Tetrahydrofurfuryl bromide Chemical Properties

Boiling point:

170-171 °C (755 mmHg)

Density 

1.45

refractive index 

1.4853-1.4873

Flash point:

63 °C

storage temp. 

Refrigerator

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Oil

color 

Clear Light Yellow

BRN 

102717

InChI

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

InChIKey

VOHILFSOWRNVJJ-UHFFFAOYSA-N

SMILES

O1CCCC1CBr

CAS DataBase Reference

1192-30-9(CAS DataBase Reference)

EPA Substance Registry System

Furan, 2-(bromomethyl)tetrahydro- (1192-30-9)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

24/25

RIDADR 

1993

RTECS 

LU6000000

TSCA 

Yes

HS Code 

29321900

Toxicity

mouse,LD50,intravenous,180mg/kg (180mg/kg),U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#03416,

MSDS

• Language:English Provider:2-(Bromomethyl)tetrahydrofuran
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Tetrahydrofurfuryl bromide Usage And Synthesis

Chemical Properties

Colorless to light yellow liqui

Uses

(±)-Tetrahydrofurfuryl Bromide is a general chemical reagent used in the synthesis of tubulin polymerization inhibitors.

Synthesis

In a 500-ml three-necked flask equipped with a stirrer, thermometer, dropping funnel, and calcium chloride tube, place 96 g of redistilled PBr₃ and 50 ml of dry benzene. Add 15 g of dry pyridine dropwise with stirring over 15 minutes.
Cool the flask in an ice-salt bath to -5°C. Then, slowly add a mixture of 102 g of tetrahydrofurfuryl alcohol and 5 g of dry pyridine over 4 hours, maintaining the internal temperature between -5° and -3°C. Stir for an additional hour and allow the mixture to warm to room temperature.
Let the mixture stand for 24-48 hours. Transfer it to a Claisen flask, rinse with a little benzene, and remove the benzene by distillation under reduced pressure (bath temperature ≤90°C). Finally, distill the product under high vacuum (5-10 mm Hg) with the bath temperature up to 150-155°C.
The crude product is redistilled to give pure tetrahydrofurfuryl bromide, boiling at 69-70°C/22 mm Hg. The yield is 90-102 g (53-61%)^[1].

References

[1] Org. Synth. 1943, 23, 88. DOI: 10.15227/orgsyn.023.0088.

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