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2,5-Norbornadiene
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Name

2,5-Norbornadiene

 EINECS 204-472-0
CAS No. 121-46-0 Density 1.003 g/cm3
PSA 0.00000 LogP 1.74850
Solubility Immiscible with water. Melting Point -20--19 °C
Formula C7H8 Boiling Point 89.5 °C at 760 mmHg
Molecular Weight 92.1405 Flash Point 12 °F
Transport Information UN 2251 3/PG 2 Appearance Clear colorless to slightly yellow liquid
Safety 16-23 Risk Codes 11
Molecular Structure Molecular Structure of 121-46-0 (2,5-Norbornadiene) Hazard Symbols FlammableF
Synonyms

2,5-Norbornadiene(8CI);3,6-Methano-1,4-cyclohexadiene;Bicyclo[2.2.1]heptadiene;NSC 13672;Norbornadiene;Bicyclo[2.2.1]hepta-2,5-diene;

Article Data 106

2,5-Norbornadiene Synthetic route

278-06-8

quadricyclo[2.2.1.0.0]heptane

121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
x In nitromethane at 25℃;100%
cadmium(II) sulphide In dichloromethane for 3h; Product distribution; Irradiation; other semiconducters, presence of methylviologen dication and diphenylamine;1.8%
3,3-dimethyldioxirane In dichloromethane; acetone at 0℃; for 0.0166667h;60 % Turnov.
278-06-8

tetracyclo-[3.2.0.0.2,7.04,6]heptane

121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
With 1-Cyanonaphthalene In methanol Irradiation;
dichloro(norbornadiene)palladium(II) In dichloromethane at 25℃; for 1h; Product distribution; Quantum yield; Mechanism; Irradiation; different Q concentration, solvent, times, intensity and wavelenght of irradiation, effect of free radical scavenger;
With 9,10-Dicyanoanthracene In hexane Quantum yield; Mechanism; Rate constant; Ambient temperature; Irradiation; exciplex isomerization, var. of sensitizer, solv.;
With aluminum oxide; 4-Aminosalicylic acid; tetrasodium (5,10,15,20-tetrakis(4-sulfonatophenyl)porphyrinato)cobalt(II) In pentane at 24℃; Rate constant; Thermodynamic data; ΔH(activation);
With trichlorostannylacetylene at 25℃; for 1h; Inert atmosphere;
(+-)-dimethyl-norborn-5-ene-2exo-yl-amine oxide

(+-)-dimethyl-norborn-5-ene-2exo-yl-amine oxide

121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
at 200℃; under 30 - 60 Torr;
(+-)-trimethyl-norborn-5-ene-2exo-yl-ammonium hydroxide

(+-)-trimethyl-norborn-5-ene-2exo-yl-ammonium hydroxide

121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
at 110 - 125℃; under 30 - 60 Torr;
27770-83-8

endo-2,3-bis(phenylsulfonyl)bicyclo<2.2.1>hept-5-ene

121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
With methanol; sodium dihydrogenphosphate; sodium amalgam Ambient temperature;65%
With sodium dihydrogenphosphate; sodium amalgam In methanol Ambient temperature;65%
132856-14-5

exo-3-deuteriobicyclo<2.2.1>hept-5-enyl tosylate

A

74773-67-4, 92076-23-8

<2-D>Bicyclo<2.2.1>hepta-2,5-dien

B

121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
With 18-crown-6 ether; potassium tert-butylate In various solvent(s) at 60℃; Yield given. Yields of byproduct given;
With 18-crown-6 ether; potassium tri-2-norbornylmethoxide In various solvent(s) at 60℃; Yield given. Yields of byproduct given;
75612-58-7

bicyclo<2.2.1>hepta-2,5-dien-2-yl p-tolyl sulfone

121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
With sodium dihydrogenphosphate; sodium amalgam In methanol at 18℃;27%
278-06-8

quadricyclo[2.2.1.0.0]heptane

A

121-46-0

bicyclo[2.2.1]hepta-2,5-diene

exo-3-Oxa-4-thiatricyclo<4.2.1.02,5>non-7-ene 4-oxide

Conditions
ConditionsYield
With sulfur dioxide In chloroform at 0℃; under 15 Torr; rotaevaporation;
278-06-8

tetracyclo-[3.2.0.0.2,7.04,6]heptane

A

13041-10-6

7anti-Methoxy-norbornen-(2)

21516-65-4

3-methoxynortricyclene

C

121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
With Rh(pnen)3(3+) In methanol Irradiation;A n/a
B n/a
C 72%
23979-29-5

exo-3,4-diazotricyclo[4.2.1.02,5]nona-3,7-diene

A

121-46-0

bicyclo[2.2.1]hepta-2,5-diene

B

278-06-8

quadricyclo[2.2.1.0.0]heptane

Conditions
ConditionsYield
With 9,10-Dicyanoanthracene Irradiation;
With 9,10-Dicyanoanthracene In acetonitrile at 23℃; Product distribution; Mechanism; Irradiation; var. sensitizers and solvents;
In various solvent(s) at 144.85℃; Kinetics; Further Variations:; Temperatures;

2,5-Norbornadiene Chemical Properties

Product Categories: Functional Materials;Photochromic Compounds;Norbornene Derivatives ；Azobenzene, etc. (Photochromic Compounds);
Synonyms:bicyclo(2.2.1)heptadiene;bicyclo[2.2.1]hepta-2,5-diene,(Norbornadiene);Norbornadiene;2,5-DICYCLOHEPTADIENE;2,5-NORBORNADIENE ；8,9,10-trinorborna-2,5-diene;Bicyclo[2.2.1]heptadiene; 3,6-Methano-1,4-cyclohexadiene;
MF: C7H8
MW: 92.14
mp ： -20--19°C
bp ：89 °C(lit.)
EINECS: 204-472-0
density  0.906 g/mL at 25 ℃(lit.)
It is a bicyclic hydrocarbon.

 

 

 

2,5-Norbornadiene Toxicity Data With Reference

1.   

orl-rat LD50:890 mg/kg SHELL*

2.   

ihl-rat LC50:14,100 ppm/8H

   SCCUR*    Shell Chemical Company. Unpublished Report. (2401 Crow Canyon Rd., San Romon, CA 94583)
3.   

ipr-rat LD50:890 mg/kg

   SCCUR*    Shell Chemical Company. Unpublished Report. (2401 Crow Canyon Rd., San Romon, CA 94583)
4.   

orl-mus LD50:3850 mg/kg

   SCCUR*    Shell Chemical Company. Unpublished Report. (2401 Crow Canyon Rd., San Romon, CA 94583)
5.   

ihl-mus LC50:27,700 ppm/30M

   SCCUR*    Shell Chemical Company. Unpublished Report. (2401 Crow Canyon Rd., San Romon, CA 94583)
6.   

ivn-mus LD50:56 mg/kg

   

CSLNX*    U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#04158 .

 

2,5-Norbornadiene Consensus Reports

EPA Extremely Hazardous Substances List. Reported in EPA TSCA Inventory.

2,5-Norbornadiene 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.
Hazard Codes：   F
HS Code  ： 29021990
Risk Statements  ： 11
Safety Statements ： 16-23
WGK Germany  ：2
F  ：13
HazardClass ： 3
RIDADR ： UN 2251 3/PG 2

2,5-Norbornadiene Standards and Recommendations

DOT Classification:  3; Label: Flammable Liquid
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