1187-58-2

Basic information

• Product Name: N-Methylpropionamide
• Synonyms: n-methyl-propanamid;N-Methylpropanamide;N-methyl-Propanamide;n-methyl-propionamid;N-Methylpropionic acid amide;n-methylpropionicacidamide;N-Methylpropionsaureamid;Propionamide, N-methyl-
• CAS NO: 1187-58-2
• Molecular Formula: C₄H₉NO
• Molecular Weight: 87.12
• EINECS: 214-699-7
• Product Categories: Amides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 1187-58-2.mol
• Article Data: 14

Chemical Properties

• Melting Point: −43 °C(lit.)
• Boiling Point: 146 °C90 mm Hg(lit.)
• Flash Point: 222 °F
• Appearance: clear colourless liquid
• Density: 0.931 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.13mmHg at 25°C
• Refractive Index: n20/D 1.436(lit.)
• PKA: 16.61±0.46(Predicted)
• BRN: 1737640
• CAS DataBase Reference: N-Methylpropionamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methylpropionamide(1187-58-2)
• EPA Substance Registry System: N-Methylpropionamide(1187-58-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: UE4515000
• F: 3
• Hazardous Substances Data: 1187-58-2(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS LIQUID

Uses

N-Methylpropionamide has been used to investigate amide-induced phase separation of hexafluoro-2-propanol-water mixtures.

Purification Methods

The amide is a colourless, odourless, neutral liquid at room temperature with a high dielectric constant. The amount of water present can be determined directly by Karl Fischer titration, GLC and NMR have been used to detect unreacted propionic acid. Commercial material of high quality is available, probably from the condensation of anhydrous methylamine with 50% excess of propionic acid. Rapid heating to 120-140o with stirring favours the reaction by removing water either directly or as the ternary xylene azeotrope. The quality of the distillate improves during the distillation. N-Methylpropionamide can be dried over CaO. Water and unreacted propionic acid are removed as their xylene azeotropes. It is then distilled in a vacuum. Material used as an electrolyte solvent (specific conductance less than 10-6 ohm-1 cm -1) is obtained by fractional distillation under reduced pressure, and storage over BaO or molecular sieves because it readily absorbs moisture from the atmosphere on prolonged storage. [Hoover Pure Appl Chem 37 581 1974, Recommended Methods for Purification of Solvents and Tests for Impurities, Coetzee Ed., Pergamon Press, 1982, Beilstein 4 IV 183.]

InChI:InChI=1/C4H9NO/c1-3-4(6)5-2/h3H2,1-2H3,(H,5,6)

Upstream product

• 96-29-7 ethyl methyl ketone oxime 
• 79-03-8 propionyl chloride 
• 74-89-5 methylamine 
• 96-31-1 N,N'-Dimethylurea 
• 802294-64-0 propionic acid 
• 130012-50-9 dimethyl N-thiopropanoyl-N-methylphosphoramidate 
• 85462-16-4 N-Methyl-O-p-nitrophenylsulphonylhydroxylamine 
• 123-38-6 propionaldehyde 
• 10341-59-0 (Z)-2-butanone oxime 
• 74-85-1 ethene 
• 124-38-9 carbon dioxide 
• 1719-57-9 Chloro(chloromethyl)dimethylsilane 
• 79-05-0 Propionamid 
• 74-88-4 methyl iodide 

Downstream Products

• 2955-71-7 N-methylthiopropionamide 
• 67138-98-1 N-(2-Cyan-aethyl)-N-methyl-propionamid 
• 130935-25-0 N-methyl-N-(1-oxopropyl)-3-oxobutanamide 
• 205443-12-5 (3-Ethylsulfanyl-2,5-dioxo-pyrrolidin-1-yl)-acetic acid 4-(1-hydroxy-1-phenyl-2-propionylamino-ethyl)-benzyl ester 
• 205443-16-9 (3-Ethylsulfanyl-2,5-dioxo-pyrrolidin-1-yl)-acetic acid 4-(1-hydroxy-1-phenyl-2-propionylamino-ethyl)-phenyl ester 
• 16395-80-5 N-methyl-N-nitrosopropylamide 
• 798533-25-2 N-(7-[1,4]dioxepan-6-yl-4-methoxy-benzothiazol-2-yl)-4-[(methyl-propionyl-amino)-methyl]-benzamide 
• 1198293-91-2 N-(2-chloro-4-cyanophenyl)-N-methylpropionamide 
• 1257533-50-8 N'-(1,3-diphenyl-1H-pyrazol-5-yl)-N-methylpropanimidamide 
• 71-23-8 propan-1-ol 
• 74-89-5 methylamine 
• 107-10-8 propylamine 
• 142-84-7 di-n-propylamine 

Relevant articles and documents

Chemoselective methylation of amides and heterocycles using chloromethyldimethylsilyl chloride

The reaction of chloromethyldimethylsilyl chloride with an amide generates a pentacoordinate N-(amidomethyl)-halosilane that can be desilylated with cesium fluoride to give the N-methyl amide. This provides a selective method for the monoalkylation of amides in the presence of other, more nucleophilic groups. (C) 2000 Elsevier Science Ltd.

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A hydrophilic inorganic framework based on a sandwich polyoxometalate: Unusual chemoselectivity for aldehydes/ketones with in situ generated hydroxylamine

A hydrophilic inorganic porous catalyst was prepared via the hydrothermal method. The combination of [WZn3(H2O)2(ZnW9O34)2]12- and Co(ii) provides a synergistical catalytic way to promote oximation of aldehyde/ketone with in situ generated hydroxylamine that initially produces an oxime, which further either dehydrates into a nitrile or undergoes a Beckmann rearrangement to form an amide.

Direct catalytic synthesis of ε-caprolactam from cyclohexanol using [n-C16H33N (CH3)3]H2PW12O40 as a catalyst

ε-Caprolactam was synthesized directly from cyclohexanol via a tandem catalytic process using [n-C16H33N(CH3)3]H2PW12O40 as a catalyst. The highly efficient performance of the catalysts is due to the phase-transfer function of cation, improved coordination with peroxotungsten during oxidation and stabilization function of heteropoly anion on the intermediate formed during Beckmann rearrangement. A ε-caprolactam yield of 73.9% was obtained with a cyclohexanol conversion of 97.1% under optimized conditions.