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74-89-5

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Basic Information
CAS No.: 74-89-5
Name: Methanamine
Article Data: 911
Cas Database
Molecular Structure:
Molecular Structure of 74-89-5 (Methanamine)
Formula: CH5N
Molecular Weight: 31.0574
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%
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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.