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447056

Sigma-Aldrich

(S)-(−)-2-Acetoxypropionyl chloride

97%

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Synonym(s):
O-Acetyl-L-lactyl chloride, AP-Cl
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

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.)

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

WGK

WGK 3

Flash Point(F)

235.4 °F

Flash Point(C)

113 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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

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