17199-29-0

Basic information

• Product Name: (S)-(+)-Mandelic acid
• Synonyms: (s)-(+)-mandelic;(s)-benzeneaceticaci;(S)-Hydroxyphenylaceticacid;Benzeneaceticacid,alpha-hydroxy-,(S)-;L-mandelate;L-ALPHA-HYDROXYPHENYLACETIC ACID;L-A-HYDROXYPHENYLACETIC ACID;L-AMYGDALIC ACID
• CAS NO: 17199-29-0
• Molecular Formula: C₈H₈O₃
• Molecular Weight: 152.15
• EINECS: 241-240-8
• Product Categories: FINE Chemical & INTERMEDIATES;Chiral Compounds;Aromatic Phenylacetic Acids and Derivatives;chiral;Analytical Chemistry;Carboxylic Acids (Chiral);Chiral Building Blocks;e.e. / Absolute Configuration Determination (NMR);Enantiomer Excess & Absolute Configuration Determination;for Resolution of Bases;Optical Resolution;Synthetic Organic Chemistry;Chiral Compound;Activators;Cosmetic
• Mol File: 17199-29-0.mol

Chemical Properties

• Melting Point: 131-134 °C(lit.)
• Boiling Point: 234.6°C (rough estimate)
• Flash Point: 162.649 °C
• Appearance: White to beige-brown/Crystalline Powder
• Density: 1.3410
• Vapor Pressure: 0.00012mmHg at 25°C
• Refractive Index: 153.5 ° (C=1, H2O)
• Storage Temp.: Refrigerator
• Solubility: Methanol (Slightly), Water (Sparingly, Heated)
• PKA: 3.41±0.25(Predicted)
• Water Solubility: 100 g/L (25 ºC)
• Sensitive: Light Sensitive
• Stability: Stable, but light sensitive. Combustible. Incompatible with strong bases, strong oxidizing agents, strong reducing agents.
• BRN: 2208678
• CAS DataBase Reference: (S)-(+)-Mandelic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-Mandelic acid(17199-29-0)
• EPA Substance Registry System: (S)-(+)-Mandelic acid(17199-29-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26-36
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 17199-29-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-(+)-Mandelic acid is used as a key intermediate for the synthesis of various pharmaceuticals. It plays a crucial role in the development of new drugs and the improvement of existing ones, contributing to the advancement of medical treatments.
Used in Chiral Synthesis:
(S)-(+)-Mandelic acid is used as a versatile reagent in the resolution of racemates, which are mixtures of two enantiomers that are mirror images of each other. This process is essential in the production of enantiomerically pure compounds, which are often required for the desired biological activity of a drug.
Used in Organic Chemistry:
(S)-(+)-Mandelic acid is employed as a reagent in the preparation of amides, which are important functional groups in organic chemistry. Amides are found in various natural products, pharmaceuticals, and agrochemicals, making (S)-(+)-Mandelic acid a valuable compound in the synthesis of these molecules.
Used in Antimicrobial Applications:
(S)-(+)-Mandelic acid is used as an antiseptic, particularly in the treatment of urinary tract infections. Its antimicrobial properties help to inhibit the growth of harmful bacteria, promoting overall health and well-being.

Flammability and Explosibility

Notclassified

Purification Methods

Purify the mandelic acids by recrystallisation from H2O, *C6H6 or CHCl3. [Roger J Chem Soc 2168 1932,Jamison & Turner J Chem Soc 611 1942.] They have solubilities in H2O of ca 11% at 25o. [Banks & Davies J Chem Soc 73 1938.] The S-benzylisothiuronium salts has m 180o (from H2O) and [] D 25 (+) and (-) 57o (c20, EtOH) [El Masri et al. Biochem J 68 199 1958]. [Beilstein 10 IV 564.]

InChI:InChI=1/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/p-1/t7-/m0/s1

Upstream product

• 4542-46-5 2-(morpholin-4-yl)ethanethiol 
• 1075-06-5 2,2-dihydroxy-1-phenyl-ethanone 
• 56-23-5 tetrachloromethane 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 4870-65-9 2-bromophenylacetic acid 
• 1496-75-9 Ethanesulfenyl chloride 
• 3282-32-4 2-diazo-acetophenone 
• 64-17-5 ethanol 
• 60686-79-5 (R)-2-bromo-2-phenylacetic acid 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 135762-75-3 5-phenyl-5-hydroxy-2,4-pentanedione 
• 1074-12-0 phenylglyoxal hydrate 
• 142-71-2 copper diacetate 
• 2648-61-5 2,2-dichloroacetophenone 

Downstream Products

• 6454-27-9 2-methyl-5-phenyl-[1,3]dioxolan-4-one 
• 66267-71-8 mandelic acid-tetrahydrofurfuryl ester 
• 1759-00-8 2-hydroxy-2-phenyl-N-(pyridin-2-yl)acetamide 
• 1026-26-2 N-(5-methyl-[2]pyridyl)-mandelamide 
• 3373-20-4 N-(4-methyl-[2]pyridyl)-mandelamide 
• 1026-27-3 N-(5-chloro-[2]pyridyl)-mandelamide 
• 1086-87-9 N-(5-bromo-[2]pyridyl)-mandelamide 
• 62173-99-3 benzyl 2-hydroxy-2-phenylacetate 
• 21210-43-5 (S)-Methyl mandelate 
• 5413-58-1 propyl 2-hydroxy-2-phenylacetate 
• 66267-66-1 mandelic acid-(2-ethoxy-ethyl ester) 
• 29071-09-8 2-acetoxy-2-phenylacetic acid 
• 50341-27-0 4,7-dimethyl-3-phenyl-3H-benzofuran-2-one 
• 39531-27-6 5,6-dimethyl-3-phenyl-3H-benzofuran-2-one 

Relevant articles and documents

Normal Pressure Double Carbonylation of Aryl Halides Using Cobalt(II) Chloride in the Presence of either Sodium Sulfide or Sodium Borohydride

Tetracarbonylcobaltate ion generated by a treatment of cobalt(II) chloride with either sodium sulfide or sodium borohydride under a normal pressure of carbon monoxide was capable of catalyzing carbonylation of aryl halides in the presence of calcium hydroxide and methyl iodide to give arylglyoxylic acids in good selectivity.

Ultrasonically-promoted synthesis of mandelic acid by phase transfer catalysis in an ionic liquid

An efficient and facile process to synthesize mandelic acid through phase transfer catalysis (PTC; also phase transfer catalyst) using ultrasound in an ionic liquid has been developed. Mandelic acid was synthesized from benzaldehyde with chloroform in an

A combination of phase transfer catalyst and ultrasonic irradiation promotes synthesis of mandelic acid

A combination of phase transfer catalyst and ultrasonic irradiation used to promotes synthesis of mandelic acid from benzaldehyde with chloroform. The main advantages of this method are that the reaction time is much shorter and the yield is higher than t

Effect of the concentration of organic modifier in an aqueous-ethanol mobile phase on the chromatographic retention and thermodynamic characteristics of the adsorption of enantiomers of α-phenylcarboxylic acids on silica gel with immobilized eremomycin antibiotic

Regularities of the chromatographic retention and thermodynamics of the adsorption of enantiomers of α-phenylcarboxylic acids on a chiral stationary phase with immobilized macrocyclic antibiotic eremomycin under conditions of reversed-phase liquid chromatography with aqueous-ethanol mobile phases are studied. Relationships between the retention characteristics of the acids, the enantioselectivity of their separation, and the concentration of organic modifier in the mobile phase are found. It is shown that the sterical structure of substituents on the chiral atoms of the acids affect the mechanism of retention. The compensation effect in the studied systems is considered.

Improved solution- and solid-phase preparation of hydroxamic acids from esters

The addition of small amounts of solid KCN to solution and solid-phase esters in THF/MeOH/50% aqueous NH2OH increases the efficiency of their transformation to the corresponding hydroxamic acids.

Solvent-induced reversed stereoselectivity in reciprocal resolutions of mandelic acid and erythro -2-amino-1,2-diphenylethanol

Solvent-induced chirality switching in reciprocal optical resolution between mandelic acid (1) and erythro-2-amino-1,2-diphenylethanol (2) has been demonstrated. The stereochemistry of the deposited salts was controlled by changing the crystallization solvent from 1-PrOH or 1-BuOH to 1,4-dioxane. It was revealed from 1H NMR spectra, thermogravimetric analysis, and X-ray crystallography of the salts that an equimolar amount of the crystallization solvent was incorporated in each diastereomeric salt. On the basis of the crystal structures, it was found that both the hydrogen-bonding ability and the size of the solvent molecule played an important role. Differences in the formed hydrogen-bonding networks (columnar or sheetlike structure) and their packing manner were found to be crucial for the reversed stereoselectivity. Furthermore, pseudopolymorphic salt crystals that incorporated 1,4-dioxane were obtained during the enantioseparation of racemic 2, and their solid-state properties were examined by measurement of their IR spectra. This solvent-induced dual stereocontrol technique was successfully applied to the successive resolution process, eliminating the need to change the resolving agent for access to both enantiomers of 1 and 2.

Effect of Alkaloid Concentration in Asymmetric Electrosynthesis

The preferred absolute configurations of mandelic acid and C-phenylglycine, obtained from the asymmetric electroreduction of phenylglyoxylic acid and the related oxime in the presence of adsorbed strychnine acting as a chiral inductor, depend on the alkaloid concentration.

Medium effects on Zwitterionic-biradicaloid intermediates from two phenyl-α-oxoamides. Irradiations in fluid and solid protic media, neat solid phases, and the solid, smectic and isotropic phases of a completely saturated phosphonium salt at different tem

The photochemical processes of two N,N-dialkyl phenyl-α-oxoamides, N,N-diisopropyl phenyl-α-oxoamide (1) and N,N-dibenzyl phenyl-α-oxoamide (2), are investigated at different temperatures in methanol and ethylene glycol (to probe the influences of H-bondi

Light-assisted preparation of a cyclodextrin-based chiral stationary phase and its separation performance in liquid chromatography

A cyclodextrin-based chiral stationary phase (CD-CSP) is one of the most widely applied CSPs due to its powerful enantioseparation ability. In this study, a facile method was developed to prepare a CD-CSP via carboxyl methyl β-cyclodextrin (CD-COOH) and diazo-resin (DR). Monodisperse silica particles were synthesized using a modified St?ber method. Then DR and CD-COOH were coated on the silica particles via ionic bonding successively and UV light was finally used to couple silica, DR and CD-COOH and the ionic bonds turned into covalent bonds. The resultant CD-DR silica particles were characterized using Fourier transform infrared spectroscopy (FT-IR), thermo-gravimetric analysis (TGA) and scanning electron microscopy (SEM). The enantioselectivity of the CD@SiO2 particles was explored in reversed phase high-performance liquid chromatography (RP-HPLC). Baseline separation of chiral drugs was achieved and the effects of separation parameters (elution mode, buffer and analyte mass) were investigated in detail. By using water soluble non-toxic DR to replace a highly toxic and moisture sensitive silane agent to modify silica microspheres, this light-assisted strategy can provide a green and effective technique to manufacture packing materials for enantioseparation applications.

Biocatalysis for sustainable organic synthesis

Biocatalysis offers mild reaction conditions, an environmentally attractive catalyst-solvent system, high activities, and chemo-, regio-, and stereoselectivities, while the use of enzymes generally circumvents the need for functional group activation and