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( R e d i r e c t e d f r o m M e t h y l a m i n e s )
Organic chemical compound
Methylamine
Ball and stick model of methylamine Spacefill model of methylamine
Names
Pronunciation
METH -ə-lə-MEEN METH -ə-LA mə-THIL -ə-meen [2]
Preferred IUPAC name
Other names
Monomethylamine
Identifiers
CAS Number
3D model (JSmol )
3DMet
Abbreviations
MMA
Beilstein Reference
741851
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.746
EC Number
Gmelin Reference
145
KEGG
MeSH
methylamine
PubChem CID
RTECS number
UNII
UN number
1061
CompTox Dashboard (EPA )
InChI=1S/CH5N/c1-2/h2H2,1H3 Y
Key: BAVYZALUXZFZLV-UHFFFAOYSA-N Y
Properties
Chemical formula
CH 3 NH 2
Molar mass
−1
Appearance
Colorless gas
Odor
Fishy, ammoniacal
Density
0.6562 g/cm3
Melting point
−93.10 °C; −135.58 °F; 180.05 K
Boiling point
−6.6 to −6.0 °C; 20.0 to 21.1 °F; 266.5 to 267.1 K
Solubility in water
1008 g/L (at 20 °C)
log P
−0.472
Vapor pressure
186.10 kPa (at 20 °C)
Henry's law (k H
1.4 mmol/(Pa·kg)
Acidity (p K a 10.66
Conjugate acid
[CH 3 NH 3 + (Methylammonium )
Magnetic susceptibility (χ)
-27.0·10−6 cm 3
Viscosity
230 μPa·s (at 0 °C)
Dipole moment
1.31 D
Thermochemistry
Std enthalpy of (Δf H ⦵ 298 )
−23.5 kJ/mol
Hazards
GHS labelling
Pictograms
Signal word
Danger
Hazard statements
H220 , H315 , H318 , H332 , H335
Precautionary statements
P210 , P261 , P280 , P305+P351+P338 , P410+P403
NFPA 704
Flash point
−10 °C; 14 °F; 263 K (liquid, gas is extremely flammable)[3]
Autoignition
430 °C (806 °F; 703 K )
Explosive limits
4.9–20.7%
Lethal dose or concentration (LD, LC):
LD 50 median dose )
100 mg/kg (oral, rat)
LC 50 median concentration )
1860 ppm (mouse, 2 hr)[3]
NIOSH
PEL (Permissible)
TWA 10 ppm (12 mg/m3 [3]
REL (Recommended)
TWA 10 ppm (12 mg/m3 [3]
IDLH (Immediate danger)
100 ppm[3]
Safety data sheet (SDS)
emdchemicals.com
Related compounds
Related alkanamines
ethylamine , dimethylamine , trimethylamine
Related compounds
ammonia
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound
Methylamine is an organic compound with a formula of CH 3 NH 2 ammonia , but with one hydrogen atom being replaced by a methyl group . It is the simplest primary amine .
Methylamine is sold as a solution in methanol , ethanol , tetrahydrofuran , or water , or as the anhydrous gas in pressurized metal containers. Industrially, methylamine is transported in its anhydrous form in pressurized railcars and tank trailers. It has a strong odor similar to rotten fish. Methylamine is used as a building block for the synthesis of numerous other commercially available compounds.
Industrial production [ edit ]
Methylamine has been produced industrially since the 1920s (originally by Commercial Solvents Corporation for dehairing of animal skins).[4] Kazimierz Smoleński [pl and his wife Eugenia who discovered amination of alcohols, including methanol, on alumina or kaolin catalyst after WWI, filed two patent applications in 1919[5] [4] [6]
It is now prepared commercially by the reaction of ammonia with methanol in the presence of an aluminosilicate catalyst . Dimethylamine and trimethylamine are co-produced; the reaction kinetics and reactant ratios determine the ratio of the three products. The product most favored by the reaction kinetics is trimethylamine.[4]
CH 3 3 3 NH 2 2 O
In this way, an estimated 115,000 tons were produced in 2005.[7]
Laboratory methods [ edit ]
Methylamine was first prepared in 1849 by Charles-Adolphe Wurtz via the hydrolysis of methyl isocyanate and related compounds.[7] [8] Hofmann rearrangement , to yield methylamine from acetamide and bromine .[9] [10]
In the laboratory, methylamine hydrochloride is readily prepared by various other methods. One method entails treating formaldehyde with ammonium chloride .[11]
[NH 4 2 CH 2 2 2 O
[CH 2 2 2 2 CH 3 NH 3 HCOOH
The colorless hydrochloride salt can be converted to an amine by the addition of a strong base, such as sodium hydroxide (NaOH):
[CH 3 NH 3 3 NH 2 2 O
Another method entails reducing nitromethane with zinc and hydrochloric acid.[12]
Another method of methylamine production is spontaneous decarboxylation of glycine with a strong base in water.[citation needed
Reactivity and applications [ edit ]
Methylamine is a good nucleophile as it is an unhindered amine .[13] weak base . Its use in organic chemistry is pervasive. Some reactions involving simple reagents include: with phosgene to methyl isocyanate , with carbon disulfide and sodium hydroxide to the sodium methyldithiocarbamate, with chloroform and base to methyl isocyanide and with ethylene oxide to methylethanolamines . Liquid methylamine has solvent properties analogous to those of liquid ammonia .[14]
Representative commercially significant chemicals produced from methylamine include the pharmaceuticals ephedrine and theophylline , the pesticides carbofuran , carbaryl , and metham sodium , and the solvents N N surfactants and photographic developers require methylamine as a building block.[7]
Biological chemistry [ edit ]
Methylamine arises as a result of putrefaction and is a substrate for methanogenesis .[15]
Additionally, methylamine is produced during PADI4 -dependent arginine demethylation .[16]
The LD 50 s.c. ) is 2.5 g/kg.[17]
The Occupational Safety and Health Administration (OSHA) and National Institute for Occupational Safety and Health (NIOSH) have set occupational exposure limits at 10 ppm or 12 mg/m3 [18]
Regulation [ edit ]
In the United States, methylamine is controlled as a List 1 precursor chemical by the Drug Enforcement Administration [19] methamphetamine .[20]
In popular culture [ edit ]
Fictional characters Walter White and Jesse Pinkman use methylamine as part of a process to synthesize methamphetamine in the AMC series Breaking Bad [21] [22]
See also [ edit ]
References [ edit ]
^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0398" . National Institute for Occupational Safety and Health (NIOSH).
^ a b c Corbin D.R.; Schwarz S.; Sonnichsen G.C. (1997). "Methylamines synthesis: A review". Catalysis Today . 37 24 ): 71–102. doi :10.1016/S0920-5861(97 )00003-5 .
^ PL application 90B1 PL application 91B1 https://uprp.gov.pl/sites/default/files/2019-12/KWARTALNIK_100_lat_wydanie_specjalne.pdf
^ Not Available (1922). Chemical Abstracts (1922) Vol.16, No.18
^ a b c Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry , Wiley-VCH, Weinheim, 2005. doi :10.1002/14356007.a02_001
^ Charles-Adolphe Wurtz (1849) "Sur une série d'alcalis organiques homologues avec l'ammoniaque" (On a series of homologous organic alkalis containing ammonia), Comptes rendus … , 28
^ Mann, F. G.; Saunders, B. C. (1960). Practical Organic Chemistry ISBN 9780582444072
^ Cohen, Julius (1900). Practical Organic Chemistry 72
^ Marvel, C. S.; Jenkins, R. L. (1941). "Methylamine Hydrochloride" . Organic Syntheses Collected Volumes , vol. 1, p. 347
^ Gatterman, Ludwig & Wieland, Heinrich (1937). Laboratory Methods of Organic Chemistry
^ Peter Scott, ed. (13 October 2009). Linker Strategies in Solid-Phase Organic Synthesis ISBN 9780470749050 ...an unhindered amine such as methylamine
^ Debacker, Marc G.; Mkadmi, El Bachir; Sauvage, François X.; Lelieur, Jean-Pierre; Wagner, Michael J.; Concepcion, Rosario; Kim, Jineun; McMills, Lauren E. H.; Dye, James L. (1996). "The Lithium−Sodium−Methylamine System: Does a Low-Melting Sodide Become a Liquid Metal?". Journal of the American Chemical Society . 118 (8 ): 1997. doi :10.1021/ja952634p .
^ Thauer, R. K. (1998). "Biochemistry of methanogenesis: A tribute to Marjory Stephenson:1998 Marjory Stephenson Prize Lecture" . Microbiology . 144 (9 ): 2377–406. doi :10.1099/00221287-144-9-2377 PMID 9782487 .
^ Ng, SS; Yue, WW; Oppermann, U; Klose, RJ (February 2009). "Dynamic protein methylation in chromatin biology" . Cellular and Molecular Life Sciences . 66 3 ): 407–22. doi :10.1007/s00018-008-8303-z . PMC 2794343 PMID 18923809 .
^ The Merck Index , 10th Ed. (1983), p.864, Rahway: Merck & Co.
^ CDC - NIOSH Pocket Guide to Chemical Hazards
^ Title 21 Code of Federal Regulations
^ Frank, R. S. (1983). "The Clandestine Drug Laboratory Situation in the United States". Journal of Forensic Sciences . 28 1 ): 18–31. doi :10.1520/JFS12235J . PMID 6680736 .
^ Matthews, Dylan (15 August 2013). "Here's what 'Breaking Bad' gets right, and wrong, about the meth business" . Washington Post the original on 3 February 2023.
^ Harnisch, Falk; Salthammer, Tunga. "The Chemistry of Breaking Bad" . Chemistry Views . Chemistry Europe . Archived from the original on 8 February 2024.
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=Methylamine&oldid=1227857954 " C a t e g o r i e s : ● A l k y l a m i n e s ● 1 8 4 9 i n t r o d u c t i o n s ● O r g a n i c c o m p o u n d s w i t h 1 c a r b o n a t o m ● S u b s t a n c e s d i s c o v e r e d i n t h e 1 9 t h c e n t u r y H i d d e n c a t e g o r i e s : ● A r t i c l e s w i t h s h o r t d e s c r i p t i o n ● S h o r t d e s c r i p t i o n i s d i f f e r e n t f r o m W i k i d a t a ● A r t i c l e s w i t h o u t I n C h I s o u r c e ● A r t i c l e s w i t h c h a n g e d E B I i d e n t i f i e r ● A r t i c l e s w i t h c h a n g e d D r u g B a n k i d e n t i f i e r ● E C H A I n f o C a r d I D f r o m W i k i d a t a ● C h e m b o x h a v i n g G H S d a t a ● A r t i c l e s c o n t a i n i n g u n v e r i f i e d c h e m i c a l i n f o b o x e s ● C h e m b o x i m a g e s i z e s e t ● S h o r t d e s c r i p t i o n m a t c h e s W i k i d a t a ● A l l a r t i c l e s w i t h u n s o u r c e d s t a t e m e n t s ● A r t i c l e s w i t h u n s o u r c e d s t a t e m e n t s f r o m D e c e m b e r 2 0 1 7 ● A r t i c l e s w i t h G N D i d e n t i f i e r s ● A r t i c l e s w i t h J 9 U i d e n t i f i e r s ● A r t i c l e s w i t h L C C N i d e n t i f i e r s
● T h i s p a g e w a s l a s t e d i t e d o n 8 J u n e 2 0 2 4 , a t 0 5 : 2 2 ( U T C ) . ● T e x t i s a v a i l a b l e u n d e r t h e C r e a t i v e C o m m o n s A t t r i b u t i o n - S h a r e A l i k e L i c e n s e 4 . 0 ;
a d d i t i o n a l t e r m s m a y a p p l y . B y u s i n g t h i s s i t e , y o u a g r e e t o t h e T e r m s o f U s e a n d P r i v a c y P o l i c y . W i k i p e d i a ® i s a r e g i s t e r e d t r a d e m a r k o f t h e W i k i m e d i a F o u n d a t i o n , I n c . , a n o n - p r o f i t o r g a n i z a t i o n . ● P r i v a c y p o l i c y ● A b o u t W i k i p e d i a ● D i s c l a i m e r s ● C o n t a c t W i k i p e d i a ● C o d e o f C o n d u c t ● D e v e l o p e r s ● S t a t i s t i c s ● C o o k i e s t a t e m e n t ● M o b i l e v i e w
