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447056

Sigma-Aldrich

(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/REAXYS Number:
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

signalword

Danger

Hazard Classifications

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

wgk_germany

WGK 3

flash_point_f

235.4 °F

flash_point_c

113 °C

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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L1750

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

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