Basic information
- CAS
121-46-0- Standard SMILES
C1=CC2C=CC1C2- InChIKey
SJYNFBVQFBRSIB-UHFFFAOYSA-N- Molecular formula
- C7H8
- Average molar mass
- 92.14 g/mol
- Monoisotopic mass
- 92.06260026
Overview
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.
Names & identifiers
- Preferred name
- Norbornadiene
- IUPAC
- bicyclo[2.2.1]hepta-2,5-diene
- English name
- 2,5-Norbornadiene
- Molecular formula
- C7H8
- Molecular weight
- 92.14
Names & synonyms
2,5-NorbornadieneBicyclo[2.2.1]hepta-2,5-diene121-46-0NorbornadieneDicycloheptadieneBICYCLO(2.2.1)HEPTA-2,5-DIENEBicyclo(2.2.1)heptadieneUN2251W9ZTQ75ZUS3,6-Methano-1,4-cyclohexadieneNSC-13672DTXSID1059523
Show more names
BICYCLO[2.2.1]-2,5-HEPTADIENENorborna-2,5-dieneBicyclo[2.2.1]hepta-2,5-diene, 97%, stabilized with 0.05 - 0.25% BHT, 97%Norbornadine2,5-NORBORNADINE
UN-2251Bicyclo[2.2.1]heptadieneRefChem:83016DTXCID6033669204-472-0BicycloheptadieneMFCD00082301NSC 13672
Database identifiers
- CAS
121-46-0、16422-76-7- PubChem CID
- 8473
- DTXSID
DTXSID1059523- UNII
- W9ZTQ75ZUS
- EC Number
- 204-472-0
- Nikkaji
- J36.833D、J398.207F
Properties
Computed structural properties
- XLogP
- 2.1
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 0
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 103
Experimental & physicochemical properties
Chemical Classes
Other Classes -> Aliphatics, Unsaturated
Flammable agents - 3rd degree
SpringerMaterials PropertiesCoriolis coupling
LogP2.67
Flash Point-6 °F (NFPA, 2010)
Vapor Pressure25.5 [mmHg]
Physical 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.
Liquid
Liquid with a foul odor; [Merck Index] Colorless liquid; [CAMEO]
Physicochemical properties
- Melting point
- -20 · -20--19°C
- Boiling point
- 89 °C · 89 °C(lit.)
Safety & regulation
GHS classification
GHS Classification
Danger
H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]
P210, P233, P240, P241, P242, P243, P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P321, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 84 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Bicyclo[2.2.1]hepta-2,5-diene
Bicyclo[2.2.1]hepta-2,5-diene is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Bicyclo[2.2.1]hepta-2,5-diene are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 22-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/26780
2,5-Norbornadiene: Does not have an individual approval but may be used under an appropriate group standard
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
DOT LabelFlammable Liquid
Fire Hazards
Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible); polymerization hazard]:
· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.
· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.
Health Hazards
Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible); polymerization hazard]:
CAUTION: Petroleum crude oil (UN1267) may contain TOXIC hydrogen sulphide gas.
CAUTION: Petroleum crude oil (UN1267) may contain TOXIC hydrogen sulphide gas.
Chemistry & industry
Uses & manufacturing
UsesUsed to make synthetic rubber; [ChemIDplus] Used in organic, organometallic, and petrochemical synthesis; Used as an intermediate for aldrin; [Merck Index]
U.S. Production2023: 50,000 - <250,000 lb
Industry UsesIntermediate
General Manufacturing Information
Pharmaceutical and Medicine Manufacturing
Bicyclo[2.2.1]hepta-2,5-diene: ACTIVE
Applications
Uses2,5-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.
Uses2,5-Norbornadiene is industrially available as a chemical intermediate. It was not intended for use in perfumes, and it is only occasionally used as such. It serves mainly as a starting material for the manufacture of industrial chemicals, etc.2,5-Norbornadiene has occasionally been used in Pine needle fragrances to improve the diffusiveness of the fragrance, and to lend initial power and short life to the fragrances which are intended for "short-effect" purposes, e.g. dishwashing detergent fragrances, etc. It is also used as a masking agent when a volatile and powerful material is needed at low cost.
General Description2,5-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.
Preparation methods
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.
Related reactions
44 records
Compound notes
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