| Identification | More | [Name]
Diethyl bromodifluoromethanephosphonate | [CAS]
65094-22-6 | [Synonyms]
BROMODIFLUOROMETHANE DIETHYL PHOSPHATE
BROMODIFLUOROMETHYL DIETHYLPHOSPHONATE
Diethyl bromodifluoromethanephosphonate
DIETHYL (BROMODIFLUOROMETHYL)PHOSPHONATE
Bromodifluoromethyl diethyl phosphonate~Diethyl bromodifluoromethanephosphonate
BromodifluoromethylphosphonicAcidDiethylEsterDiethylBromodifluoromethylphosphonate
Bromodifluoromethyl diethylphosphonate 97%
Bromodifluoromethyldiethylphosphonate97%
1-[[Bromo(difluoro)methyl]-ethoxyphosphoryl]oxyethane | [Molecular Formula]
C5H10BrF2O3P | [MDL Number]
MFCD00069118 | [Molecular Weight]
267.01 | [MOL File]
65094-22-6.mol |
| Chemical Properties | Back Directory | [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.)
| [Fp ]
>230 °F
| [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [solubility ]
Chloroform, Ethyl Acetate | [form ]
liquid | [color ]
colorless | [Specific Gravity]
1.503 | [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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R21/22:Harmful in contact with skin and if swallowed .
R36/38:Irritating to eyes and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
3278 | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [TSCA ]
No | [HazardClass ]
IRRITANT, IRRITANT-HARMFUL | [PackingGroup ]
III | [HS Code ]
29319090 |
| Hazard Information | Back Directory | [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. | [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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