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2,5-Norbornadiene

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2,5-Norbornadiene Basic information

Product Name:
2,5-Norbornadiene
Synonyms:
  • Bicyclo[2.2.1]hepta-2,5-diene, 97%, stabilized with 0.05 - 0.25% BHT, 97%
  • (1s,4s)-Bbicyclo[2.2.1]hepta-2,5-diene
  • Bicyclo[2.2.1]hepta-2,5-diene 98%
  • 2,5-Norbornadiene 
  • Bicyclo[2.2.1]hepta-2,5-diene, stabilized with 0.05 - 0.25% BHT
  • Bicycol(2.2.1)hepta-2.5-diene (2.5-norbornadiene)
  • Bicyclo[2.2.1]hepta-2,5-diene, stabilized
  • Bicycloheptadiene
CAS:
121-46-0
MF:
C7H8
MW:
92.14
EINECS:
204-472-0
Product Categories:
  • Norbornene Derivatives
  • Pharmaceutical intermediate
  • Azobenzene, etc. (Photochromic Compounds)
  • Functional Materials
  • Photochromic Compounds
  • Alicyclic/Etch-Resistant Monomers
  • Alkenes
  • Building Blocks
  • Chemical Synthesis
  • Contact Printing
  • Cyclic
  • Lithography Monomers
  • Materials Science
  • Micro/NanoElectronics
  • Organic Building Blocks
  • Self Assembly &amp
Mol File:
121-46-0.mol
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2,5-Norbornadiene Chemical Properties

Melting point:
-20--19°C
Boiling point:
89 °C(lit.)
Density 
0.906 g/mL at 25 °C(lit.)
vapor pressure 
69 hPa (20 °C)
refractive index 
n20/D 1.470(lit.)
Flash point:
12 °F
storage temp. 
Store below +30°C.
solubility 
Chloroform (Sparingly)
form 
A liquid
color 
Colorless to Almost colorless
explosive limit
1.6-6.3%(V)
Water Solubility 
Immiscible with water.
λmax
195nm(EtOH)(lit.)
BRN 
506224
Stability:
Volatile
InChIKey
SJYNFBVQFBRSIB-UHFFFAOYSA-N
LogP
2.67 at 25℃ and pH7
Surface tension
64.3-64.4mN/m at 900μg/L and 20.3℃
CAS DataBase Reference
121-46-0(CAS DataBase Reference)
NIST Chemistry Reference
2,5-Norbornadiene(121-46-0)
EPA Substance Registry System
2,5-Norbornadiene (121-46-0)
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Safety Information

Hazard Codes 
F
Risk Statements 
11
Safety Statements 
16-23
RIDADR 
UN 2251 3/PG 2
WGK Germany 
2
RTECS 
RB6535000
13
Autoignition Temperature
350 °C
TSCA 
Yes
HazardClass 
3
PackingGroup 
II
HS Code 
29021990
Toxicity
LD50 orl-rat: 890 mg/kg SHELL*

MSDS

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2,5-Norbornadiene Usage And Synthesis

Chemical Properties

2,5-Norbornadiene, also known as dicycloheptadiene, is a clear colorless to slightly yellow liquid that is soluble in petroleum ether and insoluble in water. Commercially available goods usually contain 500 ppm of 2,6-di-tert-butyl-p-methylphenol (BHT) as a stabilizer. Analyzing the structural characteristics of NBD, it can be found that it has good reaction properties and can synthesize a variety of organic compounds through addition or substitution reactions at the double bond.

Uses

2,5-Norbornadiene has an anti-ethylene effect on plants and inhibits polyphenol oxidase, peroxidase and phenylalanine ammonia lyase activities.

Uses

2,5-Norbornadiene is used as an intermediate in prostaglandin synthesis and shows anti-ethylene effect on plants. It acts as a starting material for the synthesis of diamantane and as an acetylene transfer agent for instance, in reaction with 3,6-di-2-pyridyl-1,2,4,5-tetrazine. It is also a useful dienophile in Diels-Alder reactions.

Preparation

2,5-Norbornadiene is of interest as a metal-binding ligand, whose complexes are useful for homogeneous catalysis. Norbornadiene can be formed by a Diels-Alder reaction between cyclopentadiene and acetylene.

General Description

2,5-norbornadiene, stabilized appears as a colorless liquid. Insoluble in water and less dense than water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion, inhalation and skin absorption. When heated will polymerize and at decomposition emits acrid smoke and irritating fumes.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

2,5-NORBORNADIENE may react vigorously with strong oxidizing agents. May react exothermically with reducing agents to release hydrogen gas. In the presence of various catalysts (such as acids) or initiators, may undergo exothermic addition polymerization reactions. Violent explosions at low temperatures in ammonia synthesis gas units have been traced to the addition products of dienes and nitrogen dioxide [Bretherick, 5th Ed., 1995].

Health Hazard

Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Safety Profile

Poison by intravenous route. Moderately toxic by ingestion and intraperitoneal routes. Mildly toxic by inhalation. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

Purify the diene by distillation from activated alumina [Landis & Halpern J Am Chem Soc 109 1746 1987]. [Beilstein 5 IV 879.]

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