15023-38-8

Basic information

• Product Name: (2E)-N,N-dimethyl-N'-(3-phenyl-allylidene)-hydrazine
• Synonyms: (2E)-N,N-dimethyl-N'-(3-phenyl-allylidene)-hydrazine
• CAS NO: 15023-38-8
• Molecular Weight: 174.246
• Mol File: 15023-38-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (2E)-N,N-dimethyl-N'-(3-phenyl-allylidene)-hydrazine(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-N,N-dimethyl-N'-(3-phenyl-allylidene)-hydrazine(15023-38-8)
• EPA Substance Registry System: (2E)-N,N-dimethyl-N'-(3-phenyl-allylidene)-hydrazine(15023-38-8)

Safety Data

• Hazardous Substances Data: 15023-38-8(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 131286-55-0 diethyl formylmethylphosphonate N,N-dimethylhydrazone 
• 57-14-7 N,N-Dimethylhydrazine 
• 104-55-2 3-phenyl-propenal 
• 57294-86-7 (E)-cinnamyl azide 
• 14371-10-9 (E)-3-phenylpropenal 

Downstream Products

• 1885-38-7 cinnamic nitrile 
• 14371-10-9 (E)-3-phenylpropenal 
• 1365828-08-5 (E)-1-methyl-3-styryl-1H-indazole 
• 127280-07-3 4-Phenyl-1,4-dihydro-1-azaanthracene-9,10-dione 
• 127280-12-0 cis-2,3-Dihydro-5-hydroxy-3-phenylbenzofuran-2-carboxaldehyde N,N-dimethylhydrazone 
• 127280-11-9 trans-2,3-Dihydro-5-hydroxy-3-phenylbenzofuran-2-carboxaldehyde N,N-dimethylhydrazone 
• 54125-41-6 N-methylmethyleneamine N-oxide 

Relevant articles and documents

Two-carbon homologation of aldehydes and ketones to α,β- unsaturated aldehydes

Phosphonate reagents were developed for the two-carbon homologation of aldehydes or ketones to unbranched- or methyl-branched α,β- unsaturated aldehydes. The phosphonate reagents, diethyl methylformyl-2- phosphonate dimethylhydrazone and diethyl ethylformyl-2-phosphonate dimethylhydrazone, contained a protected aldehyde group instead of the usual ester group. A homologation cycle entailed condensation of the reagent with the starting aldehyde, followed by removal of the dimethylhydrazone protective group with a biphasic mixture of 1 M HCl and petroleum ether. This robust two-step process worked with a variety of aldehydes and ketones. Overall isolated yields of unsaturated aldehyde products ranged from 71% to 86% after the condensation and deprotection steps.

A novel, one-pot synthesis of α-C-cyanohydrazines in the presence of lithium perchlorate/diethylether solution (5.0 M)

Condensation of N,N-dimethylhydrazine, an aldehyde in lithium perchlorate/diethylether solution (5.0 M) gave N,N-dimethylhydrazone, which were treated with trimethylsilylcyanide to afford α-C-cyanohydrazine. These compounds are important precursors of nitrogen-substituted reagents.

α-Alkylation of α,β-Unsaturated Aldehyde Dimethylhydrazones Accompanied with the Double Bond Migration to β,γ

Lithiated α,β-unsaturated aldehyde N,N-dimethylhydrazones reacted with alkyl halides accompanied by double bond migration to give α-alkylated β,γ-unsaturated aldehyde N,N-dimethylhydrazones in satisfactory yields.This reaction was found to be caused at the first step by deprotonation from a γ-carbon atom by lithium diisopropylamide.In the case of hydrazones with two kinds of γ-protons, deprotonation from the less hindered γ-carbon occurred selectively.Using this reaction, a novel sesquiterpene, 2,5,9-trimethyl-2-vinyl-4,8-decadienal, which has a vinyl group at the α-position, was synthesized in a good yield.