823-78-9

Basic information

• Product Name: 3-Bromobenzyl bromide
• Synonyms: ALPHA,3-DIBROMOTOLUENE;ALPHA,M-DIBROMOTOLUENE;3-BROMOBENZYL BROMIDE;3-Brombenzyl bromide;3-Bromo Benzyl Bromide m-Bromobenzyl Bromide;3-BromobenzylBromide98%;3-Bromobenzylbromide,99%;m-Bromobenzyl
• CAS NO: 823-78-9
• Molecular Formula: C₇H₆Br₂
• Molecular Weight: 249.93
• EINECS: 212-519-1
• Product Categories: Aromatic Halides (substituted);Benzyl;alkyl bromide
• Mol File: 823-78-9.mol
• Article Data: 26

Chemical Properties

• Melting Point: 39-41 °C(lit.)
• Boiling Point: 130 °C12 mm Hg
• Flash Point: >230 °F
• Appearance: White/Adhering Crystals or Crystalline Powder
• Density: 1,56 g/cm3
• Vapor Pressure: 0.0224mmHg at 25°C
• Refractive Index: 1.6066 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• Water Solubility: Insoluble in water.
• BRN: 2078683
• CAS DataBase Reference: 3-Bromobenzyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromobenzyl bromide(823-78-9)
• EPA Substance Registry System: 3-Bromobenzyl bromide(823-78-9)

Safety Data

• Hazard Codes: C
• Statements: 34-37
• Safety Statements: 26-36/37/39-45-25
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 19
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 823-78-9(Hazardous Substances Data)

Usage

Chemical Properties

White to yellow solid

Uses

Different sources of media describe the Uses of 823-78-9 differently. You can refer to the following data:
1. 3-Bromobenzyl bromide was used in the synthesis of, 1,7-di(3-bromobenzyl)cyclen and substituted 8-arylquinoline, phosphodiesterase 4 (PDE4) inhibitors.
2. 3-Bromobenzyl bromide was used in the synthesis of:1,7-di(3-bromobenzyl)cyclensubstituted 8-arylquinoline, phosphodiesterase 4 (PDE4) inhibitors

General Description

3-Bromobenzyl bromide undergoes reduction with diethylzinc in the presence of Pd(PPh3)4 to yield corresponding hydrocarbon.

InChI:InChI=1/C7H6Br2/c8-5-6-2-1-3-7(9)4-6/h1-4H,5H2

Upstream product

• 15852-73-0 (3-Bromophenyl)methanol 
• 3132-99-8 m-bromobenzoic aldehyde 
• 1878-67-7 3-Bromophenylacetic acid 
• 7791-25-5 sulfuryl dichloride 
• 591-17-3 meta-bromotoluene 
• 94-36-0 dibenzoyl peroxide 
• 7726-95-6 bromine 
• 56-23-5 tetrachloromethane 
• 78-67-1 2,2'-azobis(isobutyronitrile) 
• 123-72-8 butyraldehyde 
• 158526-66-0 m-bromobenzyl n-butyl telluride 
• 71323-99-4 (3-bromo-benzyl)-trimethyl-ammonium; bromide 
• 506-68-3 bromocyane 
• 857825-62-8 (3-bromo-benzyl)-(3-iodo-benzyl)-methyl-amine 

Downstream Products

• 20600-29-7 1-bromo-3-(phenoxymethyl)benzene 
• 14064-45-0 (E)-3-bromostilbene 
• 82732-03-4 1,1'-(1,2-ethanediyl)bis-3-bromobenzene 
• 174367-69-2 1-[(3-bromophenyl)methyl]-1H-indole-3-carboxaldehyde 
• 552887-06-6 methyl (2R,3R)-2-(3-bromobenzyloxy)-3,4-dihydroxy-3,4-O-isopropylidene-butyrate 
• 552887-07-7 methyl (2S,3S)-2-(3-bromobenzyloxy)-3,4-dihydroxy-3,4-O-isopropylidene-butyrate 
• 544481-57-4 3-(3-bromo-benzyloxy)-5-hydroxymethyl-benzoic acid ethyl ester 
• 54887-20-6 1-bromo-3-n-butylbenzene 
• 741683-46-5 1-(3-Bromo-benzyloxy)-3,5-bis-trifluoromethyl-benzene 
• 850453-98-4 (2S,5R)-2-(3-bromobenzyl)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine 
• 130891-01-9 1-bromo-3-((phenylsulfonyl)methyl)benzene 
• 848475-23-0 (2S,4S)-4-(3-Bromo-benzyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 

Relevant articles and documents

Synthesis, inhibition properties against xanthine oxidase and molecular docking studies of dimethyl N-benzyl-1H-1,2,3-triazole-4,5-dicarboxylate and (N-benzyl-1H-1,2,3-triazole-4,5-diyl)dimethanol derivatives

This study focused on synthesis various dimethyl N-benzyl-1H-1,2,3-triazole-4,5-dicarboxylate and (N-benzyl-1H-1,2,3-triazole-4,5-diyl)dimethanol derivatives under the conditions of green chemistry without the use of solvent and catalysts. Their inhibition properties were also investigated on xanthine oxidase (XO) activity. All dimethanol and dicarboxylate derivatives exhibited significant inhibition activities with IC50 values ranging from 0.71 to 2.25 μM. Especially, (1-(3-bromobenzyl)-1H-1,2,3-triazole-4,5-diyl)dimethanol (5c) and dimethyl 1-(4-chlorobenzyl)-1H-1,2,3-triazole-4,5-dicarboxylate (6 g) compounds were found to be the most promising derivatives on the XO enzyme inhibition with IC50 values 0.71 and 0.73 μM, respectively. Moreover, the double docking procedure was to evaluate compound modes of inhibition and their interactions with the protein (XO) at atomic level. Surprisingly, the docking results showed a good correlation with IC50 [correlation coefficient (R2 = 0.7455)]. Also, the docking results exhibited that the 5c, 6f and 6 g have lowest docking scores ?4.790, ?4.755, and ?4.730, respectively. These data were in agreement with the IC50 values. These results give promising beginning stages to assist in the improvement of novel and powerful inhibitor against XO.

Design, synthesis and biological evaluation of low molecular weight CXCR4 ligands

The chemokine receptor CXCR4/stromal cell-derived factor-1 (SDF-1: CXCL12) signaling axis represents a crucial drug target due to its relevance to several diseases such as HIV-1 infection, cancer, leukemia, and rheumatoid arthritis. With the aim of enhancing the binding affinity and anti-HIV activity of a potent CXCR4 ligand as a lead, 23 low molecular weight compounds containing dipicolylamine (Dpa) and cyclam cationic moieties with varying spacers and spatial positioning were designed, synthesized and biologically evaluated. All of the synthesized compounds screened at 1.0 μM in the NanoBRET assay system exhibited >70% inhibition of the binding of a competitive probe TAMRA-Ac-TZ14011 (10 nM) to CXCR4 in the presence of zinc (II) ion. Furthermore, selected compounds 3, 8, 9, 19 and 21 with spatial distances between the next carbon to Dpa and the next carbon to cyclam within the range of 6.5–7.5 ? showed potent binding affinity selective for CXCR4 with IC50 values of 1.6, 7.9, 5.7, 3.5 and 4.5 nM, respectively, with corresponding high anti-HIV activity with EC50s of 28, 13, 21, 28 and 61 nM, respectively, in the presence of zinc (II) ion. Some compounds with remarkably more potent CXCR4-binding affinity than that of an initial lead were obtained. These compounds interact with different but overlapping amino acid residues of CXCR4. The present studies have developed new low molecular weight CXCR4 ligands with high CXCR4-binding and anti-HIV activities, which open avenue into the development of more potent CXCR4 ligands.

Silver-Catalyzed Decarboxylative Bromination of Aliphatic Carboxylic Acids

The silver-catalyzed Hunsdiecker bromination of aliphatic carboxylic acids is described. With Ag(Phen)2OTf as the catalyst and dibromoisocyanuric acid as the brominating agent, various aliphatic carboxylic acids underwent decarboxylative bromination to provide the corresponding alkyl bromides under mild conditions. This method not only is efficient and general but also enjoys wide functional group compatibility. An oxidative radical mechanism involving Ag(II) intermediates is proposed.