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

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

Uses

Used in Chemical Research:
N-Methylpropionamide is used as a research chemical for investigating the effects of amides on phase separation in hexafluoro-2-propanol-water mixtures. Its ability to induce phase separation makes it a valuable compound for studying the behavior of mixtures and their potential applications in various industries.
Used in Pharmaceutical Industry:
N-Methylpropionamide is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical properties allow it to be a versatile building block for the development of new drugs and medications.
Used in Material Science:
N-Methylpropionamide can be used in the development of new materials with specific properties, such as phase separation behavior. This can be useful in creating materials with tailored characteristics for various applications, including coatings, adhesives, and other industrial products.

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 
• 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 
• 78-92-2 iso-butanol 

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.

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.

Selective α-Oxyamination and Hydroxylation of Aliphatic Amides

Compared to the α-functionalization of aldehydes, ketones, even esters, the direct α-modification of amides is still a challenge because of the low acidity of α-CH groups. The α-functionalization of N?H (primary and secondary) amides, containing both an unactived α-C?H bond and a competitively active N?H bond, remains elusive. Shown herein is the general and efficient oxidative α-oxyamination and hydroxylation of aliphatic amides including secondary N?H amides. This transition-metal-free chemistry with high chemoselectivity provides an efficient approach to α-hydroxy amides. This oxidative protocol significantly enables the selective functionalization of inert α-C?H bonds with the complete preservation of active N?H bond.

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.

Carboxyl activation of 2-mercapto-4,6-dimethylpyrimidine through n-acyl-4,6-dimethylpyrimidine-2-thione: A chemical and spectrophotometric investigation

2-Mercapto-4,6-dimethylpyrimidine, as effective carboxyl activating group, has been successfully proved by converting it into respective acyl derivatives and the subsequent conversion to the amides and esters respectively using amines, amino alcohols and alcohols. The aminolysis and esterification were monitored chemically and spectrophotometrically. This paved way to establish that the above mercaptopyrimidine derivative is an efficient carboxyl activating group applicable in solid phase peptide synthesis.

Recyclable, highly efficient and low cost nano-MgO for amide synthesis under SFRC: A convenient and greener 'NOSE' approach

A clean synthesis of amide derivatives has successfully been accomplished utilizing reusable nano-MgO under 'SFRC' (solvent free reaction condition). The 'green-ness' of this protocol makes it a benign alternative for the large scale synthesis.

Efficient iodine-mediated beckmann rearrangement of ketoximes to amides under mild neutral conditions

Aryl ketoximes readily underwent Beckmann rearrangement to give N-substituted amides in excellent yields on electrophilic activation by elemental iodine in anhydrous acetonitrile under reflux. The main advantages of this environmentally friendly protocol include a high selectivity as a result of the absence of any accompanying deprotection to form the parent ketones as byproducts, mild neutral conditions, procedural simplicity, and particularly ease of isolation of the products.

Towards supramolecular fixation of NOx gases: Encapsulated reagents for nitrosation

The use of simple calix[4]arenes for chemical conversion of NO2/ N2O4 gases is demonstrated in solution and in the solid state. Upon reacting with these gases, calixarenes 1 encapsulate nitrosonium (NO+) cations within their cavities with the formation of stable calixarene-NO+ complexes 2. These complexes act as encapsulated nitrosating reagents; cavity effects control their reactivity and selectivity. Complexes 2 were effectively used for nitrosation of secondary amides 5, including chiral derivatives. Unique size-shape selectivity was observed, allowing for exclusive nitrosation of less crowded N-Me amides 5a-e (up to 95% yields). Bulkier N-Alk (Alk > Me) substrates 5 did not react due to the hindered approach to the encapsulated NO+ reagents. Robust, silica gel based calixarene material 3 was prepared, which reversibly traps NO 2/ N2O4 with the formation of NO +-storing silica gel 4. With material 4, similar size-shape selectivity was observed for nitrosation. The N-Me-N-nitroso derivatives 6d,e were obtained with ～30% yields, while bulkier amides were nitrosated with much lower yields (+ species, which can be generated by a number of NOx gases, these supramolecular reagents and materials may be useful for NOx entrapment and separation in the environment and biomedical areas.

Encapsulated reagents for nitrosation

(Matrix presented) A novel class of stable, mild, and size-shape-selective nitrosating agents for secondary amides is introduced. These are based on reversible entrapment and release of reactive nitrosonium species by calix[4]arenes. The NO+ encapsulation controls the reaction selectivity.

A facile beckmann rearrangement of oximes with AlCl3 in the solid state

A facile and efficient synthetic procedure, for Beckmann rearrangement of oximes with AlCl3 in the absence of solvent is developed. We have been able to convert cyclohexanone oxime to εcaprolactam in a quantitative yield.