(E)-(3-chloroprop-1-enyl)-4-bromobenzene

Base Information

• Chemical Name: (E)-(3-chloroprop-1-enyl)-4-bromobenzene
• CAS No.: 104293-07-4
• Molecular Formula: C9H8BrCl
• Molecular Weight: 231.52
• Hs Code.: 2902900000
• European Community (EC) Number: 692-901-6
• DSSTox Substance ID: DTXSID00546650
• Nikkaji Number: J1.598.458I
• Mol file: 104293-07-4.mol

Synonyms:104293-07-4;(E)-(3-chloroprop-1-enyl)-4-bromobenzene;1-bromo-4-[(1E)-3-chloroprop-1-en-1-yl]benzene;1-bromo-4-[(E)-3-chloroprop-1-enyl]benzene;(E)-1-bromo-4-(3-chloroprop-1-en-1-yl)benzene;Benzene, 1-bromo-4-[(1E)-3-chloro-1-propenyl]-;SCHEMBL5230238;DTXSID00546650;MWYBPNFKLPDFBX-OWOJBTEDSA-N;MFCD01861828;AKOS015991233;AG-0700;1-bromo-4-((E)-3-chloropropenyl)benzene;CS-0440159;J-501823

Chemical Property of (E)-(3-chloroprop-1-enyl)-4-bromobenzene

Chemical Property:

• PSA: 0.00000
• LogP: 3.70110
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 229.94979
• Heavy Atom Count: 11
• Complexity: 126

Purity/Quality:

98%min ^*data from raw suppliers

(E)-(3-Chloroprop-1-enyl)-4-bromobenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=CCCl)Br
• Isomeric SMILES: C1=CC(=CC=C1/C=C/CCl)Br

Technology Process of (E)-(3-chloroprop-1-enyl)-4-bromobenzene

There total 7 articles about (E)-(3-chloroprop-1-enyl)-4-bromobenzene 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: 100.0%

(2E)-3-(4-bromophenyl)prop-2-en-1-ol (105515-33-1) → (E)-1-bromo-4-(3-chloroprop-1-en-1-yl)benzene (104293-07-4)

Guidance literature:

With thionyl chloride; In dichloromethane;

DOI:10.1016/j.bmc.2019.01.006

Reference yield:

1,4-bromoiodobenzene (589-87-7) → (E)-1-bromo-4-(3-chloroprop-1-en-1-yl)benzene (104293-07-4)

Guidance literature:

Multi-step reaction with 3 steps

1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / 24 h / 20 °C / Inert atmosphere

2: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 - 20 °C

3: triphenylphosphine; N-chloro-succinimide / dichloromethane / 1 h / 23 °C

With bis-triphenylphosphine-palladium(II) chloride; N-chloro-succinimide; copper(l) iodide; lithium aluminium tetrahydride; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jacs.0c00147

Reference yield:

4-bromo-benzaldehyde (1122-91-4) → (E)-1-bromo-4-(3-chloroprop-1-en-1-yl)benzene (104293-07-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium chloride / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: diisobutylaluminium hydride / cyclohexane; dichloromethane / 4 h / -78 - 20 °C / Inert atmosphere

3.1: sulfuryl dichloride / diethyl ether / 20 °C / Cooling with ice; Inert atmosphere

With sulfuryl dichloride; diisobutylaluminium hydride; lithium chloride; In tetrahydrofuran; diethyl ether; dichloromethane; cyclohexane; 1.1: |Horner-Wadsworth-Emmons Olefination / 1.2: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1002/chem.201502843

upstream raw materials:

(2E)-3-(4-bromophenyl)prop-2-en-1-ol

4-bromo-benzaldehyde

ethyl (E)-3-(4-bromophenyl)-2-propenoate

trans-4-bromocinnamic acid

Downstream raw materials:

1-[(E)-3-(4-bromo-phenyl)-allyl]-4-methyl-piperidin-4-ol

(E)-(3-(4-bromophenyl)allyl)(trifluoromethyl)sulfane

1-(4-bromophenyl)-3-(trimethylsilyl)propene

Refernces

• 1、 Dykstra, Ryan,Gutierrez, Osvaldo,Martin, Robert T.,Tambar, Uttam K.,Troian-Gautier, Ludovic,Xu, Bin. "Photocatalyzed Diastereoselective Isomerization of Cinnamyl Chlorides to Cyclopropanes". supporting information. p. 6206 - 6215. Retrieved 2020/04/27.
• 2、 Karnakanti, Shuklachary,Zang, Zhong-Lin,Zhao, Sheng,Shao, Pan-Lin,Hu, Ping,He, Yun. "Palladium-catalyzed oxidative arylacetoxylation of alkenes: Synthesis of indole and indoline derivatives". supporting information. p. 11205 - 11208. Retrieved 2017/10/17.