4'-Bromo-4-chlorobutyrophenone

Base Information

• Chemical Name: 4'-Bromo-4-chlorobutyrophenone
• CAS No.: 4559-96-0
• Molecular Formula: C10H10 Br Cl O
• Molecular Weight: 261.546
• Hs Code.: 2914700090
• European Community (EC) Number: 224-930-3
• UNII: 6D2RTW7CSC
• DSSTox Substance ID: DTXSID00196558
• Nikkaji Number: J297.816D
• Wikidata: Q83069590
• Mol file: 4559-96-0.mol

Synonyms:1-(4-bromophenyl)-4-chlorobutan-1-one;4559-96-0;4'-Bromo-4-chlorobutyrophenone;1-(4-Bromophenyl)-4-chloro-1-butanone;C10H10BrClO;6D2RTW7CSC;1-Butanone, 1-(4-bromophenyl)-4-chloro-;EINECS 224-930-3;UNII-6D2RTW7CSC;p-Bromo-g-chlorobutyrophenone;4-Chloro-p-bromobutyrophenone;C10-H10-Br-Cl-O;SCHEMBL1502426;4-Chloro-4'-bromobutyrophenone;4''-Bromo-4-chlorobutyrophenone;4/'-Bromo-4-chlorobutyrophenone;DTXSID00196558;4'-Bromo-gamma-chlorobutyrophenone;p-Bromo-.gamma.-chlorobutyrophenone;4-Bromophenyl 3-chloropropyl ketone;Butyrophenone, 4'-bromo-4-chloro-;MFCD00001006;AKOS000120283;4'-Bromo-4-chlorobutyrophenone, 98%;AS-49956;1-(4-bromo-phenyl)-4-chloro-butan-1-one;1-(4-Bromophenyl)-4-chloro-1-butanone #;CS-0204753;EN300-20323;O10286;A872355;4?Bromo-4-chlorobutyrophenone

Chemical Property of 4'-Bromo-4-chlorobutyrophenone

Chemical Property:

• Melting Point: 35.5-38 °C(lit.)
• Refractive Index: 1.5963 (estimate)
• Boiling Point: 352.8°Cat760mmHg
• Flash Point: 167.2°C
• PSA: 17.07000
• Density: 1.44g/cm³
• LogP: 3.65080
• Water Solubility.: Insoluble in water.
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 259.96036
• Heavy Atom Count: 13
• Complexity: 164

Purity/Quality:

99% ^*data from raw suppliers

1-(4-Bromophenyl)-4-chlorobutan-1-one ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(=O)CCCCl)Br
• Uses: 4'-Bromo-4-chlorobutyrophenone is used as a pharmaceutical & syntheses material intermediates.

Technology Process of 4'-Bromo-4-chlorobutyrophenone

There total 4 articles about 4'-Bromo-4-chlorobutyrophenone 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: 92.0%

1-(4-bromophenyl)cyclobutan-1-ol (19936-14-2) → 1-(4-bromophenyl)-4-chlorobutan-1-one (4559-96-0)

Guidance literature:

With 1,10-Phenanthroline; tert-butylhypochlorite; silver trifluoromethanesulfonate; In acetonitrile; at 20 ℃; for 6h; regioselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.5b03649

Reference yield: 90.0%

bromobenzene (108-86-1,52753-63-6) + 4-Chlorobutanoyl chloride (4635-59-0) → 1-(4-bromophenyl)-4-chlorobutan-1-one (4559-96-0)

Guidance literature:

4-Chlorobutanoyl chloride; With aluminum (III) chloride; In dichloromethane; for 2h;

bromobenzene; In dichloromethane; at 20 ℃; Solvent;

Reference yield:

1,4-bromoiodobenzene (589-87-7) → 1-(4-bromophenyl)-4-chlorobutan-1-one (4559-96-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere; Sealed tube

1.2: -78 - 20 °C / Inert atmosphere; Sealed tube

2.1: acetic acid; manganese(II) triflate; magnesium chloride; lithium perchlorate / acetonitrile / 3.5 h / 25 °C / Inert atmosphere; Electrochemical reaction; Sealed tube

With n-butyllithium; manganese(II) triflate; lithium perchlorate; acetic acid; magnesium chloride; In tetrahydrofuran; hexane; acetonitrile;

DOI:10.1021/acs.orglett.9b03652

upstream raw materials:

bromobenzene

4-Chlorobutanoyl chloride

1-(4-bromophenyl)cyclobutan-1-ol

1,4-bromoiodobenzene

Downstream raw materials:

4'-bromo-4-iodobutyrophenone

5-(4-bromophenyl)-5-oxopentanenitrile

thioacetic acid S-[4-(4-bromo-phenyl)-4-oxo-butyl] ester

5-(4-bromophenyl)-3,4-dihydro-2H-pyrrole

Refernces

• 1、 Allen, Benjamin D. W.,Hareram, Mishra Deepak,Seastram, Alex C.,McBride, Tom,Wirth, Thomas,Browne, Duncan L.,Morrill, Louis C.. "Manganese-Catalyzed Electrochemical Deconstructive Chlorination of Cycloalkanols via Alkoxy Radicals". supporting information. p. 9241 - 9246. Retrieved 2019/11/19.
• 2、 Huang, Feng-Qing,Xie, Jian,Sun, Jian-Guo,Wang, Yue-Wei,Dong, Xin,Qi, Lian-Wen,Zhang, Bo. "Regioselective Synthesis of Carbonyl-Containing Alkyl Chlorides via Silver-Catalyzed Ring-Opening Chlorination of Cycloalkanols". supporting information. p. 684 - 687. Retrieved 2016/03/01.