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14774-37-9

14774-37-9 Structure

14774-37-9 Structure
IdentificationMore
[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 PropertiesBack 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 DataBack Directory
[Symbol(GHS) ]

Corrosion (GHS05)Exclamation Mark (GHS07)
GHS05,GHS07
[Signal word ]

Warning
[Hazard statements ]

H227-H315-H318-H335
[Precautionary statements ]

P210e-P261-P280a-P305+P351+P338-P405-P501a
[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
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Ethanol-->Tetrahydrofuran-->Sodium-->Potassium hydroxide-->Acetone-->Lithium Aluminum Hydride-->Diethyl malonate-->Tetrahydro-2H-pyran-4-carboxylic acid-->2,2'-Dichlorodiethyl ether-->Methyl tetrahydropyran-4-carboxylate
[Preparation Products]

Tetrahydropyran-4-carbaldehyde-->1-azabicyclo[2.2.1]heptane--> 4-(Iodomethyl)tetrahydro-2H-pyran-->Tetrahydropyranyl-4-acetic acid-->4-(Bromomethyl)tetrahydropyran-->Tetrahydro-2H-pyran-2-ylmethyl 4-methylbenzenesulfonate
Hazard InformationBack 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 Tetrahydropyran-4-Carboxylate

96835-17-5

(TETRAHYDRO-2H-PYRAN-4-YL)METHANOL

14774-37-9

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
Spectrum DetailBack Directory
[Spectrum Detail]

(TETRAHYDRO-2H-PYRAN-4-YL)METHANOL(14774-37-9)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

tetrahydro-2H-pyran-4-ylmethanol(14774-37-9)
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