Welcome to LookChem.com Sign In|Join Free

CAS

  • or

586-75-4

Post Buying Request

586-75-4 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

586-75-4 Usage

Description

4-Bromobenzoyl chloride is an organic compound with the chemical formula C7H4BrClO2. It is a white to light brown low melting solid, which is widely utilized in the synthesis of various pharmaceutical compounds and organic molecules.

Uses

1. Used in Pharmaceutical Industry:
4-Bromobenzoyl chloride is used as a key intermediate for the synthesis of HIV-1 protease inhibitors. These inhibitors play a crucial role in the treatment of HIV/AIDS by blocking the activity of the HIV-1 protease enzyme, which is essential for the replication of the virus.
2. Used in Organic Synthesis:
4-Bromobenzoyl chloride is used as a building block in the synthesis of oxazoles, which are important heterocyclic compounds with a wide range of applications in the pharmaceutical, agrochemical, and materials science industries.
3. Used in Analgesic and Antimicrobial Agents:
4-Bromobenzoyl chloride is also employed in the synthesis of cyclohexanone derivatives, which have been found to possess analgesic (pain-relieving) and antimicrobial properties. These derivatives can be used in the development of new drugs for the treatment of pain and infections.

Purification Methods

Check IR of a film to see if OH bands are present. If absent then recrystallise from pet ether and dry it in vacuo. If OH bands are weak, then distil it in vacuo and recrystallise if necessary. If OH bands are very strong, then treat with an equal volume of redistilled SOCl2 reflux for 2hours, then evaporate excess of SOCl2 and distil the residual oil or low melting solid. Store it in the dark away from moisture. LACHRYMATORY. [Martin & Partington J Chem Soc 1175 1936, Beilstein 9 IV 1023.]

Check Digit Verification of cas no

The CAS Registry Mumber 586-75-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,8 and 6 respectively; the second part has 2 digits, 7 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 586-75:
(5*5)+(4*8)+(3*6)+(2*7)+(1*5)=94
94 % 10 = 4
So 586-75-4 is a valid CAS Registry Number.
InChI:InChI=1/C7H4BrClO/c8-6-3-1-5(2-4-6)7(9)10/h1-4H

586-75-4 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (L03794)  4-Bromobenzoyl chloride, 98+%   

  • 586-75-4

  • 10g

  • 268.0CNY

  • Detail
  • Alfa Aesar

  • (L03794)  4-Bromobenzoyl chloride, 98+%   

  • 586-75-4

  • 50g

  • 1075.0CNY

  • Detail
  • Aldrich

  • (B59209)  4-Bromobenzoylchloride  98%

  • 586-75-4

  • B59209-10G

  • 267.93CNY

  • Detail
  • Aldrich

  • (B59209)  4-Bromobenzoylchloride  98%

  • 586-75-4

  • B59209-25G

  • 946.53CNY

  • Detail

586-75-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Bromobenzoyl chloride

1.2 Other means of identification

Product number -
Other names 4-bromophenylcarbonyl chloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:586-75-4 SDS

586-75-4Synthetic route

4-Bromobenzoic acid
586-76-5

4-Bromobenzoic acid

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

Conditions
ConditionsYield
With thionyl chloride In dichloromethane for 18h; Heating;100%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 1h; Product distribution / selectivity;100%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h; Reflux;100%
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

4-nitro-benzoyl chloride
122-04-3

4-nitro-benzoyl chloride

A

p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

B

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

Conditions
ConditionsYield
With (Xantphos)Pd(4-C6H4NO2)(I) In benzene at 90℃; for 20h; Sealed tube; Inert atmosphere;A n/a
B 93%
bromobenzene
108-86-1

bromobenzene

oxalyl dichloride
79-37-8

oxalyl dichloride

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

Conditions
ConditionsYield
Stage #1: oxalyl dichloride With aluminum (III) chloride In dichloromethane for 0.0833333h;
Stage #2: bromobenzene In dichloromethane at 20 - 25℃; for 1h;
75.9%
With aluminium trichloride In dichloromethane at 20℃; for 14h; chlorocarbonylation; Friedel-Crafts reaction;
oxalyl dichloride
79-37-8

oxalyl dichloride

4-Bromobenzoic acid
586-76-5

4-Bromobenzoic acid

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

4-bromobenzoyl radical
121776-79-2

4-bromobenzoyl radical

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

Conditions
ConditionsYield
With tetrachloromethane In various solvent(s) at 22.9℃; Rate constant;
oxalyl dichloride
79-37-8

oxalyl dichloride

sodium-4-bromo benzoate

sodium-4-bromo benzoate

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

Conditions
ConditionsYield
With benzene
tetrachloromethane
56-23-5

tetrachloromethane

(4-bromo-benzoyl)-trityl-diazene

(4-bromo-benzoyl)-trityl-diazene

A

1-(4-bromo-phenyl)-2,2,2-triphenyl-ethanone

1-(4-bromo-phenyl)-2,2,2-triphenyl-ethanone

B

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

C

nitrogen

nitrogen

para-bromoacetophenone
99-90-1

para-bromoacetophenone

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium carbonate; [Pd2(2,3-bis[(phenylthio)methyl]quinoxaline(-1H))2Cl2] / water; N,N-dimethyl-formamide / 12 h / 90 °C
1.2: 72 h / 90 °C
2.1: thionyl chloride / Reflux
View Scheme
2-(4,5-Dihydro-1,3-oxazol-2-yl)aniline
3416-93-1

2-(4,5-Dihydro-1,3-oxazol-2-yl)aniline

4-Bromobenzoic acid
586-76-5

4-Bromobenzoic acid

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

Conditions
ConditionsYield
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

Conditions
ConditionsYield
With tert.-butylhydroperoxide; N-chloro-succinimide; tris(2,2'-bipyridyl)ruthenium dichloride In acetonitrile at 20℃; for 24h; Sealed tube; Irradiation;
With N-chloro-succinimide; thio-xanthene-9-one In acetonitrile at 20℃; for 7h; Irradiation;
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

terephthaloyl chloride
100-20-9

terephthaloyl chloride

A

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

B

4-iodobenzoic acid chloride
1711-02-0

4-iodobenzoic acid chloride

Conditions
ConditionsYield
With (Xantphos)Pd(4-C6H4NO2)(I) In benzene at 110℃; for 20h; Sealed tube; Inert atmosphere;A 92 %Spectr.
B n/a
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

aroyl chloride

aroyl chloride

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 100℃; for 12h;
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

butyryl chloride
141-75-3

butyryl chloride

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 100℃; for 16h; Sealed tube; Inert atmosphere;
methoxybenzene
100-66-3

methoxybenzene

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

4-bromo-4'-methoxybenzophenone
54118-75-1

4-bromo-4'-methoxybenzophenone

Conditions
ConditionsYield
aluminum (III) chloride In dichloromethane at 5 - 20℃; for 3h; Friedel Crafts Acylation;100%
With aluminum (III) chloride In dichloromethane at 0℃; for 3h;99%
With aluminum (III) chloride In dichloromethane for 3h;99%
ammonium thiocyanate
1147550-11-5

ammonium thiocyanate

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

4-bromobenzoyl isothiocyanate
66090-34-4

4-bromobenzoyl isothiocyanate

Conditions
ConditionsYield
With PEG-400 In ethyl acetate at 20℃;100%
In acetone
polyethylene glycol-600 (PEG-600) In dichloromethane at 20℃; for 1h; Substitution; solid-liquid phase transfer catalysis;
(5R,7S)-1-(1,6-Dioxa-spiro[4.6]undec-7-yl)-methanol
135158-83-7

(5R,7S)-1-(1,6-Dioxa-spiro[4.6]undec-7-yl)-methanol

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

4-Bromo-benzoic acid (5R,7S)-1-(1,6-dioxa-spiro[4.6]undec-7-yl)methyl ester
135158-84-8

4-Bromo-benzoic acid (5R,7S)-1-(1,6-dioxa-spiro[4.6]undec-7-yl)methyl ester

Conditions
ConditionsYield
With triethylamine; dmap In dichloromethane at 25℃; for 3h;100%
5,6-dihydro-6(S)-(hydroxymethyl)-1,2,3-trimethoxy-9-(methylthio)-8H-cycloheptanaphthalen-8-one
146311-27-5

5,6-dihydro-6(S)-(hydroxymethyl)-1,2,3-trimethoxy-9-(methylthio)-8H-cycloheptanaphthalen-8-one

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

5,6-dihydro-6(S)-<<(4'-bromobenzoyl)oxy>methyl>-1,2,3-trimethoxy-9-(methylthio)-8H-cycloheptanaphthalen-8-one

5,6-dihydro-6(S)-<<(4'-bromobenzoyl)oxy>methyl>-1,2,3-trimethoxy-9-(methylthio)-8H-cycloheptanaphthalen-8-one

Conditions
ConditionsYield
With pyridine Ambient temperature;100%
(-)-(1R,6S,7R)-7-endo-hydroxy-1-methylbicyclo<4.2.0>octan-3-one
152519-75-0

(-)-(1R,6S,7R)-7-endo-hydroxy-1-methylbicyclo<4.2.0>octan-3-one

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

(+)-(1R,6S,7R)-7-endo-(4-bromobenzoyl)oxy-1-methylbicyclo<4.2.0>octan-3-one

(+)-(1R,6S,7R)-7-endo-(4-bromobenzoyl)oxy-1-methylbicyclo<4.2.0>octan-3-one

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane for 2h; Ambient temperature;100%
potassium tert-butylate
865-47-4

potassium tert-butylate

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

tert-butyl-4-bromobenzoate
59247-47-1

tert-butyl-4-bromobenzoate

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;100%
In diethyl ether for 1h; Substitution;95%
In tetrahydrofuran at -78 - 20℃; for 2h;95%
4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

benzylamine
100-46-9

benzylamine

4-bromo-N-benzylbenzamide
80311-89-3

4-bromo-N-benzylbenzamide

Conditions
ConditionsYield
Stage #1: 4-chlorobenzoyl chloride With pyridine; Pyrimidin-2(1H)-one In dichloromethane for 0.05h; microwave irradiation;
Stage #2: benzylamine In dichloromethane for 0.05h; microwave irradiation;
100%
Stage #1: 4-chlorobenzoyl chloride With pyridine; Merrifield's resin-bound 6-methyl-2-thiouracil In dichloromethane at 80℃; for 0.0833333h; microwave irradiation;
Stage #2: benzylamine In dichloromethane at 80℃; for 0.0833333h; microwave irradiation;
100%
With triethylamine In dichloromethane at 20℃;83%
(4R,5R,6S,7R,8S,13S)-5-(2-Benzyloxy-ethyl)-6,7-dihydroxy-1-aza-tricyclo[6.3.2.04,13]tridecan-12-one

(4R,5R,6S,7R,8S,13S)-5-(2-Benzyloxy-ethyl)-6,7-dihydroxy-1-aza-tricyclo[6.3.2.04,13]tridecan-12-one

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

C35H35Br2NO6

C35H35Br2NO6

Conditions
ConditionsYield
With dmap; triethylamine In chloroform at 20℃; for 24h;100%
anthranilic acid
118-92-3

anthranilic acid

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

2-(4-bromobenzamido)benzoic acid
100874-12-2

2-(4-bromobenzamido)benzoic acid

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran100%
With triethylamine In dichloromethane at 20℃;
(1R,2R,3R,3aS,4S,5R,7aR)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-2,6-dimethyl-1-triisopropylsilanyloxy-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carboxylic acid methyl ester

(1R,2R,3R,3aS,4S,5R,7aR)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-2,6-dimethyl-1-triisopropylsilanyloxy-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carboxylic acid methyl ester

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

(1R,2R,3R,3aR,4R,5S,7aS)-3-(4-Bromo-benzoyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,6-dimethyl-1-triisopropylsilanyloxy-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carboxylic acid methyl ester

(1R,2R,3R,3aR,4R,5S,7aS)-3-(4-Bromo-benzoyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,6-dimethyl-1-triisopropylsilanyloxy-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carboxylic acid methyl ester

Conditions
ConditionsYield
With dmap100%
With dmap94%
methyl (cis-3-azido-4-hydroxy-1-cyclohexene)carboxylate

methyl (cis-3-azido-4-hydroxy-1-cyclohexene)carboxylate

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

4-Bromo-benzoic acid (1R,2S)-2-azido-4-methoxycarbonyl-cyclohex-3-enyl ester

4-Bromo-benzoic acid (1R,2S)-2-azido-4-methoxycarbonyl-cyclohex-3-enyl ester

Conditions
ConditionsYield
With dmap In dichloromethane at 20℃; for 1h;100%
(E)-5-((1R,2S)-2-Hydroxy-1-methyl-5-oxo-cyclopentyl)-pent-2-enoic acid methyl ester
915286-32-7

(E)-5-((1R,2S)-2-Hydroxy-1-methyl-5-oxo-cyclopentyl)-pent-2-enoic acid methyl ester

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

4-Bromo-benzoic acid (1S,2R)-2-((E)-4-methoxycarbonyl-but-3-enyl)-2-methyl-3-oxo-cyclopentyl ester

4-Bromo-benzoic acid (1S,2R)-2-((E)-4-methoxycarbonyl-but-3-enyl)-2-methyl-3-oxo-cyclopentyl ester

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane for 96h; Heating;100%
4-[3-aminobenzoyl]-1-methylpiperidine
288156-90-1

4-[3-aminobenzoyl]-1-methylpiperidine

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

4-[3-(4-bromobenzamidyl)benzoyl]-1-methylpiperidine
288157-36-8

4-[3-(4-bromobenzamidyl)benzoyl]-1-methylpiperidine

Conditions
ConditionsYield
100%
(3S)-(+)-1-benzyl-3-(methylamino)pyrrolidine
169749-99-9

(3S)-(+)-1-benzyl-3-(methylamino)pyrrolidine

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

C19H21BrN2O
762285-66-5

C19H21BrN2O

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; for 3h;100%
C24H38N2O7
864936-95-8

C24H38N2O7

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

(2S,3S)-N-t-butoxycarbonyl-2-[3-(4-bromobenzoylamino)benzyloxy]aspartic acid di-t-butyl ester

(2S,3S)-N-t-butoxycarbonyl-2-[3-(4-bromobenzoylamino)benzyloxy]aspartic acid di-t-butyl ester

Conditions
ConditionsYield
With triethylamine In chloroform for 0.5h;100%
4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

1-t-Butoxycarbonylpiperazine
57260-71-6

1-t-Butoxycarbonylpiperazine

4-(4-bromobenzoyl)piperazine-1-carboxylic acid tert-butyl ester
867333-30-0

4-(4-bromobenzoyl)piperazine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;100%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 6h;96%
With triethylamine In dichloromethane at 20℃; for 15h;95%
ammonium thiocyanate

ammonium thiocyanate

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

4-bromobenzoyl isothiocyanate
66090-34-4

4-bromobenzoyl isothiocyanate

Conditions
ConditionsYield
With PEG-400 In ethyl acetate at 20℃;100%
In acetone at 20℃; for 1h; Inert atmosphere;

586-75-4Relevant articles and documents

Orthogonally reactive SAMs as a general platform for bifunctional silica surfaces

Azam, Md. Shafiul,Fenwick, Sean L.,Gibbs-Davis, Julianne M.

, p. 741 - 750 (2011)

We report the synthesis and self-assembly of azide and amine trimethoxysilanes that result in mixed monolayers on silica. The amine and azide functional groups can be independently reacted with acid chlorides and terminal alkynes, respectively. Consequent

Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates

Chattopadhyay, Buddhadeb,Hassan, Mirja Md Mahamudul,Hoque, Md Emdadul

supporting information, p. 5022 - 5037 (2021/05/04)

Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.

Palladium-Catalyzed Chlorocarbonylation of Aryl (Pseudo)Halides Through In Situ Generation of Carbon Monoxide

Bismuto, Alessandro,Boehm, Philip,Morandi, Bill,Roediger, Sven

supporting information, p. 17887 - 17896 (2020/08/19)

An efficient palladium-catalyzed chlorocarbonylation of aryl (pseudo)halides that gives access to a wide range of carboxylic acid derivatives has been developed. The use of butyryl chloride as a combined CO and Cl source eludes the need for toxic, gaseous carbon monoxide, thus facilitating the synthesis of high-value products from readily available aryl (pseudo)halides. The combination of palladium(0), Xantphos, and an amine base is essential to promote this broadly applicable catalytic reaction. Overall, this reaction provides access to a great variety of carbonyl-containing products through in situ transformation of the generated aroyl chloride. Combined experimental and computational studies support a reaction mechanism involving in situ generation of CO.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 586-75-4