4-Fluorobenzyl bromide Chemical Properties

Boiling point:

85 °C15 mm Hg(lit.)

Density 

1.517 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.547(lit.)

Flash point:

>230 °F

storage temp. 

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

solubility 

soluble in Chloroform

form 

Liquid

Specific Gravity

1.517

color 

Clear colorless to yellow

Sensitive 

Lachrymatory

BRN 

636507

InChIKey

NVNPLEPBDPJYRZ-UHFFFAOYSA-N

CAS DataBase Reference

459-46-1(CAS DataBase Reference)

NIST Chemistry Reference

«alpha»-Bromo-4-fluorotoluene(459-46-1)

EPA Substance Registry System

4-Fluorobenzyl bromide (459-46-1)

Safety Information

Hazard Codes 

C

Risk Statements 

34-36

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3265 8/PG 2

WGK Germany 

3

Hazard Note 

Corrosive/Lachrymatory

TSCA 

Yes

HazardClass 

8

PackingGroup 

III

HS Code 

29039990

MSDS

• Language:English Provider:4-Fluorobenzyl bromide
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Fluorobenzyl bromide Usage And Synthesis

Chemical Properties

4-Fluorobenzyl bromide (C7H6BrF, CAS registry No. 459-46-1) is a colorless to light yellow liquid. Its flash point is 74.8 oC. It is stable at room temperature in closed containers under normal storage and handling conditions. 1,3-Difluorobenzene can react with water to form toxic fumes. Therefore, it should be stored in a tightly closed container and should be stored in a cool, dry and well-ventilated area away from incompatible substances.

Uses

4-Fluorobenzyl bromide is an important intermediate in organic chemistry. 4-Fluorobenzyl bromide can be used as alkylating reagent to participate in the alkylation reaction with sulfamic esters (R-O-SO2-NH2) in liquid-liquid phase transfer conditions, resulting in the preparation of the N-dialkyled products or the corresponding ethers by scission of the O-SO2 bond, depending on the nature of R.
4-Fluorobenzyl bromide can be used for the synthesis of glycyrrhetinic acid (GA) derivatives, which are slow-binding inhibitors of tyrosinase and have inhibitory effects on melanogenesis.

Chemical Properties

Colorless to light yellow liqui

Uses

4-Fluorobenzyl bromide was used in the preparation of:

• 3-acetyl-1-(4-fluorobenzyl)-4-hydroxy-1H-indole
• 1-(4-fluorobenzyl)-5-(pyrrolidine-1-sulfonyl)isatin
• (S)-1-(4-fluorobenzyl)-5-(2-(4-fluorophenoxymethyl)pyrrolidine-1-sulfonyl)isatin
• 8-bromo 9-(4-fluorobenzyl) adenine
• 8-bromo 3-(4-fluorobenzyl) adenine

Uses

4-Fluorobenzyl Bromide is a substituted benzyl bromide reagent used in the preparation of wide range of biologically active compounds such as bronchodialators, neurochemicals and antibacterials.

Synthesis

GENERAL METHOD: Benzyl alcohol (1 mmol) was dissolved in anhydrous benzene (15 mL), phosphorus tribromide (0.5 mL) was added and the reaction was stirred at room temperature. Upon completion of the reaction, the target product 4-fluorobenzyl bromide was obtained in quantitative yield by conventional post-processing steps.

References

[1] Journal of Steroid Biochemistry and Molecular Biology, 2013, vol. 137, p. 332 - 344
[2] Bulletin of the Chemical Society of Ethiopia, 2012, vol. 26, # 2, p. 305 - 309
[3] Tetrahedron Letters, 2016, vol. 57, # 22, p. 2430 - 2433
[4] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 8, p. 2989 - 3002
[5] Chem, 2018, vol. 4, # 1, p. 124 - 137

4-Fluorobenzyl bromide(459-46-1)Related Product Information

• Rocuronium bromide
• [2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]methyl 2,2-dimethyl-3-pro p-1-enyl-cyclopropane-1-carboxylate
• Diethylstilbestrol
• Ethyl bromodifluoroacetate
• Fluorobenzene
• Ethidium bromide
• 4-Fluorobenzyl chloride
• BRETYLIUM TOSYLATE
• Allyl bromide
• Sodium bromate
• alpha-Chloro-o-fluorotoluene
• 4-n-Propoxyphenylacetylene
• Bromine
• 1,2-Bis(bromomethyl)benzene
• 9-BROMOFLUORENE
• 2-(Trifluoromethyl)benzyl bromide
• 1,2,4,5-TETRAKIS(BROMOMETHYL)BENZENE
• Methyl bromide