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Cas Database

Name	Diethyl bromodifluoromethanephosphonate	EINECS	N/A
CAS No.	65094-22-6	Density	1.551 g/cm³
PSA	45.34000	LogP	3.19770
Solubility	Not miscible or difficult to mix in water.	Melting Point	N/A
Formula	C₅H₁₀BrF₂O₃P	Boiling Point	195.7 °C at 760 mmHg
Molecular Weight	267.007	Flash Point	72.2 °C
Transport Information	N/A	Appearance	N/A
Safety	26-36/37/39	Risk Codes	21/22-36/38
Molecular Structure		Hazard Symbols	Xi
Synonyms	Phosphonicacid, (bromodifluoromethyl)-, diethyl ester (9CI);(Bromodifluoromethyl)phosphonic acid diethyl ester;Diethylbromodifluoromethylphosphonate;	Article Data	17

Diethyl bromodifluoromethanephosphonate Synthetic route

: 75-61-6
dibromodifluoromethane

: 122-52-1
triethyl phosphite

: 65094-22-6
diethyl (bromodifluoromethyl)phosphonate

Conditions

Conditions	Yield
In tetrahydrofuran at 60℃; for 0.5h;	96%
In diethyl ether for 24h; Heating;	96%
In diethyl ether for 20h; Heating / reflux;	96%

: 180627-08-1
O,O-diethyl 1,1-difluoro-1-bromomethane phosphonothioate

: 65094-22-6
diethyl (bromodifluoromethyl)phosphonate

Conditions

Conditions	Yield
With perfluoro-cis-2-n-hexyl-3-n-pentyloxaziridine In various solvent(s) for 0.0833333h; Ambient temperature; further reagent;	96%

: 58201-66-4
(bromodifluormethyl)triphenylphosphonium bromide

: 122-52-1
triethyl phosphite

: 65094-22-6
diethyl (bromodifluoromethyl)phosphonate

Conditions

Conditions	Yield
In dichloromethane for 0.166667h; Ambient temperature;	92%

: 58201-66-4
(bromodifluormethyl)triphenylphosphonium bromide

: 122-52-1
triethyl phosphite

A: 74-96-4
ethyl bromide

B: 65094-22-6
diethyl (bromodifluoromethyl)phosphonate

C: 603-35-0
triphenylphosphine

Conditions

Conditions	Yield
In dichloromethane for 0.166667h; Product distribution; Mechanism; Ambient temperature;	A n/a B 92% C 65%

: 58201-66-4
(bromodifluormethyl)triphenylphosphonium bromide

: 122-52-1
triethyl phosphite

A: 65094-22-6
diethyl (bromodifluoromethyl)phosphonate

B: 603-35-0
triphenylphosphine

Conditions

Conditions	Yield
In dichloromethane at 20℃;	A 67% B n/a

: 353-59-3
halon-1211

: 122-52-1
triethyl phosphite

: 65094-22-6
diethyl (bromodifluoromethyl)phosphonate

Conditions

Conditions	Yield
at 120℃; under 3811.31 Torr; for 240h; Michaelis-Arbuzov reaction; Autoclave;	20%

: 65094-22-6
diethyl (bromodifluoromethyl)phosphonate

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

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

Conditions

Conditions	Yield
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%

: 65094-22-6
diethyl (bromodifluoromethyl)phosphonate

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

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

Conditions

Conditions	Yield
With potassium hydroxide In water; acetonitrile at -78 - 20℃;	99%

: 65094-22-6
diethyl (bromodifluoromethyl)phosphonate

: 121-44-8
triethylamine

: Triethyl(difluoromethyl)ammoniumbromid

Conditions

Conditions	Yield
With methanol; cesium fluoride In dichloromethane at 25℃; for 3h; Inert atmosphere; Sealed tube; chemoselective reaction;	99%

: 65094-22-6
diethyl (bromodifluoromethyl)phosphonate

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

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

Conditions

Conditions	Yield
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%

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: Irritant Xi
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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