CAS 65094-22-6 Bromodifluoromethyl diethylphosphonate (HCID 144101)

Substructure search Find similar structures

Basic information

CAS: 65094-22-6
Standard SMILES: CCOP(=O)(OCC)C(F)(F)Br
InChIKey: QRADKVYIJIAENZ-UHFFFAOYSA-N
Molecular formula: C5H10BrF2O3P
Average molar mass: 267.01 g/mol
Monoisotopic mass: 265.9519

Names & identifiers

Preferred name: Bromodifluoromethyl diethylphosphonate
IUPAC: 1-[[bromo(difluoro)methyl]-ethoxyphosphoryl]oxyethane
English name: Diethyl bromodifluoromethanephosphonate
Molecular formula: C5H10BrF2O3P
Molecular weight: 267.01

Names & synonyms

65094-22-6Diethyl (bromodifluoromethyl)phosphonateBromodifluoromethyl diethylphosphonateDTXSID40215398RefChem:570343DTXCID40137889671-628-6diethyl bromodifluoromethanephosphonatediethyl bromodifluoromethylphosphonateMFCD000691181-[[bromo(difluoro)methyl]-ethoxyphosphoryl]oxyethaneC5H10BrF2O3P

Show more names

Diethyl P-(bromodifluoromethyl)phosphonateDiethyl bromodifluoromethanephosphonatBROMODIFLUOROMETHANE DIETHYL PHOSPHATEBromodifluoromethyldiethylphosphonate97%Bromodifluoromethyl diethylphosphonate 97%Diethyl (Bromodifluoromethyl)phosphonate >Diethyl [bromo(difluoro)methyl]phosphonate 97%

(bromodifluoromethyl)phosphonic acid diethyl ester1-[[bromo(difluoro)methyl]-ethoxy-phosphoryl]oxyethanediethyl(bromodifluoromethyl)phosphonate(bromo-difluoro-methyl)-phosphonic acid diethyl esterP-(Bromodifluoromethyl)phosphonic Acid Diethyl Ester; (Bromodifluoromethyl)phosphonic Acid Diethyl Ester;Phosphonic acid, (bromodifluoromethyl)-, diethyl esterSCHEMBL263167CHEMBL5181377

Database identifiers

Properties

Computed structural properties

XLogP: 1.8
Topological polar surface area: 35.5 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 5
Rotatable bonds: 5
Heavy atoms: 12
Formal charge: 0
Complexity: 178

Physicochemical properties

Boiling point: 40 · 40-41 °C/0.05 mmHg (lit.)
Density: 1.503 g/mL · 1.503 g/mL at 25 °C (lit.)
refractive index: 20 · n20/D 1.417(lit.)
Flash point: 230 °F · >230 °F
storage temp.: Keep in dark place,Inert atmosphere,Room temperature
solubility: Chloroform, Ethyl Acetate
form: liquid
Specific Gravity: 1.503 · 1.503
color: colorless
Water Solubility: Not miscible or difficult to mix in water.
BRN: 1944045 · 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 · 65094-22-6(CAS DataBase Reference)

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (54.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 11 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)；Eye Irrit. 2A (100%)；STOT SE 3 (54.5%)

Safety data

PPE: Eyeshields, Gloves
wgk: 3
tsca: No
ridadr: 3278
hs_code: 29319090
risk_code: 21/22-36/38-38-36
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
hazard_note: Irritant
safety_code: 26-36/37/39-60-37-23
hazard_class

Chemistry & industry

Applications · 2 items

UsesEfficient 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.

UsesDiethyl (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.