191874-94-9

Basic information

• Product Name: 3-chloro-4-(dimethylamino)cinnamic aldehyde
• CAS NO: 191874-94-9
• Molecular Weight: 209.675
• Mol File: 191874-94-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 3-chloro-4-(dimethylamino)cinnamic aldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3-chloro-4-(dimethylamino)cinnamic aldehyde(191874-94-9)
• EPA Substance Registry System: 3-chloro-4-(dimethylamino)cinnamic aldehyde(191874-94-9)

Safety Data

• Hazardous Substances Data: 191874-94-9(Hazardous Substances Data)

Upstream product

• 68-12-2 N,N-dimethyl-formamide 
• 2124-31-4 4'-dimethylaminoacetophenone 
• 121-69-7 N,N-dimethyl-aniline 

Downstream Products

• 1026921-69-6 [(Z)-1-(4-Dimethylamino-phenyl)-3-oxo-propenylsulfanyl]-phenyl-acetic acid methyl ester 

Relevant articles and documents

3,3-Dichloroprop-2-ene iminium salts (vinylogous Viehe salts): A study of their reactivity towards nucleophiles

The title compounds 3 react regioselectively at either the 1- or 3- position depending on the reaction partner. Chloro substitution affording new propene iminium salts is preferred e.g. in the reaction with mercaptans (to 10, 11), amines (to 7, 14, 15) and some activated arenes and hetarenes (to 26, 27). Nucleophilic attack at the 1-position providing an allyl or allylidene structure is observed e.g. in the reaction with water (to 41, alcohol (to 6), trialkyl phosphite (to 21, 22), trimethylsilyl cyanide (to 30), Grignard reagents (to 31), and acceptor activated methylene compounds (to 33-44). Reaction at both positions with heterocyclization to 13 occurs with thioamide functions. The regiochemistry depends on a complex interplay of several factors in contrast to the FMO predicted orientation. The utility of 3 and some consecutive products as versatile C3-building blocks for further syntheses is foreseeable.