4-Aminotetrahydropyran Chemical Properties

Boiling point:

60 °C

Density 

0.977 g/cm3 at 25 °C

refractive index 

n20/D 1.463

Flash point:

54°C

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

pka

9.63±0.20(Predicted)

form 

liquid

color 

Colourless

InChI

InChI=1S/C5H11NO/c6-5-1-3-7-4-2-5/h5H,1-4,6H2

InChIKey

AHVQYHFYQWKUKB-UHFFFAOYSA-N

SMILES

C1OCCC(N)C1

CAS DataBase Reference

38041-19-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

10-34-41-22-37/18

Safety Statements 

16-26-36/37/39-39

RIDADR 

2734

WGK Germany 

1

HazardClass 

IRRITANT

PackingGroup 

Ⅲ

HS Code 

29321900

4-Aminotetrahydropyran Usage And Synthesis

Description

4-Aminotetrahydropyran contains the tetrahydropyran ring, which is the most frequently reported three-dimensional ring system in marketed drugs, and is second only to the phenyl ring when two-dimensional rings are included. It can be used as reactant/reagent in synthesis of aminothiazole compounds for use in treatment of cancer. Its scaffold is very useful in the drug discovery for cancer treatment.

Application

4-Aminotetrahydropyran can be used as reactant/reagent in synthesis of aminothiazole compounds for use in treatment of cancer.

Synthesis

General procedure for the synthesis of 4-aminotetrahydropyran from dihydro-2H-pyran-4(3H)-one oxime: Raney Ni (10%) was added to a stirred solution of compound 2.2 (1.0 g, 8.7 mmol) in methanol (50 mL) and the resulting mixture was stirred for 5 hr at room temperature in a hydrogen atmosphere. The progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the catalyst was removed by filtration and the methanol solvent in the filtrate was concentrated in vacuum to afford the target product 4-aminotetrahydropyran (Compound 2.3, 0.5 g, 57% yield).

References

[1] Journal of Medicinal Chemistry, 2006, vol. 49, # 7, p. 2210 - 2221
[2] Patent: US2009/82423, 2009, A1. Location in patent: Page/Page column 23
[3] Patent: US5707989, 1998, A
[4] Patent: US5821240, 1998, A
[5] Patent: US5977102, 1999, A

4-Aminotetrahydropyran(38041-19-9)Related Product Information

• Tetrahydro-2H-pyran-4-carboxylic acid
• Tetrahydropyran
• Centchroman
• Tetrahydro-4H-pyran-4-one
• AMINOACETONITRILE HYDROGEN SULFATE
• 4-AMINOTETRAHYDROPYRAN, HCL,4-AMINOTETRAHYDROPYRAN HYDROCHLORIDE,4-AMINOTETRAHYDROPYRAN HYDROCHLORIDE (TETRAHYDRO-2H-PYRAN-4-AMINE HYDROCHLORIDE)
• tetrahydropyran-4,4-dicarboxylic acid
• Tetrahydropyran-4-carbaldehyde
• Tetrahydropyran-4-boronic acid pinacol ester
• TETRAHYDRO-PYRAN-4-CARBOXYLIC ACID METHYLAMIDE
• TETRAHYDRO-PYRAN-3-YLAMINE HYDROCHLORIDE
• 4,4,5,5-Tetramethyl-2-(tetrahydro-2H-pyran-3-yl)-1,3,2-dioxaborolane
• Gentamicin
• KANAMYCIN
• MEPARTRICIN
• Geneticin
• Nystatin
• picromycin