Tetrahydropyran

HCID 8894
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Basic information

CAS
142-68-7
Standard SMILES
C1CCOCC1
InChIKey
DHXVGJBLRPWPCS-UHFFFAOYSA-N
Molecular formula
C5H10O
Average molar mass
86.13 g/mol
Monoisotopic mass
86.07316494

Overview

Oxane is a saturated organic heteromonocyclic parent that is cyclohexane in which one of the carbon atoms has been replaced by an oxygen atom.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

Names & identifiers

Preferred name
Tetrahydropyran
IUPAC
oxane
English name
Tetrahydropyran
Molecular formula
C5H10O
Molecular weight
86.13

Names & synonyms

TETRAHYDROPYRAN142-68-7OxaneTetrahydro-2H-pyranOxacyclohexane2H-Pyran, tetrahydro-Pentamethylene oxideTetrahydropyrane2H-tetrahydropyranV06I3ILG6BNSC-65448DTXSID3059719
Show more names
THPUMODEtrahydropyranTHGPMKCD2MCKD2Tamm-Horsfall
CHEBI:46941RefChem:188700DTXCID3034612205-552-8MFCD00006585PYETetrahydro-4H-pyranOxane (VAN)

Database identifiers

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

Properties

Computed structural properties

XLogP
0.9
Topological polar surface area
9.2 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
6

Experimental & physicochemical properties

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

log Kow = 0.95

0.95

Odor · 2 items

PUNGENT, SWEETISH ODOR

ETHER-LIKE

Density0.8814 @ 20 °C/4 °C

Physicochemical properties

Melting point
-45 °C · -45 °C (lit.)
Boiling point
88 °C · 88 °C (lit.)
Density
0.881 g/mL · 0.881 g/mL at 25 °C (lit.)
vapor density
3 · 3 (vs air)
refractive index
20 · n20/D 1.42(lit.)
Flash point
4 °F · 4 °F

Safety & regulation

GHS classification

GHS Classification · 6 items

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]

Hazard information

Regulatory Information · 2 items

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 items

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 items

Tetrahydropyran

D: Other compounds that may form peroxides

Kelly

Hazard Classes and Categories · 2 items

Flam. Liq. 2 (100%)

Flammable liquids - Category 2

Safety & protection

Fire Fighting ProceduresALCOHOL FOAM.

Toxicology

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

Safety data

PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
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

Chemistry & industry

Uses & manufacturing

U.S. Exports · 2 items

(1972) No Data

(1975) No Data

U.S. Imports · 2 items

(1972) No Data

(1975) No Data

U.S. Production · 2 items

(1972) No Data

(1975) No Data

Methods of Manufacturing · 2 items

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 items

2H-Pyran, tetrahydro-: ACTIVE

ALL TECHNICAL TETRAHYDROPYRAN IS STABILIZED AGAINST PEROXIDE FORMATION.

Applications · 2 items

DescriptionTetrahydropyran (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.

UsesIt 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.

Upstream & downstream products

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海康朗生物科技有限公司021-61998208 18217752821 · [email protected]
湖北成丰化工有限公司13125175253 · [email protected]

Additional notes

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

Related reactions

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Compound notes

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