フラン
フラン · オキソール · ジビニレンオキシド · フルフラン · テトロール · オキサシクロペンタジエン · ACETYLFURAN · ACF
識別子と物理属性
| CAS No. | 110-00-9 |
|---|---|
| 分子式 | C4H4O |
| 平均分子量 | 68.07 g/mol |
| 単同位体質量 | 68.02621475 g/mol |
| SMILES | c1ccoc1 |
| InChIKey | YLQBMQCUIZJEEH-UHFFFAOYSA-N |
| PubChem CID | 8029 |
| ChEMBL | CHEMBL278980 |
| ChEBI | CHEBI:35559 |
| EC No. | 203-727-3 |
| DTXSID | DTXSID6020646 |
| 現地名 | フラン |
化学・物理的性質
| XLogP | 1.3 |
|---|---|
| 極性表面積 | 13.1 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 1 |
| 回転可能結合数 | 0 |
| 重原子数 | 5 |
| 形式電荷 | 0 |
| 複雑度 | 22.8 |
| 物質分類 | Other Classes -> Ethers, OtherCarcinogens |
| SpringerMaterials Properties | Coriolis coupling |
| 農薬 | Pesticide -> EPA IRIS |
| LogP（分配係数） | log Kow = 1.34 |
| 臭い | Etherealプロピレングリコール中0.10％。エーテル的な |
| 密度 | 0.9371 at 66.92 °F (EPA, 1998) - Less dense than waterwill float0.9731 at 19.4 °C/4 °CDensity = 0.9514 g/cu cm at 20 °CRelative density (water = 1): 0.940.9514 @ 20°C0.936 g/mL at 25 °C(lit.) |
| Viscosity | 0.38 cP at 20 °C0.38 mPa*s |
| Color/Form | Colorless liquid, turns brown upon standingcolor change is retarded if a small amount of water is added |
| 溶解度 | less than 1 mg/mL at 72 °F (NTP, 1992)Soluble in alcohol and etherSlightly soluble in chloroformvery soluble in ethanol, ethersoluble in acetone, benzeneIn water, 1X10+4 mg/L at 25 °C10 mg/mL at 25 °CSolubility in water, g/l at 25 °C: 10アルコール: 溶けやすい不溶性 |
| 引火点 | Less than 32F (EPA, 1998)-32 °F (-35 °C) (Closed cup)160 °F |
| 沸点 | 90 °F at 758 mmHg (EPA, 1998)31.5 °C32.00 °C. @ 758.00 mm Hg31.3 °C31.5 °C @760 [mm Hg]67 °C10 mm Hg(lit.) |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating fumes.Furan is a heat-stable compound although, @ 670 °C in the absence of catalyst, or @ 360 °C in the presence of nickel, it decomposes to form a mixture consisting mainly of carbon monoxide, hydrogen, and hydrocarbons. |
| 融点 | -85.6 °C |
| 蒸気密度 | 2.35 (vs air) |
| 蒸気圧 | 1672 mm Hg ( 55 °C) |
| 屈折率 | n20/D 1.5070(lit.) |
| 貯蔵条件 | Store below +30°C. |
| 外観・状態 | 液体 |
| 色 | 無色透明～黄色 |
| 比重 | 0.94 |
| 臭気閾値 | 9.9ppm |
| 爆発限界 | 2.3-14.3%(V) |
| 比熱容量 | Cp(liquid): 1.69 J/(g·K)Cp(gas): 0.96 J/(g·K), at 25℃ |
| Merck | 14,4296 |
| BRN | 103221 |
| ヘンリー定数 | 1.8×10-3 mol/(m3Pa) at 25℃, HSDB (2015) |
| 誘電率 | 3.0(25℃) |
| 安定性 | 安定。避けるべき物質には、強力な酸化剤、酸、過酸化物、酸素が含まれます。可燃性が高く、空気と爆発性混合物を形成する可能性があります。 |
| InChI | 1S/C4H4O/c1-2-4-5-3-1/h1-4H |
| InChIKey | YLQBMQCUIZJEEH-UHFFFAOYSA-N |
| SMILES | [o]1cccc1 |
| LogP（分配係数） | 1.34 |
| CAS データベース | 110-00-9(CAS DataBase Reference) |
| NISTの化学物質情報 | Furan(110-00-9) |
| EPAの化学物質情報 | Furan (110-00-9) |
化学的特性
Furan is a cyclic dienic ether stabilized by benzene-like resonance. Because of its conjugated unsaturation and heterocyclic atom, furan will undergo many types of reactions. It is, therefore, of interest as a chemical intermediate for pharmaceuticals, insecticides and fine chemicals. The heterocyclic oxygen atom in a ring with conjugated unsaturation gives furan a combination of ether, aromatic and olefinic characteristics. This polyfunctionality permits it to undergo a variety of reactions. Compared to benzene, the furan ring has greater reactivity, and is more susceptible to cleavage, thus resembling the vinyl ethers. Like the vinyl ethers, the furan ring is cleaved by aqueous acids. This reaction is accompanied by resinification .
安全性と法規制
| GHS 分類 | DangerH224: Extremely flammable liquid and vapor [Danger Flammable liquids]P203, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P317, P318, P319, P321, P330, P332+P317, P362+P364, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)H224 (100%): Extremely flammable liquid and vapor [Danger Flammable liquids] |
|---|---|
| 規制情報 | Chemical: FuranRegulation (EC) No 1333/2008 (amended)Furan is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Furan 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: 27-02-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/10633Substance: FuranFuran: HSNO Approval: HSR001255 Approved with controls |
| その他の安全情報 | IMAP assessments - Furan: Human health tier II assessment |
| 輸送ラベル（DOT） | Flammable Liquid |
| 火災危険 | Very dangerous, upon exposure to heat or flame. It may form unstable peroxides on exposure to air. Contact with acids can initiate a violent, heat producing reaction. Avoid acids, oxidizing agents. Upon standing in air, it may form unstable peroxides. (EPA, 1998)· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.Extremely flammable. Vapour/air mixtures are explosive. |
| 火災の可能性 | A very dangerous fire hazard when exposed to heat or flame. |
| 健康有害性 | The vapors are narcotic. Acute exposure to furan by inhalation may involve both reversible and irreversible changes. Acute exposure by ingestion or skin absorption, as well as chronic exposure, are associated with high toxicity. (EPA, 1998)CAUTION: Petroleum crude oil (UN1267) may contain TOXIC hydrogen sulphide gas. |
| 有害性の概要 | Inhalation can cause anesthesiaAbsorbed through skin[Merck Index] May cause liver damageCorrosive to the mouth and GI tract in toxicology studies |
用途
解説
フラン，マツの木から得られるタール中に存在する．フルフラールを酸化すると得られる2-フランカルボン酸を，加熱脱炭酸すると得られる．クロロホルム臭をもつ無色の液体．沸点32 ℃(10 kPa)．d19.440.9371．n20D1.4216．エタノール，エーテル，石油エーテルに易溶，水に微溶．アルカリには安定であるが，無機酸では樹脂化する．マツ材-塩酸反応で緑色を呈する．フラン誘導体は植物の精油成分として存在するものが多い．フランは芳香族性が比較的小さく，ジエン性が高いため，ディールス-アルダー反応を起こしやすい．ナトリウムアマルガムでは還元されないが，ニッケル触媒による水素添加により，テトラヒドロフランを生成する．カチオノイド試薬による置換反応はα位で起こりやすい．脱水剤の存在下にアンモニアあるいは硫化水素と加熱すると，それぞれピロール，チオフェンを生成する．蒸気は麻酔作用があるので注意を要する．ラットの致死濃度は30400 ppm．また，エーテルと同様に過酸化物を形成するので，蒸留には注意が必要である．
用途
合成樹脂原料,有機合成原料,溶剤,洗浄剤
説明
Furan occurs naturally in oils distilled from rosin containing pinewood. In addition, many natural foods contain the furan ring structure and substituted furans may be formed through cooking of simple carbohydrates. Furan is also found in tobacco smoke as well as wood smoke and gas emissions from gasoline and diesel engines. Furan has also been detected in industrial effluents and can be emitted to the air from petroleum refineries and coal-mining and gasification plants.
使用
Furan is a five-membered heterocyclic aromatic ring. Furan is used as a building block for the preparation of many heterocyclic compounds.
一般的な説明
Furan is a stable, colourless chemical liquid. It is highly flammable and forms explosive mixtures with air. It is incompatible with many other chemical substances, for example, strong oxidising agents, acids, peroxides, and oxygen. Furan is produced commercially by decarbonylation of furfural. It is used mainly in the production of tetrahydrofuran, thiophene, and pyrrole. It also occurs naturally in certain woods and during the combustion of coal and is found in engine exhausts, wood smoke, and tobacco smoke.
使用用途
フランは多くの複素環式化合物を合成するための中間体として利用されています。また、合成樹脂、溶剤、洗浄剤などの原料にも広く使用されています。
製法・合成法
純化方法
Shake it with aqueous 5% KOH, dry it with CaSO4 or Na2SO4, then distil it under nitrogen, from KOH or sodium, immediately before use. A trace of hydroquinone could be added as an inhibitor of oxidation. [Beilstein 17 H 27, 17 I 16, 17 II 34, 17/1 V 291.]