2-Fluoro-5-methylbenzonitrile

Base Information

• Chemical Name: 2-Fluoro-5-methylbenzonitrile
• CAS No.: 64113-84-4
• Molecular Formula: C8H6FN
• Molecular Weight: 135.141
• Hs Code.: 29269090
• European Community (EC) Number: 625-630-9
• DSSTox Substance ID: DTXSID90379111
• Nikkaji Number: J1.546.166G
• Wikidata: Q72474513
• Mol file: 64113-84-4.mol

Synonyms:2-Fluoro-5-methylbenzonitrile;64113-84-4;BENZONITRILE, 2-FLUORO-5-METHYL-;MFCD00134542;6-Fluoro-m-tolunitrile;2-fluoro-5-methyl-benzonitrile;3-CYANO-4-FLUOROTOLUENE;SCHEMBL253758;2-fluoro-5 methyl benzonitrile;ETHYLALUMINUMSESQUICHLORIDE;DTXSID90379111;CMAOLVNGLTWICC-UHFFFAOYSA-N;CK1050;2-Fluoro-5-methylbenzonitrile, 99%;AKOS005254738;AC-4081;CS-W011066;DS-0900;PS-9126;BP-11296;SY016256;A8800;AM20060073;F0573;FT-0612363;FT-0640924;FT-0657799;EN300-75460;J-509456;Z1079179202

Chemical Property of 2-Fluoro-5-methylbenzonitrile

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 0.161mmHg at 25°C
• Melting Point: 50-52 °C(lit.)
• Refractive Index: 1.507
• Boiling Point: 204
• Flash Point: 94 ºC
• PSA: 23.79000
• Density: 1.11 g/cm³
• LogP: 2.00578
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 135.048427358
• Heavy Atom Count: 10
• Complexity: 158

Purity/Quality:

99.5% ^*data from raw suppliers

2-Fluoro-5-methylbenzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,T
• Hazard Codes: Xn,T
• Statements: 20/21/22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(C=C1)F)C#N
• Uses: 2-Fluoro-5-methylbenzonitrile is used in the synthesis of indazoles which have the potential to be selective for the α2-adrenoceptor and central and peripheral nervous systems.

Technology Process of 2-Fluoro-5-methylbenzonitrile

There total 4 articles about 2-Fluoro-5-methylbenzonitrile 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: 86.0%

3-bromo-4-fluorotoluene (452-62-0) + copper(I) cyanide (544-92-3) → 2-fluoro-5-methylbenzonitrile (64113-84-4)

Guidance literature:

In N,N-dimethyl-formamide; at 160 ℃; for 24h;

DOI:10.1002/hlca.201700204

Reference yield: 82.0%

benzaldehyde dimethyl acetal (1125-88-8) + 5-Bromo-2-fluoro-benzonitrile (179897-89-3) → 2-fluoro-5-methylbenzonitrile (64113-84-4)

Guidance literature:

With nickel(II) bromide dimethoxyethane; potassium phosphate; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; tetrabutylammomium bromide; 4,4'-di-tert-butyl-2,2'-bipyridine; In acetonitrile; benzene; for 24h; Glovebox; Sealed tube; Irradiation;

DOI:10.1021/jacs.1c12203

Reference yield:

2-nitro-5-methylbenzonitrile (64113-86-6) → 2-fluoro-5-methylbenzonitrile (64113-84-4)

Guidance literature:

Multi-step reaction with 2 steps

1: Fe, AcOH

2: (i) HNO₂, aq. HBF₄, (ii) (pyrolysis)

With iron; acetic acid;

DOI:10.1021/jo00396a009

upstream raw materials:

2-amino-5-methylbenzonitrile

2-nitro-5-methylbenzonitrile

3-bromo-4-fluorotoluene

copper(I) cyanide

Downstream raw materials:

2-(4-chloro-2-nitrophenylamino)-5-methylbenzonitrile

2-(4-fluoro-2-nitrophenylamino)-5-methylbenzonitrile

5-(4',5'-difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-benzo[d]isoxazol-3-ylamine

{[5-(4',5'-difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-benzo[d]isoxazol-3-yl]-methyl-amino}-acetic acid

Refernces

• 1、 Milicevic Sephton, Selena,Vetterli, Peter T.,Pedani, Valentina,Cermak, Stjepko,Chiotellis, Aristeidis,Roscales, Sylvia,Müller Herde, Adrienne,Schibli, Roger,Auberson, Yves P.,Ametamey, Simon M.. "Synthesis and Biological Evaluation of Quinoxaline Derivatives for PET Imaging of the NMDA Receptor". . . Retrieved 2017/12/08.