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Merck
CN

N32407

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24897631
EC Number:
207-866-0
Beilstein/REAXYS Number:
1098544
MDL number:
MFCD00082304

Key Documents

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Product Name

Bicyclo[2.2.1]hept-2-ene, 99%

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

SMILES string

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

assay

99%

form

solid

bp

96 °C (lit.)

mp

44-46 °C (lit.)

Quality Level

100

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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.

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.

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Danger

Hazard Classifications

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

Storage Class

4.1B - Flammable solid hazardous materials

wgk

WGK 1

flash_point_f

17.6 °F - closed cup

flash_point_c

-8 °C - closed cup

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ6418
MKCZ6417
MKCZ6348
MKCX1896
MKBQ5062V

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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)
A novel catalytic route to 2-bicyclo [2.2. 1] hept-2-ylidenebicyclo [2.2. 1]-heptane involving CH bond activation of bicyclo [2.2. 1] hept-2-ene
Malinowska, et al.
Journal of Molecular Catalysis. B, Enzymatic, 226, 259-262 (2005)
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)
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)
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.
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