trans-1-Bromo-2-phenylcyclopropane

Base Information

• Chemical Name: trans-1-Bromo-2-phenylcyclopropane
• CAS No.: 32523-77-6
• Molecular Formula: C9H9Br
• Molecular Weight: 197.074
• European Community (EC) Number: 864-012-5
• Nikkaji Number: J562.584J
• Mol file: 32523-77-6.mol

Synonyms:trans-1-bromo-2-phenylcyclopropane;32523-77-6;[(1S,2R)-2-bromocyclopropyl]benzene;2-[bromocyclopropyl]benzene;SCHEMBL23088903;1beta-Phenyl-2alpha-bromocyclopropane;AT36059;TRANS-(2-BROMOCYCLOPROPYL)BENZENE;rac-[(1R,2S)-2-bromocyclopropyl]benzene;EN300-206403;EN300-255320

Chemical Property of trans-1-Bromo-2-phenylcyclopropane

Chemical Property:

• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 195.98876
• Heavy Atom Count: 10
• Complexity: 116

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C1Br)C2=CC=CC=C2
• Isomeric SMILES: C1[C@H]([C@@H]1Br)C2=CC=CC=C2

Technology Process of trans-1-Bromo-2-phenylcyclopropane

There total 48 articles about trans-1-Bromo-2-phenylcyclopropane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

1,1-dibromo-2-phenylcyclopropane (3234-51-3) → trans-1-bromo-2-phenylcyclopropane (32523-77-6)

Guidance literature:

With n-butyllithium; lithium bromide; In tetrahydrofuran; diethyl ether; hexane; at -100 ℃; for 1h;

DOI:10.1016/j.tet.2004.10.099

Reference yield: 57.0%

trans-2-phenylcyclopropane-1-carboxylic acid (939-90-2) → trans-2-(4-bromophenyl)cyclopropanecarboxylic acid (77255-26-6,2137065-16-6) + trans-1-bromo-2-phenylcyclopropane (32523-77-6) + 1-(p-bromophenyl)-2-bromocyclopropane (77197-86-5)

Guidance literature:

With bromine; mercury(II) oxide; In tetrachloromethane; at 40 ℃; for 0.25h;

Reference yield: 43.0%

(3-bromo-4,4-difluorobut-1-yn-1-yl)triisopropylsilane + C9H9ClZn → cis-1-Bromo-2-phenyl-cyclopropan (32523-76-5,32523-77-6,36617-02-4) + ((1S,2S)-2-bromocyclopropyl)benzene (32523-76-5,32523-77-6,36617-02-4) + ((S)-4,4-difluoro-3-((1R,2S)-2-phenylcyclopropyl)but-1-yn-1-yl)triisopropylsilane

Guidance literature:

(3-bromo-4,4-difluorobut-1-yn-1-yl)triisopropylsilane; With nickel(II) bromide dimethoxyethane; C₂₃H₃₁N₃O₂; In 1,4-dioxane; at 20 ℃; for 0.416667h;

C₉H₉ClZn; In tetrahydrofuran; 1,4-dioxane; at -20 ℃; for 24h; enantioselective reaction; Further stages;

DOI:10.1021/jacs.0c04462

upstream raw materials:

styrene

cis-1-bromo-2-phenylcyclopropane

1,1-dibromo-2-phenylcyclopropane

(3-bromo-3,3-difluoroprop-1-yn-1-yl)triethylsilane

Downstream raw materials:

trans-1-(1,1-Dimethyl-2-propenyl)-2-phenylcyclopropan

trans-1-(3-methyl-2-butenyl)-2-phenylcyclopropane

(1E,5E)-1,6-diphenyl-1,5-hexadiene

2,2'-Diphenyl-1,1'-bicyclopropan