Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

327956

Sigma-Aldrich

(1R)-(+)-Nopinone

98%

Synonym(s):

6,6-Dimethylbicyclo[3.1.1]heptan-2-one

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C9H14O
CAS Number:
38651-65-9
Molecular Weight:
138.21
MDL number:
MFCD08447116
UNSPSC Code:
12352115
PubChem Substance ID:
24859704
NACRES:
NA.22

Assay

98%

form

liquid

optical activity

[α]20/D +16°, neat

refractive index

n20/D 1.479 (lit.)

bp

209 °C (lit.)

density

0.981 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CC1(C)[C@H]2CCC(=O)[C@@H]1C2

InChI

1S/C9H14O/c1-9(2)6-3-4-8(10)7(9)5-6/h6-7H,3-5H2,1-2H3/t6-,7-/m0/s1

InChI key

XZFDKWMYCUEKSS-BQBZGAKWSA-N

Related Categories

Application

(1R)-(+)-Nopinone may be used in the preparation of a chiral annulated indene derivative, which can be a potentially useful chiral ligand for transition metal complexes in asymmetric transformations. It may also react with secondary amines in cyclohexane to form the corresponding enamines.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

167.0 °F - closed cup

Flash Point(C)

75 °C - closed cup

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Synthesis of (1R)-(+)-nopinone-and (1S)-(-)-verbenone-derived chiral annulated indenes via electrocyclic reactions.
Liu C and Sowa JR.
Tetrahedron Letters, 37(40), 7241-7244 (1996)
Boranes in synthesis-VII. Synthesis of 2-dialkylamino-6, 6-dimethylbicyclo [3.1. 1] heptan-3-ols from (R)-(+)-nopinone. Chiral auxiliaries for the addition of diethylzinc to aromatic aldehydes.
Goralski CT, et al.
Tetrahedron Asymmetry, 8(23), 3863-3871 (1997)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service