基本情報
- CAS
121-46-0- 標準SMILES
C1=CC2C=CC1C2- InChIKey
SJYNFBVQFBRSIB-UHFFFAOYSA-N- 分子式
- C7H8
- 平均分子量
- 92.14 g/mol
- 単同位体質量
- 92.06260026
概要
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.
名称と識別子
- 優先名称
- Norbornadiene
- IUPAC
- bicyclo[2.2.1]hepta-2,5-diene
- 現地名
- 2,5-ノルボルナジエン
- 英語名
- 2,5-Norbornadiene
- 分子式
- C7H8
- 分子量
- 92.14
名称と別名
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
名称をさらに表示
2,5-ノルボルナジエンノルボルナ-2,5-ジエンビシクロ[2.2.1]ヘプタン-2,5-ジエンノルボルナジエンビシクロ[2.2.1]ヘプタ-2,5-ジエン3,6-メチレン-1,4-シクロヘキサジエンジシクロ（２．２．１）ヘプタジエンビシクロ（2?2?1）ヘプタ-2，5-ジエン2,5‐ノルボルナジエン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
データベース識別子
- CAS
物性
構造計算による物性
- XLogP
- 2.1
- 極性表面積
- 0 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 0
- 回転可能結合数
- 0
- 重原子数
- 7
- 形式電荷
- 0
- 複雑度
- 103
実験および物理化学的性質
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]
物理化学的性質
- 融点
- -20 · -20--19°C
- 沸点
- 89 °C · 89 °C(lit.)
- 比重(密度)
- 0.906 g/mL · 0.906 g/mL at 25 °C(lit.)
- 蒸気圧
- 69 hPa · 69 hPa (20 °C)
- 屈折率
- 20 · n20/D 1.470(lit.)
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
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.
危険有害性情報
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.
化学と産業
用途と製造
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
応用分野
解説2,5-ノルボルナジエンともいう,融点－20 ℃，沸点90 ℃．可燃性液体．加熱すれば1,3,5-シクロヘプタトリエンを生じる．光照射すれば，光のエネルギーを吸収してクアドリシクランに異性化するので，光エネルギー変換物質として注目されている．森北出版「化学辞典（第2版）
用途2,5-ノルボルナジエン,有機化合物である。この二環式の炭化水素は、ノルボルナンとノルボルネンから誘導される最も安定したジオレフィンである。ノルボルナジエンは、均一系触媒における配位子として主に関心が持たれたが、その高い反応性や異性化できないジエンとしての独特の構造的な特性により盛んに研究されている。
使用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.
一般的な説明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.
調製方法
製造方法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.
純化方法Purify the diene by distillation from activated alumina [Landis & Halpern J Am Chem Soc 109 1746 1987]. [Beilstein 5 IV 879.]
関連反応
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化合物ノート
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