Bromozinc(1+);ethylbenzene

Base Information

• Chemical Name: Bromozinc(1+);ethylbenzene
• CAS No.: 308796-14-7
• Molecular Formula: C₈H₉BrZn
• Molecular Weight: 250.453
• DSSTox Substance ID: DTXSID70410536
• Mol file: 308796-14-7.mol

Synonyms:bromozinc(1+);ethylbenzene;phenethylzinc bromide;DTXSID70410536

Chemical Property of Bromozinc(1+);ethylbenzene

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 0.00000
• Density: g/cm³
• LogP: 3.03980
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Water Solubility.: Reacts with water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 247.91790
• Heavy Atom Count: 10
• Complexity: 53.1

Purity/Quality:

98%,99%, ^*data from raw suppliers

Phenethylzinc bromide solution 0.5 M in THF ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F,Xn
• Statements: 14-19-22-36/38-40-36/37-11
• Safety Statements: 16-26-33-36-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: [CH2-]CC1=CC=CC=C1.[Zn+]Br
• Uses: Phenethylzinc bromide can be used as a reagent: In the transition metal-catalyzed Negishi cross-coupling reaction to prepare aryl or heteroaryl derivatives by reacting with organic halides or triflates via carbon-carbon bond formation. To prepare (4-phenyl-1-butyn-1-yl)benzene by reacting with phenylacetylene via palladium-catalyzed cross-coupling reaction. To synthesize benzyl substituted thienopyrimidine derivatives.

Technology Process of Bromozinc(1+);ethylbenzene

There total 2 articles about Bromozinc(1+);ethylbenzene 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:

1-phenyl-2-bromoethane (103-63-9) + zinc (7440-66-6) → phenethylzinc(II) bromide (308796-14-7)

Guidance literature:

With iodine; In N,N-dimethyl acetamide; at 80 ℃; for 12h; Inert atmosphere;

DOI:10.1002/anie.201503297

Reference yield:

1-phenyl-2-bromoethane (103-63-9) + ethylene dibromide (106-93-4) + zinc (7440-66-6) → phenethylzinc(II) bromide (308796-14-7)

Guidance literature:

ethylene dibromide; zinc; With lithium chloride; In tetrahydrofuran; at 85 ℃; for 0.5h; Inert atmosphere;

With chloro-trimethyl-silane; iodine; In tetrahydrofuran; for 0.333333h; Inert atmosphere; Reflux;

1-phenyl-2-bromoethane; In tetrahydrofuran; at 65 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.0c02515

Reference yield: 76.0%

2-(1-chloroethyl)naphthalene (58464-06-5) + 1-ethyl-2-isocyanobenzene (63212-32-8) + phenethylzinc(II) bromide (308796-14-7) → 2-(naphthalen-2-yl)-5-phenylpentan-3-one

Guidance literature:

2-(1-chloroethyl)naphthalene; 1-ethyl-2-isocyanobenzene; phenethylzinc(II) bromide; With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In N,N-dimethyl-formamide; at 60 ℃; for 2h; Schlenk technique; Inert atmosphere; Sealed tube;

With hydrogenchloride; water; In N,N-dimethyl-formamide; at 25 ℃; for 0.25h; Schlenk technique; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.orglett.0c02515

upstream raw materials:

1-phenyl-2-bromoethane

zinc

ethylene dibromide

Downstream raw materials:

2-(2-chlorophenyl)-7-(2-phenethyl)imidazo[4,5-c]quinolin-4(5H)-one

N-benzyl-3-phenylpropanamide

Refernces

• 1、 Wu, Xianqing,Li, Xiaobin,Huang, Wenyi,Wang, Yun,Xu, Hui,Cai, Liangzhen,Qu, Jingping,Chen, Yifeng. "Direct transformation of aryl 2-pyridyl esters to secondary benzylic alcohols by nickel relay catalysis". supporting information. p. 2453 - 2458. Retrieved 2019/03/29.
• 2、 Liang, Yufan,Fu, Gregory C.. "Nickel-Catalyzed Alkyl-Alkyl Cross-Couplings of Fluorinated Secondary Electrophiles: A General Approach to the Synthesis of Compounds having a Perfluoroalkyl Substituent". supporting information. p. 9047 - 9051. Retrieved 2015/08/03.