamine
107-15-3

ethylenediamine

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

A

methylamine
74-89-5

methylamine

B

N-benzylethylenediamine
4152-09-4

N-benzylethylenediamine

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

4-Aminobutanol

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
79483-05-9

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

A

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

4,5-diethyl-2,2,3-trimethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclodecene
129363-50-4

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

C

methylamine
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%
6-methyl-8-nitro-1,6-naphthyridin-5(6H)-one
79878-19-6

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

A

8-methylpyrido<2,3-d>pyridazin-5-one
90004-07-2

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

B

methylamine
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
4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
79483-05-9

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

ethanolamine
141-43-5

ethanolamine

A

4,5-diethyl-2,2,3-trimethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclooctene
129363-47-9

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

B

methylamine
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%
(2R)-2-aminobutan-1-ol
5856-63-3

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

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
79483-05-9

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

A

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

(R)-4,5,7-triethyl-2,2,3-trimethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclooctene
129444-00-4

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

C

methylamine
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%
pyrrolidine
123-75-1

pyrrolidine

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

A

N-benzylcyclohexylamine
4383-25-9

N-benzylcyclohexylamine

B

N-phenyl(methylidene)cyclohexanamine
2211-66-7

N-phenyl(methylidene)cyclohexanamine

C

methylamine
74-89-5

methylamine

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

2-aminobutanol

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
79483-05-9

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

A

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

4,5,7-triethyl-2,2,3-trimethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclooctene
129363-48-0

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

C

methylamine
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%
N-methylisoephedrine
160745-23-3

N-methylisoephedrine

A

2-hydroxy-1-phenylpropylamine
52500-61-5

2-hydroxy-1-phenylpropylamine

B

formaldehyd
50-00-0

formaldehyd

C

benzaldehyde
100-52-7

benzaldehyde

D

acetaldehyde
75-07-0

acetaldehyde

E

dimethyl amine
124-40-3

dimethyl amine

F

methylamine
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%
4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
79483-05-9

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

m-Hydroxyaniline
591-27-5

m-Hydroxyaniline

A

C30H48B2N2O2Si2
129390-09-6

C30H48B2N2O2Si2

B

methylamine
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%
N-methylalanine
3913-67-5

N-methylalanine

A

carbon dioxide
124-38-9

carbon dioxide

B

acetaldehyde
75-07-0

acetaldehyde

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 n/a
B 87%
C n/a
2-methylamino-1-phenylpropanol
299-42-3

2-methylamino-1-phenylpropanol

A

formaldehyd
50-00-0

formaldehyd

B

benzaldehyde
100-52-7

benzaldehyde

C

acetaldehyde
75-07-0

acetaldehyde

D

benzoic acid
65-85-0

benzoic acid

E

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
Mechanism; Product distribution; anodic oxidation;A 12%
B 65%
C 68%
D 12%
E 87%
4,5-diethyl-2,5-dihydro-3-isopropenyl-1,2,2-trimethyl-1,2,5-azasilaborole
81620-70-4

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

ethanolamine
141-43-5

ethanolamine

A

4,5-diethyl-3-isopropenyl-2,2-dimethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclooctene
129363-59-3

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

B

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

methylamine
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%
4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
79483-05-9

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

propan-1-ol-3-amine
156-87-6

propan-1-ol-3-amine

A

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

4,5-Diethyl-2,2,3-trimethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclononene
129363-49-1

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

C

methylamine
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%
pseudoephedrine
90-82-4

pseudoephedrine

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
79483-05-9

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

A

(4S,5S)-2-Ethyl-4-methyl-5-phenyl-1,3,2-oxazaborolan
129363-65-1

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

B

{(1S,2S)-2-[Dimethyl-((E)-1-methyl-but-1-enyl)-silanyloxy]-1-methyl-2-phenyl-ethyl}-methyl-amine
129363-66-2

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

C

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

methylamine
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%
acetamide
60-35-5

acetamide

methylamine
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;
benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

A

N-methyldibenzylamine
102-05-6

N-methyldibenzylamine

B

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
palladium at 120℃; for 20h;A 85%
B n/a
2-(N,N-dimethylamino)ethanol
108-01-0

2-(N,N-dimethylamino)ethanol

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
79483-05-9

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

A

(E)-3-<<2-(Dimethylamino)ethoxy>ethylboryl>-2-<<2-(dimethylamino)ethoxy>dimethylsilyl>-2-penten
129363-54-8

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

B

methylamine
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%
(2-hydroxyethyl)(methyl)amine
109-83-1

(2-hydroxyethyl)(methyl)amine

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
79483-05-9

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

A

4,5-diethyl-2,2,3,6-tetramethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclooctene
129363-52-6

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

B

methylamine
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%
trimethyl-borane; compound with methylamine
854457-30-0

trimethyl-borane; compound with methylamine

A

trimethylborane
593-90-8

trimethylborane

B

methylamine
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%
L(-)-ephedrine hemihydrate
299-42-3

L(-)-ephedrine hemihydrate

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
79483-05-9

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

A

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

methylamine
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%
N-n-butyl-N-methylamine
110-68-9

N-n-butyl-N-methylamine

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

A

N-Butyl-N-methylbenzenemethanamine
31844-65-2

N-Butyl-N-methylbenzenemethanamine

B

methylamine
74-89-5

methylamine

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

Succinimide

methylamine
74-89-5

methylamine

N-methyl-succinic diamide
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;
Indole-3-carboxaldehyde
487-89-8

Indole-3-carboxaldehyde

methylamine
74-89-5

methylamine

3-(N-methylformimidoyl)-1H-indole
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;
2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

methylamine
74-89-5

methylamine

2-methylisoindolin-1-one
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
phthalimide
136918-14-4

phthalimide

methylamine
74-89-5

methylamine

N1,N2-dimethylphthalamide
19532-98-0

N1,N2-dimethylphthalamide

Conditions
ConditionsYield
at -20℃; under 75.006 Torr; Addition; solid-gas reaction; ring cleavage;100%
In ethanol55%
1,8-Naphthalic anhydride
81-84-5

1,8-Naphthalic anhydride

methylamine
74-89-5

methylamine

N-methylnaphthalimide
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%
4-chloro-2-methylquinoline
4295-06-1

4-chloro-2-methylquinoline

methylamine
74-89-5

methylamine

N,2-dimethylquinolin-4-amine
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℃;
4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

methylamine
74-89-5

methylamine

p-methylbenzylidene-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%
6-Chloropurine riboside
2004-06-0

6-Chloropurine riboside

methylamine
74-89-5

methylamine

N6-methyladenosine
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%
benzaldehyde
100-52-7

benzaldehyde

methylamine
74-89-5

methylamine

N-Benzylidenemethylamine
622-29-7

N-Benzylidenemethylamine

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

4-hydroxy-benzaldehyde

methylamine
74-89-5

methylamine

4-(Methylimino-methyl)-phenol
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℃;
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

methylamine
74-89-5

methylamine

4-methoxybenzyl-N-methylimine
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%
salicylaldehyde
90-02-8

salicylaldehyde

methylamine
74-89-5

methylamine

2-(methyliminomethyl)phenol
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%
N,N,N',N'-Tetramethylphosphorodiamidic chloride
1605-65-8

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

methylamine
74-89-5

methylamine

Pentamethylphosphoramide
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%
3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

methylamine
74-89-5

methylamine

N-(3,4-dimethoxybenzylidene)methanamine
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;
meta-hydroxybenzaldehyde
100-83-4

meta-hydroxybenzaldehyde

methylamine
74-89-5

methylamine

3-(Methylimino-methyl)-phenol
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;
methyl thioisocyanate
556-61-6

methyl thioisocyanate

methylamine
74-89-5

methylamine

N,N-dimethylthiourea
534-13-4

N,N-dimethylthiourea

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

acrylic acid methyl ester

methylamine
74-89-5

methylamine

methyl 3-(methylamino)propanoate
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%
acetophenone
98-86-2

acetophenone

methylamine
74-89-5

methylamine

N-(1-phenylethylidene)methanamine
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%
3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

methylamine
74-89-5

methylamine

N-(3-methoxybenzylidene)methanamine
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%
ortho-anisaldehyde
135-02-4

ortho-anisaldehyde

methylamine
74-89-5

methylamine

1-(2-methoxyphenyl)-N-methylmethanimine
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
4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

methylamine
74-89-5

methylamine

4-(dimethylamino)-N-methylbenzylimine
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
ortho-nitrofluorobenzene
1493-27-2

ortho-nitrofluorobenzene

methylamine
74-89-5

methylamine

2-nitro-N-methylaniline
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%
1-chloro-2,4-dinitro-benzene
97-00-7

1-chloro-2,4-dinitro-benzene

methylamine
74-89-5

methylamine

N-methyl-2,4-dinitroaniline
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%
1-isothiocyanatonaphthalene
551-06-4

1-isothiocyanatonaphthalene

methylamine
74-89-5

methylamine

1-methyl-3-naphthalene-1-yl-thiourea
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
p-nitrophenyl isothiocyanate
2131-61-5

p-nitrophenyl isothiocyanate

methylamine
74-89-5

methylamine

1-(4-nitrophenyl)-3-methyl-thiourea
16361-69-6

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

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

methylamine

β-naphthol
135-19-3

β-naphthol

2-N-methylaminonaphthalene
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;
methylamine
74-89-5

methylamine

3-(bromomethyl)benzonitrile
28188-41-2

3-(bromomethyl)benzonitrile

3-((methylamino)methyl)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%
methylamine
74-89-5

methylamine

4-Bromophenyl isothiocyanate
1985-12-2

4-Bromophenyl isothiocyanate

1-(4-bromophenyl)-3-methyl-thiourea
61449-55-6

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

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

methylamine

2,3-dimethyoxybenzaldehyde
86-51-1

2,3-dimethyoxybenzaldehyde

(2,3-dimethoxy-benzylidene)-methyl-amine
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
methylamine
74-89-5

methylamine

2,4-Dichloro-5-nitropyrimidine
49845-33-2

2,4-Dichloro-5-nitropyrimidine

2-chloro-4-(methylamino)-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%

Methylamine History

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

Methylamine Consensus Reports

Reported in EPA TSCA Inventory.

Methylamine 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)

Methylamine Analytical Methods

For occupational chemical analysis use OSHA: #40.

Methylamine 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.

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