| Identification | More | [Name]
(TETRAHYDRO-2H-PYRAN-4-YL)METHANOL | [CAS]
14774-37-9 | [Synonyms]
TERTAHYDROPYRAN-4-METHANOL
(TETRAHYDRO-2H-PYRAN-4-YL)METHANOL
TETRAHYDROPYRAN-4-METHANOL
(TETRAHYDRO-PYRAN-4-YL)-METHANOL
4-(Hydroxymethyl)tetrahydro-2H-pyran
4-(Hydroxymethyl)tetrahydropyr
(Tetrahydro-pyran-4-yl)-methanol ,97% | [Molecular Formula]
C6H12O2 | [MDL Number]
MFCD00457804 | [Molecular Weight]
116.16 | [MOL File]
14774-37-9.mol |
| Chemical Properties | Back Directory | [Boiling point ]
105 °C | [density ]
1.000±0.06 g/cm3(Predicted) | [Fp ]
61°(142°F) | [refractive index ]
1.4600 | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
clear liquid | [pka]
14.85±0.10(Predicted) | [color ]
Colorless to Light yellow to Light orange | [Water Solubility ]
Slightly soluble in water. | [Detection Methods]
GC | [InChI]
InChI=1S/C6H12O2/c7-5-6-1-3-8-4-2-6/h6-7H,1-5H2 | [InChIKey]
YSNVSVCWTBLLRW-UHFFFAOYSA-N | [SMILES]
C1OCCC(CO)C1 | [CAS DataBase Reference]
14774-37-9(CAS DataBase Reference) | [Storage Precautions]
Store under nitrogen |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) . | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29329990 |
| Hazard Information | Back Directory | [Chemical Properties]
Colorless liquid | [Uses]
Used as a reagent in the identification and optimization of pteridinone Toll-like receptor 7 agonists, which can be used for the oral treatment of viral hepatitis. 4-(Hydroxymethyl)tetrahydropyran is also a starting material for [1-[(Tetrahydro-2H-pyran-4-yl)methyl]-1H-indol-3-yl](2,2,3,3-tetramethylcyclopropyl)methanone which is a drug that acts as CB2 cannabinoid receptor agonist. | [Synthesis]
Ethyl tetrahydro-2H-pyran-4-carboxylate (5.0 g, 34.7 mmol) was slowly added to a stirred suspension of lithium aluminum hydride (LiAlH4, 4.0 g, 104 mmol) in tetrahydrofuran (THF, 100 mL) at 0 °C. The reaction mixture was kept stirred at 0 °C for 1 hour. Subsequently, ethyl acetate (20 mL) was added slowly and dropwise to the reaction mixture to quench the excess LiAlH4, followed by the addition of 10% aqueous sodium hydroxide (NaOH). The resulting mixture was continued to be stirred for 30 minutes. Upon completion of the reaction, the reaction mixture was filtered through a diatomaceous earth pad to remove insoluble impurities. The filtrate was concentrated under reduced pressure to give the target product (tetrahydro-2H-pyran-4-yl) methanol (9) as a colorless oil. The yield was 3.9 g in 96% yield. The product was characterized by 1H NMR (400 MHz, DMSO-d5): δ 4.46 (broad single peak, 1H), 3.82 (double peak, J=8.0 Hz, 2H), 3.25-3.22 (multiple peaks, 4H), 1.62-1.52 (multiple peaks, 3H), 1.18-1.04 (multiple peaks, 1H). | [References]
[1] Patent: US2014/275043, 2014, A1. Location in patent: Paragraph 0415; 0416
[2] Justus Liebigs Annalen der Chemie, 1936, vol. 525, p. 292,294
[3] Patent: WO2010/96371, 2010, A2. Location in patent: Page/Page column 156 |
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