720681-64-1

Basic information

• Product Name: 4-chloro-2-(prop-1-en-2-yl)aniline
• Synonyms: 4-chloro-2-(prop-1-en-2-yl)aniline
• CAS NO: 720681-64-1
• Molecular Weight: 167.638
• Mol File: 720681-64-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 4-chloro-2-(prop-1-en-2-yl)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chloro-2-(prop-1-en-2-yl)aniline(720681-64-1)
• EPA Substance Registry System: 4-chloro-2-(prop-1-en-2-yl)aniline(720681-64-1)

Safety Data

• Hazardous Substances Data: 720681-64-1(Hazardous Substances Data)

Upstream product

• 21740-91-0 2-(2-amino-5-chloro-phenyl)-propan-2-ol 
• 5922-60-1 2-amino-5-chlorobenzonitrile 
• 1685-19-4 2-amino-5-chloroacetophenone 
• 1779-49-3 Methyltriphenylphosphonium bromide 

Downstream Products

• 2585-04-8 6-chloro-4-methylquinolin-2(1H)-one 

Relevant articles and documents

NH2-directed C-H alkenylation of 2-vinylanilines with vinylbenziodoxolones

The first directing-group-mediated C-H alkenylation with alkenyl-λ3-iodanes as electrophilic alkene-transfer reagents has been developed. The application of free aromatic amines as challenging but synthetically valuable directing groups in combination with an IrIII catalyst enabled the synthesis of highly desirable 1, 3- dienes in excellent yields of up to 98% with high to perfect (Z, E) stereoselectivity. A broad substrate scope and further synthetic modifications are demonstrated.

Pd-catalyzed regiodivergent synthesis of diverse oxindoles enabled by the versatile heck reaction of carbamoyl chlorides

We report herein a miscellaneous oxindole synthesis bearing an all-carbon quaternary center, enabled by Pd-catalyzed intramolecular cyclization followed by multiple intermolecular Heck reactions of both easily accessible alkene-tethered carbamoyl chlorides and olefins. This protocol obviates the use of prefunctionalized olefinic reagents, exhibits excellent functional group tolerance, and features fascinating reactive versatility.

Direct Electrophilic C?H Alkynylation of Unprotected 2-Vinylanilines

Unprotected aromatic amines can be used as directing groups in metal-catalyzed C?H alkynylations of alkenes. By using low amounts of an IrIIIcatalyst in combination with alkynylbenziodoxolones as electrophilic alkyne-transfer reagents, highly desirable 1,3-enynes were isolated in excellent yields of up to 98 % with Z stereoselectivity. A broad substrate scope as well as the high synthetic utility of the 1,3-enynes render this new method an efficient approach for the synthesis of five- and six-membered heterocycles. Further derivatizations of the 1,3-enynes to highly substituted quinolines through AuI- and N-bromosuccinimide-mediated exo-dig cyclizations were demonstrated.