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Merck
CN

B33803

Bicyclo[2.2.1]hepta-2,5-diene

98%

Synonym(s):

2,5-Norbornadiene, NBD

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About This Item

Empirical Formula (Hill Notation):
C7H8
CAS Number:
121-46-0
Molecular Weight:
92.14
UNSPSC Code:
12352300
NACRES:
NA.23
PubChem Substance ID:
24891712
MDL number:
MFCD00082301
Beilstein/REAXYS Number:
506224

Key Documents

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InChI key

SJYNFBVQFBRSIB-KNVOCYPGSA-N

SMILES string

C1[C@H]2C=C[C@@H]1C=C2

InChI

1S/C7H8/c1-2-7-4-3-6(1)5-7/h1-4,6-7H,5H2/t6-,7+

assay

98%

form

liquid

contains

0.05-0.25% BHT as inhibitor

Quality Level

200

bp

89 °C (lit.)

density

0.906 g/mL at 25 °C (lit.)

Related Categories

Application

Intermediate in prostaglandin synthesis.

Features and Benefits

Intermediate in prostaglandin synthesis.

pictograms

Flame
GHS02

signalword

Danger

hcodes

H225,H412

Hazard Classifications

Aquatic Chronic 3 - Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk

WGK 2

flash_point_f

-5.8 °F - closed cup

flash_point_c

-21 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
SHBS4112
SHBQ8972
SHBQ2191
SHBQ6191
SHBP3930

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Bianka Steffens et al.
Planta, 223(3), 604-612 (2005-09-15)
Growth of adventitious roots is induced in deepwater rice (Oryza sativa L.) when plants become submerged. Ethylene which accumulates in flooded plant parts is responsible for root growth induction. Gibberellin (GA) is ineffective on its own but acts in a
Yusuke Kamiyoshihara et al.
Plant physiology, 160(1), 488-497 (2012-07-17)
Perception of the plant hormone ethylene is essential to initiate and advance ripening of climacteric fruits. Since ethylene receptors negatively regulate signaling, the suppression is canceled upon ethylene binding, permitting responses including fruit ripening. Although receptors have autophosphorylation activity, the
Tanner J Kettles et al.
The Journal of organic chemistry, 76(16), 6951-6957 (2011-07-08)
Ruthenium-catalyzed homo Diels-Alder [2 + 2 + 2] cycloadditions between alkynyl phosphonates and bicyclo[2.2.1]hepta-2,5-diene were studied. The observed reactivity was found to be dependent on the presence of the phosphonate moiety. The Ru-catalyzed cycloaddition was compatible with a variety of
Paulo M Nunes et al.
The journal of physical chemistry. A, 113(23), 6524-6530 (2009-05-20)
The energetics of tert-butoxyl radical addition reaction to norbornadiene was investigated by time-resolved photoacoustic calorimetry (TR-PAC). The result, together with the C-O bond dissociation enthalpy (BDE) in the addition product, allowed us to calculate the pi-bond dissociation enthalpy in norbornadiene.
Praew Thansandote et al.
The Journal of organic chemistry, 74(4), 1673-1678 (2009-01-16)
A general procedure for the palladium-catalyzed annulation of substituted haloanilines with norbornadiene gives functionalized indolines in 51-98% yield. These indolines can be rapidly converted to benzenoid-substituted indoles and tricyclic indolines. Extension to the use of substituted halobenzamides gives functionalized isoquinolinones
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