182210-43-1

Basic information

• Product Name: syn-(1R,2R)-2-chloro-1-phenyl-3-buten-1-ol
• Synonyms: syn-(1R,2R)-2-chloro-1-phenyl-3-buten-1-ol
• CAS NO: 182210-43-1
• Molecular Weight: 182.65
• Mol File: 182210-43-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: syn-(1R,2R)-2-chloro-1-phenyl-3-buten-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: syn-(1R,2R)-2-chloro-1-phenyl-3-buten-1-ol(182210-43-1)
• EPA Substance Registry System: syn-(1R,2R)-2-chloro-1-phenyl-3-buten-1-ol(182210-43-1)

Safety Data

• Hazardous Substances Data: 182210-43-1(Hazardous Substances Data)

Upstream product

• 1357478-20-6 C₈H₁₄BClO₂ 
• 100-52-7 benzaldehyde 
• 542-75-6 E/Z-1,3-Dichloropropene 
• 107-05-1 3-chloroprop-1-ene 

Downstream Products

• 182210-51-1 cis-(1R,2S)-1,2-epoxy-1-phenyl-3-butene 
• 182210-57-7 cis-(1S,2R)-1,2-epoxy-1-phenyl-3-butene 

Relevant articles and documents

Chiral zinc-catalyzed asymmetric α-alkylallylation and α-chloroallylation of aldehydes

Two birds with one stone: In the presence of Zn(OH)2 and a chiral bipyridine ligand, racemic α-substituted allylboronates 2 reacted with aldehydes 1 (see scheme) exclusively in an α-addition fashion to afford various homoallylic alcohols 3 bear

Diastereo- and enantioselective synthesis of syn-α-vinylchlorohydrins and cis-vinylepoxides

A new method to generate chiral syn-vinylchlorohydrins and cis-vinyloxiranes is reported. Reaction of (α-haloallyl)lithiums with methoxy-9-BBN or Ipc2BOMe followed by treatment with BF3·OEt2 leads to (Z)-(γ-haloallyl)boranes which react with aldehydes to yield cis-vinylepoxides (de ≥ 90%) upon oxidative workup. Alternatively, addition of ethanolamine to the allylboration product yields syn-α-halohydrins (de ≥ 90%) that are also easily cyclized to cis-vinylepoxides. Extension of this protocol using [(Z)-γ-chloroallyl]BIpc2 leads to chiral syn-α-chlorohydrins and cis-vinylepoxides in high de (≥90%) and ee (90-99%). Enantioselectivity of reactions of chiral (Z)-(γ-chloroallyl)boranes with aldehydes are more sensitive to reaction conditions than enantioselectivity of reactions of other α-or γ-substituted allylboranes. The effects of proportion of BP3·OEt2 and the relative efficacies of LiNR2 bases on diastereo- and enantioselectivity of the chloroallylation are reported.