3-Fluoro-4-hydroxybenzonitrile

Base Information

• Chemical Name: 3-Fluoro-4-hydroxybenzonitrile
• CAS No.: 405-04-9
• Molecular Formula: C7H4FNO
• Molecular Weight: 137.113
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID90382367
• Nikkaji Number: J1.298.337I
• Wikidata: Q72479964
• Mol file: 405-04-9.mol

Synonyms:3-Fluoro-4-hydroxybenzonitrile;405-04-9;4-cyano-2-fluorophenol;Benzonitrile, 3-fluoro-4-hydroxy-;MFCD00215834;3-fluoro-4-hydroxy-benzonitrile;4-cyano-2-fluoro phenol;SCHEMBL200168;4-CYANO-2-FLLUOROPHENOl;DTXSID90382367;DPSSSDFTLVUJDH-UHFFFAOYSA-N;STL450321;AKOS005257724;AC-4071;AM61511;CS-W002523;DS-1510;PS-9100;SB74070;SY014168;3-Fluoro-4-hydroxybenzonitrile, AldrichCPR;A6774;F0638;FT-0632100;EN300-68178

Chemical Property of 3-Fluoro-4-hydroxybenzonitrile

Chemical Property:

• Vapor Pressure: 0.0111mmHg at 25°C
• Melting Point: 133-135 °C
• Refractive Index: 1.558
• Boiling Point: 253.9 °C at 760 mmHg
• PKA: 6.58±0.18(Predicted)
• Flash Point: 107.4 °C
• PSA: 44.02000
• Density: 1.35 g/cm³
• LogP: 1.40298
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: soluble in Methanol
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 137.027691913
• Heavy Atom Count: 10
• Complexity: 162

Purity/Quality:

99% ^*data from raw suppliers

3-Fluoro-4-hydroxybenzonitrile ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C#N)F)O

Technology Process of 3-Fluoro-4-hydroxybenzonitrile

There total 11 articles about 3-Fluoro-4-hydroxybenzonitrile 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: 98.0%

zinc(II) cyanide (557-21-1) + 4-bromo-2-fluorophenol (2105-94-4) → 3-fluoro-4-hydroxybenzonitrile (405-04-9)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 120 ℃; for 2h;

DOI:10.1055/s-0035-1561346

Reference yield: 94.0%

3-fluoro-4-methoxybenzonitrile (331-62-4) → 3-fluoro-4-hydroxybenzonitrile (405-04-9)

Guidance literature:

With boron tribromide; In dichloromethane; at 0 ℃; for 72h; Inert atmosphere; Reflux;

Reference yield: 64.0%

4-cyanophenol (767-00-0) → 3-fluoro-4-hydroxybenzonitrile (405-04-9) + 3,5-difluoro-4-hydroxybenzonitrile (2967-54-6)

Guidance literature:

With formic acid; fluorine; at 10 ℃; for 1.75h;

DOI:10.1016/S0022-1139(99)00238-9

upstream raw materials:

3-fluoro-4-methoxybenzonitrile

4-bromo-2-fluorophenol

4-cyanophenol

2-fluorophenol

Downstream raw materials:

3-fluoro-4-hydroxybenzoic acid

4-(benzyloxy)-3-fluorobenzonitrile

3-fluoro-4-(2-hydroxyethoxy)benzonitrile

2-(4-cyano-2-fluorophenoxy)ethyl toluene-4-sulfonate

Refernces

• 1、 Lalwani, Komal G.,Sudalai, Arumugam. "A Concise Enantioselective Synthesis of (+)-L-733,060 and (+)-T-2328 via Sequential Proline Catalysis". supporting information. p. 1339 - 1343. Retrieved 2016/06/01.
• 2、 -. "New oxabispidine compounds for the treatment of cardiac arrhythmias". Page/Page column 59. . Retrieved 2008/06/13.