(S)-(+)-TETRAHYDROFURFURYL ALCOHOL Chemical Properties

Boiling point:

176.8±8.0 °C(Predicted)

Density 

1.038±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

form 

liquid

pka

14.44±0.10(Predicted)

color 

Clear, colourless

CAS DataBase Reference

57203-01-7

Safety Information

HS Code 

2932990090

(S)-(+)-TETRAHYDROFURFURYL ALCOHOL Usage And Synthesis

Uses

(S)-(Tetrahydrofuran-2-yl)methanol is used during aminopyrrolopyrimidine derivatives preparation and IGF-1R inhibition in tumors.

Synthesis

Under argon protection, (R)-tetrahydrofuran-2-carboxylic acid (2 g, 17.22 mmol) was dissolved in 20 mL of tetrahydrofuran (THF) and the reaction flask was cooled in an ice bath. Borane-dimethyl sulfide complex (BH3-SMe2, 2M THF solution, 10 mL, 20.0 mmol) was slowly added to the reaction solution over 10 min. After removing the ice bath, the reaction mixture was stirred at room temperature for 1 hour. Subsequently, the reaction mixture was again cooled in an ice bath and methanol was slowly added until no gas escaped. Finally, the reaction solution was concentrated under reduced pressure to afford the target product tetrahydrofurfuryl alcohol as an oil (1 g, 60% yield). The product was characterized by 1H NMR (300 MHz, CDCl3): δ 1.55-1.70 (m, 1H), 1.72-1.98 (m, 3H), 3.35-4.00 (m, 6H).

References

[1] European Journal of Organic Chemistry, 2001, # 23, p. 4537 - 4542
[2] Patent: WO2016/16238, 2016, A1. Location in patent: Page/Page column 184
[3] Patent: WO2017/134188, 2017, A1. Location in patent: Page/Page column 48; 49
[4] Journal of Medicinal Chemistry, 1995, vol. 38, # 15, p. 2830 - 2841
[5] Journal of Organic Chemistry, 1997, vol. 62, # 2, p. 242 - 243

(S)-(+)-TETRAHYDROFURFURYL ALCOHOL(57203-01-7)Related Product Information

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• L-BORNYL ACETATE
• D(+)-Carnitine
• 8-BROMOADENOSINE
• α-Chloralose
• 2,2'-Cyclouridine
• DIACETONE-D-GLUCOSE
• 6-THIOGUANOSINE
• XANTHOSINE
• 2-Chloroadenosine
• D-SACCHARIC ACID 1,4-LACTONE
• Span 20
• Span 60
• tetrahydrofurfuryl alcohol propionate
• Tetrahydrofurfuryl alcohol
• (R)-(-)-TETRAHYDROFURFURYL ALCOHOL
• GLYCOFUROL
• 2-Amino-6-chloropurine Riboside