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Key Documents

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:
Molecular Weight:
150.56
Beilstein:
1722943
EC Number:
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22

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

Signal Word

Danger

Hazard Statements

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

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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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)
Tetrahedron Asymmetry, 2, 987-987 (1991)
Burlina, F. et al.
Tetrahedron Letters, 35, 8151-8151 (1994)

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