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328227

Sigma-Aldrich

(1S)-(−)-Camphanic acid

98%

Synonym(s):

(−)-Camphanic acid, (1S)-3-Oxo-4,7,7-trimethyl-2-oxabicyclo[2.2.1]heptane-1-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C10H14O4
CAS Number:
13429-83-9
Molecular Weight:
198.22
Beilstein/REAXYS Number:
84570
EC Number:
236-552-6
MDL number:
MFCD00044948
UNSPSC Code:
12352005
PubChem Substance ID:
24859723
NACRES:
NA.22

assay

98%

optical activity

[α]20/D −18°, c = 1 in dioxane

optical purity

ee: 98% (GLC)

mp

201-204 °C (lit.)

SMILES string

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

InChI

1S/C10H14O4/c1-8(2)9(3)4-5-10(8,6(11)12)14-7(9)13/h4-5H2,1-3H3,(H,11,12)/t9-,10+/m0/s1

InChI key

KPWKPGFLZGMMFX-VHSXEESVSA-N

General description

(1S)-(-)-Camphanic acid is commonly used as a chiral auxiliary for the separation of racemates.[1]

Application

(1S)-(-)-Camphanic acid may be used in the preparation of (-)-(1S,4R)-camphanoyl chloride by reacting with thionyl chloride.[2]

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCBW3631
BCBR8155V
BCBP1655V
BCBM8108V
1384490V

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(-)-(1S, 4R)-Camphanoyl Chloride.
Gerlach H, et al.
Organic Syntheses, 48-48 (1993)
Conformational study of a-arylethylamides of (-)-camphanic acid.
Hamersak Z, et al.
Tetrahedron Asymmetry, 9(11), 1891-1897 (1998)

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