4-(2-Bromoacetyl)benzonitrile

Base Information

• Chemical Name: 4-(2-Bromoacetyl)benzonitrile
• CAS No.: 20099-89-2
• Molecular Formula: C9H6BrNO
• Molecular Weight: 224.057
• Hs Code.: 29269090
• European Community (EC) Number: 606-435-8
• NSC Number: 157569
• UNII: E6T2NP32GC
• DSSTox Substance ID: DTXSID00173920
• Nikkaji Number: J534.052G
• Wikidata: Q72453822
• ChEMBL ID: CHEMBL1801622
• Mol file: 20099-89-2.mol

Synonyms:4-(2-bromoacetyl)benzonitrile;20099-89-2;4-Cyanophenacyl bromide;4-(Bromoacetyl)benzonitrile;2-Bromo-4'-cyanoacetophenone;Benzonitrile, 4-(bromoacetyl)-;p-Cyanophenacyl bromide;E6T2NP32GC;CHEMBL1801622;4-(2-bromo-acetyl)-benzonitrile;Benzonitrile, 4-(2-bromoacetyl)-;NSC 157569;NSC-157569;4-Cyanophenacyl Bromide 97%;MFCD00052931;p-Bromoacetylbenzonitrile;4-bromoacetylbenzonitrile;4-bromoacetyl benzonitrile;4-Bromoacetyl-benzonitrile;UNII-E6T2NP32GC;SCHEMBL250688;a-bromo-4'-cyano-acetophenone;4-(Bromoacetyl)benzonitrile #;2-bromo-4'-cyano acetophenone;2-bromo-4'-cyano-acetophenone;4-(2-bromoacetyl)-benzonitrile;The intermideate of Isavuconazole;DTXSID00173920;AM835;2-bromo-1-(4-cyanophenyl)ethanone;BCP10300;CS-M3110;STR07969;BDBM50347519;CK2151;NSC157569;STK279014;2-Bromo-1-(4-cyanophenyl)-ethanone;2-Bromo-4'-cyanoacetophenone, 96%;2-BROMO-4-CYANO ACETOPHENONE;AKOS000117765;UPCMLD0ENAT5695579:001;AC-31070;BP-13004;FT-0611444;EN300-13898;J-013010;2-Bromo-4 inverted exclamation marka-cyanoacetophenone;F0001-0711;Z104496340

Chemical Property of 4-(2-Bromoacetyl)benzonitrile

Chemical Property:

• Appearance/Colour: off-white to light yellow crystalline powder
• Melting Point: 92-96 °C(lit.)
• Refractive Index: 1.59
• Boiling Point: 342.4 °C at 760 mmHg
• Flash Point: 160.9 °C
• PSA: 40.86000
• Density: 1.56 g/cm³
• LogP: 2.13588
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: soluble in Methanol
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 222.96328
• Heavy Atom Count: 12
• Complexity: 210

Purity/Quality:

99%, ^*data from raw suppliers

4-(2-Bromoacetyl)benzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 20/21/22-34
• Safety Statements: 26-27-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1C#N)C(=O)CBr
• Uses: 4-(2-Bromoacetyl)benzonitrile is useful for the irreversible inhibitory activity of Glycogen synthase kinase 3 (GSK-3). Phenylhalomethylketones can be used in the study of novel GSK-3 inhibitors. 2-Bromo-4′-cyanoacetophenone may be used to synthesize:3-acylindolizines(2R,3R)-3-[4-(4-cyanophenyl)thiazol-2-yl]-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol1-[2-(4-cyanophenyl)-2-oxoethyl]-1,10-phenanthrolinium bromide

Technology Process of 4-(2-Bromoacetyl)benzonitrile

There total 14 articles about 4-(2-Bromoacetyl)benzonitrile 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: 100.0%

4-cyanophenyl methyl ketone (1443-80-7) → 4-Cyanophenacyl bromide (20099-89-2)

Guidance literature:

With bromine;

DOI:10.1002/ardp.19803130407

Reference yield: 85.0%

4-(2-bromoethynyl)-benzonitrile (157729-39-0) → 4-Cyanophenacyl bromide (20099-89-2)

Guidance literature:

With water; In 1,2-dichloro-ethane; at 20 ℃; for 14h;

DOI:10.1080/00397911.2018.1528616

Reference yield: 80.0%

benzonitrile (100-47-0) + 2-Bromoacetyl bromide (598-21-0) → 4-Cyanophenacyl bromide (20099-89-2)

Guidance literature:

With aluminum (III) chloride; at 0 ℃; for 4h;

upstream raw materials:

4-cyanophenyl methyl ketone

methanol

4-ethylbenzonitrile

4-(2-bromoethynyl)-benzonitrile

Downstream raw materials:

4-[(pyridine-3-sulfonyl)-acetyl]-benzonitrile

ω-ethythio-p-cyanoacetophenone

4-[2-(4-Butyl-phenyl)-imidazo[2,1-b][1,3,4]thiadiazol-6-yl]-benzonitrile

2-<4-butylcyclohexyl>-6-<4-cyanophenyl>imidazo-<2,1-b>-1,3,4-thiadiazole

Refernces

• 1、 Jagatheesan,Joseph Santhana Raj,Lawrence,Christopher. "Electroselective α-bromination of acetophenone using: In situ bromonium ions from ammonium bromide". . p. 35602 - 35608. Retrieved 2016.
• 2、 Kang, Lei,Zhang, Jinlong,Yang, Huameng,Qian, Jinlong,Jiang, Gaoxi. "Base-Catalyzed Intramolecular Defluorination/O-Arylation Reaction for the Synthesis of 3-Fluoro-1,4-oxathiine 4,4-Dioxide". supporting information. p. 785 - 789. Retrieved 2021/04/09.
• 3、 Shang, Xiao,Liu, Xuan,Sun, Yujie. "Flexible on-site halogenation paired with hydrogenation using halide electrolysis". supporting information. p. 2037 - 2043. Retrieved 2021/03/26.