N -methylacetamide

Structural formula
General
Surname	N -methylacetamide
other names	N -methylacetamide; Monomethylacetamide; Methylacetamide;
Molecular formula	C 3 H 7 NO
Brief description	colorless solid with a faint odor
External identifiers / databases
EC number	201-182-6
ECHA InfoCard	100.001.075
PubChem	6582
Wikidata	Q12871952
properties
Molar mass	73.09 g mol −1
Physical state	firmly
density	0.94 g cm −3
Melting point	27-30.6 ° C
boiling point	206-208 ° C
Vapor pressure	1.1 hPa (50 ° C)
solubility	soluble in water; soluble in chloroform , ethanol , ether , acetone and benzene ;
Refractive index	1.433 (20 ° C)
safety instructions
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger
H and P phrases	H: 360D
	P: 201-308 + 313
Authorization procedure under REACH	of particular concern : toxic for reproduction ( CMR )
Toxicological data	5000 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

N -Methylacetamide is a chemical compound from the group of carboxamides . The compound is one of the substances of very high concern of the European Chemicals Agency (ECHA).

Extraction and presentation

N -Methylacetamide can be obtained by reacting hot acetic acid or acetic anhydride with methylamine . It is also possible to produce it by reacting N , N '-dimethylurea with acetic acid or by reacting acetone oxime with sulfuric acid .

properties

N -Methylacetamide is a flammable, hardly inflammable, hygroscopic , crystalline, colorless solid with a faint odor, which is soluble in water. Several isomeric forms are known. In solution it is 97–100% as a ( Z ) isomer with a polymeric structure. The compound has a high dielectric constant of 191.3 at 32 ° C.

use

N -Methylacetamide is used as an intermediate in the manufacture of agrochemicals and as a solvent in electrochemistry.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on N-methylacetamide in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
↑ ^a ^b J. F. Coetzee: Recommended Methods for Purification of Solvents and Tests for Impurities International Union of Pure and Applied Chemistry . Elsevier, 2013, ISBN 978-1-4831-3845-9 , pp. 50 ( limited preview in Google Book search).
↑ ^a ^b Data sheet N-Methylacetamide, 99% from AlfaAesar, accessed on April 17, 2017 ( PDF )(JavaScript required) .
↑ Data sheet N-Methylacetamide, ≥99% from Sigma-Aldrich , accessed on April 17, 2017 ( PDF ).
↑ Entry on N-methylacetamide in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on April 29, 2017. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Entry in the SVHC list of the European Chemicals Agency , accessed on April 21, 2020.
↑ ^a ^b Entry on N-methylacetamide in the Hazardous Substances Data Bank , accessed April 17, 2017.
↑ ^a ^b D.R. Buhler, DJ Reed: Nitrogen and Phosphorus Solvents . Elsevier, 2013, ISBN 978-1-4832-9020-1 , pp. 166 ( limited preview in Google Book search).
↑ Joachim Buddrus, Bernd Schmidt: Fundamentals of organic chemistry . Walter de Gruyter GmbH & Co KG, 2015, ISBN 978-3-11-033105-9 , p. 581 ( limited preview in Google Book search).
↑ Noemi G. Mirkin, Samuel Krimm: Conformers of cis-N-methylacetamide. In: Journal of Molecular Structure: THEOCHEM. 236, 1991, p. 97, doi : 10.1016 / 0166-1280 (91) 87010-J .
↑ Ab initio vibrational analysis of hydrogen-bonded trans- and cis-N-methylacetamide . In: Journal of the American Chemical Society . tape 113 , no. 26 , December 1, 1991, pp. 9742-9747 , doi : 10.1021 / ja00026a005 .
↑ K.-H. Hellwich: Basic stereochemistry terms . Springer-Verlag, 2013, ISBN 978-3-662-10051-6 , pp. 43 ( limited preview in Google Book search).
^ A. Covington: Physical Chemistry of Organic Solvent Systems . Springer Science & Business Media, 2012, ISBN 978-1-4684-1959-7 , pp. 247 ( limited preview in Google Book search).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on N-methylacetamide in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .

[J._F._Coetzee-2] J. F. Coetzee: Recommended Methods for Purification of Solvents and Tests for Impurities International Union of Pure and Applied Chemistry . Elsevier, 2013, ISBN 978-1-4831-3845-9 , pp. 50 ( limited preview in Google Book search).

[Alfa-3] Data sheet N-Methylacetamide, 99% from AlfaAesar, accessed on April 17, 2017 ( PDF )(JavaScript required) .

[Sigma-4] Data sheet N-Methylacetamide, ≥99% from Sigma-Aldrich , accessed on April 17, 2017 ( PDF ).

[CLP_100.001.075-5] Entry on N-methylacetamide in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on April 29, 2017. Manufacturers or distributors can expand the harmonized classification and labeling .

[SVHC-6] Entry in the SVHC list of the European Chemicals Agency , accessed on April 21, 2020.

[HSDB-7] Entry on N-methylacetamide in the Hazardous Substances Data Bank , accessed April 17, 2017.

[D.R._Buhler,_D.J._Reed-8] D.R. Buhler, DJ Reed: Nitrogen and Phosphorus Solvents . Elsevier, 2013, ISBN 978-1-4832-9020-1 , pp. 166 ( limited preview in Google Book search).

[Joachim_Buddrus,_Bernd_Schmidt-9] Joachim Buddrus, Bernd Schmidt: Fundamentals of organic chemistry . Walter de Gruyter GmbH & Co KG, 2015, ISBN 978-3-11-033105-9 , p. 581 ( limited preview in Google Book search).

[10] Noemi G. Mirkin, Samuel Krimm: Conformers of cis-N-methylacetamide. In: Journal of Molecular Structure: THEOCHEM. 236, 1991, p. 97, doi : 10.1016 / 0166-1280 (91) 87010-J .

[11] Ab initio vibrational analysis of hydrogen-bonded trans- and cis-N-methylacetamide . In: Journal of the American Chemical Society . tape 113 , no. 26 , December 1, 1991, pp. 9742-9747 , doi : 10.1021 / ja00026a005 .

[K.-H._Hellwich-12] K.-H. Hellwich: Basic stereochemistry terms . Springer-Verlag, 2013, ISBN 978-3-662-10051-6 , pp. 43 ( limited preview in Google Book search).

[A._Covington-13] A. Covington: Physical Chemistry of Organic Solvent Systems . Springer Science & Business Media, 2012, ISBN 978-1-4684-1959-7 , pp. 247 ( limited preview in Google Book search).