2,4-Difluorophenylacetic acid Chemical Properties

Melting point:

115-118 °C (lit.)

Boiling point:

219°C (rough estimate)

Density 

1.3010 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Powder

pka

3.98±0.10(Predicted)

color 

White

BRN 

3649727

InChI

InChI=1S/C8H6F2O2/c9-6-2-1-5(3-8(11)12)7(10)4-6/h1-2,4H,3H2,(H,11,12)

InChIKey

QPKZIGHNRLZBCL-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

81228-09-3(CAS DataBase Reference)

NIST Chemistry Reference

2,4-Difluorophenylacetic acid(81228-09-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2,4-Difluorophenylacetic acid Usage And Synthesis

Chemical Properties

white powder

Uses

2,4-Difluorophenylacetic acid is used in the synthesis of nonpolar peptide nucleic acid monomers containing fluoroaromatics (F-PNA).

Uses

2,4-Difluorophenylacetic acid has been used in the synthesis of nonpolar peptide nucleic acid monomers containing fluoroaromatics (F-PNA).

Synthesis

(a) 25.7 g of 2,4-difluorobenzyl bromide was dissolved in 100 mL of tetrahydrofuran and slowly added dropwise over 0.5 h to a stirred suspension containing 3.0 g of magnesium chips and 30 mL of tetrahydrofuran. After the dropwise addition was completed, stirring of the reaction mixture was continued for 10 minutes. Subsequently, a steady stream of carbon dioxide was continuously passed into the resulting Grignard reagent for 1 hour. After completion of the reaction, the mixture was evaporated to dryness and the residue was partitioned with ether and dilute hydrochloric acid. The ether phase was separated and extracted with 2 N sodium hydroxide solution. The basic extract was acidified with concentrated hydrochloric acid and extracted with ether to give 5.1 g (24% yield) of crude 2,4-difluorophenylacetic acid. The crude product was dissolved directly in 25 mL of tetrahydrofuran without further purification and added slowly dropwise to a stirred mixture of 2.0 g of lithium aluminum hydride suspended in 100 mL of tetrahydrofuran.

References

[1] Patent: US4649160, 1987, A

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