3,4-ジヒドロ-2H-ピラン
3,4-ジヒドロ-2H-ピラン · ジヒドロピラン · 2,3-ジヒドロ-4H-ピラン · 5,6-ジヒドロ-4H-ピラン · 3,4-ジヒドロ2H-ピラン · Δ2-ジヒドロピラン · 2,3-ジヒドロピラン · 2,3‐ジヒドロピラン
識別子と物理属性
| CAS No. | 110-87-2 |
|---|---|
| 分子式 | C5H8O |
| 平均分子量 | 84.12 g/mol |
| 単同位体質量 | 84.05751488 g/mol |
| SMILES | C1=COCCC1 |
| InChIKey | BUDQDWGNQVEFAC-UHFFFAOYSA-N |
| PubChem CID | 8080 |
| ChEMBL | CHEMBL3184439 |
| EC No. | 203-810-4 |
| DTXSID | DTXSID6041426 |
| 現地名 | 3,4-ジヒドロ-2H-ピラン |
化学・物理的性質
| XLogP | 0.7 |
|---|---|
| 極性表面積 | 9.2 |
| 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 | 6 |
| 形式電荷 | 0 |
| 複雑度 | 57 |
| 物質分類 | Other Classes -> Ethers, OtherFlammable agents - 3rd degree |
| SpringerMaterials Properties | Coriolis coupling |
| LogP（分配係数） | 0.69 |
| 密度 | 0.922 @ 19°C0.922 g/mL at 25 °C (lit.) |
| 引火点 | 0 °F (NFPA, 2010)4 °F |
| Physical Description | Dihydro-2h-pyran appears as a clear colorless liquid with an ethereal odor. Less dense than water. Vapors heavier than air.Clear colorless liquid with an ethereal odor[CAMEO] Unpleasant odor[Alfa Aesar MSDS] |
| 融点 | -70 °C (lit.) |
| 沸点 | 86 °C (lit.) |
| 蒸気密度 | 2.9 (vs air) |
| 蒸気圧 | 77.8 hPa (20 °C) |
| 屈折率 | n20/D 1.440(lit.) |
| 貯蔵条件 | Store below +30°C. |
| 溶解度 | 7.7g/リットル20g/L(20℃) |
| 外観・状態 | 液体 |
| 色 | 無色透明～黄色 |
| pH | 7 (5g/l, H2O, 20℃) |
| 爆発限界 | 1.1-13.8%(V) |
| BRN | 103493 |
| 安定性 | 揮発性 |
| InChI | 1S/C5H8O/c1-2-4-6-5-3-1/h2,4H,1,3,5H2 |
| InChIKey | BUDQDWGNQVEFAC-UHFFFAOYSA-N |
| SMILES | C1COC=CC1 |
| LogP（分配係数） | 0.690 |
| CAS データベース | 110-87-2(CAS DataBase Reference) |
| NISTの化学物質情報 | 2H-Pyran, 3,4-dihydro-(110-87-2) |
| EPAの化学物質情報 | 2H-Pyran, 3,4-dihydro- (110-87-2) |
化学的特性
colorless to light yellow liqui
安全性と法規制
| GHS 分類 | DangerH225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P272, P280, P302+P352, P303+P361+P353, P305+P351+P338, P321, P332+P317, P333+P317, P337+P317, P362+P364, P370+P378, P403+P235, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 180 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.WarningH317: May cause an allergic skin reaction [Warning Sensitization, Skin] |
|---|---|
| 規制情報 | Chemical: 2H-Pyran, 3,4-dihydro-2H-Pyran, 3,4-dihydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2H-Pyran, 3,4-dihydro- 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: 29-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/120422H-Pyran, 3,4-dihydro-: HSNO Approval: HSR001129 Approved with controlsThe 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 127 [Flammable Liquids (Water-Miscible)]:· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. |
| 健康有害性 | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:· Inhalation or contact with material may irritate or burn skin and eyes. |
| 有害性の概要 | A skin and strong eye irritant[Alfa Aesar MSDS] |
| 輸送番号・ガイド（DOT） | 2376 127 |
| 反応性グループ | Ethers |
| Reactivity Alerts | Highly Flammable |
| Reactivity Profile | Ethers, such as DIHYDRO-2H-PYRAN, can act as bases. They form salts with strong acids and addition complexes with Lewis acids. The complex between diethyl ether and boron trifluoride is an example. Ethers may react violently with strong oxidizing agents. In other reactions, which typically involve the breaking of the carbon-oxygen bond, ethers are relatively inert. |
| DOT Hazard Classification | 2,3-DihydropyranUN2376Class 3 Flammable and combustible liquid (49 eCFR § 173.120)PG II: the degree of danger presented by the material is medium |
| Air and Water Reactions | Highly flammable. Slightly soluble in water. |
| Hazard Classes and Categories | Flam. Liq. 2 (100%)Flammable liquids - Category 2Skin sensitization - Category 1BFlammable agents - 3rd degree, Reactive agents - 1st degree |
| 消火 | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]: |
| 漏出応急措置 | · CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. |
| 応急処置 | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:General First Aid: |
| 暴露管理・個人防護 | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| 非火災時の漏出対応 | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]: |
| Isolation and Evacuation | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:Immediate precautionary measure |
| Protective Action Criteria (PAC) | 14 [mg/m3]150 [mg/m3]910 [mg/m3] |
| Personal Protective Equipment (PPE) | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]: |
| Emergency Response Planning Guidelines | CAUTION: The majority of these products have a very low flash point. Use of water spray when fighting fire may be inefficient. |
| Toxicity Data | LC50 (rat) > 10,700 mg/m3/4hr |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | UP7700000 |
| 輸送番号（UN） | UN 2376 |
| 毒性 | LD50 orally in Rabbit: > 4000 mg/kg |
| 税関コード | 29329995 |
| 危険文句（R） | 11-36/37/38-36/38-19 |
| 化審法 | (5)-670 |
| 消防法 | 危-4-1-II |
| 危険表示 | F,Xi |
| hazard_note | Highly Flammable/Irritant |
| 安全措置（S） | 16-26-36-37/39-33-7/9 |
| 危険等級 | 3Aquatic Chronic 3Eye Irrit. 2Flam. Liq. 2Skin Irrit. 2Skin Sens. 1B |
| 包装等級 | II |
| 自然発火温度 | 240 °C |
| 貯蔵分類 | 3 - Flammable liquids |
用途
用途
有機合成用、OH基の保護試薬。
用途
水酸基(アルコール、フェノール)の保護試薬。
使用
Widely used hydroxyl-protecting reagent3,4-Dihydro-2H-pyran is used as a hydroxyl-protecting reagent in organic synthesis. It acts as an intermediate in synthetic chemistry. It is used to protect various reactive functional groups. It is involved in the polymerization reaction either alone or with unsaturated compound and finds application in polymer industries. Further, it is employed in the preparation of bicyclic compounds of epoxide-fused, halo compounds and allenic alcohols.
使用用途
ジヒドロピランの主な使用用途は、有機合成原料・有機合成試薬です。特に、アルコールやフェノールなどの水酸基の保護に用いられます。酸触媒を用いてジヒドロピランをアルコールと反応させると、テトラヒドロピラニル基を生成し、アルコールの保護基の役割を果たします。 また、ジヒドロピランはやテトラヒドロピラニルエーテルを生成する原料としても用いられる化合物です。
製法・合成法
純化方法
Partially dry dihydropyran with Na2CO3, then fractionally distil it. The fraction b 84-85o is refluxed with Na until hydrogen no longer evolves when fresh Na is added. It is then dried, and distilled again through a 60 x 1.2cm column packed with glass rings [Brandon et al. J Am Chem Soc 72 2120 1950, UV: Elington et al. J Chem Soc 2873 1952, NMR: Bushweller & O'Neil Tetrahedron Lett 4713 1969]. It has been characterised as the 3,5-dinitrobenzoyloxy-tetrahydrofuran derivative, m 103o which forms pale yellow crystals from dihydropyran/Et2O [Woods & Kramer J Am Chem Soc 69 2246 1947]. [Beilstein 17/1 V 181.]