(2-Bromoethyl)benzene

Base Information

• Chemical Name: (2-Bromoethyl)benzene
• CAS No.: 103-63-9
• Molecular Formula: C8H9Br
• Molecular Weight: 185.063
• Hs Code.: 29036990
• European Community (EC) Number: 203-130-8
• NSC Number: 33926
• UNII: 96O442668X
• DSSTox Substance ID: DTXSID1033876
• Nikkaji Number: J44.198H
• Wikipedia: 2-Phenylethyl_bromide
• Wikidata: Q4596916
• ChEMBL ID: CHEMBL1340745
• Mol file: 103-63-9.mol

Synonyms:(2-bromoethyl)benzene

Chemical Property of (2-Bromoethyl)benzene

Chemical Property:

• Appearance/Colour: Colourless to yellow liquid
• Vapor Pressure: 0.167mmHg at 25°C
• Melting Point: -56 °C
• Refractive Index: n20/D 1.556(lit.)
• Boiling Point: 220.5 °C at 760 mmHg
• Flash Point: 89.4 °C
• PSA: 0.00000
• Density: 1.366 g/cm³
• LogP: 2.62400
• Storage Temp.: 2-8°C
• Solubility.: 0.039g/l
• Water Solubility.: INSOLUBLE
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 183.98876
• Heavy Atom Count: 9
• Complexity: 65

Purity/Quality:

99% min ^*data from raw suppliers

(2-Bromoethyl)benzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36-36/37/38
• Safety Statements: 26-37/39-39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Monoaromatics
• Canonical SMILES: C1=CC=C(C=C1)CCBr
• Description: Phenethylbromide is an analytical reference material that is structurally categorized as an organobromide. It is used in the synthesis of a variety of compounds, including fentanyl. Phenethylbromide is combined with 4-piperidinone to produce N-phenethyl-4-piperidone, which, as a precursor in the synthesis of fentanyl (Item Nos. ISO60197 | 14719), is scheduled as a List I chemical in the United States. Phenethylbromide may be found as in impurity in samples of fentanyl produced using this pathway.
• Uses: (2-Bromoethyl)benzene is used in the preparation of phenelzine by reacting with hydrazine. It is also used as a starting material to prepare various beta-phenethyl derivatives, active pharmaceutical ingredients, and fragrances. It finds application as a flame retardant.

Technology Process of (2-Bromoethyl)benzene

There total 70 articles about (2-Bromoethyl)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: 72.0%

2-phenylethyl mesylate (20020-27-3) → styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + 1-phenyl-2-bromoethane (103-63-9)

Guidance literature:

With lithium bromide; In N,N-dimethyl-formamide; at 120 ℃; Inert atmosphere;

DOI:10.1002/adsc.201100736

Reference yield: 72.0%

2-phenylethanol (60-12-8) + triphenylphosphine (603-35-0) → 1-phenyl-2-bromoethane (103-63-9) + Triphenylphosphine oxide (791-28-6)

Guidance literature:

With carbon tetrabromide; In 1,2-dichloro-ethane;

DOI:10.1016/j.tet.2010.03.039

Reference yield: 64.0%

2-phenylethanol (60-12-8) → dibenzyl ether (103-50-4) + 1-phenyl-2-bromoethane (103-63-9)

Guidance literature:

2-phenylethanol; With N,N-dimethylthiourea; In dichloromethane; at 20 ℃;

With N-Bromosuccinimide; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/acs.joc.0c01431

upstream raw materials:

styrene

bromocyane

N,N-diethylphenethylamine

2-phenylethanol

Downstream raw materials:

1-(2-phenylethyl)-2,5-dimethyl-4-piperidone

5-ethyl-2-methyl-1-phenethyl-pyridinium; bromide

3-methyl-2-phenethyl-isoquinolinium; bromide

6-chloro-1-phenethyl-quinolinium; bromide

Refernces

• 1、 Fan, Ji-Cai,Shang, Zhi-Cai,Liang, Jun,Liu, Xiu-Hong,Liu, Yang. "The oxidation of alcohols to aldehydes and ketones with N-bromosuccinimide in polyethylene glycol: An experimental and theoretical study". . p. 945 - 953. Retrieved 2008.
• 2、 Pluempanupat, Wanchai,Chantarasriwong, Oraphin,Taboonpong, Piyada,Jang, Doo Ok,Chavasiri, Warinthorn. "Reactivity of chlorinating agents/PPh3 for the chlorination of alcohols and carboxylic acids: a comparative study". . p. 223 - 226. Retrieved 2007.
• 3、 Hojo,K.,Mukaiyama,T.. "-". . p. 619 - 622. Retrieved 1976.
• 4、 Dou, Xiaozheng,Nath, Dinesh,Shin, Henry,Nurmemmedov, Elmar,Bourne, Philip C.,Ma, Jian-Xing,Duerfeldt, Adam S.. "Evolution of a 4-Benzyloxy-benzylamino Chemotype to Provide Efficacious, Potent, and Isoform Selective PPARα Agonists as Leads for Retinal Disorders". . p. 2854 - 2876. Retrieved 2020.
• 5、 Barton,Jaszberenyi,Tang. "Photolytic generation of carbon radicals from Barton esters: Recent developments". . p. 3381 - 3384. Retrieved 1993.
• 6、 Skell, P. S.,Baxter, H. N.,Tanko, J. M.. "REACTIONS OF BrCl WITH ALKYL RADICALS.". . p. 5181 - 5184. Retrieved 1986.
• 7、 Neumann, Ronny,Vega, Fernando de la,Bar-On, Adva. "α-Bromo Carbonyl Compounds as Promoters for the Synthesis of (2-Bromoethyl)benzene by the Anti-Markovnikov Addition of Hydrogen Bromide to Styrene". . p. 1315 - 1318. Retrieved 1995.
• 8、 Hayami et al.. "-". . p. 1628,1629. Retrieved 1971.
• 9、 Mohite, Amar R.,Phatake, Ravindra S.,Dubey, Pooja,Agbaria, Mohamed,Shames, Alexander I.,Lemcoff, N. Gabriel,Reany, Ofer. "Thiourea-Mediated Halogenation of Alcohols". . p. 12901 - 12911. Retrieved 2020/11/26.
• 10、 Buonomo, Joseph A.,Cole, Malcolm S.,Eiden, Carter G.,Aldrich, Courtney C.. "1,3-Diphenyldisiloxane Enables Additive-Free Redox Recycling Reactions and Catalysis with Triphenylphosphine". . p. 3583 - 3594. Retrieved 2020/09/15.