1711-09-7

Basic information

• Product Name: 3-Bromobenzoyl chloride
• Synonyms: 3-bromo-benzoylchlorid;Benzoyl chloride, 3-bromo-;Benzoyl chloride, m-bromo-;M-BROMOBENZOYL CHLORIDE;3-BROMOBENZOYL CHLORIDE;Methoxyisopropyl Acetoacetate;m-Bromobenzoyl Chloride 3-Bromobenzoyl Chloride;OZNB , also named:4-(1,3-Oxazole-4-yl)nitro-benzene
• CAS NO: 1711-09-7
• Molecular Formula: C₇H₄BrClO
• Molecular Weight: 219.46
• EINECS: 216-978-9
• Product Categories: Acid Halides;Carbonyl Compounds;Organic Building Blocks;Pyridines ,Halogenated Heterocycles
• Mol File: 1711-09-7.mol
• Article Data: 115

Chemical Properties

• Boiling Point: 74-75 °C0.5 mm Hg(lit.)
• Flash Point: 225°F
• Appearance: colorless liquid
• Density: 1.662 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0114mmHg at 25°C
• Refractive Index: n20/D 1.595(lit.)
• Sensitive: Moisture Sensitive
• BRN: 1635505
• CAS DataBase Reference: 3-Bromobenzoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromobenzoyl chloride(1711-09-7)
• EPA Substance Registry System: 3-Bromobenzoyl chloride(1711-09-7)

Safety Data

• Hazard Codes: C
• Statements: 34-37
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• F: 19-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 1711-09-7(Hazardous Substances Data)

Usage

Chemical Properties

Clear light yellow liquid

Uses

3-Bromobenzoyl chloride was used in the synthesis of 2-(3-bromophenyl)-5-phenyl-1,3,4-oxadiazole and (4-benzhydryl-1,4-diazepan-1-yl)(3-bromophenyl)methanone.

InChI:InChI=1/C7H4BrClO/c8-6-3-1-2-5(4-6)7(9)10/h1-4H

Upstream product

• 591-18-4 1-Bromo-3-iodobenzene 
• 79-37-8 oxalyl dichloride 
• 585-76-2 m-bromobenzoic acid 
• 201230-82-2 carbon monoxide 
• 98-88-4 benzoyl chloride 

Downstream Products

• 349405-35-2 3-bromo-N-(4-nitrophenyl)benzamide 
• 83868-06-8 3-bromo-benzoic acid-(N'-phenyl-hydrazide) 
• 872279-52-2 4'-ethoxy-3-bromo-benzophenone 
• 102092-51-3 3-bromo-4′-methylbenzophenone 
• 1016-77-9 3-bromobenzophenone 
• 177171-17-4 3-bromo-N-tert-butyl-N-methylbenzamide 
• 6239-03-8 2-(m-Brombenzamido)phenoxyessigsaeure 
• 211388-38-4 3-bromo-N-(2-hydroxy-1,1-dimethylethyl)benzamide 
• 98979-16-9 1,2-Bis-<3-brom-benzoyl>cyclopentadien 
• 24167-51-9 3-bromo-N,N-dimethylbenzamide 
• 35309-74-1 3-bromo-N,N-dibutylbenzamide 
• 138407-37-1 N,N-dibenzyl-3-bromobenzamide 

Relevant articles and documents

A sustainable and simple catalytic system for direct alkynylation of C(sp2)-H bonds with low nickel loadings

A sustainable and simple catalytic system for the atom-economical alkynylation of benzamides with low nickel loadings is described. No organic or metallic oxidants and expensive ligands are required. A broad range of benzamides and bromoalkynes bearing various synthetically useful functional groups are compatible with this reaction. The versatility of this operationally simple protocol has been further demonstrated by the controllable mono- and di-alkynylation. Importantly, substrate/catalyst ratios of up to 200, and a turnover number of 196 were achieved, highlighting the potential of this protocol for synthetic applications.

Copper-catalyzed ortho-halogenation of arenes and heteroarenes directed by a removable auxiliary

Copper-catalyzed ortho-halogenation of C(sp2)-H bonds directed by a PIP directing group with NXS (X = Cl, Br, I) has been developed. The reaction is scalable and tolerates a broad range of functional groups and heteroarenes, providing an efficient access to halogenated arenes and heteroarenes.

Synthesis, Characterization, and Catalytic Studies of Unsymmetrical Chiral NCC Pincer Pd(II) and Ni(II) Complexes Bearing (Imidazolinyl)aryl NHC Ligands

A series of palladium(II) and nickel(II) complexes based on unsymmetrical chiral (imidazolinyl)aryl NHC ligands are reported. The new ligand presursors 3a-g were prepared from commercially available 3-bromobenzoic acid, in which the carboxyl and bromo fun

Palladium-Catalyzed 5-exo-dig Cyclization Cascade, Sequential Amination/Etherification for Stereoselective Construction of 3-Methyleneindolinones

An cascade intramolecular 5-exo-dig cyclization of N-(2-iodophenyl)propiolamides and sequential amination/etherification (with N-hydroxybenzamides, phenyl hydroxycarbamate) protocol for the synthesis of amino- and phenoxy-substituted 3-methyleneindolinones using unexpensive Pd(PPh3)4 as catalyst has been developed. The protocol enables the assembly of structurally important oxindole cores featuring moderate functional group tolerance (particularly the halo group), affording a broad spectrum of products with diverse substituents in good to excellent yields. (Figure presented.).

Structure-Activity Relationship of Phenylpyrazolones against Trypanosoma cruzi

Chagas disease is a neglected parasitic disease caused by the parasitic protozoan Trypanosoma cruzi and currently affects around 8 million people. Previously, 2-isopropyl-5-(4-methoxy-3-(pyridin-3-yl)phenyl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one (NPD-0227) was discovered to be a sub-micromolar inhibitor (pIC50=6.4) of T. cruzi. So far, SAR investigations of this scaffold have focused on the alkoxy substituent, the pyrazolone nitrogen substituent and the aromatic substituent of the core phenylpyrazolone. In this study, modifications of the phenyldihydropyrazolone scaffold are described. Variations were introduced by installing different substituents on the phenyl core, modifying the geminal dimethyl and installing various bio-isosteres of the dihydropyrazolone group. The anti T. cruzi activity of NPD-0227 could not be surpassed as the most potent compounds show pIC50 values of around 6.3. However, valuable additional SAR data for this interesting scaffold was obtained, and the data suggest that a scaffold hop is feasible as the pyrazolone moiety can be replaced by a oxazole or oxadiazole with minimal loss of activity.