3-Fluoro-4-hydroxybenzoic acid

Base Information

• Chemical Name: 3-Fluoro-4-hydroxybenzoic acid
• CAS No.: 350-29-8
• Molecular Formula: C7H5FO3
• Molecular Weight: 156.113
• Hs Code.: 29163990
• DSSTox Substance ID: DTXSID60188530
• Nikkaji Number: J732.581I
• Wikidata: Q27460292
• Mol file: 350-29-8.mol

Synonyms:3-fluoro-4-hydroxybenzoate

Chemical Property of 3-Fluoro-4-hydroxybenzoic acid

Chemical Property:

• Vapor Pressure: 0.000234mmHg at 25°C
• Melting Point: 154-158 °C(lit. )
• Boiling Point: 311.9 °C at 760 mmHg
• PKA: 4.23±0.10(Predicted)
• Flash Point: 142.4 °C
• PSA: 57.53000
• Density: 1.492 g/cm³
• LogP: 1.22950
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility.: Slightly soluble in water.
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 156.02227218
• Heavy Atom Count: 11
• Complexity: 160

Purity/Quality:

99% ^*data from raw suppliers

3-Fluoro-4-hydroxybenzoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C, Xi
• Hazard Codes: Xi,C
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C(=O)O)F)O
• Uses: 3-Fluoro-4-hydroxybenzoic acid may be used in the preparation of (S)-2-methylbutyl-3-fluoro-4-hydroxy benzoate and 4-n-alkoxy-3-fluorobenzoic acids. It may also be used in the synthesis of bis 3-fluoro-4-hydroxybenzoates, which are potent KCa2/3 pan-inhibitors.

Technology Process of 3-Fluoro-4-hydroxybenzoic acid

There total 19 articles about 3-Fluoro-4-hydroxybenzoic acid 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: 71.0%

(4R,5R)-3,3-Difluoro-4,5-dihydroxy-cyclohex-1-enecarboxylic acid methyl ester (257876-95-2) → 3-fluoro-4-hydroxybenzoic acid (350-29-8) + (4R,5R)-3,3-Difluoro-4,5-dihydroxy-cyclohex-1-enecarboxylic acid

Guidance literature:

With potassium trimethylsilonate; In tetrahydrofuran; at 20 ℃; for 20h;

DOI:10.1016/S0957-4166(99)00447-4

Reference yield: 44.0%

(3,4-difluoro-phenyl)-amide (85118-04-3) → 3-fluoro-4-hydroxybenzamide (1155354-10-1) + 3-fluoro-4-hydroxybenzoic acid (350-29-8)

Guidance literature:

(3,4-difluoro-phenyl)-amide; With potassium trimethylsilonate; In diethylene glycol dimethyl ether; at 120 ℃; for 5h; Inert atmosphere;

With hydrogenchloride; water; In diethylene glycol dimethyl ether; at 20 ℃; Inert atmosphere;

DOI:10.1055/s-0028-1087564

Reference yield:

methylammonium carbonate (15719-64-9,15719-76-3,97762-63-5) → 3-fluoro-4-hydroxybenzoic acid (350-29-8) + 3-fluorosalicylic acid (341-27-5)

Guidance literature:

at 150 - 160 ℃; under 41188.4 Torr;

DOI:10.1021/ja01216a020

upstream raw materials:

3-fluoro-4-hydroxybenzonitrile

methylammonium carbonate

4-hydroxy-benzoic acid

(4R,5R)-3,3-Difluoro-4,5-dihydroxy-cyclohex-1-enecarboxylic acid methyl ester

Downstream raw materials:

4-butoxy-3-fluoro-benzoic acid

methyl 3-fluoro-4-hydroxybenzoate

4-n-hexyloxy-3-fluorobenzoic acid

3-fluoro-4-octyloxybenzoic acid

Refernces

• 1、 Li, Jianqing,Smith, Daniel,Qiao, Jennifer X.,Huang, Stella,Krishnananthan, Subramaniam,Wong, Henry S.,Salvati, Mark E.,Balasubramanian, Balu N.,Chen, Bang-Chi. "Preparation of monofluorophenols via the reaction of difluorobenzene derivatives with potassium trimethylsilanoate". scheme or table. p. 633 - 637. Retrieved 2009/07/01.
• 2、 Chambers, Richard D.,Hutchinson, John,Sparrowhawk, Matthew E.,Sandford, Graham,Moilliet, John S.,Thomson, Julie. "Elemental fluorine Part 12. Fluorination of 1,4-disubstituted aromatic compounds". . p. 169 - 173. Retrieved 2007/10/03.