Diethyl bromodifluoromethanephosphonate

Base Information

• Chemical Name: Diethyl bromodifluoromethanephosphonate
• CAS No.: 65094-22-6
• Molecular Formula: C5H10BrF2O3P
• Molecular Weight: 267.007
• Hs Code.: 29319090
• Mol file: 65094-22-6.mol

Synonyms:Phosphonicacid, (bromodifluoromethyl)-, diethyl ester (9CI);(Bromodifluoromethyl)phosphonic acid diethyl ester;Diethylbromodifluoromethylphosphonate;

Chemical Property of Diethyl bromodifluoromethanephosphonate

Chemical Property:

• Vapor Pressure: 0.58mmHg at 25°C
• Refractive Index: n20/D 1.417(lit.)
• Boiling Point: 195.7 °C at 760 mmHg
• Flash Point: 72.2 °C
• PSA: 45.34000
• Density: 1.551 g/cm³
• LogP: 3.19770
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Chloroform, Ethyl Acetate
• Water Solubility.: Not miscible or difficult to mix in water.

Purity/Quality:

99.0% ^*data from raw suppliers

Diethyl (Bromodifluoromethyl)phosphonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 21/22-36/38-38-36
• Safety Statements: 26-36/37/39-60-37-23

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• 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.

Technology Process of Diethyl bromodifluoromethanephosphonate

There total 12 articles about Diethyl bromodifluoromethanephosphonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

dibromodifluoromethane (75-61-6) + triethyl phosphite (122-52-1) → diethyl (bromodifluoromethyl)phosphonate (65094-22-6)

Guidance literature:

In tetrahydrofuran; at 60 ℃; for 0.5h;

DOI:10.1016/S0022-328X(96)06541-2

Reference yield: 96.0%

O,O-diethyl 1,1-difluoro-1-bromomethane phosphonothioate (180627-08-1) → diethyl (bromodifluoromethyl)phosphonate (65094-22-6)

Guidance literature:

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

DOI:10.1021/jo970572a

Reference yield: 92.0%

(bromodifluormethyl)triphenylphosphonium bromide (58201-66-4) + triethyl phosphite (122-52-1) → ethyl bromide (74-96-4) + diethyl (bromodifluoromethyl)phosphonate (65094-22-6) + triphenylphosphine (603-35-0)

Guidance literature:

In dichloromethane; for 0.166667h; Product distribution; Mechanism; Ambient temperature;

DOI:10.1021/jo00168a068

upstream raw materials:

phosgene

[(diethoxyphosphoryl)difluoromethyl]zinc bromide

(diethylphosphono)difluoromethyl cadmium bromide

dibromodifluoromethane

Downstream raw materials:

diethyl (2E)-1,1-difluoro-3-(phenyl)prop-2-enylphosphonate

(3-cyclohexylidene-1,1-difluoro-allyl)-phosphonic acid diethyl ester

(S)-2-{[(9H-fluoren-9-yl)methoxy]carbonylamino}-3-{4-[(diethoxyphosphoryl)difluoromethyl]phenyl}propanoic acid

1,1,1-trifluoro-2-difluoromethoxypropane

Refernces

• 1、 Yang, Xueyan,Zhu, Yaoping,Fang, Xiang,Yang, Xianjin,Wu, Fanhong,Shen, Yongjia. "Synthesis of γ-butyrolactones containing α,α-difluoromethylenyl bisphosphonate initiated by Na2S2O4". . p. 174 - 178. Retrieved 2007.
• 2、 Flynn, Richard M.,Burton, Donald J.. "Synthetic and mechanistic aspects of halo-F-methylphosphonates". experimental part. p. 815 - 828. Retrieved 2011/10/08.