Diethyl (2-bromoethyl)phosphonate

Base Information

• Chemical Name: Diethyl (2-bromoethyl)phosphonate
• CAS No.: 5324-30-1
• Molecular Formula: C6H14BrO3P
• Molecular Weight: 245.053
• Hs Code.: 29319090
• European Community (EC) Number: 226-193-3
• NSC Number: 119421,2672
• DSSTox Substance ID: DTXSID00201333
• Nikkaji Number: J236.439E
• Wikidata: Q83074525
• Mol file: 5324-30-1.mol

Synonyms:5324-30-1;Diethyl 2-bromoethylphosphonate;Diethyl (2-bromoethyl)phosphonate;1-bromo-2-diethoxyphosphorylethane;Phosphonic acid, (2-bromoethyl)-, diethyl ester;(2-Bromoethyl)phosphonic acid diethyl ester;2-Bromoethylphosphonic Acid Diethyl Ester;EINECS 226-193-3;O,O-Diethyl (2-bromoethyl)phosphonate;diethyl(2-bromoethyl)phosphonate;MFCD00000239;C6H14BrO3P;diethyl bromoethylphosphonate;SCHEMBL331812;C6-H14-Br-O3-P;diethyl-2-bromoethyl phosphonate;diethyl-2-bromoethyl-phosphonate;PINITSMLVXAASM-UHFFFAOYSA-;diethyl-(2-bromoethyl)phosphonate;DTXSID00201333;NSC2672;BrCH2CH2P(O)(OC2H5)2;NSC 2672;NSC-2672;1-Bromo-2-diethoxyphosphoryl-ethane;BBL100179;NSC119421;STL512351;AKOS015903184;Diethyl 2-bromoethylphosphonate, 97%;4-Pyridineethanamine,2-methoxy-(9CI);CS-W016702;NSC 119421;NSC-119421;1-(2-bromoethyl-ethoxyphosphoryl)oxyethane;B1781;FT-0624771;EN300-99423;F14033;A870787;Diethyl 2-bromoethanephosphonate;2-Bromoethylphosphonic acid diethyl ester;Diethyl2-bromoethylphosphonate, (2-Bromoethylphosphonicacid diethylester)

Chemical Property of Diethyl (2-bromoethyl)phosphonate

Chemical Property:

• Appearance/Colour: clear colorless to slightly yellow liquid
• Vapor Pressure: 0.0285mmHg at 25°C
• Refractive Index: n20/D 1.461(lit.)
• Boiling Point: 253.9 °C at 760 mmHg
• Flash Point: 114.4 °C
• PSA: 45.34000
• Density: 1.379g/cm³
• LogP: 2.64740
• Storage Temp.: Refrigerator
• Water Solubility.: Soluble in water(20 g/L) (25°C).
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 243.98639
• Heavy Atom Count: 11
• Complexity: 130

Purity/Quality:

98%,99%, ^*data from raw suppliers

Diethyl 2-Bromoethylphosphonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOP(=O)(CCBr)OCC
• Uses: It is employed as a reactant involved in radical coupling, synthesis of organosoluble zirconium phosphonate nanocomposites, click-chemistry, asymmetric epoxidation of unfunctionalized olefins, Negishi alkyl-aryl cross-coupling, and in synthesis of hydrolytically stable phosphonic acids for use as dental adhesives.

Technology Process of Diethyl (2-bromoethyl)phosphonate

There total 10 articles about Diethyl (2-bromoethyl)phosphonate 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: 95.0%

ethylene dibromide (106-93-4) + triethyl phosphite (122-52-1) → diethyl 2-bromoethylphosphonate (5324-30-1)

Guidance literature:

for 2h; Reflux;

Reference yield: 70.0%

nickel(II) chloride hexahydrate + salicylaldehyde (90-02-8) + diaminomaleonitrile (1187-42-4) → Ni((NCCNCHC6H4O)2) (64696-98-6)

Guidance literature:

In ethanol; byproducts: H2O, HCl; soln. of the dinitrile in 95% EtOH and a hot soln. of salicylaldehyde succesively added to a hot soln. of the metal salt kept at 70°C, heated; filtered off, washed with hot EtOH, dried over silica gel, elem. anal.;

DOI:10.1016/0022-1902(81)90005-1

Reference yield:

ethylmagnesium bromide (925-90-6) + diethyl chlorophosphate (814-49-3) → diethyl 2-bromoethylphosphonate (5324-30-1)

Guidance literature:

ethylmagnesium bromide; With zirconocene dichloride; In tetrahydrofuran; diethyl ether;

diethyl chlorophosphate; In tetrahydrofuran; diethyl ether; at 20 ℃; for 24h;

With N-Bromosuccinimide; In tetrahydrofuran; at 20 ℃; for 3h; Further stages.;

DOI:10.1039/b107755d

upstream raw materials:

ethylene dibromide

triethyl phosphite

ethanol

ethylmagnesium bromide

Downstream raw materials:

Diethyl vinylphosphonate

diethyl <2-(diethylamino)ethyl>phosphonate

ethylphosphonic acid diethyl ester

diethyl 5-oxo-n-hexylphosphonate

Refernces

• 1、 Sheikhshoaie, Iran,Lotfi, Najmeh,Sieler, Joachim,Krautscheid, Harald,Khaleghi, Moj. "Synthesis, structures and antimicrobial activities of nickel(II) and zinc(II) diaminomaleonitrile-based complexes". . p. 555 - 562. Retrieved 2018.
• 2、 Li, Jing,Ni, Xufeng,Ling, Jun,Shen, Zhiquan. "Syntheses and properties of poly(diethyl vinylphosphonate) initiated by lanthanide tris(borohydride) complexes: Polymerization controllability and mechanism". . p. 2409 - 2415. Retrieved 2013.
• 3、 Ali,Assiri,Yahia,Zahran,Meselhy,Hussien. "Regioselective Synthesis of Novel Functionalized Pyrano[2′,3′:4,5]pyrimido[1,6-b][1,2,4,5]triazaphosphepines". . p. 79 - 84. Retrieved 2021/03/04.
• 4、 -. "Compounds and compositions as TLR activity modulators". Page/Page column 134. . Retrieved 2018/05/04.