2-Fluoro-5-hydroxyphenylacetic acid

Base Information

• Chemical Name: 2-Fluoro-5-hydroxyphenylacetic acid
• CAS No.: 149029-89-0
• Molecular Formula: C₈H₇FO₃
• Molecular Weight: 170.14
• Hs Code.: 2918199890
• European Community (EC) Number: 806-158-4
• DSSTox Substance ID: DTXSID90564227
• Wikidata: Q82448850
• Mol file: 149029-89-0.mol

Synonyms:149029-89-0;2-(2-fluoro-5-hydroxyphenyl)acetic acid;2-FLUORO-5-HYDROXYPHENYLACETIC ACID;SCHEMBL3907433;DTXSID90564227;AKOS006330310;(2-Fluoro-5-hydroxyphenyl)acetic acid;2-(2-fluoro-5-hydroxyphenyl)aceticacid;Benzeneacetic acid, 2-fluoro-5-hydroxy-;E89135;2-fluoro-5-hydroxyphenylacetic acid, AldrichCPR

Chemical Property of 2-Fluoro-5-hydroxyphenylacetic acid

Chemical Property:

• Boiling Point: 362.1±27.0 °C(Predicted)
• PKA: 3.93±0.10(Predicted)
• PSA: 57.53000
• Density: 1.423±0.06 g/cm3(Predicted)
• LogP: 1.15840
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 170.03792224
• Heavy Atom Count: 12
• Complexity: 172

Purity/Quality:

99%min ^*data from raw suppliers

2-Fluoro-5-hydroxyphenylacetic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1O)CC(=O)O)F

Technology Process of 2-Fluoro-5-hydroxyphenylacetic acid

There total 11 articles about 2-Fluoro-5-hydroxyphenylacetic 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: 90.0%

2-(5-(benzyloxy)-2-fluorophenyl)acetic acid (459215-67-9) → 2-(2-fluoro-5-hydroxyphenyl)acetic acid (149029-89-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1016/S0022-1139(02)00013-1

Reference yield:

2-(2-fluoro-5-methoxyphenyl)acetic acid (798563-50-5) → 2-(2-fluoro-5-hydroxyphenyl)acetic acid (149029-89-0)

Guidance literature:

With bromic acid; In water; at 105 ℃; for 5h;

DOI:10.1002/chem.201201895

Reference yield:

methyl 2-amino-3-(2-fluoro-5-hydroxyphenyl)propanoate (103438-84-2) → 2-(2-fluoro-5-hydroxyphenyl)acetic acid (149029-89-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 82 percent / NaBH₄ / tetrahydrofuran / 3.5 h / 20 °C

2: 83 percent / SO₂Cl / 1 h / Heating

3: 95 percent / dimethylsulfoxide / 3 h / 20 °C

4: HCl / diethyl ether / 2 h

5: 320 mg / H₂O / 3 h / 20 °C

6: 99 percent / aq. NaOH / methanol / 4 h / 20 °C

7: 90 percent / H₂ / 10 percent Pd/C / ethanol

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; sulfuryl dichloride; water; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dimethyl sulfoxide;

DOI:10.1016/S0022-1139(02)00013-1

upstream raw materials:

2-(5-(benzyloxy)-2-fluorophenyl)acetic acid

methyl 2-amino-3-(2-fluoro-5-hydroxyphenyl)propanoate

5-benzyloxy-2-fluorobenzaldehyde

2-fluoro-5-benzyloxybenzyl chloride

Downstream raw materials:

2-(5-(benzyloxy)-2-fluorophenyl)acetyl chloride

3-((6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)-4-fluorophenol

2-(5-(benzyloxy)-2-fluorophenyl)-N-(3,4-dimethoxyphenethyl)-N-methylacetamide

1-(5-(benzyloxy)-2-fluorobenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

Refernces

• 1、 Resch, Verena,Lechner, Horst,Schrittwieser, Joerg H.,Wallner, Silvia,Gruber, Karl,MacHeroux, Peter,Kroutil, Wolfgang. "Inverting the regioselectivity of the berberine bridge enzyme by employing customized fluorine-containing substrates". . p. 13173 - 13179. Retrieved 2013/01/15.