[(1E)-1-Bromo-1-propen-1-yl]benzene

Base Information

• Chemical Name: [(1E)-1-Bromo-1-propen-1-yl]benzene
• CAS No.: 31076-47-8
• Molecular Formula: C9H9Br
• Molecular Weight: 197.074
• DSSTox Substance ID: DTXSID901295356
• Mol file: 31076-47-8.mol

Synonyms:[(1E)-1-Bromo-1-propen-1-yl]benzene;SCHEMBL16933770;DTXSID901295356;31076-47-8

Chemical Property of [(1E)-1-Bromo-1-propen-1-yl]benzene

Chemical Property:

• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 195.98876
• Heavy Atom Count: 10
• Complexity: 121

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC=C(C1=CC=CC=C1)Br
• Isomeric SMILES: C/C=C(\C1=CC=CC=C1)/Br

Technology Process of [(1E)-1-Bromo-1-propen-1-yl]benzene

There total 14 articles about [(1E)-1-Bromo-1-propen-1-yl]benzene 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: 69.0%

1-Phenylprop-1-yne (673-32-5) → [(1E)-1-bromoprop-1-en-1-yl]benzene (31076-47-8)

Guidance literature:

With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); 1,2-dibromo-1,1,2,2-tetrachloroethane; diphenylsilane; 2-tert-butylphenol potassium salt; In toluene; at 45 ℃; for 1h; stereoselective reaction; Glovebox; Inert atmosphere; Schlenk technique;

DOI:10.1021/ja503944n

Reference yield:

1-Phenylprop-1-yne (673-32-5) → (E)-(2-bromoprop-1-en-1-yl)benzene (54624-37-2) + [(1E)-1-bromoprop-1-en-1-yl]benzene (31076-47-8)

Guidance literature:

With ammonia borane; 1,2-dibromo-1,1,2,2-tetrachloroethane; C₂₈H₃₈ClN₂; sodium hydroxide; In tetrahydrofuran; ethanol; at 0 ℃; for 3h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.8b02055

Reference yield:

1-Phenylprop-1-yne (673-32-5) → [(1E)-1-bromoprop-1-en-1-yl]benzene (31076-47-8) + cis-1-bromo-2-methyl-1-phenylethene (31026-78-5)

Guidance literature:

With aluminum oxide; phosphorus tribromide; In dichloromethane; for 3h;

DOI:10.1021/jo00090a031

upstream raw materials:

(1,2-dibromopropyl)benzene

1-Phenylprop-1-yne

erythro-1-phenyl-1,2-dibromopropylphosphonic acid

Z-1-phenyl-1-propenylphosphonic acid

Downstream raw materials:

4-methyl-1-(cis-2-methyl-1-phenylethenyl)-4-phenyl-1-cyclohexene

1-hydroxy-4-methyl-1-(cis-2-methyl-1-phenylethenyl)-4-phenylcyclohexane

trimethyl[(Z)-(1-phenyl-1-propenyl)oxy]silane

(E)-1-phenyl-1-(trimethylsiloxy)propene

Refernces

• 1、 Das, Manas,Kaicharla, Trinadh,Teichert, Johannes F.. "Stereoselective Alkyne Hydrohalogenation by Trapping of Transfer Hydrogenation Intermediates". supporting information. p. 4926 - 4929. Retrieved 2018/08/24.
• 2、 Shimizu, Makoto,Okura, Kanako,Arai, Takuya,Hachiya, Iwao. "Titanium tetraiodide-promoted tandem prins reaction of alkynes with acetals: Synthesis of (Z,Z)-1,5-Diiodo-1,3,5-triarylpenta-1,4-dienes". scheme or table. p. 1052 - 1054. Retrieved 2011/01/10.