Diethyl bromodifluoromethanephosphonate
- Product Name
- Diethyl bromodifluoromethanephosphonate
- CAS No.
- 65094-22-6
- Chemical Name
- Diethyl bromodifluoromethanephosphonate
- Synonyms
- DIETHYL (BROMODIFLUOROMETHYL)PHOSPHONATE;BROMODIFLUOROMETHYL DIETHYLPHOSPHONATE;BROMODIFLUOROMETHANE DIETHYL PHOSPHATE;Diethyl bromodifluoromethanephosphonat;Diethyl bromodifluoromethanephosphonate;Bromodifluoromethyldiethylphosphonate97%;Bromodifluoromethyl diethylphosphonate 97%;Diethyl P-(bromodifluoromethyl)phosphonate;Diethyl (Bromodifluoromethyl)phosphonate >Diethyl [bromo(difluoro)methyl]phosphonate 97%
- CBNumber
- CB8333674
- Molecular Formula
- C5H10BrF2O3P
- Formula Weight
- 267.01
- MOL File
- 65094-22-6.mol
Diethyl bromodifluoromethanephosphonate Property
- 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
- 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
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
- Precautionary statements
-
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P321Specific treatment (see … on this label).
P332+P313IF SKIN irritation occurs: Get medical advice/attention.
P337+P313IF eye irritation persists: Get medical advice/attention.
N-Bromosuccinimide Price
- Product number
- 411361
- Product name
- Diethyl (bromodifluoromethyl)phosphonate
- Purity
- 96%
- Packaging
- 5g
- Price
- $83.68
- Updated
- 2025/07/31
- Product number
- D3071
- Product name
- Diethyl (Bromodifluoromethyl)phosphonate
- Purity
- >97.0%(GC)
- Packaging
- 5g
- Price
- $38
- Updated
- 2025/07/31
- Product number
- D3071
- Product name
- Diethyl (Bromodifluoromethyl)phosphonate
- Purity
- >97.0%(GC)
- Packaging
- 25g
- Price
- $149
- Updated
- 2025/07/31
- Product number
- D443845
- Product name
- Diethyl (Bromodifluoromethyl)phosphonate
- Packaging
- 5g
- Price
- $80
- Updated
- 2021/12/16
- Product number
- 6177-B-01
- Product name
- Bromodifluoromethyl diethylphosphonate
- Purity
- 97%
- Packaging
- 1g
- Price
- $10
- Updated
- 2021/12/16
Diethyl bromodifluoromethanephosphonate Chemical Properties,Usage,Production
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
75-61-6
122-52-1
65094-22-6
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
Diethyl bromodifluoromethanephosphonate Preparation Products And Raw materials
Raw materials
Preparation Products
Diethyl bromodifluoromethanephosphonate Suppliers
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View Lastest Price from Diethyl bromodifluoromethanephosphonate manufacturers
- Product
- Diethyl bromodifluoromethanephosphonate 65094-22-6
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 1Ton
- Release date
- 2025-04-01
- Product
- bromodifluoromethane diethyl phosphate 65094-22-6
- Price
- US $0.10/kg
- Min. Order
- 0.005kg
- Purity
- 99.99%
- Supply Ability
- 20 tons
- Release date
- 2024-04-15
- Product
- Diethyl bromodifluoromethanephosphonate 65094-22-6
- Price
- US $15.00-10.00/KG
- Min. Order
- 1KG
- Purity
- 99%+ HPLC
- Supply Ability
- Monthly supply of 1 ton
- Release date
- 2021-06-27