5449-26-3

Basic information

• Product Name: 3-hydroxy-2,3-diphenylpropionic acid
• Synonyms: 3-hydroxy-2,3-diphenylpropionic acid;2,3-Diphenyl-3-hydroxypropanoic acid;β-Hydroxy-α-phenylbenzenepropionic acid
• CAS NO: 5449-26-3
• Molecular Formula: C₁₅H₁₄O₃
• Molecular Weight: 242.26986
• EINECS: 226-673-2
• Mol File: 5449-26-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 384.8 °C at 760 mmHg
• Flash Point: 200.7 °C
• Appearance: /
• Density: 1.254 g/cm³
• Vapor Pressure: 4.44E-20mmHg at 25°C
• Refractive Index: 1.626
• CAS DataBase Reference: 3-hydroxy-2,3-diphenylpropionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxy-2,3-diphenylpropionic acid(5449-26-3)
• EPA Substance Registry System: 3-hydroxy-2,3-diphenylpropionic acid(5449-26-3)

Safety Data

• Hazardous Substances Data: 5449-26-3(Hazardous Substances Data)

Usage

General Description

3-hydroxy-2,3-diphenylpropionic acid, also known as DCDPA, is a chemical compound that belongs to the class of phenylpropionic acids. It is a white solid with a molecular formula of C15H14O3 and a molecular weight of 242.27 g/mol. DCDPA is used in various industries including pharmaceuticals, agrochemicals, and polymers. It has anti-inflammatory properties and is commonly used as a chiral building block in the synthesis of pharmaceutical drugs. DCDPA is also used as a stabilizer in polyvinyl chloride (PVC) polymers, helping to improve their thermal stability and weather resistance. Additionally, it is used as an intermediate in the production of fragrance and flavor compounds.

InChI:InChI=1/C29H31ClN2O5S/c1-3-8-22-15-21(16-24(36-2)27(22)37-19-20-9-11-23(30)12-10-20)17-25-28(34)32(29(35)38-25)18-26(33)31-13-6-4-5-7-14-31/h3,9-12,15-17H,1,4-8,13-14,18-19H2,2H3

Upstream product

• 103-30-0 (E)-1,2-diphenyl-ethene 
• 100-52-7 benzaldehyde 
• 103-82-2 phenylacetic acid 
• 15082-44-7 dilithium phenyl acetic acid 
• 31491-21-1 2-phenyl-1,1-bis(trimethylsilyloxy)ethene 
• 920-39-8 isopropylmagnesium bromide 
• 4870-65-9 2-bromophenylacetic acid 
• 95777-19-8 phenylacetic acid magnesium enediolate 

Downstream Products

• 92791-30-5 (2RS,3RS)-2,3-dicyclohexyl-3-hydroxy-propionic acid 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 17226-93-6 (2R,3R)-und (2S,3S)-3-Hydroxy-2,3-diphenylpropansaeure-methylester 
• 645-49-8 cis-stilben 
• 17226-93-6 α-benzenessigsaeure-methylester 
• 82575-09-5 (2R,3S)-3-Hydroxy-2,3-diphenyl-propionatetetramethyl-ammonium; 
• 342804-72-2 3,4-Diphenyl-oxetan-2-one 
• 103-82-2 phenylacetic acid 
• 100-52-7 benzaldehyde 
• 108896-24-8 (2RS,3SR)-3-hydroxy-2,3-diphenyl-propionic acid hydrazide 
• 95135-80-1 (2RS,3RS)-2,3-dicyclohexyl-3-hydroxy-propionic acid-(2-diethylamino-ethyl ester); hydrochloride 
• 14367-02-3 1,2-anti-1,2-Diphenylpropan-1,3-diol 
• 91-48-5 (E)-2,3-diphenylpropenoic acid 

Relevant articles and documents

Organometallic reactions in aqueous media - Bismuth-mediated crossed aldol type reactions

Bismuth metal, upon activation by zinc fluoride, can effect the crossed aldol reaction between α-bromocarbonyl compounds and aldehydes in aqueous media. The reaction was found to be regiospecific and syndiastereoselective.

Kinetics and Mechanism of the Ivanov Reaction: Reaction of Aldehydes and Ketones with Phenylacetic Acit Magnesium Enediolate

Stopped-flow kinetics of the reaction between aldehydes or ketones and the magnesium enediolate of phenylacetic acid in THF are second order at enediolate concentrations -3 M.At concentrations of 10-3 - 3*10-2 M, the formation of a bis(enediolate) requires a more complex kinetic equation.Second-order rate constans are reported for the reaction of the enediolate with a number of aldehydes and ketones at 25 deg C.Entropies of activation for cyclohexanone, benzaldehyde, 2-methylpropanal, and 2,2-dimethylpropanal are positive, and enthalpy-entropy compensation is observed.Ef fects of cycloalkanone ring size and benzaldehyde substituents are small and are ascribable to a transition state with a very small C-C bond order.A two-step mechanism is proposed, with preequilibrium formation of a coordination intermediate which, in some cases, is accompanied by a change in the magnesium coordination number.Effects of alkyl groups on aldehyde and ketone reactivity stem mainly from steric desolvation.

Ketene bis(trimethylsilyl) acetals. Cross-aldol condensation with aldehydes. Stereochemistry of the reaction

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