21678-37-5

Basic information

• Product Name: N,N,2-TRIMETHYLPROPIONAMIDE
• Synonyms: N,N-DIMETHYLISOBUTYRAMIDE;N,N,2-TRIMETHYLPROPIONAMIDE;AKOS 130;N,N-Dimethyl-2-methylpropanamide;N,N-Dimethylisobutylamide;N,N,2-Trimethylpropionamide,99%;PropanaMide, N,N,2-triMethyl-;N,N-Dimethyl-2-methylpropionamide
• CAS NO: 21678-37-5
• Molecular Formula: C₆H₁₃NO
• Molecular Weight: 115.17
• Mol File: 21678-37-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 175-176 °C744 mm Hg(lit.)
• Flash Point: 158 °F
• Appearance: /
• Density: 0.892 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.28mmHg at 25°C
• Refractive Index: n20/D 1.439(lit.)
• PKA: -0.47±0.70(Predicted)
• Water Solubility: Soluble in water.
• BRN: 1742178
• CAS DataBase Reference: N,N,2-TRIMETHYLPROPIONAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N,2-TRIMETHYLPROPIONAMIDE(21678-37-5)
• EPA Substance Registry System: N,N,2-TRIMETHYLPROPIONAMIDE(21678-37-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 21678-37-5(Hazardous Substances Data)

Usage

Description

N,N,2-TRIMETHYLPROPIONAMIDE, also known as N,N-Dimethylisobutyramide, is an N,N-disubstituted amide that can be prepared by acylation of secondary amines with acyl chloride. It is a clear colorless to slightly yellow liquid.

Uses

Used in Chemical Synthesis:
N,N,2-TRIMETHYLPROPIONAMIDE is used as a reagent in the preparation of 1-chloro-N,N,2-trimethylpropenylamine, which is readily prepared from N,N-dimethylisobutyramide. N,N,2-TRIMETHYLPROPIONAMIDE is further used in the synthesis of isoxazoles by deprotonation of N,N-dimethylisobutyramide.
Used in Pharmaceutical Industry:
N,N,2-TRIMETHYLPROPIONAMIDE is used as a solvent or intermediate in the synthesis of various pharmaceutical compounds due to its ability to form hydrogen bonds and its compatibility with a wide range of chemical reactions.

InChI:InChI=1/C6H13NO/c1-5(2)6(8)7(3)4/h5H,1-4H3

Upstream product

• 504-61-0 (E)-but-2-enol 
• 106-24-1 Geraniol 
• 106-28-5 Farnesol 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 26189-59-3 1-chloro-1-(dimethylamino)-2-methyl-1-propene 
• 65560-29-4 N,N-dimethyl-1-fluoro-2-methylpropenamine 
• 73630-93-0 1-bromo-N,N,2-trimethyl-1-propen-1-amine 
• 107-19-7 propargyl alcohol 
• 100-51-6 benzyl alcohol 
• 71-36-3 butan-1-ol 
• 71-41-0 pentan-1-ol 

Downstream Products

• 565-69-5 ethyl isopropyl ketone 
• 78-84-2 isobutyraldehyde 
• 24331-71-3 N,N-dimethylpivalamide 
• 13019-20-0 2-methylheptan-3-one 
• 72873-39-3 2,2,N,N-Tetramethyl-3-oxo-3-phenyl-propionamide 
• 72873-38-2 3-Cyclohexyl-2,2,N,N-tetramethyl-3-oxo-propionamide 
• 6976-91-6 N,N-dimethylmethacrylamide 
• 26189-59-3 1-chloro-1-(dimethylamino)-2-methyl-1-propene 
• 81391-08-4 2,2-dimethyl-3-phenylcyclobutanone 
• 122969-83-9 N-methyl-N-(3-methyl-2-oxobutyl)-2-methylpropanamide 
• 122968-47-2 N,N,2,-trimethyl-2-(3'-oxocyclohexyl)propanamide 
• 122968-46-1 N,N,2,2,3-pentamethyl-5-oxo-5-phenylpentanamide 
• 89578-39-2 N-((S)-1-Phenyl-2-propyl)-3,3-dimethyl-4(S)-phenyl-azetidin-2-one 
• 89578-40-5 N-((S)-1-Phenyl-2-propyl)-3,3-dimethyl-4(R)-phenyl-azetidin-2-one 

Relevant articles and documents

A mild method for the replacement of a hydroxyl group by halogen: 2. unified procedure and stereochemical studies

N,N-Dimethyl- and N,N-diisopropyl-1-halo-2-methyl-l-propenylamines are readily available reagents for the mild deoxyhalogenation of alcohols and hydroxyacids. In this study we showed that the reactivity of the reagents can be tuned by varying the size of the alkyl groups on the reagents: the replacement of methyl by isopropyl groups led to a significant increase of reactivity. We then described a unified procedure for all deoxyhalogenations using the readily available α-chloroenamines as reagents with (bromination, iodination) or without (chlorination) an alkaline bromide or iodide. Finally, we showed that deoxyhalogenation reactions of secondary alcohols were highly stereospecific and generally occurred with inversion of configuration.

SYNTHESIS OF ALKYL HALIDES UNDER NEUTRAL CONDITIONS

Primary and secondary alcohols are efficiently converted to the corresponding alkyl halides under neutral conditions.