2,4-Difluorotoluene

2,4-Difluorotoluene Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P403+P235Store in a well-ventilated place. Keep cool.

P405Store locked up.

P501Dispose of contents/container to..…

2,4-Difluorotoluene Chemical Properties,Usage,Production

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