4-Bromobenzonitrile

Base Information

• Chemical Name: 4-Bromobenzonitrile
• CAS No.: 623-00-7
• Molecular Formula: C7H4BrN
• Molecular Weight: 182.019
• Hs Code.: 29269095
• European Community (EC) Number: 210-764-9
• NSC Number: 3978
• UNII: 32L8XG37J4
• DSSTox Substance ID: DTXSID60211352
• Nikkaji Number: J42.017D
• Wikidata: Q63408716
• ChEMBL ID: CHEMBL3248210
• Mol file: 623-00-7.mol

Synonyms:4-bromo benzonitrile

Chemical Property of 4-Bromobenzonitrile

Chemical Property:

• Appearance/Colour: white to light yellow powder or flakes
• Vapor Pressure: 0.046mmHg at 25°C
• Melting Point: 110-115 °C(lit.)
• Refractive Index: 1.606
• Boiling Point: 236.796 °C at 760 mmHg
• Flash Point: 97.011 °C
• PSA: 23.79000
• Density: 1.609 g/cm³
• LogP: 2.32078
• Storage Temp.: Store below +30°C.
• Solubility.: 0.2g/l
• Water Solubility.: Very slightly soluble in water(0.2g/L). Soluble in alcohol and ether.
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 180.95271
• Heavy Atom Count: 9
• Complexity: 127

Purity/Quality:

99% ^*data from raw suppliers

4-Bromobenzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, T, Xi
• Hazard Codes: Xn,T,Xi
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 61-36/37/39-26-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1C#N)Br
• Uses: 4- Bromobenzonitrile is classified as organic nitriles, which are commonly use solvents and are reacted further for various applications such as manufacture of polymers and intermediates for pharmaceu ticals and other organic chemicals, 4-Bromobenzonitrile is used as reagents and solvents. Reaction of 2-propanol, 4-bromobenzonitrile, and NaH in the presence of 1.5 mol % Pd2(dba)3 and 3 mol % (S)-(-)2,2?-bis(di-p-tolylphosphino)- 1,1?-binaphthyl at 50°C afforded 4-isopropoxy- benzonitrile in 80% isolated yield. The synthesis of 4-cyanobiphenyl at room temperature in a flow injection microreactor, using a supported catalyst, without the addition of a base gave a product yield of 67±7% (n=6). This was achieved by injecting 4-bromobenzonitrile. The 3-arylation of 2,5-dimethylthiophene with 4-bromopropiophenone, 4-trifluoromethylbromobenzene or 4-bromobenzonitrile gave 3-5 in only 38-50% yields in Palladium-catalysed direct 3-or 4-arylation of thiophene derivatives using aryl bromides.

Technology Process of 4-Bromobenzonitrile

There total 148 articles about 4-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:

Reference yield: 99.0%

4-bromobenzaldehyde Oxime (25062-46-8,34158-73-1,40979-16-6) → 4-bromobenzenecarbonitrile (623-00-7)

Guidance literature:

With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In tetrahydrofuran; ethyl acetate; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tetlet.2010.12.090

Reference yield: 98.0%

4-bromo-benzaldehyde (1122-91-4) → 4-bromobenzenecarbonitrile (623-00-7)

Guidance literature:

With hydroxylamine hydrochloride; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In ethyl acetate; N,N-dimethyl-formamide; at 100 ℃; for 1h; Inert atmosphere;

DOI:10.1055/s-0029-1218388

Reference yield: 97.0%

4-cyanophenylboronic acid (126747-14-6) → 4-bromobenzenecarbonitrile (623-00-7)

Guidance literature:

With N-Bromosuccinimide; In acetonitrile; at 80 ℃; for 12h;

DOI:10.1039/c6ra25666j

upstream raw materials:

p-bromobenzamide

4-bromo-N,N-dimethylbenzamide

4-cyanobenzenesulfonic acid

4-Bromobenzoic acid

Downstream raw materials:

4-(piperidin-1-yl)benzonitrile

ethyl 4-bromobenzimidate hydrochloride

(4-bromophenyl)(2,3-dihydro-1H-indol-7-yl)methanone

4-[5-Oxo-dihydro-furan-(2E)-ylidenemethyl]-benzonitrile

Refernces

• 1、 Clarke,Read. "-". . p. 1003. Retrieved 1924.
• 2、 Bagirzade. "Kinetics of oxidative ammonolysis of 4-bromo-o-xylene: I. Transformations of 4-bromo-o-xylene and 4-bromo-o-tolunitrile". . p. 1672 - 1676. Retrieved 2010.
• 3、 Abe, Masahiro,Nitta, Sayasa,Miura, Erina,Kimachi, Tetsutaro,Inamoto, Kiyofumi. "Nitrile Synthesis via Desulfonylative-Smiles Rearrangement". . p. 4460 - 4467. Retrieved 2022/03/15.
• 4、 Hua, Manli,Song, Jinliang,Huang, Xin,Liu, Huizhen,Fan, Honglei,Wang, Weitao,He, Zhenhong,Liu, Zhaotie,Han, Buxing. "Highly Efficient Oxidative Cyanation of Aldehydes to Nitriles over Se,S,N-tri-Doped Hierarchically Porous Carbon Nanosheets". supporting information. p. 21479 - 21485. Retrieved 2021/08/23.