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74-89-5 Usage

Fire Hazard

FLAMMABLE. POISONOUS GASES MAY BE PRODUCED IN FIRE. Containers may explode in fire. Flashback along vapor trail may occur. Vapor may explode if ignited in an enclosed area. Toxic nitrogen oxides may be formed. Vapors are heavier than air and may travel considerable distance to a source of ignition and flash back.

Definition

ChEBI: The simplest of the methylamines, consisting of ammonia bearing a single methyl substituent.

Uses

Methylamine is an important kind of fatty amines organic chemicals and is used in a variety of industries such as manufacture of dyestuffs, treatment of cellulose, acetate rayon, as fuel additive, rocket propellant, and leather tanning processes. It can be used in the synthesis of the N-methyl-chloroacetamide that is the intermediate of the organic phosphorus insecticide dimethoate and omethoate; synthesis of the intermediate of the monocrotophos, α-chloro acetoacetyl methylamine; synthesis of the intermediates of carbamate pesticide, carbamoyl chloride and methyl isocyanate; as well as the synthesis of other pesticides varieties such as formamidine, amitraz, and tribenuron, etc. In addition, it can also be used in medicine, rubber, dyes, leather industry and photosensitive materials.

General Description

A colorless gas or a liquid. Pungent fishy odor resembling odor of ammonia. The liquid boils at 20.3°F hence vaporizes rapidly when unconfined. Vapors are heavier than air and may collect in low-lying areas. Easily ignited under most conditions. Under prolonged exposure to intense heat the containers may rupture violently and rocket. Used for making pharmaceuticals, insecticides, paint removers, surfactants, rubber chemicals.

Health Hazard

VAPOR: Irritating to eyes, nose and throat. If inhaled will cause coughing or difficult breathing. LIQUID: Will burn skin and eyes.

Reactivity Profile

METHYLAMINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated in combination with strong reducing agents, such as hydrides.

Chemical Properties

colourless gas (or solution in water or methanol)

Purification Methods

Dry the amine with sodium or BaO. It is commercially available in metal cylinders. [Beilstein 4 IV 118.]

Organic Chemicals

Methylamine, also known as amino methane, is an important kind of organic chemical raw materials and intermediates and is a flammable colorless gas at normal temperature and pressure. Upon being liquefied or compressed at high concentrations, it has a strong odor of ammonia. It has fishy odor at very low concentrations. It is easily soluble in water and soluble in alcohol and ether. It is flammable and can form explosive mixtures with air with the explosive limit being 4.3% to 21%. It has weak alkalinity with the alkaline being stronger than ammonia. It can interact with inorganic acid to form water-soluble salts. It is obtained through the reaction between methanol and ammonia at high pressure and high temperature in the action of catalyst. Alternatively, it can be obtained through the reaction between formaldehyde and ammonium chloride upon being heated to 300 ℃ in the presence of zinc chloride. Methylamine can be used to make pesticides, pharmaceuticals, rubber vulcanization accelerator, dyes, explosives, leather, petroleum, surfactants, and ion exchange resin, paint strippers, and coatings as well as additives. It is an important raw material for the manufacturing of pesticide dimethoate, carbaryl, and chlordimeform. The inhalation toxicity of methylamine belongs to low toxicity category. The maximum allowable air concentration is 5mg/m3 (0.4ppm). It is corrosive and can cause irritation of the eyes, skin and mucous membranes. In case of fire, high heating temperature, it can cause risk of fire with cylinders and accessories damage being capable of causing an explosion.

Poisoning

Methylamine belongs to moderate-poisoning drug with a strong irritant and corrosive property. During the process of production and in transit, when there is leakage occurring due to accident, it can cause acute poisoning of contacted people.
This product can be subject to inhalation in its gaseous state from the respiratory tract. Its solution can be absorbed through the skin. Its salt can cause poisoning upon mistakenly oral administration. This product has a strong stimulating effect on eye; upper respiratory tract, skin and mucous membranes. Inhalation of it at high concentrations can cause damage to the lungs with people in severe cases getting pulmonary edema and respiratory distress syndrome, finally leading to death. However, it has been no yet reported of cases of systemic poisoning around the world. Liquid methylamine has strong irritation and corrosion effect and can cause eye and skin chemical burning. In case of 40% aqueous methylamine being splashed into the eyes, the victims can get burning eyes, photophobia, lacrimation, conjunctival hyperemia, eyelid irritation, corneal edema and superficial ulcers with those symptoms being able to last 1 to 2 weeks. Long-term exposure to low concentrations of methylamine can cause dryness and discomfort of the eyes, nose, and throat.
[first-aid]
Upon skin contact, the victim should immediately remove the contaminated clothing, wash it thoroughly with a large amount of flowing water. For first-aid, the victim can apply 1 to 2% acetic acid, 0.5% citric acid to wash the skin, mucous membranes and mouth.
When the eyes are contaminated, they should raise the eyelid and wash the eyes with flowing clean water and saline for at least 15 minutes, followed by fluorescein staining. If there is corneal injury occurring, the victims should be invited to an ophthalmologist for treatment.
For patients inhaling nitric methylamine gas and getting poisoned, they should be rapidly transferred from the scene of fresh air and keep the airway open. For patients with breathing difficulties, they should be given oxygen. Patients of respiratory and cardiac arrest should be immediately subject to artificial respiration and sent to hospital immediately after treatment in a timely manner.
This information is edited by Xiongfeng Dai from Chemicalbook.

Production method

There are a lot of ways for manufacturing of methylamine. But in industry, people mainly apply methanol amination.
CH3OH + NH3 → CH3NH2 + H2O
2CH3OH + NH3 → (CH3) 2NH + 2H2O
3CH3OH + NH3 → (CH3) 3N + 3H2O
It is obtained through the following process: methanol and ammonia is at a ratio of 1.5 to 4 and subject to continuous vapor phase catalytic amination at high temperature and high pressure with activated alumina as a catalyst to generate the mixture crude product of mono-, di-, trimethylamine. The crude mixture further goes through a series of distillation column for continuous pressure and distillation separation, have cooling for deamination, dehydration can yield respectively mono-, di-, trimethylamine products.

Air & Water Reactions

Highly flammable. Very soluble in water; the solutions are strongly basic and therefore corrosive. Liquid fumes in air.
InChI:InChI=1/CH5N/c1-2/h2H2,1H3

74-89-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name METHYLAMINE

1.2 Other means of identification

Product number -
Other names Methanamine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Agricultural chemicals (non-pesticidal),Intermediates,Processing aids, not otherwise listed,Processing aids, specific to petroleum production,Solvents (for cleaning or degreasing),Solvents (which become part of product formulation or mixture),Viscosity adjustors
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:74-89-5 SDS

74-89-5Synthetic 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%