3,4-dihydro-2H-pyran

• ChemBase ID: 69501
• Molecular Formular: C5H8O
• Molecular Mass: 84.11642
• Monoisotopic Mass: 84.05751488
• SMILES: C1CCC=CO1
• Canonical SMILES: C1COC=CC1
• InChI: InChI=1S/C5H8O/c1-2-4-6-5-3-1/h2,4H,1,3,5H2
• InChIKey: BUDQDWGNQVEFAC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,4-dihydro-2H-pyran
• IUPAC Traditional name: dihydropyran
• Synonyms: 2,3-Dihydro-4H-pyran; 3,4-Dihydro-2H-pyran; 3,4-Dihydro-2H-pyran; 2,3-Dihydropyran; DIHYDROPYRAN; 3,4-二氢-2H-吡喃

Database IDs

• CAS Number: 110-87-2
• EC Number: 203-810-4
• MDL Number: MFCD00006558
• Beilstein Number: 103493
• PubChem SID: 24893341; 24863242; 162035227
• PubChem CID: 8080
• Chemspider ID: 7789
• Wikipedia Title: Dihydropyran

CALCULATED PROPERTIES

• Lipinski's Rule of Five: true
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.9868946
• LogD (pH = 7.4): 0.9868946
• Log P: 0.9868946
• Molar Refractivity: 25.2476 cm^3
• Polarizability: 9.660139 Å^3
• Polar Surface Area: 9.23 Å^2
• Rotatable Bonds: 0

PROPERTIES

Physical Property

• Apperance: Colorless liquid
• Melting Point: -70 °C(lit.); -70°C; -70°C
• Boiling Point: 85-86°C; 85-86°C; 86 °C(lit.); 86°C
• Flash Point: -15.5°C; -15°C(5°F); -16 °C; -16°C; 3.2 °F
• Density: 0.922; 0.922 g/ml; 0.922 g/mL; 0.922 g/mL at 25 °C(lit.); 0.926; 1 g/ml
• Refractive Index: 1.441; 1.4420; n20/D 1.440(lit.); n20/D 1.441
• Vapor Density: 2.9 (vs air)

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Highly Flammable/Irritant/Air Sensitive/Light Sensitive/Store under Argon; IRRITANT
• European Hazard Symbols: Flammable (F); Irritant (Xi)
• UN Number: 2376; UN2376
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2; II
• Australian Hazchem: 2YE
• Risk Statements: 11-36/37/38; R:11-36/37/38
• Safety Statements: 16-26-36; 7/9-16-23-26-37; S:16-20-25-26-37/39
• EU Classification: F1
• EU Hazard Identification Number: 3B
• Emergency Response Guidebook(ERG) Number: 127
• TSCA Listed: false; 是
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H315-H319-H335
• GHS Precautionary statements: P210-P261-P280G-P305+P351+P338-P403+P233; P210-P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2376 3/PG 2

Product Information

• Purity: ~97-98%; ≥95.0% (GC); 95+%; 97%; 98%; 99%
• Grade: purum
• Impurities: ≤3% tetrahydropyran
• Empirical Formula (Hill Notation): C5H8O

DETAILS

MP Biomedicals - 05204025

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02150907

Purity: Approx. 97-98%
Widely used hydroxyl-protecting (-OH) reagent.

Sigma Aldrich - D106208

Application
Widely used OH-protecting reagent.1
Packaging
100, 500 mL in glass bottle

Sigma Aldrich - 37350

Other Notes
Protecting group reagent for alcohols1,2

REFERENCES

• Synth. Commun. , 9 : 271 (1979).
• Protects OH groups as their tetrahydropyranyl, (THP) ethers, stable to bases, Grignard or organolithium reagents, metal hydrides, etc., but readily removed by mild acid. Introduction (acetal formation) generally employs an acid catalyst, often p-TsOH. For example of protection, reaction with Grignard, and deprotection, see: Org. Synth. Coll., 7, 334 (1990). For alternative catalysts for THP ether formations, see: Pyridinium p-toluenesulfonate, A15708, Triphenylphosphine hydrobromide, L14290, Boron trifluoride diethyl etherate, A15275, Amberlyst? 15, 89079, Montmorillonite K10, L15160, Acetonyltriphenylphosphonium bromide, B22434, Indium(III) trifluoromethanesulfonate, 40131. Sulfuric acid/silica gel: Synth. Commun., 22, 159 (1992), allows the catalyst to be removed by simple filtration. POCl₃, described for the protection of diethyl hydroxymethylphosphonate, permits use in the Horner-Wadsworth-Emmons reaction: Org. Synth. Coll., 7, 160 (1990). See also Iodotrimethylsilane, A12902, providing non-acidic conditions; cf also Tetrahydropyran, A13392. For selective monotetrahydropyranylation of symmetrical diols, catalyzed by acidic ion-exchange resin, Dowex? 50WX2 50-100 (H), L13943, see: J. Org. Chem., 63, 8183 (1998).
• For selective deprotection of THP ethers under non-acidic conditions with LiCl in wet DMSO, see: J. Org. Chem., 61, 6038 (1996).
• The lithio-derivative, formed with tert-BuLi, reacts with, e.g. alkyl iodides or carbonyl compounds: Tetrahedron Lett., 4187 (1977).
• Acetals and ortho esters, in the presence of Lewis acid catalysts, add readily to the vinyl ether system: Chem. Lett., 1101 (1988).