33603-89-3

Basic information

• Product Name: (Z)-2-chloro-3-phenyl-prop-2-enal
• CAS NO: 33603-89-3
• Molecular Formula: C₉H₇ClO
• Molecular Weight: 166.607
• Mol File: 33603-89-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 265.9°Cat760mmHg
• Flash Point: 130.7°C
• Density: 1.199g/cm³
• CAS DataBase Reference: (Z)-2-chloro-3-phenyl-prop-2-enal(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-2-chloro-3-phenyl-prop-2-enal(33603-89-3)
• EPA Substance Registry System: (Z)-2-chloro-3-phenyl-prop-2-enal(33603-89-3)

Safety Data

• Hazardous Substances Data: 33603-89-3(Hazardous Substances Data)

Upstream product

• 104-55-2 3-phenyl-propenal 
• 100-52-7 benzaldehyde 
• 75-87-6 chloral 
• 515-83-3 chloral ethyl hemiacetal 
• 14371-10-9 (E)-3-phenylpropenal 
• 20473-36-3 2,3-dichloro-3-phenyl-propionaldehyde 
• 71996-30-0 2-phenylselenenyl-3-phenyl-2-propenal 
• 79-35-6 1,1'-dichloro-2,2'-difluoroethene 

Downstream Products

• 160721-87-9 (Z)-2-Chloro-1-phenyl-1,3-butadiene 
• 160721-89-1 (Z)-2-Chloro-4-methyl-1-phenyl-1,3-pentadiene 
• 130996-38-2 2-chloro-1,3-diphenyl-prop-2-en-1-ol 
• 393827-56-0 3-chloro-3-phenyl-prop-2(Z)-en-1-ol 
• 1356450-51-5 [(1Z,3E)-2-chlorohexa-1,3,5-trien-1-yl]benzene 
• 1582784-05-1 (Z)-2-(ethylthio)-3-phenylacrylaldehyde 
• 1463930-84-8 C₁₈H₁₅Cl 
• 1463930-86-0 (1Z,3E)-2-chloro-1-phenyl-4-(o-styrenyl)-1,3-butadiene 
• 1463930-98-4 (1Z,3Z)-4-{o-[(1Z,3Z)-3-chloro-4-phenyl-1,3-butadienyl]phenyl}-2-chloro-1-phenyl-1,3-butadiene 
• 1463931-00-1 C₂₆H₂₀Cl₂ 
• 1463930-92-8 (1E,3Z)-4-{o-[(1E,3Z)-3-chloro-4-phenyl-1,3-butadienyl]phenyl}-2-chloro-1-phenyl-1,3-butadiene 
• 1266333-85-0 2-[(2Z)-2-anilino-3-phenylprop-2-enoyl]-1,4,5-trimethyl-1H-imidazole 
• 1252684-79-9 (1Z,3S)-(-)-2-chloro-1-phenylhexa-1,5-dien-3-ol 
• 1252684-74-4 (1Z,3R)-(+)-2-chloro-1-phenylhexa-1,5-dien-3-ol 

Relevant articles and documents

Modular Synthesis of α-Substituted Alkenyl Acetals by a Palladium-Catalyzed Suzuki Reaction of α-Haloalkenyl Acetals with Organoboranes

A modular and straightforward synthetic strategy for the preparation of α-substituted alkenyl acetals has been developed. α-Haloalkenyl acetals react smoothly with (het)aryl boronic acids, aryl boronates, or B-Alkyl-9-borabicyclo[3.3.1]nonanes through Pd-catalyzed Suzuki cross-coupling under mild conditions with good to high yields. This protocol features a broad substrate scope and good functional-group compatibility, and is easily scaled up.

Convenient preparation of (Z)-α-halo-α,β-unsaturated aldehydes: synthesis of a Laurencia flexilis toxin

The CrCl2-mediated two-carbon halo-homologation of aryl, alkenyl, and aliphatic aldehydes with chloral ethyl hemiacetal or bromal affords (Z)-α-chloro- and (Z)-α-bromo-α,β-unsaturated aldehydes, respectively, in good to excellent yields and high stereoselectivity. The utility of this methodology was illustrated by a synthesis of 2-chloropentadec-2(Z)-enal, a toxin isolated from the marine red alga Laurencia flexilis.

A convenient halogenation of α,β-unsaturated carbonyl compounds with OXONE and hydrohalic acid (HBr,HCl)

Mixtures of OXONE and hydrobromic acid or hydrochloric acid afford solutions of bromine or chlorine, respectively, α-Bromo- or α-chloro-α,β-unsaturated carbonyl compounds were prepared by addition of hydrobromic acid or hydrochloric acid to the mixture of