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51019-43-3 molecular structure
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(2R)-2-(acetyloxy)-2-phenylacetic acid

ChemBase ID: 148983
Molecular Formular: C10H10O4
Molecular Mass: 194.184
Monoisotopic Mass: 194.0579088
SMILES and InChIs

SMILES:
CC(=O)O[C@H](c1ccccc1)C(=O)O
Canonical SMILES:
OC(=O)[C@@H](c1ccccc1)OC(=O)C
InChI:
InChI=1S/C10H10O4/c1-7(11)14-9(10(12)13)8-5-3-2-4-6-8/h2-6,9H,1H3,(H,12,13)/t9-/m1/s1
InChIKey:
OBCUSTCTKLTMBX-SECBINFHSA-N

Cite this record

CBID:148983 http://www.chembase.cn/molecule-148983.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2R)-2-(acetyloxy)-2-phenylacetic acid
IUPAC Traditional name
(R)-(acetyloxy)(phenyl)acetic acid
Synonyms
(R)-(-)-α-Acetoxyphenylacetic acid
(-)-O-Acetyl-D-mandelic acid
(R)-(-)-O-Acetylmandelic acid
(R)-2-Acetoxy-2-phenylacetic acid
(-)-O-乙酰基-D-扁桃酸
(R)-(-)-α-乙酰氧基苯乙酸
CAS Number
51019-43-3
MDL Number
MFCD00004249
Beilstein Number
2694110
PubChem SID
162243153
24855256
PubChem CID
2733814

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 3.6172729  H Acceptors
H Donor LogD (pH = 5.5) -0.5417314 
LogD (pH = 7.4) -1.9999727  Log P 1.336961 
Molar Refractivity 47.8553 cm3 Polarizability 19.013554 Å3
Polar Surface Area 63.6 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Melting Point
97-99 °C(lit.) expand Show data source
98-101 °C expand Show data source
Optical Rotation
[α]20/D -152.4°, c = 2 in acetone expand Show data source
[α]20/D -155±3°, c = 2% in acetone expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥98.0% (T) expand Show data source
95+% expand Show data source
98% expand Show data source
99% expand Show data source
Grade
purum expand Show data source
Optical Purity
ee: 98% (GLC) expand Show data source
Linear Formula
CH3CO2CH(C6H5)CO2H expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 253030 external link
Packaging
5 g in glass bottle
Application
The (R)- and (S)-isomers are chiral derivatizing agents for NMR determination of enantiomeric purity of α-deuterated carboxylic acids, alcohols, and amines.1
Sigma Aldrich - 00875 external link
Other Notes
Chiral auxiliary used for determining the enantiomeric purity and for the resolution of alcohols1,2; Review 3

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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