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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)

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(-)-(1S, 4R)-Camphanoyl Chloride.
Gerlach H, et al.
Organic Syntheses, 71, 48-48 (1993)
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)
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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