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N32407

Sigma-Aldrich

Bicyclo[2.2.1]hept-2-ene

99%

Synonym(s):

2-Norbornene, Norbornylene

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About This Item

Empirical Formula (Hill Notation):
C7H10
CAS Number:
498-66-8
Molecular Weight:
94.15
Beilstein:
1098544
EC Number:
207-866-0
MDL number:
MFCD00082304
UNSPSC Code:
12352100
PubChem Substance ID:
24897631
NACRES:
NA.22

Assay

99%

form

solid

bp

96 °C (lit.)

mp

44-46 °C (lit.)

SMILES string

C1C[C@H]2C[C@@H]1C=C2

InChI

1S/C7H10/c1-2-7-4-3-6(1)5-7/h1-2,6-7H,3-5H2/t6-,7+

InChI key

JFNLZVQOOSMTJK-KNVOCYPGSA-N

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General description

Bicyclo[2.2.1]hept-2-ene is a cyclic olefin used in the transition metal-catalyzed dimerization of alkene.

The vinylic polymerization of bicyclo[2.2.1]hept-2-ene (norbornene) with Co(II) compounds and the metallocene [η5-(C5Me5)Co-η2-Cl]2, in chlorobenzene activated with methylaluminoxane (MAO) has been reported. Co(II) catalyzed polymerization of bicyclo[2.2.1]hept-2-ene in the presence of ethene has been reported.

Application

Bicyclo[2.2.1]hept-2-ene may be used in the preparation of cis,exo-2,3-diarylsubstituted bicyclo[2.2.1]heptanes or bicyclo [2.2.1] hept-2-enes.

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Description
Pricing

Signal Word

Danger

Hazard Statements

H228,H319,H361,H411

Hazard Classifications

Aquatic Chronic 2 - Eye Irrit. 2 - Flam. Sol. 1 - Repr. 2

Storage Class Code

4.1B - Flammable solid hazardous materials

WGK

WGK 1

Flash Point(F)

17.6 °F - closed cup

Flash Point(C)

-8 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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A new palladium catalyzed synthesis of cis, exo-2, 3-diarylsubstituted bicyclo [2.2. 1] heptanes or bicyclo [2.2. 1] hept-2-enes.
Catellani M, et al.
Tetrahedron, 45(16), 5263-5268 (1989)
Co (II)-catalyzed polymerization of bicyclo [2.2. 1] hept-2-ene in the presence of ethene.
Alt FP and Heitz W.
Acta Polym., 49(9), 477-481 (1998)
Vinylic polymerization of bicyclo [2.2. 1] hept-2-ene by Co (II)-catalysis.
Alt FP and Heitz W.
Macromolecular Chemistry and Physics, 199(9), 1951-1956 (1998)
P Veeraraghavan Ramachandran et al.
Organic letters, 12(20), 4474-4477 (2010-09-21)
The first boron-mediated enolization-aldolization of 3,3,3-trifluoropropionates has been reported. The preparation and application of bis-exo-bicyclo[2.2.1]heptan-2-ylboron triflate as a superior reagent for diastereospecific enolization has also been described.
The Non-planarity of the Bicyclo [2.2. 1] hept-2-ene Double bond. Crystal Structures of Bicyclo [2.2. 2] oct-2-ene, Bicyclo [2.2. 1] hept-2-ene, and Bicyclo [2.1. 1] hex-2-ene Systems
Pinkerton, et al.
Helvetica Chimica Acta, 67, 1136-1153 (1984)
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