Diethyl bromodifluoromethanephosphonate Chemical Properties

Boiling point:

40-41 °C/0.05 mmHg (lit.)

Density 

1.503 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.417(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform, Ethyl Acetate

form 

liquid

Specific Gravity

1.503

color 

colorless

Water Solubility 

Not miscible or difficult to mix in water.

BRN 

1944045

InChI

InChI=1S/C5H10BrF2O3P/c1-3-10-12(9,11-4-2)5(6,7)8/h3-4H2,1-2H3

InChIKey

QRADKVYIJIAENZ-UHFFFAOYSA-N

SMILES

P(=O)(OCC)(OCC)C(F)(F)Br

CAS DataBase Reference

65094-22-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

21/22-36/38-38-36

Safety Statements 

26-36/37/39-60-37-23

RIDADR 

3278

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

No

HazardClass 

IRRITANT, IRRITANT-HARMFUL

PackingGroup 

III

HS Code 

29319090

MSDS

• Language:English Provider:Diethyl bromodifluoromethanephosphonate
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Diethyl bromodifluoromethanephosphonate Usage And Synthesis

Uses

Efficient difluoroalkylation of aryl boronic acids via palladium catalysis. Novel, moisture-stable bromodifluoromethylated phosphonate, ester, and amide. Efficient coupling with aryl boronic acids via Pd catalysis.

Uses

Diethyl (bromodifluoromethyl)phosphonate is used as a reactant for the preparation of phosphopeptide mimetic prodrugs targeted to Src homology 2 (SH2) domain of signal transducer and activator of transcription 3 (Stat3), synthesis of Mycobacterium tuberculosis protein tyrosine phosphatase inhibitory difluoromethylphosphonic acid derivatives via multi step synthesis with Suzuki coupling and resolution as key steps and P-C bond cleavage on basic hydrolysis.

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 3437, 1984 DOI: 10.1021/jo00192a056

reaction suitability

reaction type: C-C Bond Formation

Synthesis

Dibromodifluoromethane (209.8 g, 1 mol) was slowly added dropwise to a solution of triethyl phosphite (153.5 g, 0.925 mol) in anhydrous ether (450 mL) equipped with a magnetic stirrer under nitrogen protection. After the dropwise addition, the reaction system was slowly warmed to room temperature and subsequently heated to reflux for 20 hours. Upon completion of the reaction, the volatile solvent was removed by distillation under reduced pressure and the fraction with a boiling point of 50-52 °C (1 mmHg) was collected to afford the colorless liquid product diethyl (bromodifluoromethyl) phosphonate (256.3 g, 96% yield). The structure of the product was confirmed by 1H NMR (CDCl3): δ 4.35 (m, 4H), 1.35 (m, 6H); 13C NMR (CDCl3): δ 122.9, 119.8, 118.6, 115.4, 114.2, 111.1, 66.59, 66.50, 16.56, 16.48.

References

[1] Journal of Organometallic Chemistry, 1997, vol. 529, # 1-2, p. 267 - 278
[2] Phosphorus, Sulfur and Silicon and Related Elements, 1997, vol. 122, p. 247 - 259
[3] Patent: US2004/225146, 2004, A1. Location in patent: Page 4
[4] Journal of Fluorine Chemistry, 2011, vol. 132, # 10, p. 815 - 828
[5] Patent: WO2006/78698, 2006, A1. Location in patent: Page/Page column 64-65

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