2-(3-Bromopropoxy)tetrahydro-2H-pyran Chemical Properties

Boiling point:

64.5 °C/0.8 mmHg (lit.)

Density 

1.317 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.478(lit.)

Flash point:

222 °F

storage temp. 

-20°C

form 

liquid

Appearance

Colorless to light yellow Liquid

BRN 

106236

InChI

InChI=1S/C8H15BrO2/c9-5-3-7-11-8-4-1-2-6-10-8/h8H,1-7H2

InChIKey

HJNHUFQGDJLQRS-UHFFFAOYSA-N

SMILES

C1(OCCCBr)OCCCC1

CAS DataBase Reference

33821-94-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

23-24/25

WGK Germany 

3

F 

8-10

Hazard Note 

Irritant

HS Code 

29329900

MSDS

• Language:English Provider:SigmaAldrich

2-(3-Bromopropoxy)tetrahydro-2H-pyran Usage And Synthesis

Chemical Properties

Clear colorless to yellow liquid

Uses

2-(3-Bromopropoxy)tetrahydro-2H-pyran may be used in organic synthesis studies.

General Description

The latent alcohol functionality of this bifunctional building block can be generated using aqueous acid.

Synthesis

GENERAL STEPS: The synthesis of the compound was reported in the literature (Pinchuk, A.N. et al. J. Med. Chem. 2006, 49, 2155-2165). A solution of 3-bromo-1-propanol (6.95 g, 50 mmol, 1 eq.) in DCM (25 mL) was added to a 125 mL round-bottomed flask, and 3,4-dihydro-2H-pyran (5.93 mL, 65 mmol, 1.3 eq.) was added slowly with stirring. The reaction mixture was stirred at room temperature overnight and the progress of the reaction was monitored by TLC (Spreader: 20% EtOAc in hexane solution, Color Developer: KMnO4) to confirm complete consumption of 3-bromo-1-propanol. After completion of the reaction, the solvent was evaporated under reduced pressure, and the resulting crude product was purified by rapid column chromatography on silica gel (silica gel dosage: 20 g, column diameter: 1.5 cm, eluent: 10% EtOAc/hexane, 100 mL) to afford 2-(3-bromopropoxy)tetrahydro-2H-pyran as a colorless, transparent oil in 86.4% yield (9.637 g). The product was detected by TLC (20% EtOAc in hexane solution) with Rf = 0.85. The NMR data were as follows: 1H NMR (400 MHz, CDCl3) δ: 4.59 (t, 1H, J = 3.52 Hz, H-7), 3.90-3.81 (m, 2H, H-6), 3.55-3.47 (m, 4H, H-4 + H-5), 2.16-2.08 (m, 2H, H-3), 1.90-1.64 (m, 2H, H-2), 1.57-1.50 (m, 4H, H-1); 13C NMR (100 MHz, CDCl3) δ: 98.90 (C-7), 64.88 (C-6), 62.26 (C-5), 32.90 (C-3), 30.59 (d, 2J-3) 30.59 (d, 2J = 6.04 Hz, C-4), 25.41 (C-2), 19.48 (C-1).

References

[1] Synthetic Communications, 2007, vol. 37, # 12, p. 2031 - 2037
[2] Journal of Medicinal Chemistry, 2006, vol. 49, # 7, p. 2155 - 2165
[3] Organic Letters, 2014, vol. 16, # 11, p. 2818 - 2821
[4] Angewandte Chemie - International Edition, 2015, vol. 54, # 51, p. 15497 - 15500
[5] Angew. Chem., 2015, vol. 127, # 51, p. 15717 - 15720

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