3,5-Difluoromandelic acid

Base Information

• Chemical Name: 3,5-Difluoromandelic acid
• CAS No.: 132741-31-2
• Molecular Formula: C8H6F2O3
• Molecular Weight: 188.131
• Hs Code.: 29181990
• European Community (EC) Number: 670-875-7
• DSSTox Substance ID: DTXSID10343273
• Nikkaji Number: J3.016.605A
• Mol file: 132741-31-2.mol

Synonyms:3,5-Difluoromandelic acid;132741-31-2;2-(3,5-difluorophenyl)-2-hydroxyacetic acid;Benzeneacetic acid, 3,5-difluoro-alpha-hydroxy-;MFCD00061300;(S)-3,5-Difluoromandelic acid;3,5-Difluoromandelicacid;3,5-difluoro-mandelic acid;SCHEMBL851355;DTXSID10343273;(r/s)-3,5-difluoromandelic acid;3,5-Difluoromandelic acid, 97%;CS-B0381;racemic 3,5-difluoro-mandelic acid;3,5-difluorophenylhydroxyacetic acid;AKOS006223926;(3,5-Difluorophenyl)hydroxyacetic acid;PS-6482;AC-10451;SY018788;(3,5-Difluoro-phenyl)-hydroxy-acetic acid;(3,5-Difluorophenyl)(hydroxy)acetic acid #;AM20060915;FT-0601473;EN300-1693517;A806491;J-511329;Z1203161883

Chemical Property of 3,5-Difluoromandelic acid

Chemical Property:

• Appearance/Colour: similar to white solid
• Vapor Pressure: 0.000336mmHg at 25°C
• Melting Point: 135-139 °C(lit.)
• Boiling Point: 306.5 °C at 760 mmHg
• PKA: 3.10±0.10(Predicted)
• Flash Point: 139.1 °C
• PSA: 57.53000
• Density: 1.522 g/cm³
• LogP: 1.08280
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 188.02850037
• Heavy Atom Count: 13
• Complexity: 188

Purity/Quality:

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

3,5-Difluoromandelic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(C=C(C=C1F)F)C(C(=O)O)O

Technology Process of 3,5-Difluoromandelic acid

There total 2 articles about 3,5-Difluoromandelic 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: 80.0%

3,5-difluoromandelonitrile (132741-32-3) → S-(+)-3.5-Difluoromandelic Acid (132741-31-2)

Guidance literature:

With hydrogenchloride; at 110 ℃;

DOI:10.1016/j.bmcl.2007.07.062

Reference yield:

3,5-difluorobenzaldehyde (32085-88-4) → S-(+)-3.5-Difluoromandelic Acid (132741-31-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydrogensulfite; water / diethyl ether / 2 h / 20 °C

1.2: 20 °C

2.1: water; hydrogenchloride / 1,4-dioxane / 6 h / Reflux

With hydrogenchloride; water; sodium hydrogensulfite; In 1,4-dioxane; diethyl ether;

DOI:10.1016/j.tetlet.2014.02.095

Reference yield: 97.0%

S-(+)-3.5-Difluoromandelic Acid (132741-31-2) + methanol (67-56-1) → methyl 2-(3,5-difluorophenyl)-2-hydroxyacetate (208259-37-4,209982-92-3)

Guidance literature:

With sulfuric acid; at 60 ℃;

DOI:10.1016/j.bmcl.2018.01.059

upstream raw materials:

3,5-difluoromandelonitrile

3,5-difluorobenzaldehyde

Downstream raw materials:

N-(3,5-difluoromandelyl)-L-alanine tert-butyl ester

methyl 2-(3,5-difluorophenyl)-2-hydroxyacetate

N-(3,5-difluoromandelyl)-L-alanine

methyl N-[(2S)-2-(3,5-difluorophenyl)-2-hydroxylacetyl]-L-alaninate

Refernces

• 1、 Fauq, Abdul H.,Simpson, Katherine,Maharvi, Ghulam M.,Golde, Todd,Das, Pritam. "A multigram chemical synthesis of the γ-secretase inhibitor LY411575 and its diastereoisomers". . p. 6392 - 6395. Retrieved 2008/09/16.