4-BROMO-TETRAHYDROPYRAN Chemical Properties

Boiling point:

178℃

Density 

1.467 g/cm3 at 25 °C

refractive index 

n20/D1.497

Flash point:

69℃

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

clear liquid

color 

Colorless to Yellow to Orange

InChI

InChI=1S/C5H9BrO/c6-5-1-3-7-4-2-5/h5H,1-4H2

InChIKey

IVBVKTPDEWDNRW-UHFFFAOYSA-N

SMILES

C1OCCC(Br)C1

CAS DataBase Reference

25637-16-5

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

WGK Germany 

2

HS Code 

29321900

4-BROMO-TETRAHYDROPYRAN Usage And Synthesis

Chemical Properties

Light yellow liquid

Uses

Reactant for:

• Nickel-catalyzed alkyl-alkyl Suzuki coupling reactions with boron reagents
• Preparation of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humans
• Preparation of aliphatic hydrocarbons via nickel-catalyzed Suzuki cross-coupling with alkylboranes
• Preparation of anthranilic acids as antibacterial agents with human serum albumin binding affinity
• Preparation of antiatherogenic antioxidant di-tert-butyldihydrobenzofuranols via Grignard reactions with di-tert-butyl(hydroxy)benzaldehyde derivatives
• Synthesis of gephyrotoxin via the Schmidt reaction

Uses

4-Bromo-tetrahydropyran is a useful reactant in organic synthesis.

Synthesis

General procedure for the synthesis of 4-bromotetrahydropyran from tetrahydropyran-4-ol: A. Preparation of 4-bromotetrahydropyran. Tetrahydropyran-4-ol (1.0 g, 10 mmol), carbon tetrabromide (3.6 g, 11 mmol) and triphenylphosphine (3.1 g, 12 mmol) were dissolved in dichloromethane (25 mL) and the reaction was stirred at room temperature overnight. Upon completion of the reaction, the crude reaction mixture was concentrated and subsequently purified by rapid chromatography on silica gel (eluent ratio ethyl acetate:hexane = 1:20) to afford the target product 4-bromotetrahydropyran as a colorless oil (1.4 g, 87% yield).

References

[1] Journal of Medicinal Chemistry, 2017, vol. 60, # 7, p. 2780 - 2789
[2] Patent: WO2005/9973, 2005, A1. Location in patent: Page/Page column 85; 86
[3] Angewandte Chemie - International Edition, 2007, vol. 46, # 19, p. 3556 - 3558
[4] Justus Liebigs Annalen der Chemie, 1937, vol. 532, p. 80
[5] Chem.Abstr., 1940, p. 4396

4-BROMO-TETRAHYDROPYRAN(25637-16-5)Related Product Information

• TETRAHYDRO-2H-PYRAN-3-OL
• 4-IODOTETRAHYDRO-2H-PYRAN
• (TETRAHYDRO-2H-PYRAN-4-YL)METHANOL
• 3,4-Dihydro-2H-pyran
• TETRAHYDRO-2H-PYRAN-4-CARBOXAMIDE
• Tetrahydro-2H-pyran-4-carboxylic acid
• 4-Aminotetrahydropyran
• Tetrahydro-4H-pyran-4-one
• 3,6-dihydro-2H-pyran
• Methyl tetrahydropyran-4-carboxylate
• 2-methyloxan-4-one
• Tetrahydro-4-pyranol
• 4-BROMOMETHYLTETRAHYDROPYRAN
• Tetrahydropyran
• 4-BROMO-TETRAHYDROPYRAN