5-Bromo-2-fluorobenzonitrile

Base Information

• Chemical Name: 5-Bromo-2-fluorobenzonitrile
• CAS No.: 179897-89-3
• Molecular Formula: C7H3NBrF
• Molecular Weight: 200.01
• Hs Code.: 29269090
• DSSTox Substance ID: DTXSID10369276
• Nikkaji Number: J835.876A
• Wikidata: Q72455870
• Mol file: 179897-89-3.mol

Synonyms:5-Bromo-2-fluorobenzonitrile;179897-89-3;2-FLUORO-5-BROMOBENZONITRILE;Benzonitrile, 5-bromo-2-fluoro-;MFCD00143424;3-CYANO-4-FLUOROBROMOBENZENE;3-cyano-4-fluoro-bromobenzene;5-bromo-2-fluoro-benzonitrile;2-fluoro5-bromobenzonitrile;3-cyano-4-flurobromobenzene;SCHEMBL80153;3-bromo-6-fluorobenzonitrile;5-Bromo-2-Fluoro Benzonitrile;DTXSID10369276;3-bromo-6-fluorobenzenecarbonitrile;CS-D0996;5-Bromo-2-fluorobenzonitrile, 97%;AKOS005254287;AC-3080;AM61364;PS-8214;BP-12095;SY003785;5-bromanyl-2-fluoranyl-benzenecarbonitrile;B2425;FT-0620089;EN300-81406;A812495;J-011475;J-516927;Z57900355;InChI=1/C7H3BrFN/c8-6-1-2-7(9)5(3-6)4-10/h1-3

Chemical Property of 5-Bromo-2-fluorobenzonitrile

Chemical Property:

• Appearance/Colour: white to off-white powder or crystals
• Vapor Pressure: 0.114mmHg at 25°C
• Melting Point: 76-81 °C
• Refractive Index: 1.577
• Boiling Point: 220.4 °C at 760 mmHg
• Flash Point: 87.1 °C
• PSA: 23.79000
• Density: 1.69 g/cm³
• LogP: 2.45988
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 198.94329
• Heavy Atom Count: 10
• Complexity: 162

Purity/Quality:

98% ^*data from raw suppliers

5-Bromo-2-fluorobenzonitrile ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1Br)C#N)F
• Uses: 5-Bromo-2-fluorobenzonitrile may be used for the preparation of the following compounds:(E)-5-(2-cyclopropylvinyl)-2-fluorobenzonitrile and methyl-3-amino-5-bromobenzo[b]thiophene-2-carboxylate(S)-[2-[5-(3-cyano-4-fluoro-phenyl)-pyridin-3-yloxy]-1-(1H-indol-3-ylmethyl)-ethyl]-carbamic acid tert-butyl ester4-fluoro-3-cyano-3′-tributyltinbenzhydrol4-fluoro-3-cyano-3′-iodobenzhydrol

Technology Process of 5-Bromo-2-fluorobenzonitrile

There total 2 articles about 5-Bromo-2-fluorobenzonitrile 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:

C7H5BrFNO (202865-65-4) → 5-Bromo-2-fluoro-benzonitrile (179897-89-3)

Guidance literature:

With acetic anhydride; In tetrahydrofuran; at 140 ℃;

DOI:10.1016/j.bmcl.2008.08.064

Reference yield:

5-bromo-2-fluorobenzaldehyde (93777-26-5) → 5-Bromo-2-fluoro-benzonitrile (179897-89-3)

Guidance literature:

Multi-step reaction with 2 steps

1: hydroxylamine hydrochloride; sodium carbonate / dimethyl sulfoxide / 20 °C

2: sodium carbonate; fluorosulfonyl fluoride / dimethyl sulfoxide / 12 h / 20 °C

With fluorosulfonyl fluoride; hydroxylamine hydrochloride; sodium carbonate; In dimethyl sulfoxide;

DOI:10.1021/acs.joc.8b03164

Reference yield: 100.0%

benzophenone hydrazone (5350-57-2) + 5-Bromo-2-fluoro-benzonitrile (179897-89-3) → benzophenone N-4-fluoro-3-cyanophenylhydrazone

Guidance literature:

With sodium hydroxide; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tert-Amyl alcohol; at 103 ℃; for 12h;

upstream raw materials:

C₇H₅BrFNO

5-bromo-2-fluorobenzaldehyde

Downstream raw materials:

3-cyano-4-fluorobenzoic acid

5-bromo-2-{3-[2-(4-dimethylamino-piperidin-1-yl)-ethyl]-benzo[b]thiophen-2-ylmethoxy}-benzonitrile

tert-butyl 4-(4-bromo-2-cyanophenyl)piperazine-1-carboxylate

2-fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile

Refernces

• 1、 Antonysamy, Stephen,Hirst, Gavin,Park, Frances,Sprengeler, Paul,Stappenbeck, Frank,Steensma, Ruo,Wilson, Mark,Wong, Melissa. "Fragment-based discovery of JAK-2 inhibitors". scheme or table. p. 279 - 282. Retrieved 2009/04/16.