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B33803

Sigma-Aldrich

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
Beilstein/REAXYS Number:
506224
MDL number:
MFCD00082301
UNSPSC Code:
12352300
PubChem Substance ID:
24891712
NACRES:
NA.23

Quality Level

200

assay

98%

form

liquid

contains

0.05-0.25% BHT as inhibitor

refractive index

n20/D 1.470 (lit.)

bp

89 °C (lit.)

density

0.906 g/mL at 25 °C (lit.)

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+

InChI key

SJYNFBVQFBRSIB-KNVOCYPGSA-N

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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_germany

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBQ8972
SHBQ2191
SHBQ6191
SHBP3930
SHBP0983

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cis,cis-1,3-Cyclooctadiene 98%

Sigma-Aldrich

274100

cis,cis-1,3-Cyclooctadiene

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.
M Victoria Jiménez et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 17(29), 8115-8128 (2011-06-03)
The treatment of [{Rh(μ-SH){P(OPh)(3)}(2)}(2)] with [{M(μ-Cl)(diolef)}(2)] (diolef=diolefin) in the presence of NEt(3) affords the hydrido-sulfido clusters [Rh(3)(μ-H)(μ(3)-S)(2)(diolef){P(OPh)(3)}(4)] (diolef=1,5-cyclooctadiene (cod) for 1, 2,5-norbornadiene (nbd) for 2, and tetrafluorobenzo[5,6]bicyclo[2.2.2]octa-2,5,7-triene (tfb) for 3) and [Rh(2)Ir(μ-H)(μ(3)-S)(2)(cod){P(OPh)(3)}(4)] (4). Cluster 1 can be also obtained by
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
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
Ehud Katz et al.
Journal of experimental botany, 56(415), 1359-1367 (2005-03-16)
Although leaves and other vegetative tissues are generally considered as non-climacteric, citrus leaves show a climacteric system II behaviour after detachment. Upon harvest, young, fully expanded 'Valencia' orange (Citrus sinensis) leaves ( approximately 60-d-old) exhibited two phases of ethylene production.
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