2038-24-6

Usage

Physical state

Colorless to pale yellow liquid

Odor

Strong ammonia-like odor

Uses

Chemical intermediate in the production of pharmaceuticals, agrochemicals, and other organic compounds

Reactivity

Highly reactive and can form stable complexes with certain metal ions

Safety

Mild irritant to the skin and eyes; should be handled with care

Carcinogenicity

Not found to be carcinogenic in studies conducted to date

Mutagenicity

Not found to be mutagenic in studies conducted to date

Upstream product

• 85389-63-5 lithium N-butylcyclopropylamide 
• 123-38-6 propionaldehyde 
• 109-73-9 N-butylamine 

Downstream Products

• 20193-21-9 N-propyl-1-butylamine 
• 131270-40-1 1-butyl-3,5-dimethyl-2-oxo-2-phenyl-1,2-dihydro-1,2-azaphosphinine 
• 123-72-8 butyraldehyde 
• 77597-07-0 3,5-diphenyl-4-propylisoxazoline N-oxide 
• 131270-24-1 1-butyl-3,5-dimethyl-2-phenyl-1,2-dihydro-1,2-λ³-azaphosphinine 
• 80118-54-3 1-butyl-3-ethyl-4-methyl-2-phenyl-2-oxo-1,2,4-azaphospholene 

Relevant academic research and scientific papers

Imidoylstannanes from acylstannanes and primary amines - A simple and versatile method of preparation

Imidoylstannanes 3 can be obtained by condensation of primary aliphatic and aromatic amines 2 with acylstannanes 1. The versatile and easy to perform method fails only with tertiary alkyl groups on the nitrogen atom of the amine as well as on the carbon atom of the acylstannane. Only one stereoisomer of 3 could be detected, to which the Z-configuration is tentatively ascribed. Some transformations of 3 to give the hitherto unknown secondary 1-stannylamines 4, 1-stannyl-2-silylimines 5 or 1-stannyl-N-silylenamines 6 are described.

Some reactions of ammonia and primary amines with propanal, 2-chloroethanal, 2,2-dichloroethanal and 2,2,2-trichloroethanal in acetonitrile

The reaction of ammonia with propanal in acetonitrile produces the hexahydrotriazine, 1, in good yield. The corresponding reaction of chloroethanal yields the cyclic trimer 16 but only in poor yield. Increasing chloro-substitution in the aldehyde stabilises the initially formed carbinolamines and disfavours trimerisation. Imines formed by reaction of primary amines with the aldehydes are relatively stable. Those formed from aliphatic amines may undergo slow dimerisation by C-C bond formation and this may be accompanied by loss of amine to yield products containing a conjugated double-bond system. Kinetic and equilibrium data are reported for both the forward and reverse reactions involving interconversion of propanal and ammonia with 1 in acetonitrile-water mixtures. The results indicate that dehydration of the carbinolamine is rate determining.

A Versatile New Synthesis of Quinolines and Related Fused Pyridines. Part 12. A General Synthesis of 2-Chloropyridines and 2-Pyridons

The Vilsmeier formylation of tertiary and secondary enamides leads to 2-pyridons and 2-chloropyridines, respectively.The reaction appears to be quite general allowing substitution in the 1-, 3-, 5-, or 6-position or combinations of these.The major limitation arises with enamides which are unsymmetrically substituted on the double bond with alkyl groups, when mixtures can result.Attempts to introduce a 4-substituent by a variation of the Vilsmeier reagent had limited success.

ISOMERIZATIONS OF SMALL RING LITHIUM DIALKYLAMIDES

Lithium N-butylcyclopropylamide (1) and lithium N-propylcyclobutylamide (2) rearrange in etheral solvents by nucleophilic eliminative ring fission process; amide 1 is highly reactive whereas 2 is somewhat stable.