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21327

Sigma-Aldrich

(1R,E)-(+)-Camphorquinone 3-oxime

purum, ≥97.0% (sum of enantiomers, HPLC)

Synonym(s):

(1R,E)-(+)-2,3-Bornanedione 3-oxime, anti-(1R)-(+)-Camphorquinone 3-oxime

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About This Item

Empirical Formula (Hill Notation):
C10H15NO2
CAS Number:
31571-14-9
Molecular Weight:
181.23
Beilstein:
3200377
MDL number:
MFCD00074848
UNSPSC Code:
12352000

grade

purum

Assay

≥97.0% (sum of enantiomers, HPLC)

optical activity

[α]20/D +199±3°, c = 1% in ethanol

mp

153-156 °C (lit.)
153-156 °C

storage temp.

2-8°C

SMILES string

[H][C@@]12CC[C@@](C)(C(=O)\C1=N/O)C2(C)C

InChI

1S/C10H15NO2/c1-9(2)6-4-5-10(9,3)8(12)7(6)11-13/h6,13H,4-5H2,1-3H3/b11-7-/t6-,10+/m1/s1

InChI key

YRNPDSREMSMKIY-HAKKTOSXSA-N

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Other Notes

Chiral intermediate; starting material for the synthesis of cis-3-amino-borneol and -isoborneol, versatile chiral auxiliaries

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Certificates of Analysis (COA)

Lot/Batch Number
046007/1
046766/1
46766/1
46007/1

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N. Ikota et al.
Chemical & Pharmaceutical Bulletin, 34, 1050-1050 (1986)
R.A. Chittenden et al.
Journal of the Chemical Society, 49-49 (1970)
T.R. Kelly et al.
Tetrahedron Letters, 25, 39-39 (1984)
Catalytic asymmetric induction. Highly enantioselective addition of dialkylzincs to aldehydes.
M Kitamura et al.
Journal of the American Chemical Society, 108(19), 6071-6072 (1986-09-01)

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