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Key Documents

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:
Molecular Weight:
92.14
Beilstein:
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

Signal Word

Danger

Hazard Statements

Hazard Classifications

Aquatic Chronic 3 - Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

-5.8 °F - closed cup

Flash Point(C)

-21 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Krystyna Oracz et al.
Journal of experimental botany, 59(8), 2241-2251 (2008-05-02)
Freshly harvested sunflower (Helianthus annuus L.) seeds are considered to be dormant because they fail to germinate at relatively low temperatures (10 degrees C). This dormancy results mainly from an embryo dormancy and disappears during dry storage. Although endogenous ethylene
New extensions of the bicyclo[2.2.1]heptane route to prostaglandins.
J S Bindra et al.
Journal of the American Chemical Society, 95(22), 7522-7523 (1973-10-31)
B L Parsons et al.
Plant molecular biology, 17(3), 453-464 (1991-09-01)
Regulation of three cDNA clones (pT52, pT53, and pT58) was analyzed in terms of wounding alone and wounding in conjunction with developmental and environmental cues (ripening, ethylene, and light) in tomato fruit tissue. The pT52-specific transcript level is induced by
S Mita et al.
Plant & cell physiology, 39(11), 1209-1217 (1999-01-19)
An increase in the enzyme activity of 1-aminocyclopropane-1-carboxylic acid (ACC) synthase and ACC oxidase induces the evolution of ethylene during the ripening of passion fruit. A much higher level of ethylene is produced in arils than in seeds or peels
Brenton T Smith et al.
Organic letters, 4(15), 2577-2579 (2002-07-19)
[reaction: see text] The total synthesis of (+)-sparteine was accomplished from 2,5-norbornadione in 15 steps and 15.7% overall yield. The key steps were two ring-expansion reactions, one involving an intramolecular Schmidt reaction and one using a novel variant of the

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