Product Name

  • Name

    Diethyl bromodifluoromethanephosphonate

  • EINECS
  • CAS No. 65094-22-6
  • Article Data17
  • CAS DataBase
  • Density 1.551 g/cm3
  • Solubility Not miscible or difficult to mix in water.
  • Melting Point
  • Formula C5H10BrF2O3P
  • Boiling Point 195.7 °C at 760 mmHg
  • Molecular Weight 267.007
  • Flash Point 72.2 °C
  • Transport Information
  • Appearance
  • Safety 26-36/37/39
  • Risk Codes 21/22-36/38
  • Molecular Structure Molecular Structure of 65094-22-6 (Diethyl bromodifluoromethanephosphonate)
  • Hazard Symbols IrritantXi
  • Synonyms Phosphonicacid, (bromodifluoromethyl)-, diethyl ester (9CI);(Bromodifluoromethyl)phosphonic acid diethyl ester;Diethylbromodifluoromethylphosphonate;
  • PSA 45.34000
  • LogP 3.19770

Synthetic route

dibromodifluoromethane
75-61-6

dibromodifluoromethane

triethyl phosphite
122-52-1

triethyl phosphite

diethyl (bromodifluoromethyl)phosphonate
65094-22-6

diethyl (bromodifluoromethyl)phosphonate

Conditions
ConditionsYield
In tetrahydrofuran at 60℃; for 0.5h;96%
In diethyl ether for 24h; Heating;96%
In diethyl ether for 20h; Heating / reflux;96%
O,O-diethyl 1,1-difluoro-1-bromomethane phosphonothioate
180627-08-1

O,O-diethyl 1,1-difluoro-1-bromomethane phosphonothioate

diethyl (bromodifluoromethyl)phosphonate
65094-22-6

diethyl (bromodifluoromethyl)phosphonate

Conditions
ConditionsYield
With perfluoro-cis-2-n-hexyl-3-n-pentyloxaziridine In various solvent(s) for 0.0833333h; Ambient temperature; further reagent;96%
(bromodifluormethyl)triphenylphosphonium bromide
58201-66-4

(bromodifluormethyl)triphenylphosphonium bromide

triethyl phosphite
122-52-1

triethyl phosphite

diethyl (bromodifluoromethyl)phosphonate
65094-22-6

diethyl (bromodifluoromethyl)phosphonate

Conditions
ConditionsYield
In dichloromethane for 0.166667h; Ambient temperature;92%
(bromodifluormethyl)triphenylphosphonium bromide
58201-66-4

(bromodifluormethyl)triphenylphosphonium bromide

triethyl phosphite
122-52-1

triethyl phosphite

A

ethyl bromide
74-96-4

ethyl bromide

B

diethyl (bromodifluoromethyl)phosphonate
65094-22-6

diethyl (bromodifluoromethyl)phosphonate

C

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
In dichloromethane for 0.166667h; Product distribution; Mechanism; Ambient temperature;A n/a
B 92%
C 65%
...Expand
(bromodifluormethyl)triphenylphosphonium bromide
58201-66-4

(bromodifluormethyl)triphenylphosphonium bromide

triethyl phosphite
122-52-1

triethyl phosphite

A

diethyl (bromodifluoromethyl)phosphonate
65094-22-6

diethyl (bromodifluoromethyl)phosphonate

B

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
In dichloromethane at 20℃;A 67%
B n/a
...Expand
halon-1211
353-59-3

halon-1211

triethyl phosphite
122-52-1

triethyl phosphite

diethyl (bromodifluoromethyl)phosphonate
65094-22-6

diethyl (bromodifluoromethyl)phosphonate

Conditions
ConditionsYield
at 120℃; under 3811.31 Torr; for 240h; Michaelis-Arbuzov reaction; Autoclave;20%
diethyl (bromodifluoromethyl)phosphonate
65094-22-6

diethyl (bromodifluoromethyl)phosphonate

tert-butyl (E)-3-iodobut-2-enoate
292601-91-3

tert-butyl (E)-3-iodobut-2-enoate

tert-butyl (E)-3-(diethylphosphonodifluoromethyl)but-2-enoate
292601-92-4

tert-butyl (E)-3-(diethylphosphonodifluoromethyl)but-2-enoate

Conditions
ConditionsYield
Stage #1: diethyl (bromodifluoromethyl)phosphonate With zinc In N,N-dimethyl-formamide at 20℃; for 3h; Metallation;
Stage #2: tert-butyl (E)-3-iodobut-2-enoate With copper(I) bromide In N,N-dimethyl-formamide at 20℃; for 3h; Alkylation; cross-coupling; Further stages.;		99.4%
diethyl (bromodifluoromethyl)phosphonate
65094-22-6

diethyl (bromodifluoromethyl)phosphonate

2',6'-dichloro-4'-nitro-[1,1'-biphenyl]-2-ol

2',6'-dichloro-4'-nitro-[1,1'-biphenyl]-2-ol

2,6-dichloro-2'-(difluoromethoxy)-4-nitro-1,1'-biphenyl

2,6-dichloro-2'-(difluoromethoxy)-4-nitro-1,1'-biphenyl

Conditions
ConditionsYield
With potassium hydroxide In water; acetonitrile at -78 - 20℃;99%
diethyl (bromodifluoromethyl)phosphonate
65094-22-6

diethyl (bromodifluoromethyl)phosphonate

triethylamine
121-44-8

triethylamine

Triethyl(difluoromethyl)ammoniumbromid

Triethyl(difluoromethyl)ammoniumbromid

Conditions
ConditionsYield
With methanol; cesium fluoride In dichloromethane at 25℃; for 3h; Inert atmosphere; Sealed tube; chemoselective reaction;99%
diethyl (bromodifluoromethyl)phosphonate
65094-22-6

diethyl (bromodifluoromethyl)phosphonate

<(Ethinyl)(isopropyl)methyl>-p-toluolsulfonat
79157-49-6

<(Ethinyl)(isopropyl)methyl>-p-toluolsulfonat

(1,1-difluoro-5-methyl-hexa-2,3-dienyl)-phosphonic acid diethyl ester
334940-73-7

(1,1-difluoro-5-methyl-hexa-2,3-dienyl)-phosphonic acid diethyl ester

Conditions
ConditionsYield
Stage #1: diethyl (bromodifluoromethyl)phosphonate With copper(I) bromide; zinc In N,N-dimethyl-formamide
Stage #2: <(Ethinyl)(isopropyl)methyl>-p-toluolsulfonat With copper(I) bromide In N,N-dimethyl-formamide at 20℃; for 12h;		98%
4-nitro-phenol
100-02-7

4-nitro-phenol

diethyl (bromodifluoromethyl)phosphonate
65094-22-6

diethyl (bromodifluoromethyl)phosphonate

1-difluoromethoxy-4-nitrobenzene
1544-86-1

1-difluoromethoxy-4-nitrobenzene

Conditions
ConditionsYield
With potassium hydroxide In water; acetonitrile at -78 - 20℃; for 0.333333h;98%
With potassium hydroxide In water; acetonitrile at 25℃; Cooling;
diethyl (bromodifluoromethyl)phosphonate
65094-22-6

diethyl (bromodifluoromethyl)phosphonate

Na+[O2P(OEt)CF2Br]-
1333210-85-7

Na+[O2P(OEt)CF2Br]-

Conditions
ConditionsYield
With sodium iodide In acetone for 3h; Reflux;98%

Diethyl bromodifluoromethanephosphonate Chemical Properties

Molecule structure of Phosphonic acid,P-(bromodifluoromethyl)-, diethyl ester (CAS NO.65094-22-6):

IUPAC Name: 1-[[Bromo(difluoro)methyl]-ethoxyphosphoryl]oxyethane
Molecular Weight: 267.005667 [g/mol]
Molecular Formula: C5H10BrF2O3P 
Index of Refraction: 1.42
Molar Refractivity: 43.6 cm3
Molar Volume: 172 cm3
Surface Tension: 31.8 dyne/cm
Density: 1.551 g/cm3
Flash Point: 72.2 °C
Enthalpy of Vaporization: 41.42 kJ/mol
Boiling Point: 195.7 °C at 760 mmHg
Vapour Pressure: 0.58 mmHg at 25 °C
XLogP3-AA: 1.8
H-Bond Acceptor: 5
Rotatable Bond Count: 5
Exact Mass: 265.9519
MonoIsotopic Mass: 265.9519
Topological Polar Surface Area: 35.5
Heavy Atom Count: 12
Canonical SMILES: CCOP(=O)(C(F)(F)Br)OCC
InChI: InChI=1S/C5H10BrF2O3P/c1-3-10-12(9,11-4-2)5(6,7)8/h3-4H2,1-2H3
InChIKey: QRADKVYIJIAENZ-UHFFFAOYSA-N
Product Categories Phosphonic acid,P-(bromodifluoromethyl)-, diethyl ester (CAS NO.65094-22-6): C-C Bond Formation; Horner-Wadsworth-Emmons Reagents; Olefination

Diethyl bromodifluoromethanephosphonate Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 21/22-36/38
R21/22:Harmful in contact with skin and if swallowed. 
R36/38:Irritating to eyes and skin.
Safety Statements: 26-36/37/39 
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
HazardClass: IRRITANT, IRRITANT-HARMFUL
PackingGroup: III

Diethyl bromodifluoromethanephosphonate Specification

 Phosphonic acid,P-(bromodifluoromethyl)-, diethyl ester (CAS NO.65094-22-6) is also called Bromodifluoromethyl diethylphosphonate ; Diethyl bromodifluoromethanephosphonate ; Diethyl [bromo(difluoro)methyl]phosphonate .

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