シクロペンタジエン
ペントール · 1,3-シクロペンタジエン · シクロペンタ-1,3-ジエン · ピロペンチレン · 2,4-シクロペンタジエン · R-ペンチン · １，３シクロペンタジエン · シクロペンタジエン
識別子と物理属性
| CAS No. | 542-92-7 |
|---|---|
| 分子式 | C5H6 |
| 平均分子量 | 66.1 g/mol |
| 単同位体質量 | 66.04695019 g/mol |
| SMILES | C1=CCC=C1 |
| InChIKey | ZSWFCLXCOIISFI-UHFFFAOYSA-N |
| PubChem CID | 7612 |
| ChEMBL | CHEMBL3188826 |
| ChEBI | CHEBI:30664 |
| EC No. | 208-835-4 |
| DTXSID | DTXSID0027191 |
| 現地名 | シクロペンタジエン |
化学・物理的性質
| XLogP | 1.8 |
|---|---|
| 極性表面積 | 0 |
| 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 | 5 |
| 形式電荷 | 0 |
| 複雑度 | 58.1 |
| 物質分類 | Other Classes -> Aliphatics, UnsaturatedFlammable agents - 3rd degree |
| SpringerMaterials Properties | Coriolis coupling |
| 臭い | MONOMERIC FORM HAS TERPENE ODOR IN VAPOR STATEIrritating terpene-like odor |
| 密度 | 0.8 (NIOSH, 2024) - Less dense than waterwill float0.8021 g/cu cm at 20 °CRelative density (water = 1): 0.8d40 0.8235d410 0.8131d420 0.8021d425 0.7966d430 0.7914 |
| Color/Form | Colorless liquid |
| 溶解度 | Insoluble (NIOSH, 2024)In water, 1,800 mg/L at 25 °CMiscible with carbon tetrachloridesoluble in carbon disulfide, aniline, acetic acid, liquid petrolatumSoluble in acetonemiscible with ethanol, ethyl ether, benzeneSolubility in water: insolubleアセトン、ベンゼン、四塩化炭素、エーテルと混和します。酢酸、アニリン、二硫化炭素に可溶 (Windholz et al., 1983)。10.3 mM、25°C (振とうフラスコ-UV 分光光度法、Streitwieser および Nebenzahl、1976) |
| 引火点 | 77 °F (NIOSH, 2024)77 °F (OPEN CUP)-20 °C(oc) 77 °F |
| 沸点 | 107 °F at 760 mmHg (NIOSH, 2024)41 °C41.5-42.0 °Cbp760 41.5-42.0° |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating fumes.It decomposes violently at high temperatures and pressures. |
| 融点 | -121 °F (NIOSH, 2024)-95.54 °C-85 °C-85°mp 32.5° |
| 蒸気密度 | (AIR= 1) AT BOILING POINT OF CYCLOPENTADIENE 2.3Relative vapor density (air = 1): 2.3 |
| 臭気閾値 | Odor Threshold Low: 1.8 [ppm]Low Threshold= 5.0 mg/cu mHigh threshold= 5.0 mg/cu m. |
| 蒸気圧 | 381 at 20.6 °C, 735 at 40.6 °C, 1,380 at 60.9 °C (Stoeck and Roscher, 1977) |
| 屈折率 | nD16 1.44632 |
| pKa（酸解離定数） | 16(at 25℃) |
| 外観・状態 | 無色の液体 |
| ヘンリー定数 | 5.1 at 25 °C (approximate - calculated from water solubility and vapor pressure) |
| 安定性 | 室温で安定で、酸化剤、酸、その他多くの化合物と相溶しません。密閉型酸素貯蔵庫。 |
| InChI | InChI=1S/C5H6/c1-2-4-5-3-1/h1-4H,5H2 |
| InChIKey | ZSWFCLXCOIISFI-UHFFFAOYSA-N |
| SMILES | C1C=CC=C1 |
| EPAの化学物質情報 | Cyclopentadiene (542-92-7) |
化学的特性
1,3-Cyclopentadiene is a colorless liquid that dimerizes easily in the presence of peroxides and trichloroacetic acid to a colorless solid.
化学性质
沸点41℃の揮発性液体であるが，室温付近で容易に二量化し，沸点170℃のジシクロペンタジエン（DCPD）として存在する。
安全性と法規制
| GHS 分類 | DangerH225 (28.2%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P316, P317, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 372 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H225: Highly Flammable liquid and vapor [Danger Flammable liquids] |
|---|---|
| 規制情報 | Chemical: 1,3-Cyclopentadiene1,3-Cyclopentadiene is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Cyclopentadiene 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)SP - indicates a substance that is identified in a proposed Significant New Use Rule.Status: Active Update: 27-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/34854Cyclopentadiene: Does not have an individual approval but may be used under an appropriate group standardThe 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.) |
| 輸送ラベル（DOT） | Flammable Liquid |
| 火災危険 | Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:Flammable. Above 25 °C explosive vapour/air mixtures may be formed. Risk of fire and explosion on contact with incompatible substances. See Chemical Dangers. |
| 火災の可能性 | A dangerous fire hazard when exposed to heat or flame. |
| 健康有害性 | Excerpt from NIOSH Pocket Guide for Cyclopentadiene: |
| 有害性の概要 | Cyclopentadiene causes narcosis and liver injury in animal experiments. It has an irritating odor that is objectionable to workers. [ACGIH, 1987] A skin, eye, and respiratory tract irritant[ICSC]TLV and Documentation withdrawn. . . Since cyclopentadiene (CPD) dimerizes into DCPD [Dicyclopentadiene], we recommended using the TLV for DCPD if CPD is of concern. There is little information available on the toxicity of CPD. [ACGIH, 2019] See Dicyclopentadiene. |
用途
解説
シクロペンタジエン,無色の液体．融点－85 ℃，沸点41 ℃．d1540.8048．n20D1.4440．プロトンが引き抜かれて生成するシクロペンタジエニドイオンは，芳香族性を示す．シクロペンタジエンはディールス-アルダー反応の共役ジエンとして有機合成に広く用いられるほか，一群のシクロペンタジエニル錯体が知られている．工業的用途としては，エチレンプロピレンゴムの第三成分エチリデンノルボルネンの合成，農薬原料などがあり，またジシクロペンタジエンから誘導される化学製品が，近年，種々開発され，新しい石油化学工業分野を広げつつある．森北出版「化学辞典（第2版）
使用
manufacture of resins; in organic synthesis as the diene in the Diels-Alder reaction producing sesquiterpenes, synthetic alkaloids, camphors.
一般的な説明
1,3-Cyclopentadiene is a colorless liquid with an irritating, terpene-like odor. Bp: 42.5°C; Flash point: 77°F. Density: 0.805 g cm-3.
製法・合成法
調製方法
This compound occurs in the C6–C8 petroleum distillation fraction, and in coke oven light oil fractions. It is produced by dehydrogenation of cyclopentadiene or monomerization of its dimer.
合成方法
ナフサ分解のC5留分として生成する。CPDは，その二量化，分解反応の容易さを利用し，DCPDとして他のC5留分と分離した後に分解されて得られる。
純化方法
Dry the diene with Mg(ClO4)2 and distil it rapidly as it dimerises readily at room temperature. It should be used immediately or stored in a Dry Ice or an ice-salt bath. HIGHLY FLAMMABLE. [Moffett Org Synth Coll Vol IV 238 1963.] Cyclopentadiene Dimer (4,7-methano-3a,4,7,7a-tetrahydroindene) has [77-73-6], M 132.3, m 33o, b 170o/atm, and d2 5 0.986; add ~0.05% of 2,6-di-tert-butyl-4-methylphenol as stabilizer. Cyclopentadiene is prepared when required by de-polymerising the technical grade dimer by heating it carefully under a fractionating column [Wilkinson Org Synth Coll Vol IV 467 1963], as described by Moffett (above reference), or by adding the dimer at a steady rate onto mineral oil heated at 240-270o (Korach et al. Org Synth 42 50 1962). [Beilstein 5 II 391.]