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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:
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.

Application

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

Storage Class Code

13 - Non Combustible Solids

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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(-)-(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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