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Merck
CN

447056

(S)-(−)-2-Acetoxypropionyl chloride

97%

Synonym(s):

O-Acetyl-L-lactyl chloride, AP-Cl

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About This Item

Linear Formula:
CH3CH(O2CCH3)COCl
CAS Number:
36394-75-9
Molecular Weight:
150.56
Beilstein:
1722943
EC Number:
420-610-4
MDL number:
MFCD00145252
UNSPSC Code:
12352101
PubChem Substance ID:
24868317
NACRES:
NA.22

Key Documents

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Quality Level

100

Assay

97%

form

liquid

optical activity

[α]20/D −31°, c = 4 in chloroform

refractive index

n20/D 1.423 (lit.)

bp

50 °C/5 mmHg (lit.)

density

1.189 g/mL at 25 °C (lit.)

functional group

acyl chloride
ester

SMILES string

C[C@H](OC(C)=O)C(Cl)=O

InChI

1S/C5H7ClO3/c1-3(5(6)8)9-4(2)7/h3H,1-2H3/t3-/m0/s1

InChI key

ALHZEIINTQJLOT-VKHMYHEASA-N

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Application

Frequently used chiral building block. Also used to resolve a bicyclic α-hydroxylactone and to prepare chiral phosphonates used in an enantiomeric excess assay of unprotected amino acids. Useful chiral derivatizing agent.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H314,H317

Hazard Classifications

Acute Tox. 4 Oral - Skin Corr. 1B - Skin Sens. 1

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
STBJ7563
STBH6600
STBF6190V
STBD0194V
S23137V

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Hulst, R. et al.
Tetrahedron, 50, 11721-11721 (1994)
Zhu, J. et al.
The Journal of Organic Chemistry, 60, 6389-6389 (1995)
Kende, A.S. et al.
Journal of the American Chemical Society, 115, 9842-9842 (1993)
Burlina, F. et al.
Tetrahedron Letters, 35, 8151-8151 (1994)
Tetrahedron Asymmetry, 2, 987-987 (1991)

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