2,4-Difluorotoluene Chemical Properties

Melting point:

-35 °C

Boiling point:

113-117 °C (lit.)

Density 

1.12 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.449(lit.)

Flash point:

59 °F

storage temp. 

Sealed in dry,2-8°C

form 

Liquid

Specific Gravity

1.120

color 

Clear colorless

BRN 

1931681

InChI

InChI=1S/C7H6F2/c1-5-2-3-6(8)4-7(5)9/h2-4H,1H3

InChIKey

MPXDAIBTYWGBSL-UHFFFAOYSA-N

SMILES

C1(C)=CC=C(F)C=C1F

CAS DataBase Reference

452-76-6(CAS DataBase Reference)

NIST Chemistry Reference

2,4-Difluorotoluene(452-76-6)

Safety Information

Hazard Codes 

F,F+

Risk Statements 

11

Safety Statements 

16-29-33

RIDADR 

UN 1993 3/PG 2

WGK Germany 

3

Hazard Note 

Flammable

HazardClass 

3

PackingGroup 

II

HS Code 

29039990

MSDS

• Language:English Provider:2,4-Difluorotoluene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2,4-Difluorotoluene Usage And Synthesis

Chemical Properties

colorless to light yellow liqui

Uses

2,4-Difluorotoluene was used in the synthesis of new hydrophobic isosteres of pyrimidines and purine nucleosides.

General Description

2,4-Difluorotoluene was synthesized as a nucleotide analog and was incorporated into DNA and undergoes replication by DNA polymerase enzymes.

Synthesis

The general procedure for the synthesis of p-fluorotoluene, 2-fluorotoluene, 3-fluorotoluene, 2,4-difluorotoluene, 2,5-difluorotoluene, and 1,2-difluoro-4-methylbenzene from toluene is as follows: to a glass reactor fitted with a PTFE-lined magnetic stirring bar attached to a gas scrubbing flask were added toluene derivative (0.95-1.14 mmol), acetonitrile (1-2.5 mL/mmol of toluene derivative), and boron trifluoride ethyl ether complex (1.3-1.6 mmol/mmol of toluene derivative). mmol toluene derivative), acetonitrile (1-2.5 mL/mmol toluene derivative) and boron trifluoride ethyl ether complex (1.3-1.6 mmol/mmol toluene derivative). The reaction mixture was stirred at -25 °C for 10-15 min, followed by the addition of xenon difluoride (1.2-1.3 mmol/mmol toluene derivative) in batches. The reaction system was slowly warmed to 22 °C over 1 h and stirring was continued for 40-60 min. Upon completion of the reaction, hexafluorobenzene was added as an internal standard and samples were taken for 19F NMR analysis (Method B). The reaction mixture was quenched with saturated aqueous sodium bicarbonate and extracted with dichloromethane (1-2 mL). The combined organic phases were dried with anhydrous magnesium sulfate and subsequently analyzed by 19F NMR and GC/MS (Procedure C). The major products are listed in the table and others are shown below (GC/MS data).

References

[1] Russian Journal of Organic Chemistry, 2016, vol. 52, # 10, p. 1400 - 1407
[2] Zh. Org. Khim., 2016, vol. 52, # 10, p. 1412 - 1419,8

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