95-05-6

Basic information

• Product Name: sulfiram
• Synonyms: sulfiram;Tetraethylthiuram monosulfide;Thiodicarbonic diamide ((H2N)C(S)2S), tetraethyl-;TETRAETHYLTHIURAMMONOSULPHIDE;BIS(DIETHYLTHIOCARBAMOYL)SULPHIDE;Tetmos;diethylcarbamothioyl N,N-diethylcarbamodithioate;N,N-diethylcarbamodithioic acid diethylthiocarbamoyl ester
• CAS NO: 95-05-6
• Molecular Formula: C₁₀H₂₀N₂S₃
• Molecular Weight: 264.4742
• EINECS: 202-387-3
• Product Categories: Agro-Products;Amines;Sulfur & Selenium Compounds
• Mol File: 95-05-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: 30-32°
• Boiling Point: 329.1°Cat760mmHg
• Flash Point: 152.8°C
• Appearance: /
• Density: 1.1200
• Vapor Pressure: 0.000182mmHg at 25°C
• Refractive Index: 1.5500 (rough estimate)
• CAS DataBase Reference: sulfiram(CAS DataBase Reference)
• NIST Chemistry Reference: sulfiram(95-05-6)
• EPA Substance Registry System: sulfiram(95-05-6)

Safety Data

• RIDADR: 2811
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 95-05-6(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 95-05-6 differently. You can refer to the following data:
1. As vulcanization agent.
2. sulfiram acts as a vulcanization agent,it is used in combination pesticide compositions for controlling infestation.

Contact allergens

This rubber vulcanization accelerator is also used as an ectoparasiticide against Sarcoptes scabiei, louses, or in veterinary medicine.

InChI:InChI=1/C10H20N2S3/c1-5-11(6-2)9(13)15-10(14)12(7-3)8-4/h5-8H2,1-4H3

Synthetic route

N,N-diethylthiocarbamoyl chloride (88-11-9) → tetraethylthiuram monosulfide (95-05-6)

Conditions	Yield
With pyridine; hexamethyldisilathiane Heating;	66%

N,N-diethyldithiocarbamate triethylamine salt (2391-78-8) + N,N-diethylthiocarbamoyl chloride (88-11-9) → tetraethylthiuram monosulfide (95-05-6)

Conditions	Yield
In acetonitrile at 20℃; for 12h;	62%

thiophosgene (463-71-8) + sodium N,N-diethyldithiocarbamate (148-18-5) → tetraethylthiuram monosulfide (95-05-6)

Conditions	Yield
With diethyl ether

sodium N,N-diethyldithiocarbamate (148-18-5) + N,N-diethylthiocarbamoyl chloride (88-11-9) → tetraethylthiuram monosulfide (95-05-6)

Conditions	Yield
With water

sodium N,N-diethyldithiocarbamate (148-18-5) → tetraethylthiuram monosulfide (95-05-6)

Conditions	Yield
With sulfuric acid; dihydrogen peroxide; cyanide(1-)

disulfiram (97-77-8) → tetraethylthiuram monosulfide (95-05-6)

Conditions	Yield
With potassium cyanide In ethanol

phosgene (75-44-5) + sodium diethyl dithiocarbamate → tetraethylthiuram monosulfide (95-05-6)

Conditions	Yield
With water beim Erwaermen des Reaktionsprodukts mit Wasser auf 50grad;

{Sb(S2CN(C2H5)2)2}2CH2 → methylene-bis-(antimony(III)-sulfide) + tetraethylthiuram monosulfide (95-05-6)

Conditions	Yield
In neat (no solvent) decomposition on heating;;

triethylamine (121-44-8) → tetraethylthiuram monosulfide (95-05-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetonitrile / 16 h / 20 °C 2: acetonitrile / 12 h / 20 °C View Scheme

tetraethylthiuram monosulfide (95-05-6) + 4-Methoxyphenyl isocyanate (5416-93-3) → 1,1,5,5-tetraethyl-3-(4-methoxy-phenyl)-dithiobiuret

tetraethylthiuram monosulfide (95-05-6) → 4,4-diethyl-thiosemicarbazide (21198-48-1)

Conditions	Yield
With hydrazine hydrate In ethanol Heating;

tetraethylthiuram monosulfide (95-05-6) + copper(I) bromide (7787-70-4) → [CuBr((C2H5)2NC(S)SC(S)N(C2H5)2)] (168563-02-8) + copper diethyldithiocarbamate

Conditions	Yield
In acetonitrile addn. of the monosulfide in MeCN with stirring to an ice-cooled soln. ofCuBr in MeCN; layering with Et2O, standing (freezer, 3 h), filtration, addn. of more Et2O, standing (freezer, overnight), decantation, washing (Et2O), drying in air; elem. anal.;

copper(l) iodide (7681-65-4) + tetraethylthiuram monosulfide (95-05-6) → [Cu5I5((C2H5)2NC(S)SC(S)N(C2H5)2)2]*C2H5OH*CH3CN (205104-84-3) + copper diethyldithiocarbamate

Conditions	Yield
In acetonitrile addn. of the monosulfide in MeCN with stirring to an ice-cooled soln. ofCuI in MeCN; layering with Et2O, standing (freezer, 3 h), filtration, addn. of more Et2O, standing (freezer, overnight), decantation, washing (Et2O), drying in air;

tetraethylthiuram monosulfide (95-05-6) + copper(l) chloride → [CuCl((C2H5)2NC(S)SC(S)N(C2H5)2)] (171624-55-8) + copper diethyldithiocarbamate

Conditions	Yield
In acetonitrile addn. of the monosulfide in MeCN with stirring to an ice-cooled soln. ofCuCl in MeCN; layering with Et2O, standing (freezer, 3 h), filtration, addn. of more Et2O, standing (freezer, overnight), decantation, washing (Et2O), drying in air; elem. anal.;

copper(l) iodide (7681-65-4) + tetraethylthiuram monosulfide (95-05-6) → Cu5(tetraethylthiuram monosulfide)2I5 (203629-42-9) + copper diethyldithiocarbamate

Conditions	Yield
In acetonitrile addn. of 1 equiv. ligand to CuI (ice bath, stirring); layering with Et2O, fractional crystn. (freezer, overnight), collection (decantation), washing (ether), drying in air;

tetraethylthiuram monosulfide (95-05-6) + copper(ll) bromide (7789-45-9) → Cu(1+)*(CH3CH2)2NCS3CN(CH2CH3)2*Br(1-) (168563-02-8)

Conditions	Yield
In ethanol (N2); stirring (-10°C); washing (EtOH), extracting (CH3CN), evapn., cooling (-10°C); elem. anal.;

tetraethylthiuram monosulfide (95-05-6) + copper(ll) bromide (7789-45-9) → (CH3CH2)2NCS3CN(CH2CH3)2(2+)*Cu(1+)*3Br(1-)=[(CH3CH2)2NCS3CN(CH2CH3)2]CuBr3

Conditions	Yield
In ethanol (N2); stirring (-10°C); washing (EtOH), extracting (CH3CN), evapn.; elem. anal.;

Upstream product

• 463-71-8 thiophosgene 
• 148-18-5 sodium N,N-diethyldithiocarbamate 
• 88-11-9 N,N-diethylthiocarbamoyl chloride 
• 97-77-8 disulfiram 
• 75-44-5 phosgene 
• 2391-78-8 N,N-diethyldithiocarbamate triethylamine salt 
• 121-44-8 triethylamine 

Downstream Products

• 21198-48-1 4,4-diethyl-thiosemicarbazide 

Relevant articles and documents

THIURAM MONOSULFIDES AS A NEUTRAL CARRIER FOR COPPER(II)-SELECTIVE MEMBRANE ELECTRODE

Poly(vinyl chloride) membrane electrodes that are sensitive and selective to copper(II) ion were developed.The electrodes based on tetramethyl, tetraethyl and dipyrrolidine thiuram monosulfides as a neutral carrier, exhibit a Nernstian behavior to copper(II) ion in the activity range of 10-1 M to 10-6 M - 10-8 M.Properties of the electrodes are briefly discussed.

Syntheses, properties, crystal and molecular structure of a novel neutral pentanuclear copper(I) iodide species. Copper(I) complexes with tetraethylthiuram monosulfide

The reaction of copper(I) iodide with tetraethylthiuram monosulfide LEt afforded the novel copper(I) pentanuclear neutral complex [CU5LEt2I5]·EtOH·MeCN 1. Its crystal structure may be described as a very distorted octahedral central Cu3I3 cage having two additional CuLEt(I) units fused to the central cage by means of two iodine and one sulfur bridging atom. All copper(I) atoms in 1 are tetrahedral and both sulfur ligands are bidentate. The solvent molecules occupy intermolecular vacancies generated by the manner in which 1 is packed in space. In contrast, other copper(I) halides CuX (X = Cl or Br) with tetraethylthiuram monosulfide afforded the copper(I) complexes [CuLEt(X)] (X = Cl 2 or Br 3) which exist in the solid state as monomeric units featuring three-co-ordinate copper(I). The ligands are bidentate and co-ordination is completed by the halogen atoms. The complexes were additionally characterized by IR and 1H NMR spectra as well as magnetic susceptibility measurements. Complexes 2 and 3 can be alternatively prepared by sulfur abstraction from the disulfides, using triphenylphosphine. Copper(I) iodide and tetraethylthiuram monosulfide failed to yield a mononuclear compound under a variety of experimental conditions.

SYNTHESIS OF ORGANIC SULFUR COMPOUNDS BY MEANS OF SILICON-CONTAINING REAGENTS

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