(S)-Mandelic acid

Base Information

• Chemical Name: (S)-Mandelic acid
• CAS No.: 17199-29-0
• Deprecated CAS: 14447-36-0
• Molecular Formula: C8H8O3
• Molecular Weight: 152.15
• Hs Code.: 29181980
• European Community (EC) Number: 241-240-8
• UNII: L0UMW58G3T
• DSSTox Substance ID: DTXSID301014792
• Nikkaji Number: J74.069A
• Wikidata: Q27096314
• Metabolomics Workbench ID: 37375
• ChEMBL ID: CHEMBL58910
• Mol file: 17199-29-0.mol

Synonyms:17199-29-0;(S)-(+)-Mandelic acid;(S)-Mandelic acid;L-mandelic acid;(S)-2-Hydroxy-2-phenylacetic acid;(2S)-2-hydroxy-2-phenylacetic acid;S-(+)-Mandelic acid;L-(+)-MANDELIC ACID;Mandelic acid, (S)-;Mandelic acid, L-;l(+)-mandelic acid;D-2-Hydroxy-2-phenylacetic acid;UNII-L0UMW58G3T;L0UMW58G3T;(S)-(+)-Mandelic acid, 98% e.e.;CHEMBL58910;MLS000069517;CHEBI:32800;(S)-alpha-Hydroxyphenylacetic acid;(S)-alpha-hydroxybenzeneacetic acid;EINECS 241-240-8;Benzeneacetic acid, .alpha.-hydroxy-, (.alpha.S)-;(S)-A-HYDROXYPHENYLACETIC ACID;alpha-Hydroxybenzeneacetic acid, (S)-;SMR000058582;MFCD00004495;Benzeneacetic acid, alpha-hydroxy-, (alphaS)-;EC 241-240-8;(2S)-2-Hydroxy-2-phenylacetic Acid (L-Mandelic Acid);DL-Amygdalic Acid;SMN;(S)-(+)-Mandelic acid, ReagentPlus(R), >=99%;alpha-hydroxybenzeneacetate;Amygdalate;Paramandelate;Phenylglycolate;(+)-L-MANDELIC ACID;s-mandelic acid;DL-Amygdalate;(S)-Hydroxy-phenyl-acetic acid;DL-Mandelate;2-Phenylglycolate;(RS)-Mandelate;(S)-Mandelsaeure;Phenylhydroxyacetate;a-Hydroxy-a-toluate;a-Hydroxyphenylacetate;L-(+)mandelic acid;a-Hydroxybenzeneacetate;Benzeneacetic acid, .alpha.-hydroxy-, (S)-;(S)-L-Mandelic acid;Opera_ID_622;a-Hydroxy-a-toluic acid;(s)(+)-mandelic acid;alpha-Hydroxyphenylacetate;a-Hydroxyphenylacetic acid;Mandelic acid, L-()-;DL-Hydroxy(phenyl)acetate;(+)-(s)-mandelic acid;a-Hydroxybenzeneacetic acid;2-Phenyl-2-hydroxyacetate;(S)-hydroxyphenylaceticacid;alpha-Hydroxy-alpha-toluate;cid_1292;(S)-(+)-Amygdalic Acid;2-Hydroxy-2-phenylethanoate;(S)--(+)--mandelic acid;SCHEMBL255601;cid_439616;BDBM16420;(2s)-hydroxy(phenyl)ethanoic acid;DTXSID301014792;HMS2233J03;CS-D1423;STR07719;AKOS006343440;AKOS007930623;AC-2496;DB03357;Benzeneacetic acid, ?-hydroxy-, (S)-;Benzeneacetic acid, alpha-hydroxy-, (S)-;AM20050159;M0661;(+)-.ALPHA.-HYDROXYPHENYLACETIC ACID;EN300-97210;C01984;MLS-0090889.0001;L-(+)-Mandelic acid, purum, >=98.0% (T);J-520416;Q-201693;Q27096314;(S)-(+)-Mandelic acid, Vetec(TM) reagent grade, 99%;Z1201618616;ATOMOXETINE HYDROCHLORIDE IMPURITY E [ EP IMPURITY]

Chemical Property of (S)-Mandelic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.00012mmHg at 25°C
• Melting Point: 131-134 °C(lit.)
• Refractive Index: 153.5 ° (C=1, H2O)
• Boiling Point: 321.827 °C at 760 mmHg
• PKA: 3.41±0.25(Predicted)
• Flash Point: 162.649 °C
• PSA: 57.53000
• Density: 1.322 g/cm³
• LogP: 0.80460
• Storage Temp.: Refrigerator
• Sensitive.: Light Sensitive
• Solubility.: Methanol (Slightly), Water (Sparingly, Heated)
• Water Solubility.: 100 g/L (25 ºC)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 152.047344113
• Heavy Atom Count: 11
• Complexity: 138

Purity/Quality:

99% ^*data from raw suppliers

(S)-(+)-Mandelic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C1=CC=C(C=C1)C(C(=O)O)O
• Isomeric SMILES: C1=CC=C(C=C1)[C@@H](C(=O)O)O
• General Description: (S)-(+)-Mandelic acid, also known as L-Mandelic acid or (S)-2-hydroxy-2-phenylacetic acid, is a chiral aromatic hydroxy acid derived from the chiral pool and widely used as a starting material in asymmetric synthesis. It serves as a key precursor in the diastereoselective synthesis of β-keto-diphenylphosphine oxides and subsequent reduction to syn- and anti-dihydroxyphosphinates, demonstrating its utility in producing stereochemically defined intermediates. Additionally, it is employed in the preparation of enantiopure 2-(hydroxyalkyl)pyridine derivatives, highlighting its role in asymmetric catalysis and the synthesis of chiral ligands. Its versatility in organic transformations, including esterification, lithiation, and reduction reactions, underscores its importance in stereoselective synthetic methodologies.

Technology Process of (S)-Mandelic acid

There total 393 articles about (S)-Mandelic 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: 75.0%

[bis(acetoxy)iodo]benzene (3240-34-4) + Ethyl 2-phenylethanoate (101-97-3) → MANDELIC ACID (611-71-2,611-72-3,17199-29-0,90-64-2)

Guidance literature:

With potassium hydroxide; In water; benzene;

DOI:10.1016/S0040-4039(01)90541-6

Reference yield: 75.0%

C17H18N2O5S (85515-89-5) → MANDELIC ACID (611-71-2,611-72-3,17199-29-0,90-64-2)

Guidance literature:

With copper dichloride; In methanol; water; for 20h; Heating;

Reference yield: 50.0%

[bis(acetoxy)iodo]benzene (3240-34-4) + benzeneacetic acid methyl ester (101-41-7) → MANDELIC ACID (611-71-2,611-72-3,17199-29-0,90-64-2)

Guidance literature:

With potassium hydroxide; In water; benzene;

DOI:10.1016/S0040-4039(01)90541-6

upstream raw materials:

2-(morpholin-4-yl)ethanethiol

2,2-dihydroxy-1-phenyl-ethanone

tetrachloromethane

1-Phenyl-2-propen-1-ol

Downstream raw materials:

2-methyl-5-phenyl-[1,3]dioxolan-4-one

mandelic acid-tetrahydrofurfuryl ester

N-(5-methyl-[2]pyridyl)-mandelamide

N-(4-methyl-[2]pyridyl)-mandelamide

Refernces

A practical synthesis of syn- and anti-α,β-dihydroxyphosphinates via diastereoselective reduction of α-phosphinoyl ketones

10.1016/j.tetasy.2007.12.016

The research presents a new methodology for the diastereoselective synthesis of syn- and anti-diphenylphosphinoyl-1,2-diols through the reduction of β-keto-diphenylphosphine oxide derived from (S)-mandelic acid. Key chemicals involved include (S)-mandelic acid as the starting material, thionyl chloride and tert-butyldimethylsilyl chloride for the synthesis of the intermediate methyl ester, and lithium diphenylphosphine oxide for the formation of the β-keto-diphenylphosphine oxide. The reductions were performed using various reagents such as NaBH4, DIBAL-H, catecholborane, LiBH4, and Zn(BH4)2, with the latter two showing high diastereoselectivity for the desired products. The study also involved the use of n-tetrabutylammonium fluoride (TBAF) for deprotection and 2,2-dimethoxypropane for the formation of acetonides. The research highlights the role of these chemicals in achieving high yields and excellent diastereoselectivity, contributing to the field of asymmetric synthesis.

Preparation of chiral enantiopure 2-(hydroxyalkyl)pyridine derivatives. Use of the chiral pool

10.1039/b000269k

The research focuses on the preparation of chiral enantiopure 2-(hydroxyalkyl)pyridine derivatives, which are valuable in asymmetric catalysis. The experiments utilize naturally occurring chiral compounds such as D-mannitol, L-lactic acid, and L-mandelic acid as starting materials. Key reactants include 2-lithiopyridine, (R)-2,3-O-isopropylideneglyceraldehyde, and various esters derived from the aforementioned chiral compounds. The methodology involves the synthesis of 2-(1-hydroxyalkyl)pyridines and 6,6'-bis(1-hydroxyalkyl)-2,2'-bipyridines through a series of reactions, including lithiation, reduction with sodium borohydride, and nickel-catalyzed coupling. The analyses used to determine the success of the syntheses and the structures of the products encompass NMR spectroscopy (both 1H and 13C), optical rotation measurements, and in some cases, the preparation and analysis of Mosher's esters to determine the absolute configurations of the synthesized chiral alcohols.

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