2,5-Norbornadiene supplier

Name
2,5-Norbornadiene
EINECS 204-472-0
CAS No. 121-46-0
Article Data106
CAS DataBase
Density 1.003 g/cm³
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
Hazard Symbols F
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;
PSA 0.00000
LogP 1.74850

Synthetic route

: 278-06-8
quadricyclo[2.2.1.0.0]heptane

: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With Rh(pnen)3(3+) In methanol Irradiation;	A n/a B n/a C 72%

...Expand

: 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

Conditions	Yield
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;

: 67-56-1
methanol

: 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

Conditions	Yield
With Rh(pnen)3(3+) In methanol Irradiation; Yield given. Title compound not separated from byproducts;	A n/a B n/a C 72%

...Expand

: 16104-45-3
3,4-diazaquadricyclo[6.1.0.02,605,9]non-3-ene

A: 278-06-8
tetracyclo-[3.2.0.0.2,7.04,6]heptane

B: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

Conditions

Conditions	Yield
With Rh(pnen)3(3+) In acetonitrile Irradiation;	A 47% B 50%

(+-)-5endo,6exo-dichloro-norbornene: (+-)-5endo,6exo-dichloro-norbornene

: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

Conditions

Conditions	Yield
With diethyl ether; magnesium iodide

5endo,6endo-dichloro-norbornene: 5endo,6endo-dichloro-norbornene

: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

Conditions

Conditions	Yield
With diethyl ether; magnesium iodide

: 12146-37-1, 124717-04-0
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

: 201230-82-2
carbon monoxide

A: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

B: 13939-06-5, 199620-15-0
molybdenum hexacarbonyl

Conditions

Conditions	Yield
In tetrahydrofuran reaction in a calorimeter; CO pressure: 500 psi;	A n/a B 100%

...Expand

: 12146-37-1, 124717-04-0
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

: 6737-42-4
1,3-bis-(diphenylphosphino)propane

A: 15553-68-1
tetracarbonyl-1,3-bis(diphenylphosphino)propane-molybdenum(0)

B: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

Conditions

Conditions	Yield
In tetrahydrofuran reaction in a calorimeter under argon;	A 100% B n/a

...Expand

: 12146-37-1, 124717-04-0
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

: 2071-20-7
bis-diphenylphosphinomethane

A: 26743-81-7
tetracarbonyl-bis(diphenylphosphino)methane-molybdenum(0)

B: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

Conditions

Conditions	Yield
In tetrahydrofuran reaction in a calorimeter under argon;	A 100% B n/a

...Expand

: 12146-37-1, 124717-04-0
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

: 594-09-2
trimethylphosphane

: 16027-45-5
cis-bis(trimethylphosphine)tetracarbonylmolybdenum

B: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

Conditions

Conditions	Yield
In tetrahydrofuran reaction in a calorimeter under argon;	A 100% B n/a

...Expand

: 12146-37-1, 124717-04-0
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

: 7719-12-2, 52843-90-0
phosphorus trichloride

: 16244-51-2
bis(trichlorophosphine)molybdenum tetracarbonyl

B: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

Conditions

Conditions	Yield
In tetrahydrofuran reaction in a calorimeter under argon;	A 100% B n/a

...Expand

: 110-86-1
pyridine

: 12146-37-1, 124717-04-0
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

: 16742-99-7, 33570-29-5
cis-{molybdenum(0)(carbonyl)4(pyridine)2}

B: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

Conditions

Conditions	Yield
In tetrahydrofuran reaction in a calorimeter under argon;	A 100% B n/a

...Expand

: 1552-12-1, 111-78-4
1,5-cis,cis-cyclooctadiene

: 12146-37-1, 124717-04-0
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

A: 12109-74-9
tetracarbonyl(1,5-cyclooctadiene)molybdenum

B: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

Conditions

Conditions	Yield
In tetrahydrofuran reaction in a calorimeter under argon;	A 100% B n/a

...Expand

: 12146-37-1, 124717-04-0
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

: 13991-08-7
1,2-Bis(diphenylphosphino)benzene

A: 111189-30-1
(1,2-bis(diphenylphosphino)benzene)molybdenum tetracarbonyl

B: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

Conditions

Conditions	Yield
In tetrahydrofuran reaction in a calorimeter under argon;	A 100% B n/a

...Expand

: 12146-37-1, 124717-04-0
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

: 64065-08-3
dmpm

A: 90624-09-2
(bis(dimethylphosphino)methane)molybdenum tetracarbonyl

B: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

Conditions

Conditions	Yield
In tetrahydrofuran reaction in a calorimeter under argon;	A 100% B n/a

...Expand

: 12146-37-1, 124717-04-0
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

: 121-45-9
phosphorous acid trimethyl ester

: 15631-22-8
bis(trimethylphosphite)molybdenum tetracarbonyl

B: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

Conditions

Conditions	Yield
In tetrahydrofuran reaction in a calorimeter under argon;	A 100% B n/a

...Expand

: 12146-37-1, 124717-04-0
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

: 554-70-1
triethylphosphine

: 19217-80-2, 19217-81-3, 22614-45-5
cis-{molybdenum(0)(carbonyl)4(P(ethyl)3)2}

B: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

Conditions

Conditions	Yield
In tetrahydrofuran under argon; reaction in a calorimeter;	A 100% B n/a

...Expand

: 12146-37-1, 124717-04-0
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

: 617-75-4
triethylarsine

: 111265-67-9
bis(triethylarsine)molybdenum tetracarbonyl

B: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

Conditions

Conditions	Yield
In tetrahydrofuran under argon; reaction in a calorimeter;	A 100% B n/a

...Expand

: 12146-37-1, 124717-04-0
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

: 110-18-9
N,N,N,N,-tetramethylethylenediamine

A: 23301-98-6
(N,N,N',N'-tetramethylethylenediamine)tetracarbonylmolybdenum(0)

B: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

Conditions

Conditions	Yield
In tetrahydrofuran reaction in a calorimeter under argon;	A 100% B n/a

...Expand

: 12146-37-1, 124717-04-0
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

: 23936-60-9
1,2-bis(dimethylphosphanyl)ethane

A: 40544-97-6
(1,2-bis(dimethylphosphino)ethane)molybdenum tetracarbonyl

B: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

Conditions

Conditions	Yield
In tetrahydrofuran reaction in a calorimeter under argon;	A 100% B n/a

...Expand

: 931-53-3
Cyclohexyl isocyanide

: 12146-37-1, 124717-04-0
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

: 15227-72-2
di(cyclohexylisocyanide)molybdenum tetracarbonyl

B: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

Conditions

Conditions	Yield
In tetrahydrofuran under argon; reaction in a calorimeter;	A 100% B n/a

...Expand

: 484-11-7
2.9-dimethyl-1,10-phenanthroline

: 12146-37-1, 124717-04-0
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

A: 23301-98-6
molybdenum(0) tetracarbonyl(2,9-dimethyl-1,10-phenanthroline)

B: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

Conditions

Conditions	Yield
In tetrahydrofuran reaction in a calorimeter under argon;	A 100% B n/a

...Expand

: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

: 693-02-7
hex-1-yne

: 123186-37-8, 126518-14-7, 128163-06-4, 128163-07-5
4-n-butyldeltacyclen

Conditions

Conditions	Yield
With diphosphane; (2S,3S)-(+)-bis(diphenylphosphanyl)bicyclo[2.2.1]hept-5-ene; cobalt(III) acetylacetonate; diethylaluminium chloride In tetrahydrofuran at 35℃; for 4h;	100%

: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

: 536-74-3
phenylacetylene

: C15H14

Conditions

Conditions	Yield
With cobalt(III) acetylacetonate; diethylaluminium chloride; 1,2-bis-(diphenylphosphino)ethane In toluene; benzene Ambient temperature;	100%

: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

: 155052-20-3
4-Aza-2-oxo-1-oxaspiro<5.4>dec-3-ene 4-oxide

: rel-(5aR,6R,9S,9aR,9bS)-7,8-dehydro-6,9-methano-1-oxo-1,5a,9a,9b-tetrahydrocyclohex[f]isoxazolo[2,3-c]oxazole-3-spiro-1'-cyclohexane

Conditions

Conditions	Yield
for 9h; Ambient temperature;	100%

: 628-71-7
1-Heptyne

: 201230-82-2
carbon monoxide

: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

: 85806-43-5, 85806-49-1, 122422-23-5, 122422-24-6
(3aR,4S,7R,7aR)-2-Pentyl-3a,4,7,7a-tetrahydro-4,7-methano-inden-1-one

Conditions

Conditions	Yield
dodecacarbonyl tetracobalt In dichloromethane at 150℃; under 7600 Torr; for 6h;	100%
Co/C In tetrahydrofuran at 130℃; under 22800 Torr; for 18h; Pauson-Khand reaction;	98%
Pauson-Khand reaction;	64%

...Expand

: 938164-26-2
4-(2-bromo-phenyl)-1-methyl-1H-pyrrole-3-carboxylic acid ethyl ester

: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

: C16H15NO2

Conditions

Conditions	Yield
With caesium carbonate; palladium diacetate; triphenylphosphine In toluene at 120℃;	100%

: 2052-07-5
2-Bromobiphenyl

: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

: C19H16

Conditions

Conditions	Yield
With caesium carbonate; palladium diacetate; triphenylphosphine In toluene at 130℃;	100%

: 14104-20-2
silver tetrafluoroborate

: bis(ethylene)rhodium(I) chloride dimer

: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

: di(norbornadiene)rhodium(I) tetrafluoroborate

Conditions

Conditions	Yield
In dichloromethane under N2 or Ar, addn. of diene in CH2Cl2 to Rh-complex in CH2Cl2, then addn. of solid AgBF4, soln. is stirred for 45 min; filtn. through Celite, addn. of THF to the filtrate, concn., filtn. of deep red crystals, washed with THF, air-dried;	100%

...Expand

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

Product Name

2,5-Norbornadiene

Synthetic route

2,5-Norbornadiene Chemical Properties

2,5-Norbornadiene Toxicity Data With Reference

2,5-Norbornadiene Consensus Reports

2,5-Norbornadiene Safety Profile

2,5-Norbornadiene Standards and Recommendations

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