13113-71-8

Basic information

• Product Name: (S)-(+)-2-HYDROXY-2-PHENYLPROPIONIC ACID
• Synonyms: (S)-(+)-2-HYDROXY-2-PHENYLPROPIONIC ACID;(S)-2-HYDROXY-2-METHYLBENZENEACETIC ACID;(S)-(+)-2-Phenyllacticacid;(S)-(+)-Atrolacticacid;(S)-(+)-2-HYDROXY-2-PHENYLPROPIONIC ACID 99%;(S)-(+)-2-Hydroxy-2-phenylpropionic acid, 98+%;(+)-Atrolactate;(+)-α-Methyl-L-mandelic acid
• CAS NO: 13113-71-8
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.17
• EINECS: 243-726-5
• Mol File: 13113-71-8.mol
• Article Data: 23

Chemical Properties

• Melting Point: 112-115 °C
• Boiling Point: 254.38°C (rough estimate)
• Flash Point: 165.9 °C
• Appearance: white fluffy fine crystalline powder
• Density: 1.1708 (rough estimate)
• Vapor Pressure: 8.3E-05mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• PKA: 3.53±0.25(Predicted)
• BRN: 2208529
• CAS DataBase Reference: (S)-(+)-2-HYDROXY-2-PHENYLPROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-2-HYDROXY-2-PHENYLPROPIONIC ACID(13113-71-8)
• EPA Substance Registry System: (S)-(+)-2-HYDROXY-2-PHENYLPROPIONIC ACID(13113-71-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 24/25-26
• Hazardous Substances Data: 13113-71-8(Hazardous Substances Data)

Usage

Chemical Properties

white fluffy fine crystalline powder

Purification Methods

Recrystallise them from *C6H6 or *C6H6/pet-ether and dry them in a vacuum. [McKenzie & Clough J Chem Soc 1019 1910, Meyers & Slade Synth Commun 6 6011972, Beilstein 10 II 157, 10 III 560, 10 IV 657.]

InChI:InChI=1/C9H10O3/c1-9(12,8(10)11)7-5-3-2-4-6-7/h2-6,12H,1H3,(H,10,11)/t9-/m0/s1

Upstream product

• 63007-15-8 trans-(4S,5S)-2-benzoyl-4-(methoxymethyl)-5-phenyl-2-oxazoline 
• 75-16-1 methylmagnesium bromide 
• 266694-57-9 Phenyl-((2R,4aR,7R,8aR)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-methanone 
• 89556-32-1 2-((1'S)-1'-hydroxy-1'-phenylethyl)hexahydro-4,4,7-trimethyl-4H-1,3-benzoxathiin 
• 25726-04-9 phenylglyoxylyl chloride 
• 81036-97-7 (2S,5S)-2-tert-butyl-5-phenyl-1,3-dioxolan-4-one 
• 124-38-9 carbon dioxide 
• 98-86-2 acetophenone 
• 53651-68-6 pyruvic acid menthyl ester 
• 515-30-0 2-phenyllactic acid 
• 4361-50-6 2-hydroxy-2-phenyl-propionaldehyde 
• 67-56-1 methanol 
• 1158775-11-1 (S)-(-)-2-phenyl-2-hydroxy-N-(2-trifluoromethylphenyl)propionamide 
• 77383-14-3 (S)-2-Isopropyl-5-phenyl-[1,3]dioxolan-4-one 

Downstream Products

• 29916-14-1 (S)-ethyl 2-hydroxy-2-phenylpropanoate 
• 13448-81-2 (S)-methyl atrolactate 
• 56787-06-5 (S)-(+)-2-Hydroxy-2-phenyl-3-pentanon 
• 1219630-41-7 (2S,2’S)-N,N’-(1,2-ethynediyldi-4,1-phenylene)bis(1-((2S)-2-hydroxy-2-phenylpropanoyl)-2-pyrrolidinecarboxamide) 
• 1115954-85-2 benzyl (S)-(-)-2-hydroxy-2-phenylpropanoate 
• 1109269-07-9 (2S)-2-(2-bromopropanoyloxy)-2-phenylpropanonic acid 
• 1109268-82-7 (3S,6R)-6-isopropyl-3-methyl-3-phenyl-1,4-dioxane-2,5-dione 

Relevant articles and documents

Optical Resolution of 2-Amino-1,2-diphenylethanol by Preferential Crystallization and Its Utilization in Fractional Crystallization and Enantioselective Reduction of Prochiral Ketones

(-/+)-erythro-2-Amino-1,2-diphenylethanol prepared from benzoin oxime by catalytic reduction was successfully resolved into pair of optically active forms by preferential crystallization.The optically active amino alcohol was found to be useful as a basic resolving agent for optical resolution of tartaric acid, trans-2,3-oxiranedicarboxylic acid, 2-hydroxy-2-phenylpropionic acid, and 3-endo-benzamido-5-norbornene-2-endo-carboxylic acid.Chiral hydrides prepared from lithium aluminium hydride and optical active threo- and erythro-2-amino-1,2-diphenylethanol derivatives were applied to the enantioface differentiating reduction of prochiral ketones to give the corresponding optically active alcohols in the 26-72percent optical purities.

Improved practical asymmetric synthesis of α-alkylmandelic acids utilizing highly diastereoselective alkylation of 5-aryl-2-(1-naphthyl)-1,3- dioxolan-4-ones

A practical method for the synthesis of optically pure α- alkylmandelic acids 1 is described. The present improved robust method involved two reactions: a mild, convenient, stereo-selective preparation of chiral cis-5-aryl-2-(1-naphthyl)-1,3-dioxolan-4-ones, 9a-c, and highly diastereoselective alkylation of 9a-c, followed by the hydrolysis.

Evaluation of dalbavancin as chiral selector for HPLC and comparison with teicoplanin-based chiral stationary phases

Dalbavancin is a new compound of the macrocyclic glycopeptide family. It was covalently linked to 5 lm silica particles using two different binding chemistries. Approximately 250 racemates including (a) heterocyclic compounds, (b) chiral acids, (c) chiral amines, (d) chiral alcohols, (e) chiral sulfoxides and sulfilimines, (f) amino acids and amino acid derivatives, and (g) other chiral compounds were tested on the two new chiral stationary phases (CSPs) using three different mobile phases. As dalbavancin is structurally related to teicoplanin, the same set of chiral compounds was screened on two commercially available teicoplanin CSPs for comparison. The dalbavancin CSPs were able to separate some enantiomers that were not separated by the teicoplanin CSPs and also showed improved separations for many racemates. However, there were other compounds only separated or better separated on teicoplanin CSPs. Therefore, the dalbavancin CSPs are complementary to the teicoplanin CSPs.

Me2Zn-Mediated Catalytic Enantio- and Diastereoselective Addition of TosMIC to Ketones

The first catalytic asymmetric addition of TosMIC to unactivated ketones is presented. A combination of Me2Zn and aminoalcohol catalyst promoted the aldol addition/cyclization reaction to render oxazolines possessing a fully substituted stereocenter with excellent yields (up to 92 %), high enantioselectivities (up to 96 %), and complete diastereoselectivity. The chiral oxazolines were then used to give, after a straightforward acid hydrolysis, enantioenriched building blocks bearing tertiary alcohol motifs such as hydroxylaldehydes, hydroxylacids, and hydroxylesters without racemization.