4-Bromobenzoyl chloride

Base Information

• Chemical Name: 4-Bromobenzoyl chloride
• CAS No.: 586-75-4
• Deprecated CAS: 1350454-34-0
• Molecular Formula: C7H4BrClO
• Molecular Weight: 219.465
• Hs Code.: 29163900
• European Community (EC) Number: 209-580-1
• NSC Number: 7091
• DSSTox Substance ID: DTXSID2060412
• Nikkaji Number: J94.963I
• Wikidata: Q69999947
• Mol file: 586-75-4.mol

Synonyms:4-Bromobenzoyl chloride;586-75-4;p-Bromobenzoyl chloride;Benzoyl chloride, 4-bromo-;4-Bromobenzoylchloride;Benzoyl chloride, p-bromo-;p-Bromobenzoyl chloride, p-bromo-;C7H4BrClO;4-bromo-benzoyl chloride;MFCD00000683;4-bromobenzoic acid chloride;NSC 7091;EINECS 209-580-1;p-Brombenzoylchlorid;4bromobenzoyl chloride;p-BrC6H4COCl;4-bromo-benzoylchloride;4-bromobenzoyl-chloride;parabromobenzoyl chloride;rho-bromobenzoyl chloride;4-bromo-benzoyl-chloride;4-Bromo benzoyl chloride;SCHEMBL1088;4-Bromobenzoyl chloride, 98%;DTXSID2060412;NSC7091;4-Bromo-1-benzenecarbonyl chloride;NSC-7091;AKOS009031172;PS-10792;B0558;FT-0601037;EN300-21294;A831975;W-105370

Chemical Property of 4-Bromobenzoyl chloride

Chemical Property:

• Appearance/Colour: Pale yellow crystalline
• Vapor Pressure: 0.0267mmHg at 25°C
• Melting Point: 36-39 °C(lit.)
• Refractive Index: 1.584
• Boiling Point: 246.7 °C at 760 mmHg
• Flash Point: 103 °C
• PSA: 17.07000
• Density: 1.662 g/cm³
• LogP: 2.82810
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: Soluble in methanol. Reacts with water forming Hcl.
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 217.91341
• Heavy Atom Count: 10
• Complexity: 130

Purity/Quality:

99% ^*data from raw suppliers

4-Bromobenzoyl Chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-37
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(=O)Cl)Br
• Uses: 4-Bromobenzoyl chloride is used in the synthesis of HIV-1 protease inhibitors. It is also used in the synthesis of oxazoles, cyclohexanone derivatives as analgesic and antimicrobial agents.

Technology Process of 4-Bromobenzoyl chloride

There total 15 articles about 4-Bromobenzoyl chloride 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%

4-Bromobenzoic acid (586-76-5) → 4-chlorobenzoyl chloride (586-75-4)

Guidance literature:

With thionyl chloride; In dichloromethane; for 18h; Heating;

DOI:10.1055/s-2008-1032156

Reference yield: 93.0%

1,4-bromoiodobenzene (589-87-7) + 4-nitro-benzoyl chloride (122-04-3) → p-nitrobenzene iodide (636-98-6) + 4-chlorobenzoyl chloride (586-75-4)

Guidance literature:

With (Xantphos)Pd(4-C₆H₄NO₂)(I); In benzene; at 90 ℃; for 20h; Sealed tube; Inert atmosphere;

DOI:10.1021/jacs.8b06605

Reference yield: 75.9%

bromobenzene (108-86-1,52753-63-6) + oxalyl dichloride (79-37-8) → 4-chlorobenzoyl chloride (586-75-4)

Guidance literature:

oxalyl dichloride; With aluminum (III) chloride; In dichloromethane; for 0.0833333h;

bromobenzene; In dichloromethane; at 20 - 25 ℃; for 1h;

DOI:10.15227/orgsyn.061.0008

upstream raw materials:

oxalyl dichloride

4-Bromobenzoic acid

4-bromobenzoyl radical

bromobenzene

Downstream raw materials:

(4-bromophenyl)(1-piperidinyl)methanone

6-(4-bromo-benzoylamino)-benzo[1,3]dioxole-5-carboxylic acid methyl ester

1-(4-bromo-benzoyloxy)-3-(2-methyl-piperidino)-propane; hydrochloride

4-(4-bromo-benzoyl)-5-methyl-2-phenyl-1,2-dihydro-pyrazol-3-one

Refernces

• 1、 Chattopadhyay, Buddhadeb,Hassan, Mirja Md Mahamudul,Hoque, Md Emdadul. "Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates". supporting information. p. 5022 - 5037. Retrieved 2021/05/04.
• 2、 Li, Fangshao,Wu, Xiaofang,Guo, Fengzhe,Tang, Zi-Long,Xiao, Jing. "One-step Conversion of Amides and Esters to Acid Chlorides with PCl3". supporting information. p. 4314 - 4317. Retrieved 2021/07/16.