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226173

Sigma-Aldrich

(1S)-(−)-Camphanic chloride

98%

Synonym(s):

(−)-Camphanoyl chloride, (1S)-3-Oxo-4,7,7-trimethyl-2-oxabicyclo[2.2.1]heptane-1-carbonyl chloride

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About This Item

Linear Formula:
C10H13O3Cl
CAS Number:
39637-74-6
Molecular Weight:
216.66
Beilstein:
3590860
EC Number:
254-552-4
MDL number:
MFCD00135626
UNSPSC Code:
12352005
PubChem Substance ID:
24853548
NACRES:
NA.22

Assay

98%

optical activity

[α]23/D −18±1°, c = 2 in dioxane

mp

71-73 °C (lit.)

storage temp.

2-8°C

SMILES string

CC1(C)[C@@]2(C)CC[C@@]1(OC2=O)C(Cl)=O

InChI

1S/C10H13ClO3/c1-8(2)9(3)4-5-10(8,6(11)12)14-7(9)13/h4-5H2,1-3H3/t9-,10+/m0/s1

InChI key

PAXWODJTHKJQDZ-VHSXEESVSA-N

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General description

(1S)-(-)-Camphanic chloride is a chiral derivatizing agent. It can be prepared by reacting (-)-(1S,4R)-camphanic acid with thionyl chloride.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Chiral separations of ?-blocking drug substances using derivatization with chiral reagents and normal-phase high-performance liquid chromatography.
Olsen L, et al.
Journal of Chromatography A, 636(2), 231-241 (1993)
(-)-(1S, 4R)-Camphanoyl Chloride.
Gerlach H, et al.
Organic Syntheses, 71, 48-48 (1993)
The determination of the absolute configurations of diastereomers of (S)-camphanoyl 3-hydroxy-5-oxohexanoic acid derivatives by X-ray crystallography.
Kwai-Ming Cheung et al.
Angewandte Chemie (International ed. in English), 41(7), 1198-1202 (2002-12-20)
M Ruud-Christensen et al.
Journal of chromatography, 491(2), 355-366 (1989-07-21)
A reversed-phase high-performance liquid chromatographic assay has been developed for determination of (R)-(--)-and (S)-(+)-proxyphylline in human plasma. The procedure is based on liquid-solid extraction of proxyphylline from plasma followed by derivatization of extracted proxyphylline with (--)-camphanoyl chloride. The ratio between

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