82737-61-9

Basic information

• Product Name: 2,4-BIS(METHYLTHIO)-1,3,2,4-DITHIADIPHOSPHETANE-2,4-DISULFIDE
• Synonyms: DAVY REAGENT METHYL;DR-ME;2,4-BIS(METHYLTHIO)-1,3,2,4-DITHIADIPHOSPHETANE-2,4-DISULFIDE;2,4-BIS(METHYLTHIO)-1,3-DITHIA-2,4-DIPHOSPHETANE-2,4-DISULFIDE;Davy;DAVY REAGENT METHYL, TECH.;1,3,2,4-Dithiadiphosphetane, 2,4-bis(methylthio)-, 2,4-disulfide;2,4-Bis(methylthio)-1,3,2,4-dithiadiphosphetane-2,4-disulfide, DR-Me
• CAS NO: 82737-61-9
• Molecular Formula: C₂H₆P₂S₆
• Molecular Weight: 284.41
• Product Categories: Boron, Nitrile, Thio,& TM-Cpds;API intermediates
• Mol File: 82737-61-9.mol

Chemical Properties

• Melting Point: 165-166℃
• Boiling Point: 382.5 °C at 760 mmHg
• Flash Point: 105 °F
• Appearance: /
• Density: 1.69 g/cm³
• Vapor Pressure: 1.03E-05mmHg at 25°C
• Refractive Index: 1.754
• BRN: 4182442
• CAS DataBase Reference: 2,4-BIS(METHYLTHIO)-1,3,2,4-DITHIADIPHOSPHETANE-2,4-DISULFIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-BIS(METHYLTHIO)-1,3,2,4-DITHIADIPHOSPHETANE-2,4-DISULFIDE(82737-61-9)
• EPA Substance Registry System: 2,4-BIS(METHYLTHIO)-1,3,2,4-DITHIADIPHOSPHETANE-2,4-DISULFIDE(82737-61-9)

Safety Data

• Hazard Codes: Xn,N,F
• Statements: 22-51/53-10-61-50/53-11
• Safety Statements: 61
• RIDADR: UN 1325 4.1/PG 2
• WGK Germany: 3
• F: 13
• Hazardous Substances Data: 82737-61-9(Hazardous Substances Data)

Usage

Purification Methods

It crystallises from *C6H6 in yellow plates or from hot trichlorobenzene. The low melting point reported in the literature (112o with gradual softening at 68-102o) has been attributed to the presence of elemental sulfur in the crystals. It has a foul odour and is a suspected carcinogen. [Yousif et al. Tetrahedron 40 2663 1984, Scott et al. J Org Chem 22 789 1957.]

InChI:InChI=1/C2H6P2S6/c1-7-3(5)9-4(6,8-2)10-3/h1-2H3

Upstream product

• 756-80-9 O,O-dimethyl phosphorodithioic acid 
• 67-56-1 methanol 

Downstream Products

• 2168-78-7 methyl dithiobenzoate 
• 949-00-8 phenyl dithiobenzoate 
• 5415-95-2 methyl dithiopropionate 
• 128742-65-4 2-(methylthio)tropothione 
• 20849-26-7 methyl 2-naphthalenecarbodithioate 
• 5969-49-3 3-Methyl-dithiobenzoesaeure-methylester 
• 1613253-81-8 2,3,4-trimethoxy-thiobenzoic acid S-methyl ester 
• 377732-35-9 methyl 2-methyl-c-5-{4-[5-methyl-2-(4-methylphenyl)-1,3-thiazol-4-yl]butyl}-1,3-dioxane-r-2-carboxylate 
• 5874-05-5 methyl cyclohexanecarbodithionate 
• 100555-93-9 phenoxy-2 dithioacetate de methyle 
• 2168-84-5 methyl dithioacetate 
• 2168-85-6 methyl phenyldithioacetate 
• 137092-48-9 2-(2-Fluorphenyl)dithioessigsaeure-methylester 
• 58863-41-5 4-nitro-dithiobenzoic acid methyl ester 

Relevant articles and documents

STUDIES ON ORGANOPHOSPHORUS COMPOUNDS XLVIII Synthesis of Dithioesters from P,S-Containing Reagents and Carboxylic Acids and Their Derivatives

2,4-Bismethylthio-1,3,2,4-dithiadiphosphetane 2,4-disulfide, IIa, is prepared from O,O-dimethyldithiophosphoric acid, Ia, and P4S10 at 160 deg C. 2,4-Bis(4-phenoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide, IIc, and 2,4-bis(4-phenyl-thiolphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide, IId, are prepared at 160 deg C from P4S10 and diphenylether and diphenylsulfides, respectively.Carboxylic acids RCOOH (R=CH3, C2H5, n-C3H7, n-C4H9, C6H5CH2, C6H5) react with compound Ia at 130 deg C to give the corresponding methyl dithioesters.Carboxylic acids RCOOH (R=C6H5-CH2, C6H5) react with compound Ib at 200 deg C for 15 min to give the corresponding ethyl dithioesters, while low boiling acids (R=CH3, C2H5, n-C3H7) yielded mixtures of the corresponding ethyl dithioester and ethyl carboxylate.Carboxylic acid chlorides RCOCl (R=ClCH2, C2H5, t-C4H9, C6H5CH2, C6H5, p-NO2C6H4) react with compound IIa at 80 deg C to give the corresponding methyl dithioesters in good yields.S-Substituted thioesters react with IIc at 85 deg C to give the corresponding dithioesters in good yields.Dihydro-2(3H)-furanone, VI, and 5-methyl-2(3H)-furanone, VII, react with IIa at 80 deg C to give dihydro-2(3H)-thiophenethione, VIII and 2,2'-dithiobis(5-methyl thiophene), IX, respectively.Also XI reacts with IIa, IIc, and IId to give VIII in nearly quantitative yields.

A Direct Conversion of Carboxylic Acids into Dithioesters

A facile one-pot reaction between carboxylic acids and S-alkyl phosphorus sulphides affords the corresponding alkyl dithioesters.