Diethyl (iodomethyl)phosphonate

Base Information

• Chemical Name: Diethyl (iodomethyl)phosphonate
• CAS No.: 10419-77-9
• Molecular Formula: C5H12 I O3 P
• Molecular Weight: 278.027
• Hs Code.: 2931900090
• European Community (EC) Number: 233-895-3
• DSSTox Substance ID: DTXSID80146334
• Nikkaji Number: J129.834H
• Wikidata: Q83011137
• Mol file: 10419-77-9.mol

Synonyms:DIETHYL IODOMETHYLPHOSPHONATE;10419-77-9;Diethyl (iodomethyl)phosphonate;1-[ethoxy(iodomethyl)phosphoryl]oxyethane;Diethyl iodomethanephosphonate;Phosphonic acid, (iodomethyl)-, diethyl ester;Iodomethylphosphonic acid diethyl ester;EINECS 233-895-3;(E)-2-Styrylcyclobutanone;C5H12IO3P;SCHEMBL830528;DTXSID80146334;C5-H12-I-O3-P;CCG-2013;MFCD00041386;STK204925;AKOS005415745;Iodomethyl-phosphonic acid diethyl ester;(Iodomethyl)phosphonic acid diethyl ester;BB 0221096;CS-0063910;FT-0604980;FT-0624789;D73313;EN300-6733682;A800919;J-001130;F0001-0095

Chemical Property of Diethyl (iodomethyl)phosphonate

Chemical Property:

• Appearance/Colour: clear colorless to dark yellow liquid
• Vapor Pressure: 0.019mmHg at 25°C
• Refractive Index: 1.497-1.499
• Boiling Point: 261.2°Cat760mmHg
• Flash Point: 111.8°C
• PSA: 45.34000
• Density: 1.667g/cm³
• LogP: 2.64500
• Sensitive.: Light Sensitive
• Water Solubility.: Immiscible with water.
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 277.95688
• Heavy Atom Count: 10
• Complexity: 118

Purity/Quality:

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

DIETHYL IODOMETHYLPHOSPHONATE 95.00% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(CI)OCC
• Uses: Diethyl iodomethylphosphonate is used in the synthesis of H2N-Tyr(tBu)-vinyl sulfone.

Technology Process of Diethyl (iodomethyl)phosphonate

There total 7 articles about Diethyl (iodomethyl)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: 91.0%

diethyl (p-toluenesulfonyloxymethane)phosphonate (31618-90-3) → diethyl iodomethanephosphonate (10419-77-9)

Guidance literature:

With sodium iodide; In acetone; Reflux;

DOI:10.3762/bjoc.15.77

Reference yield: 84.0%

diiodomethane (75-11-6) + diethyl chlorophosphate (814-49-3) → diethyl iodomethanephosphonate (10419-77-9)

Guidance literature:

With methyllithium lithium bromide; In tetrahydrofuran; at -78 ℃; for 1h; chemoselective reaction; Inert atmosphere;

DOI:10.1039/d1ob00273b

Reference yield: 37.2%

diiodomethane (75-11-6) + triethyl phosphite (122-52-1) → diethyl iodomethanephosphonate (10419-77-9)

Guidance literature:

at 100 ℃; for 48h; Inert atmosphere;

DOI:10.1007/s10847-015-0490-2

upstream raw materials:

diiodomethane

triethyl phosphite

diethyl (p-toluenesulfonyloxymethane)phosphonate

diethyl (1-hydroxymethyl)phosphonate

Downstream raw materials:

phenoxymethylphosphonic acid

(2-chloro-phenoxymethyl)-phosphonic acid monoethyl ester

(2,4,6-trichloro-phenoxymethyl)-phosphonic acid monoethyl ester

(2,4,5-trichloro-phenoxymethyl)-phosphonic acid monoethyl ester

Refernces

• 1、 Kosolapoff. "-". . p. 1500. Retrieved 1953.
• 2、 Jia, Xue-Shun,Wang, Xian-Liang,Xiao, Jun-Zhao,Yin, Liang,Yin, Xing-Hao. "Asymmetric Synthesis of Chiral 1,3-Disubstituted Allylsilanes via Copper(I)-Catalyzed 1,4-Conjugate Silylation of α,β-Unsaturated Sulfones and Subsequent Julia-Kocienski Olefination". . p. 1916 - 1922. Retrieved 2021/06/07.
• 3、 Jones, David J.,O’Leary, Eileen M.,O’Sullivan, Timothy P.. "An improved synthesis of adefovir and related analogues". supporting information. p. 801 - 810. Retrieved 2019/04/17.