3433-80-5

Basic information

• Product Name: 2-Bromobenzyl bromide
• Synonyms: 2-Bromobenzyl bromide, 95+%;2-Bromobenzylbromide,98%;Benzene, 1-bromo-2-(bromomethyl)-;à,2-dibromotoluene;2-BROMOBENZYL BROMIDE 99%;alpha,2-Dibromotoluene, 1-Bromo-2-(bromomethyl)benzene;1-(Bromomethyl)-2-bromobenzene;2-Bromo-1-bromomethylbenzene
• CAS NO: 3433-80-5
• Molecular Formula: C₇H₆Br₂
• Molecular Weight: 249.93
• EINECS: 222-334-8
• Product Categories: Aromatic Halides (substituted);Benzyl;alkyl bromide
• Mol File: 3433-80-5.mol

Chemical Properties

• Melting Point: 29-32 °C(lit.)
• Boiling Point: 129 °C19 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to yellow/Liquid After Melting
• Density: 1.8246 (rough estimate)
• Vapor Pressure: 0.0298mmHg at 25°C
• Refractive Index: n20/D 1.619(lit.)
• Storage Temp.: 0-6°C
• Solubility: dioxane: soluble1g/10 mL, clear, colorless
• Water Solubility: Insoluble in water.
• BRN: 971015
• CAS DataBase Reference: 2-Bromobenzyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromobenzyl bromide(3433-80-5)
• EPA Substance Registry System: 2-Bromobenzyl bromide(3433-80-5)

Safety Data

• Hazard Codes: C,T
• Statements: 34-37-23
• Safety Statements: 26-36/37/39-45-22
• RIDADR: UN 3261 8/PG 3
• WGK Germany: 3
• F: 8-19
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 3433-80-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Bromobenzyl bromide is used as a synthetic intermediate for the production of substituted quinazoline and 1,2,3,4-tetrahydroquinazoline derivatives. These compounds have potential applications in the development of new drugs due to their diverse biological activities, including anti-cancer, anti-inflammatory, and anti-bacterial properties.
Used in Chemical Synthesis:
2-Bromobenzyl bromide is used as a synthetic intermediate for the production of 2and 3-substituted indenes. These compounds are important building blocks in the synthesis of various organic molecules, including pharmaceuticals, agrochemicals, and dyes.
Used in Material Science:
2-Bromobenzyl bromide is used as a synthetic intermediate for the production of tris-2-bromotribenzylamine. 2-Bromobenzyl bromide has potential applications in the development of new materials, such as advanced polymers and coatings, due to its unique chemical properties.

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

Upstream product

• 506-68-3 bromocyane 
• 857785-85-4 (2-bromo-benzyl)-(2-iodo-benzyl)-methyl-amine 
• 95-46-5 2-methylphenyl bromide 
• 100-39-0 benzyl bromide 
• 75-25-2 Bromoform 
• 4646-69-9 benzocyclopropene 
• 75-62-7 Bromotrichloromethane 
• 7726-95-6 bromine 
• 140-11-4 Benzyl acetate 
• 7791-25-5 sulfuryl dichloride 
• 94-36-0 dibenzoyl peroxide 
• 18982-54-2 o-bromobenzyl alcohol 
• 6630-33-7 ortho-bromobenzaldehyde 
• 850335-71-6 2-bromo-1-[(ethoxymethoxy)methyl]benzene 

Downstream Products

• 13160-93-5 N-(2-bromobenzyl)-pyridinium bromide 
• 1976-04-1 2-bromo-N,N-dimethylbenzylamine 
• 59485-34-6 1,2-bis(2-bromophenyl)ethane 
• 131887-70-2 S-(2-bromo-benzyl)-isothiourea 
• 54636-17-8 4-(2-bromo-phenyl)-3-phenyl-butan-2-one 
• 94191-73-8 1-bromo-2-(phenoxymethyl)benzene 
• 6630-33-7 ortho-bromobenzaldehyde 
• 876476-07-2 (2-bromo-benzyl)-(2-chloro-benzyl)-methyl-amine 
• 857785-85-4 (2-bromo-benzyl)-(2-iodo-benzyl)-methyl-amine 
• 52711-30-5 1-bromo-2-(methoxymethyl)benzene 
• 99180-11-7 2-<(ethylthio)methyl>bromobenzene 
• 137395-70-1 1-bromo-2-(tert-butoxymethyl)benzene 
• 74637-37-9 2,2'-(oxybis(methylene))bis(bromobenzene) 
• 18982-54-2 o-bromobenzyl alcohol 

Relevant articles and documents

Preparation of 1,5-Dihydropyrazolo[3′,4′:5,6]pyrano[3,4- b]pyridines via a Microwave-Assisted, Palladium-Catalyzed Regioselective C-H Heteroarylation of Electron-Rich Pyrazoles

Here we report the first synthesis of a family of novel heterocyclic compounds based on a 5-dihydropyrazolo[3′,4′:5,6]pyrano[3,4-b]pyridine core. In the course of our drug discovery programs, we had need to access the previously unknown 5-dihydropyrazolo[3′,4′:5,6]pyrano[3,4-b]pyridine core. Initial attempts required long reaction times, which led to degradation and side products. Reaction optimization identified a Pd-catalyzed, microwave-assisted C-H heteroarylation protocol for the rapid, general, and high yielding synthesis of this tricyclic core (as well as related analogs) suitable to drive optimization efforts.

tBuOK-Promoted Cyclization of Imines with Aryl Halides

A transition-metal-free indole synthesis using radical coupling of 2-halotoluenes and imines via the later-stage C-N bond construction was reported for the first time. It includes an aminyl radical generation by C-H cleaving addition of 2-halotoluenes to imines via the carbanion radical relay and an intramolecular coupling of aryl halides with aminyl radicals. One standard condition can be used for all halides including F, Cl, Br, and I. No extra oxidant or transition metal is required.

Thiourea-Catalyzed C?F Bond Activation: Amination of Benzylic Fluorides

We describe the first thiourea-catalyzed C?F bond activation. The use of a thiourea catalyst and Ti(OiPr)4 as a fluoride scavenger allows the amination of benzylic fluorides to proceed in moderate to excellent yields. Preliminary results with S- and O-based nucleophiles are also presented. DFT calculations reveal the importance of hydrogen bonds between the catalyst and the fluorine atom of the substrate to lower the activation energy during the transition state.

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.

Carbocation Catalyzed Bromination of Alkyl Arenes, a Chemoselective sp3 vs. sp2 C?H functionalization.

The versatility of the trityl cation (TrBF4) as a highly efficient Lewis acid organocatalyst is demonstrated in a light induced benzylic brominaion of alkyl-arenes under mild conditions. The reaction was conducted at ambient temperature under common hood light (55 W fluorescent light) with catalyst loadings down to 2.0 mol% using N-bromosuccinimide (NBS) as the brominating agent. The protocol is applicable to an extensive number of substrates to give benzyl bromides in good to excellent yields. In contrast to most previously reported strategies, this protocol does not require any radical initiator or extensive heating. For electron-rich alkyl-arenes, the trityl ion catalyzed bromination could be easily switched between benzylic sp3 C?H functionalization and arene sp2 C?H functionalization by simply alternating the solvent. This chemoselective switch allows for high substrate control and easy preparation of benzyl bromides and bromoarenes, respectively. The chemoselective switch was also applied in a one-pot reaction of 1-methylnaphthalene for direct introduction of both sp3 C?Br and sp2 C?Br functionality. (Figure presented.).

Visible-Light-Driven Oxidative Mono- and Dibromination of Benzylic sp 3 C-H Bonds with Potassium Bromide/Oxone at Room Temperature

Benzylic sp 3 C-H bonds have been successfully brominated with potassium bromide by using Oxone as an oxidant in water/dichloromethane under visible light at room temperature. Toluene, ethylbenzene and other alkylbenzenes bearing an electron-withdrawing group, such as Br, Cl, COMe, CO 2 Et, CO 2 H, CN or NO 2, provide the corresponding benzylic monobromides in good to excellent yields in this reaction. Dibromides can also be produced in the presence of excess potassium bromide in a prolonged reaction time. Control of the illuminance of visible light (~500 lux) is crucial to achieving both high yield and high selectivity in these brominations. Mono- and difluorides can be conveniently prepared through nucleophilic substitutions of the benzylic bromides with potassium fluoride.

Halogenation through Deoxygenation of Alcohols and Aldehydes

An efficient reagent system, Ph3P/XCH2CH2X (X = Cl, Br, or I), was very effective for the deoxygenative halogenation (including fluorination) of alcohols (including tertiary alcohols) and aldehydes. The easily available 1,2-dihaloethanes were used as key reagents and halogen sources. The use of (EtO)3P instead of Ph3P could also realize deoxy-halogenation, allowing for a convenient purification process, as the byproduct (EtO)3Pa?O could be removed by aqueous washing. The mild reaction conditions, wide substrate scope, and wide availability of 1,2-dihaloethanes make this protocol attractive for the synthesis of halogenated compounds.

Strategy for Overcoming Full Reversibility of Intermolecular Radical Addition to Aldehydes: Tandem C-H and C-O Bonds Cleaving Cyclization of (Phenoxymethyl)arenes with Carbonyls to Benzofurans

An intermolecular addition of carbon radicals enabled by a cascade radical coupling strategy is developed. It includes an intermolecular alkyl radical addition to a carbonyl group followed by an intramolecular alkoxy radical addition to haloarenes and produces substituted benzofurans in high yields. The radical nature of this reaction is explored by radical trapping experiments and EPR analysis. The mechanism is investigated by KIE experiments and control experiments. This method could provide rapid and practical access to the key intermediate of TAM-16, a safe and potent antibacterial agent for treating tuberculosis, and, therefore, is of great importance for organic synthesis and the pharmaceutical industry.

Copper powder-catalyzed coupling and cyclization of 1-bromoallyl bromides with amidine hydrochlorides leading to pyrimidines

1-Bromoallyl bromides are coupled and cyclized with amidine hydrochlorides in DMF at 130 °C in the presence of a catalytic amount of copper powder along with K3PO4 to give pyrimidines in moderate to good yields.

Preparation method of FSH (follicle-stimulating hormone) antagonist with benzopyran structure

The invention discloses a preparation method of an FSH (follicle-stimulating hormone) antagonist with a benzopyran structure, and belongs to the technical field of synthesis of medical intermediates. The technical scheme is mainly as shown in the description. The synthesis process is simple and low in cost, and the prepared FSH antagonist is good in action effect on FSH receptors after activity tests and can be further popularized and applied.