766-80-3

Basic information

• Product Name: 3-Chlorobenzyl bromide
• Synonyms: 3-Chlorobenzyl bromide, 98+%;Benzene, 1-(bromomethyl)-3-chloro-;à-bromo-3-chlorotoluene;3-Chlorobenzyl bromide 97%;A-BROMO-3-CHLOROTOLUENE;m-Chloro-α-bromotoluene;α-Bromo-m-chlorotoluene;3-Chlorobenzyl bromi
• CAS NO: 766-80-3
• Molecular Formula: C₇H₆BrCl
• Molecular Weight: 205.48
• EINECS: 212-171-0
• Product Categories: Benzyl
• Mol File: 766-80-3.mol
• Article Data: 27

Chemical Properties

• Melting Point: 15 °C
• Boiling Point: 109-110 °C12 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Colorless liquid
• Density: 1.565 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0675mmHg at 25°C
• Refractive Index: n20/D 1.588(lit.)
• Storage Temp.: Store at R.T.
• Water Solubility: DECOMPOSES
• Sensitive: Lachrymatory
• BRN: 636504
• CAS DataBase Reference: 3-Chlorobenzyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chlorobenzyl bromide(766-80-3)
• EPA Substance Registry System: 3-Chlorobenzyl bromide(766-80-3)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• F: 19
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 766-80-3(Hazardous Substances Data)

Usage

Description

3-Chlorobenzyl bromide is an organic compound with the chemical formula C7H6BrCl. It is a colorless to pale yellow liquid with a characteristic odor. It is a halogenated aromatic compound, which makes it a versatile building block in organic synthesis.

Uses

Used in Organic Synthesis:
3-Chlorobenzyl bromide is used as a starting reagent for the synthesis of various organic compounds. Its reactivity and functional groups make it a valuable intermediate in the preparation of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in the Synthesis of Benzyl Thioethers:
3-Chlorobenzyl bromide is used as a key intermediate in the synthesis of symmetrical and unsymmetrical benzyl thioethers. These thioethers have potential applications in the development of new drugs, agrochemicals, and materials.
Used in the Synthesis of 1-(3-chlorobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole Dihydrochloride:
3-Chlorobenzyl bromide is used as a starting reagent in the synthesis of 1-(3-chlorobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole dihydrochloride, a compound with potential biological activities. This synthesis demonstrates the versatility of 3-chlorobenzyl bromide in the preparation of complex organic molecules.

InChI:InChI=1/C7H6BrCl/c8-5-6-2-1-3-7(9)4-6/h1-4H,5H2

Upstream product

• 506-68-3 bromocyane 
• 876476-09-4 (3-bromo-benzyl)-(3-chloro-benzyl)-methyl-amine 
• 854392-02-2 (3-chloro-benzyl)-methyl-(4-nitro-benzyl)-amine 
• 108-41-8 1-chloro-3-methylbenzene 
• 873-63-2 m-chlorobenzyl alcohol 
• 70450-41-8 1-chloro-3-(iodomethyl)benzene 
• 620-20-2 1-Chloro-3-chloromethyl-benzene 
• 7726-95-6 bromine 
• 191097-25-3 2-(2-tert-butyldimethylsiloxyethyl)-3,4-dihydro-7-methyl-3-oxo-2H-1,4-benzoxazine 
• 587-04-2 m-Chlorobenzaldehyde 
• 535-80-8 3-chlorobenzoate 

Downstream Products

• 59347-49-8 1-(3-chloro-benzyl)-pyridinium; bromide 
• 15184-97-1 1-(3-chlorophenyl)-N,N-dimethylmethanamine 
• 860585-13-3 1-(3-chloro-benzyloxy)-2-methoxy-benzene 
• 872278-13-2 (+/-)-3-(3-chloro-phenyl)-2-benzyl-propionic acid 
• 89802-75-5 3-chlorobenzyl imidothiocarbamate 
• 51229-57-3 (3-chloro-benzyl)-phenyl sulfone 
• 1529-41-5 3-chloro-benzeneacetonitrile 
• 39191-07-6 3-chloro-N-methylbenzylamine 
• 25251-56-3 (3-chloro-benzyl)-trimethyl-ammonium; bromide 
• 70450-41-8 1-chloro-3-(iodomethyl)benzene 
• 67219-34-5 2-[(3-chloro-phenyl)-methanesulfonyl]-benzothiazole 
• 1754-67-2 1-(3-chlorophenyl)-2-methylpropan-2-ol 
• 67219-36-7 2-(3-chloro-benzylsulfanyl)-thiazolo[5,4-b]pyridine 
• 55614-65-8 6-Chloro-1-(4-chloro-phenyl)-3-methyl-naphthalene 

Relevant articles and documents

[1,3]-Claisen rearrangement via removable functional group mediated radical stabilization

A thermal O-to-C [1,3]-rearrangement of α-hydroxy acid derived enol ethers was achieved under mild conditions. The 2-aminothiophenol protection of carboxylic acids facilitates formation of the [1,3] precursor and its thermal rearrangement via stabilization of a radical intermediate. Experimental and theoretical evidence for dissociative radical pair formation, its captodative stability via aminothiophenol, and a unique solvent effect are presented. The aminothiophenol was deprotected from rearrangement products as well as after derivatization to useful synthons.

New 3-(1H-benzo[d]imidazol-2-yl)quinolin-2(1H)-one-based triazole derivatives: Design, synthesis, and biological evaluation as antiproliferative and apoptosis-inducing agents

A series of 1,2,3-triazole derivatives based on the quinoline–benzimidazole hybrid scaffold was designed, synthesized, and screened against a panel of NCI-60 humanoid cancer cell lines for in vitro cytotoxicity evaluation, which revealed that compound Q6 was the most potent cytotoxic agent with excellent GI50, TGI, and LC50 values on multiple cancer cell lines. Q6 was tested further on the BT-474 breast cancer line to evaluate the mechanism of action. Preliminary screening studies based on the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide assay revealed that compound Q6 had an excellent antiproliferative effect against human breast cancer cells, BT-474, with IC50 values of 0.59 ± 0.01 μM. The detailed study based on the acridine orange/ethidium bromide staining (AO/EB) and the 4′,6-diamidino-2-phenylindole (DAPI) assay suggested that the antiproliferative activity shown was due to the induction of apoptosis on exposure to Q6. Further, DCFDA staining showed the generation of reactive oxygen species, altering the mitochondrial potential and leading to the initiation of apoptosis. This was further supported by JC-1 staining, indicating that this scaffold can contribute to the development of more potent derivatives.

Synthesis of Novel Triazole-incorporated Isatin Derivatives as Antifungal, Antitubercular, and Antioxidant Agents and Molecular Docking Study

A library of 1,2,3-triazoles efficiently prepared via click chemistry and evaluated for their antifungal, antitubercular, antioxidant, cytotoxicity, molecular docking and ADME prediction.