2-Fluoro-5-methoxybenzonitrile

Base Information

• Chemical Name: 2-Fluoro-5-methoxybenzonitrile
• CAS No.: 127667-01-0
• Molecular Formula: C8H6FNO
• Molecular Weight: 151.14
• Hs Code.: 29269090
• DSSTox Substance ID: DTXSID30379094
• Nikkaji Number: J331.595I
• Wikidata: Q72474018
• Mol file: 127667-01-0.mol

Synonyms:2-Fluoro-5-methoxybenzonitrile;127667-01-0;Benzonitrile, 2-fluoro-5-methoxy-;MFCD00142921;3-Cyano-4-fluoroanisole;2-Fluoro-5-methoxy-benzonitrile;Fluoromethoxybenzonitrile2;SCHEMBL1017145;2-Fluoro-5-methoxy benzonitrile;DTXSID30379094;VBZLRHYLNXWZIU-UHFFFAOYSA-N;2-Fluoro-5-(methyloxy)benzonitrile;BBL101254;CL8165;STL555050;AKOS005258058;AC-1970;AM61296;CS-W001229;FS-1327;BP-13171;SY018198;2-Fluoro-5-methoxybenzonitrile, AldrichCPR;F0642;FT-0602515;EN300-94983;J-509447

Chemical Property of 2-Fluoro-5-methoxybenzonitrile

Chemical Property:

• Vapor Pressure: 0.0582mmHg at 25°C
• Melting Point: 77-80 °C
• Refractive Index: 1.505
• Boiling Point: 232.7 °C at 760 mmHg
• Flash Point: 94.5 °C
• PSA: 33.02000
• Density: 1.18 g/cm³
• LogP: 1.70598
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 151.043341977
• Heavy Atom Count: 11
• Complexity: 174

Purity/Quality:

98%,99%, ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 20/21/22-36/37/38-36/38
• Safety Statements: 26-36/37/39-45-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=C(C=C1)F)C#N

Technology Process of 2-Fluoro-5-methoxybenzonitrile

There total 6 articles about 2-Fluoro-5-methoxybenzonitrile 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: 67.0%

methanol (67-56-1) + 5-Bromo-2-fluoro-benzonitrile (179897-89-3) → 2-fluoro 5-methoxybenzonitrile (127667-01-0)

Guidance literature:

With t-BuBrettPhos; [(2-di-tert-butylphosphino-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1’-biphenyl)-2-(2’-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate; caesium carbonate; In 1,4-dioxane; at 80 ℃; for 20h; Sealed tube; Inert atmosphere;

DOI:10.1021/ol401796v

Reference yield:

2-fluoro-5-methoxybenzaldehyde oxime (796120-91-7) → 2-fluoro 5-methoxybenzonitrile (127667-01-0)

Guidance literature:

With triethylamine; trifluoroacetic anhydride; In tetrahydrofuran;

Reference yield:

2-fluoro-5-methoxybenzaldehyde (105728-90-3) → 2-fluoro 5-methoxybenzonitrile (127667-01-0)

Guidance literature:

Multi-step reaction with 2 steps

1: hydroxylamine hydrochloride / ethanol / 4 h / Reflux

2: trifluoroacetic anhydride; triethylamine / tetrahydrofuran

With hydroxylamine hydrochloride; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; ethanol;

upstream raw materials:

copper(I) cyanide

2-chloro-1-fluoro-4-methoxybenzene

methanol

5-Bromo-2-fluoro-benzonitrile

Downstream raw materials:

5-methoxy-2-(4-phenylpiperidino)benzonitrile

6-benzyloxy-quinazoline-2,4-diamine

2,4-diaminoquinazolin-6-yl 2,5-dimethoxybenzoate

5-(benzyloxy)-2-fluorobenzonitrile

Refernces

• 1、 -. "A preparation method of the compound [...] benzene substitution (by machine translation)". . . Retrieved 2018/03/26.
• 2、 Cheung, Chi Wai,Buchwald, Stephen L.. "Mild and general palladium-catalyzed synthesis of methyl aryl ethers enabled by the use of a palladacycle precatalyst". supporting information. p. 3998 - 4001. Retrieved 2013/09/02.