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2-Bromobenzonitrile

Base Information
  • Chemical Name:2-Bromobenzonitrile
  • CAS No.:2042-37-7
  • Molecular Formula:C7H4BrN
  • Molecular Weight:182.019
  • Hs Code.:29269095
  • European Community (EC) Number:218-045-1
  • NSC Number:59730
  • UNII:8LSJ4JR86W
  • DSSTox Substance ID:DTXSID50174366
  • Nikkaji Number:J126.353F
  • Wikidata:Q72451682
  • ChEMBL ID:CHEMBL3248212
  • Mol file:2042-37-7.mol
2-Bromobenzonitrile

Synonyms:2-bromobenzonitrile

Suppliers and Price of 2-Bromobenzonitrile
Supply Marketing:
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TCI Chemical
  • 2-Bromobenzonitrile >98.0%(GC)
  • 25g
  • $ 98.00
  • TCI Chemical
  • 2-Bromobenzonitrile >98.0%(GC)
  • 10g
  • $ 40.00
  • SynQuest Laboratories
  • 2-Bromobenzonitrile 99%
  • 100 g
  • $ 138.00
  • Sigma-Aldrich
  • 2-Bromobenzonitrile 99%
  • 1g
  • $ 27.80
  • Sigma-Aldrich
  • 2-Bromobenzonitrile 99%
  • 10g
  • $ 105.00
  • Oakwood
  • 2-Bromobenzonitrile
  • 100g
  • $ 50.00
  • Oakwood
  • 2-Bromobenzonitrile
  • 5g
  • $ 12.00
  • Oakwood
  • 2-Bromobenzonitrile
  • 25g
  • $ 20.00
  • Matrix Scientific
  • 2-Bromobenzonitrile 98%
  • 25g
  • $ 13.00
  • Matrix Scientific
  • 2-Bromobenzonitrile 98%
  • 100g
  • $ 43.00
Total 136 raw suppliers
Chemical Property of 2-Bromobenzonitrile
Chemical Property:
  • Appearance/Colour:white to light yellow crystal powder 
  • Vapor Pressure:0.0198mmHg at 25°C 
  • Melting Point:53-57 °C(lit.) 
  • Refractive Index:1.606 
  • Boiling Point:252 °C at 760 mmHg 
  • Flash Point:113.7 °C 
  • PSA:23.79000 
  • Density:1.6 g/cm3 
  • LogP:2.32078 
  • Storage Temp.:Store below +30°C. 
  • Solubility.:10.5g/l 
  • XLogP3:2.1
  • Hydrogen Bond Donor Count:0
  • Hydrogen Bond Acceptor Count:1
  • Rotatable Bond Count:0
  • Exact Mass:180.95271
  • Heavy Atom Count:9
  • Complexity:135
Purity/Quality:

99% *data from raw suppliers

2-Bromobenzonitrile >98.0%(GC) *data from reagent suppliers

Safty Information:
  • Pictogram(s): HarmfulXn, IrritantXi 
  • Hazard Codes:Xn,Xi 
  • Statements: 22-36/37/38-20/21/22 
  • Safety Statements: 22-24/25-36/37/39-26 
MSDS Files:
Useful:
  • Canonical SMILES:C1=CC=C(C(=C1)C#N)Br
  • General Description 2-Bromobenzonitrile is a brominated aromatic nitrile compound that serves as a key intermediate in organic synthesis, particularly in lithiation-trapping protocols for the preparation of substituted 2-cyanoarylboronic esters, which are useful in Suzuki cross-coupling reactions. Additionally, its electron-withdrawing cyano group enhances reactivity in photostimulated SRN1 reactions, enabling efficient arylation and heteroarylation of β-dicarbonyl compounds. These applications highlight its versatility in constructing complex aromatic and heterocyclic frameworks.
Technology Process of 2-Bromobenzonitrile

There total 55 articles about 2-Bromobenzonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:
Guidance literature:
2-methylphenyl bromide; With hydrogen bromide; dihydrogen peroxide; In tetrachloromethane; water; at 20 ℃; for 1h; Irradiation;
With ammonia; iodine; In tetrachloromethane; water; acetonitrile; at 20 - 60 ℃; for 24h;
DOI:10.1002/ejoc.201402270
Guidance literature:
With formic acid; tributyl-amine; 1,1′-(10-(4-acetylphenyl)-10H-phenothiazine-3,7-diyl)bis(ethan-1-one); In acetonitrile; at 23 ℃; for 24h; chemoselective reaction; UV-irradiation;
DOI:10.1021/acs.joc.6b01034
Guidance literature:
With oxalyl dichloride; triethylamine; Triphenylphosphine oxide; In acetonitrile; at 20 ℃; for 0.166667h;
DOI:10.1021/acs.orglett.7b03862
Refernces

Synthesis of substituted 2-cyanoarylboronic esters

10.1021/jo052400g

The research focuses on the synthesis of substituted 2-cyanoarylboronic esters, which are valuable tools in organic synthesis, particularly for the formation of biaryls through cross-coupling reactions. The study aims to develop efficient protocols for the preparation of these derivatives, addressing the growing demand for diversely substituted arylboronic acid derivatives. The researchers utilized a lithiation/in situ trapping protocol with LTMP/B(O-i-Pr)3 to synthesize the esters from various methoxy-, trifluoromethyl-, fluoro-, chloro-, and bromobenzonitriles. The process resulted in high yields and purities with good regioselectivities. The conclusion of the study is that this method is very efficient for preparing substituted 2-cyanoarylboronic esters, which are known to be effective in Suzuki couplings with aryl halides and carbamoyl chlorides, and can be further transformed into various compounds such as aryltetrazole boronic esters. The research also demonstrated the synthetic utility of these esters through a two-step synthesis of a substituted phenanthridine.

STUDIES ON SRN1 REACTIONS. PART 8 NEW AND DIRECT ARYLATION AND HETARYLATION OF β-DICARBONYL COMPOUNDS BY SRN1

10.1016/0040-4020(82)85032-1

The research investigates the arylation and heteroarylation of β-dicarbonyl compounds through a photostimulated SRN1 reaction. The purpose of the study is to explore new synthetic methods for heterocyclic compounds by extending the scope of the SRN1 reaction, which is known for its efficiency in arylation of monoketones but was previously thought not to occur between aryl halides and monoanions of β-dicarbonyl compounds. The researchers discovered that the presence of a cyano electron-withdrawing group allows high-yield SRN1 reactions to occur with β-dicarbonyl derived monoanions. Key chemicals used in the research include bromobenzonitriles, bromocyanopyridine, and various β-dicarbonyl compounds such as malonates, ethyl-cyanoacetate, and 2,4-pentanedione. The study concludes that the SRN1 reaction mechanism is supported by experimental observations, including the necessity of photostimulation and the influence of the cyano group's strong withdrawing effect on the reactivity. The research demonstrates that the SRN1 reaction can be efficiently applied to introduce aryl groups onto β-dicarbonyl compounds, offering a versatile and high-yield synthetic method for a variety of heterocyclic compounds.

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