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Merck

B33803

Sigma-Aldrich

Bicyclo[2.2.1]hepta-2,5-diene

98%

Sinónimos:

2,5-Norbornadiene, NBD

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About This Item

Fórmula empírica (notación de Hill):
C7H8
Número de CAS:
Peso molecular:
92.14
Beilstein/REAXYS Number:
506224
MDL number:
UNSPSC Code:
12352300
PubChem Substance ID:
NACRES:
NA.23

Quality Level

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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Application

Intermediate in prostaglandin synthesis.

Features and Benefits

Intermediate in prostaglandin synthesis.

pictograms

Flame

signalword

Danger

hcodes

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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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
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.
S Philosoph-Hadas et al.
Plant physiology, 110(1), 301-310 (1996-01-01)
The possible involvement of Ca2+ as a second messenger in snapdragon (Antirrhinum majus L.) shoot gravitropism, as well as the role of ethylene in this bending response, were analyzed in terms of stem curvature and gravity-induced asymmetric ethylene production rates
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.
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

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