578-51-8

Basic information

• Product Name: 2-BROMOBENZYL CHLORIDE
• Synonyms: 2-BROMOBENZYL CHLORIDE;AKOS BBS-00003988;O-BROMOBENZYL CHLORIDE;1-Bromo-2-(chloromethyl)benzene;Benzene,1-bromo-2-(chloromethyl)-;2-Bromo-alpha-chlorotoluene;2-bromo-à-chlorotoluene;2-BROMOBENZYL CHLORIDE / 2-BROMO-ALPHA-CHLOROTOLUENE
• CAS NO: 578-51-8
• Molecular Formula: C₇H₆BrCl
• Molecular Weight: 205.48
• Mol File: 578-51-8.mol

Chemical Properties

• Boiling Point: 110-111 °C (15 mmHg)
• Flash Point: 110-111°C/15mm
• Appearance: Clear colorless to pale yellow liquid
• Density: 1.541 g/cm³
• Vapor Pressure: 0.0596mmHg at 25°C
• Refractive Index: 1.586
• Water Solubility: Not miscible or difficult to mix with water.
• BRN: 471701
• CAS DataBase Reference: 2-BROMOBENZYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMOBENZYL CHLORIDE(578-51-8)
• EPA Substance Registry System: 2-BROMOBENZYL CHLORIDE(578-51-8)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 45-36/37/39-26
• RIDADR: 3265
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 578-51-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-BROMOBENZYL CHLORIDE is used as a key intermediate for the synthesis of various organic compounds. Its reactive nature allows it to participate in a wide range of chemical reactions, making it a valuable component in the creation of new molecules.
Used in Pharmaceutical Industry:
2-BROMOBENZYL CHLORIDE is used as a building block in the development of pharmaceuticals. Its unique structure and reactivity enable the synthesis of various drug molecules, contributing to the advancement of medicinal chemistry.
Used in Agrochemicals:
In the agrochemical industry, 2-BROMOBENZYL CHLORIDE is utilized as a starting material for the production of various agrochemicals, such as pesticides and herbicides. Its role in these applications is crucial for the development of effective and targeted solutions for agricultural challenges.
Used in Dyestuff Industry:
2-BROMOBENZYL CHLORIDE is employed as a raw material in the dyestuff industry, where it is used to synthesize a variety of dyes and pigments. Its versatility in chemical reactions allows for the creation of a wide range of colorants, enhancing the options available for various applications.

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

Upstream product

• 50-00-0 formaldehyd 
• 108-86-1 bromobenzene 
• 95-46-5 2-methylphenyl bromide 
• 18982-54-2 o-bromobenzyl alcohol 
• 7647-01-0 hydrogenchloride 
• 7646-78-8 tin(IV) chloride 
• 7791-25-5 sulfuryl dichloride 
• 94-36-0 dibenzoyl peroxide 

Downstream Products

• 101884-75-7 10-(2-bromobenzyl)-10H-phenothiazine 
• 6279-34-1 1-bromo-2-((p-tolyloxy)methyl)benzene 
• 5468-74-6 2-(2-bromo-benzyl)-4-methyl-phenol 
• 5422-46-8 (3-bromo-benzyl)-p-tolyl ether 
• 855358-86-0 2,6-dibromo-4-(2-bromo-benzyl)-phenol 
• 94191-73-8 1-bromo-2-(phenoxymethyl)benzene 
• 208035-00-1 2-(2-bromo-benzyl)-phenol 
• 159448-29-0 (2-bromo-benzyloxy)-acetic acid ethyl ester 
• 6279-13-6 4-(2-bromo-benzyl)-2-methyl-phenol 
• 5422-50-4 1-bromo-(2-methylphenoxymethyl)benzene 
• 5442-20-6 2-(2-bromo-benzyl)-6-methyl-phenol 
• 63909-55-7 diethyl 2-bromobenzylphosphonate 
• 58380-12-4 <(2-bromophenyl)methyl>propanedicarboxylic acid 
• 138849-94-2 o-(2-chlorotetramethyldisilanyl)benzyl chloride 

Relevant articles and documents

NMP-mediated chlorination of aliphatic alcohols with aryl sulfonyl chloride for the synthesis of alkyl chlorides

NMP-mediated chlorination of aliphatic alcohols has been developed for the synthesis of alkyl chlorides. This facile, efficient and practical approach used simple and readily available aryl sulfonyl chlorides as the chlorination reagent for the construction of C–Cl bond in good to excellent yields with mild conditions and broad substrate scope.

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.

Towards iron-catalysed suzuki biaryl cross-coupling: Unusual reactivity of 2-halobenzyl halides

The reaction of 2-halobenzyl halides with the borate anion Li[(Ph)(t-Bu)Bpin] leads not only to the expected arylation at the benzyl position, but also to some Suzuki biaryl cross-coupling. Preliminary mechanistic investigations hint towards the intermediacy of benzyl iron intermediates that can either: (a) directly cross-couple with the aryl boron reagent to give observed monoarylated species, or (b) undergo oxidative addition of the aryl halide to generate the diarylated species on reaction with the boron-based nucleophile.

Cu-Catalyzed Suzuki-Miyaura reactions of primary and secondary benzyl halides with arylboronates

A copper-catalyzed Suzuki-Miyaura coupling of benzyl halides with arylboronates is described. Varieties of primary benzyl halides as well as more challenging secondary benzyl halides with β hydrogens or steric hindrance could be successfully converted into the corresponding products. Thus it provides access to diarylmethanes, diarylethanes and triarylmethanes. This journal is the Partner Organisations 2014.

Catalytic diastereo- and enantioselective annulations between transient nitrosoalkenes and indoles

Caught in transition: An efficient catalytic system is the key to the successful development of the first highly diastereo- and enantioselective annulation reaction between indoles and transient nitrosoalkenes. This robust reaction affords structurally unique architectures with up to three new chiral centers. The products can be readily elaborated into other indoline-based chiral heterocyclic motifs, including those of pyrrolidinoindoline alkaloids. Copyright

Amide-modified prenylcysteine based Icmt inhibitors: Structure-activity relationships, kinetic analysis and cellular characterization

Human protein isoprenylcysteine carboxyl methyltransferase (hIcmt) is the enzyme responsible for the α-carboxyl methylation of the C-terminal isoprenylated cysteine of CaaX proteins, including Ras proteins. This specific posttranslational methylation event has been shown to be important for cellular transformation by oncogenic Ras isoforms. This finding led to interest in hIcmt inhibitors as potential anti-cancer agents. Previous analog studies based on N-acetyl-S-farnesylcysteine identified two prenylcysteine-based low micromolar inhibitors (1a and 1b) of hIcmt, each bearing a phenoxyphenyl amide modification. In this study, a focused library of analogs of 1a and 1b was synthesized and screened versus hIcmt, delineating structural features important for inhibition. Kinetic characterization of the most potent analogs 1a and 1b established that both inhibitors exhibited mixed-mode inhibition and that the competitive component predominated. Using the Cheng-Prusoff method, the K i values were determined from the IC50 values. Analog 1a has a KIC of 1.4 ± 0.2 μM and a KIU of 4.8 ± 0.5 μM while 1b has a KIC of 0.5 ± 0.07 μM and a KIU of 1.9 ± 0.2 μM. Cellular evaluation of 1b revealed that it alters the subcellular localization of GFP-KRas, and also inhibits both Ras activation and Erk phosphorylation in Jurkat cells.

Large-scale preparation of polyfunctional benzylic zinc reagents by direct insertion of zinc dust into benzylic chlorides in the presence of lithium chloride

Highly functionalized benzylic zinc chlorides are prepared by the direct insertion of commercially available zinc dust into the corresponding benzylic chlorides in the presence of stoichiometric amount of lithium chloride. These polyfunctional zinc organometallics react with various electrophiles leading to a broad range of functionalized products. Georg Thieme Verlag Stuttgart.

FUNGAL CELL WALL SYNTHESIS GENE

A reporter system reflecting the transport process that transports GPI-anchored proteins to the cell wall was constructed and compounds inhibiting this process were discovered. Further, genes conferring resistance to the above compounds were identified and methods of screening for compounds that inhibit the activity of the proteins encoded by these genes were developed.Therefore, through the novel compounds, the present invention showed that antifungal agents having a novel mechanism, i.e. inhibiting the process that transports GPI-anchored proteins to the cell wall, could be achieved.

Mechanical Activation of Magnesium Turnings for the Preparation of Reactive Grignard Reagents

Preactivation of magnesium by dry stirring in an inert atmosphere is highly beneficial for the clean synthesis of reactive allylic or benzylic organomagnesium chlorides.This procedure routinely produces 0.4 M solutions of the Grignard reagent in diethyl ether free from coupling products.The purity may be directly assayed by 13C spectroscopy.Using spin saturation transfer techniques, the rate constant for interconversion of the enantiomers of (1-phenyl-2-methylpropyl)magnesium chloride in Et2O at 25 deg C was shown to be -1.Electron microscopy has been used to define the surface changes occurring during the dry stirring of magnesium turnings.