テトラヒドロピラン

Tetrahydropyran

HCID 8894CAS 142-68-7
部分構造検索類似構造を探す

基本情報

標準SMILES
C1CCOCC1
InChIKey
DHXVGJBLRPWPCS-UHFFFAOYSA-N
分子式
C5H10O
平均分子量
86.13 g/mol
単同位体質量
86.07316494

概要

Oxane is a saturated organic heteromonocyclic parent that is cyclohexane in which one of the carbon atoms has been replaced by an oxygen atom. It is a saturated organic heteromonocyclic parent and a member of oxanes.

名称と識別子

優先名称
Tetrahydropyran
IUPAC
oxane
現地名
テトラヒドロピラン
英語名
Tetrahydropyran
分子式
C5H10O
分子量
86.13

名称と別名

TETRAHYDROPYRAN142-68-7OxaneTetrahydro-2H-pyranOxacyclohexane2H-Pyran, tetrahydro-Pentamethylene oxideTetrahydropyrane2H-tetrahydropyranV06I3ILG6BNSC-65448DTXSID3059719
名称をさらに表示
テトラヒドロピラン3,4,5,6-テトラヒドロ-2H-ピラン1-オキサシクロヘキサンオキサンペンタメチレンオキシド1,5-エポキシペンタンテトラヒドロ-4H-ピランオキサシクロヘキサンテトラヒドロ-2H-ピランテトラヒドロピラン, 98+%THPUMODEtrahydropyranTHGPMKCD2MCKD2Tamm-Horsfall
CHEBI:46941RefChem:188700DTXCID3034612205-552-8MFCD00006585PYETetrahydro-4H-pyranOxane (VAN)

データベース識別子

CAS
142-68-7
PubChem CID
8894
DTXSID
DTXSID3059719
ChEBI
CHEBI:46941
UNII
V06I3ILG6B
EC Number
205-552-8
Nikkaji
J5.814I

物性

構造計算による物性

XLogP
0.9
極性表面積
9.2 Ų
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

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15
SolventsSolvents -> Ethers (<C12)
SpringerMaterials PropertiesCoriolis coupling
LogP · 2 件

log Kow = 0.95

0.95

Odor · 2 件

PUNGENT, SWEETISH ODOR

ETHER-LIKE

Density0.8814 @ 20 °C/4 °C

物理化学的性質

融点
-45 °C · -45 °C (lit.)
沸点
88 °C · 88 °C (lit.)
比重(密度)
0.881 g/mL · 0.881 g/mL at 25 °C (lit.)
蒸気密度
3 · 3 (vs air)
屈折率
20 · n20/D 1.42(lit.)
闪点
4 °F · 4 °F

化学的性質

化学的特性colorless to light yellow liquid

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 51 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H225: Highly Flammable liquid and vapor [Danger Flammable liquids]

危険有害性情報

Regulatory Information · 2 件

Chemical: 2H-Pyran, tetrahydro-

Tetrahydropyran: Does not have an individual approval but may be used under an appropriate group standard

Fire PotentialFIRE HAZARD: DANGEROUS, WHEN EXPOSED TO HEAT, FLAME, OR OXIDIZERS. ...CAN REACT VIGOROUSLY WITH OXIDIZING MATERIALS.
Hazards SummaryForms peroxides on contact with air (technical products stabilized to prevent); [Merck Index] An irritant; [MSDSonline]
NFPA Hazard Classification · 3 件

2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.

3 - Liquids and solids that can be ignited under almost all ambient temperature conditions. Materials produce hazardous atmospheres with air under almost all ambient temperatures or, though unaffected by ambient temperatures, are readily ignited under almost all conditions.

1 - Materials that in themselves are normally stable but that can become unstable at elevated temperatures and pressures.

Peroxide Forming Chemical · 3 件

Tetrahydropyran

D: Other compounds that may form peroxides

Kelly

Hazard Classes and Categories · 2 件

Flam. Liq. 2 (100%)

Flammable liquids - Category 2

安全と保護具

Fire Fighting ProceduresALCOHOL FOAM.

毒性情報

Adverse EffectsNeurotoxin - Acute solvent syndrome
Non-Human Toxicity ValuesLDLO RATS ORAL 3000 MG/KG

安全データ

wgk
3
tsca
TSCA listed
ridadr
UN 1993 3/PG 2
hs_code
29321100
risk_code
11-36/37/38-9-19-52/53-22
化審法
(5)-5761

化学と産業

用途と製造

U.S. Exports · 2 件

(1972) No Data

(1975) No Data

U.S. Imports · 2 件

(1972) No Data

(1975) No Data

U.S. Production · 2 件

(1972) No Data

(1975) No Data

Methods of Manufacturing · 2 件

HYDROGENATION OF 2,3-DIHYDROPYRAN OR ACIDIC DEHYDRATION OF 1,5-PENTANEDIOL

/IT IS/ PREPARED BY HYDROGENATION OF DIHYDROPYRAN (FROM FURFURAL)...CASS, IND ENG CHEM 40, 219 (1948).

General Manufacturing Information · 2 件

2H-Pyran, tetrahydro-: ACTIVE

ALL TECHNICAL TETRAHYDROPYRAN IS STABILIZED AGAINST PEROXIDE FORMATION.

応用分野 · 5 件

解説テトラヒドロピラン (英: Tetrahydropyran) とは、無色透明液体の環状エーテルです。 IUPAC名はオキサン (英: Oxane) 、別名として、THP、オキサシクロヘキサン (英: Oxacyclohexane) 、1-オキサシクロヘキサン (英: 1-Oxacyclohexane) 、1,5-エポキシペンタン (英: 1,5-epoxypentane) 、ペンタメチレンオキシド (英: Pentamethylene oxide) とも呼ばれます。

用途医薬?農薬原料、溶剤。

説明Tetrahydropyran (THP) is the organic compound consisting of a saturated six-membered ring containing five carbon atoms and one oxygen atom. It is named by reference to pyran, which contains two double bonds, and may be produced from it by adding four hydrogens. Tetrahydropyran can be used as a solvent in various classical organic reactions such as radical reactions, palladium-catalyzed coupling, and Grignard reactions.

使用It is is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and dyestuff. They are also used as important solvents, as chemical intermediate and as monomer for ring-opening polymerization.

使用用途1. 保護基 有機合成において、2-テトラヒドロピラニル基は、アルコールの保護基として汎用されます。基質のアルコール部位に対し、酸性条件下、を作用させることでテトラヒドロピラニルエーテルへと変換可能です。 テトラヒドロピランは、酸性条件や塩基性条件、還元条件に強い耐性を持つため、反応溶媒、抽出溶媒、晶析溶媒といった様々な用途で使用できる有機溶媒です。 n-BuLiなどの強塩基性条件下では、同じ環状エーテル構造を持つ、五員環のテトラヒドロフランに比べ、テトラヒドロピランはより強い耐性を有します。そのため、医薬・農薬原料としても使用されます。

調製方法 · 1 件

純化方法Dry oxane with CaH2, then pass it through a column of silica gel to remove olefinic impurities and fractionally distil it. Free it from peroxides and moisture by refluxing with sodium, then distil it from LiAlH4. Alternatively, peroxides can be removed by treatment with aqueous ferrous sulfate and sodium bisulfate, followed by solid KOH, and fractional distillation from sodium. [Beilstein 17 H 12, 17 I 6, 17 II 18, 17 III/IV 51, 17/1 V 64.]

上流・下流製品情報

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補足説明

定義ChEBI: A saturated organic heteromonocyclic parent that is cyclohexane in which one of the carbon atoms has been replaced by an oxygen atom.

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