Diethyl [bis(methylthio)methyl]phosphonate

Base Information

• Chemical Name: Diethyl [bis(methylthio)methyl]phosphonate
• CAS No.: 62999-70-6
• Molecular Formula: C7H17 O3 P S2
• Molecular Weight: 244.316
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID50402378
• Nikkaji Number: J722.536I
• Wikidata: Q82205779
• Mol file: 62999-70-6.mol

Synonyms:62999-70-6;DIETHYL [BIS(METHYLTHIO)METHYL]PHOSPHONATE;SCHEMBL3938656;DTXSID50402378;Diethyl[bis(methylthio)methyl]phosphonate;Diethyl [bis(methylsulfanyl)methyl]phosphonate;[Bis(methylthio)methyl]phosphonic acid diethyl ester;(Bis-methylsulfanyl-methyl)-phosphonic acid diethyl ester

Chemical Property of Diethyl [bis(methylthio)methyl]phosphonate

Chemical Property:

• Vapor Pressure: 0.00164mmHg at 25°C
• Boiling Point: 303.7°C at 760 mmHg
• Flash Point: 137.5°C
• PSA: 95.94000
• Density: 1.167g/cm³
• LogP: 3.26210
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 244.03567374
• Heavy Atom Count: 13
• Complexity: 163

Purity/Quality:

99% ，98% ^*data from raw suppliers

DIETHYL [BIS(METHYLTHIO)METHYL]PHOSPHONATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(C(SC)SC)OCC

Technology Process of Diethyl [bis(methylthio)methyl]phosphonate

There total 9 articles about Diethyl [bis(methylthio)methyl]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: 61.0%

diethyl(diethoxymethyl)phosphonate (17997-33-0) → S,S-dimethylthioacetal of diethyl oxomethanephosphonate (62999-70-6)

Guidance literature:

With hydrogenchloride; methylthiol; In acetic acid;

Reference yield: 60.0%

diethyl 1-(methylthio)methylphosphonate (28460-01-7) + Dimethyldisulphide (624-92-0) → S,S-dimethylthioacetal of diethyl oxomethanephosphonate (62999-70-6)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; Mechanism; sulphenylation of the metallated phosphonates monitored by low temp. 31P-NMR;

DOI:10.1055/s-1980-28944

Reference yield:

diethyl 1-(methylthio)methylphosphonate (28460-01-7) → S,S-dimethylthioacetal of diethyl oxomethanephosphonate (62999-70-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) n-BuLi / 1.) hexane, THF, -78 deg C, 2.) -78 deg C

2: 1.) n-BuLi / 1.) Et₂O, THF, -78 deg C, 10 min, 2.) room temp., 1 h; reflux, 30 min

With n-butyllithium;

DOI:10.1055/s-1989-27163

upstream raw materials:

chlordimethylmercaptomethan

triethyl phosphite

diethyl (mercapto-methylthio-methyl)phosphonate

methyl iodide

Downstream raw materials:

(S)-1-(bis-methylsulfanyl-methylene)-3-(1-nitro-cyclopentyl)-cyclohexane

diethyl methylsulfonylmethylphosphonate

Diethyl methylphosphonate

Diethyl (2-oxopropyl)phosphonate

Refernces

• 1、 Bulpin, Andrew,Masson, Serge,Sene, Aboubacary. "THE USE OF PHOSPHONODITHIOFORMATES FOR THE SYNTHESIS OF KETENE DITHIOACETALS". . p. 3415 - 3418. Retrieved 2007/10/02.
• 2、 Mikolajczyk, Marian,Balczewski, Piotr,Grzejszczak, Slawomir. "Sulphenylation of Phosphonates. A Facile Synthesis of α-Phosphoryl Sulphides and S,S-Acetals of Oxomethanephosphonates". . p. 127 - 129. Retrieved 2007/10/02.