(R)-Benzyl 2-hydroxy-2-phenylacetate

Basic Information

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CAS Number

97415-09-3

Molecular Formula

C15H14O3

Molecular Weight

242.27 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Esters

Basic Chemical Raw Materials Organic Chemicals Ethers

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Surfactants Anionic Surfactants

Basic Physical Properties

Physical State

Powder

Melting Point

104-107 °C

Boiling Point

387 ºC

Density

1.204

Flash Point

163 ºC

Refractive Index

-34 ° (C=1, CH3CN)

Specific Rotation

-55 ° (c=1, CHCl3)

SMILES

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C1=CC=C(C=C1)COC(=O)C(C2=CC=CC=C2)O

InChI

InChI=1S/C15H14O3/c16-14(13-9-5-2-6-10-13)15(17)18-11-12-7-3-1-4-8-12/h1-10,14,16H,11H2

InChIKey

JFKWZVQEMSKSBU-UHFFFAOYSA-N

LogP

2.463400000000001

Topological Polar Surface Area

46.53 Å²

Hydrogen Bond Donor/Acceptor

1 / 3

Complexity

253

Safety Information

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Hazard Statement

H315 Causes skin irritation
Skin corrosion/irritation

H319 Causes serious eye irritation
Serious eye damage/eye irritation

H335 May cause respiratory irritation
Specific target organ toxicity, single exposure; Respiratory tract irritation

Synonyms & References

English

(R)-Benzyl 2-hydroxy-2-phenylacetate
Benzyl D-(-)-Mandelate
(R)-benzyl Mandelate
Benzyl (R)-(?)-mandelate
C15H14O3
D-(-)-Mandelic Acid Benzyl Ester
Benzyl D-mandelate
Benzyl (R)-(-)-mandelate
benzyl (2R)-2-hydroxy-2-phenylacetate
D-Mandelic Acid Benzyl Ester
(-)-Mandelic acid benzyl ester
JFKWZVQEMSKSBU-CQSZACIVSA-N
HMS3650E03
(R)-Hydroxyphenylacetic acid benzyl ester
AB0031301
M1354
X4324
ST24026442
HYDROXY-PHENYL-ACETIC ACID BENZYL ESTER
Benzeneacetic acid, α-hydroxy-, phenylmethyl ester, (R)- (ZCI)
(R)-Benzyl mandelate
(R)-Benzyl2-hydroxy-2-phenylacetate
D
F16500
97415-09-3
SCHEMBL2231648
DTXSID50357490
MFCD00674031
SR-01000946772
Benzyl (2R)-hydroxy(phenyl)acetate
Benzeneacetic acid,a-hydroxy-,phenylmethyl ester,(ar)-

MDL Number

MFCD00674031

Customs Code

29181990

FAQ

What are the physical and chemical properties of (R)-Benzyl 2-hydroxy-2-phenylacetate (CAS: 97415-09-3)?

(R)-Benzyl 2-hydroxy-2-phenylacetate is a white crystalline solid with a molecular weight of approximately 226.27 g/mol. It has a pKa of about 7.0 and dissolves poorly in water but has good solubility in organic solvents such as ethanol and acetone. The compound exhibits moderate reactivity, particularly towards nucleophilic substitution reactions and hydrogenation. It is stable under normal conditions but may undergo hydrolysis in basic media.

How is (R)-Benzyl 2-hydroxy-2-phenylacetate (CAS: 97415-09-3) typically synthesized?

(R)-Benzyl 2-hydroxy-2-phenylacetate can be synthesized via a kinetic resolution of racemic benzyl 2-phenylacetate using chiral stationary phases or via asymmetric synthesis using chiral auxiliaries. The reaction conditions typically include the use of a chiral catalyst and a base like sodium hydroxide, leading to high enantiomeric excess and good yield.

What industries use (R)-Benzyl 2-hydroxy-2-phenylacetate (CAS: 97415-09-3)?

(R)-Benzyl 2-hydroxy-2-phenylacetate finds applications in the pharmaceutical industry as a chiral building block for the synthesis of drug candidates. It is also utilized in the polymer industry for the modification of polymer properties and in the sensor industry for developing chiral sensors due to its inherent chirality.

What precautions should be taken when handling (R)-Benzyl 2-hydroxy-2-phenylacetate (CAS: 97415-09-3)?

When handling (R)-Benzyl 2-hydroxy-2-phenylacetate, wear appropriate personal protective equipment including gloves, goggles, and a lab coat. Work in a well-ventilated area or fume hood to avoid inhalation of vapors. Avoid contact with skin and eyes. In case of a spill, use appropriate absorbents and dispose of them according to local regulations. Always consult the Safety Data Sheet (SDS) for detailed handling and safety information.