3064-73-1

Basic information

• Product Name: Diisobutylthiuram disulfide
• Synonyms: tetra(isobutyl)thioperoxydicarbamic acid;TETRA-ISO-BUTYL THIURAM DISULFIDE;TiBTD;Diisobutylthiuram disulfide;ISOBUTYL TUADS;DiisobutylThiuramDisulfide(Tibtd);Thioperoxydicarbonic diamide ((H2N)C(S)2S2), tetrakis(2-methylpropyl)-;1,1'-Dithiobis(N,N-diisobutylthioformamide)
• CAS NO: 3064-73-1
• Molecular Formula: C₁₈H₃₆N₂S₄
• Molecular Weight: 296.54
• EINECS: 221-312-5
• Mol File: 3064-73-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 73.5-74.5 °C
• Boiling Point: 462.9 °C at 760 mmHg
• Flash Point: 233.7 °C
• Appearance: Light yellow crystal grain
• Density: 1.076 g/cm³
• Vapor Pressure: 9.5E-09mmHg at 25°C
• Refractive Index: 1.563
• PKA: 0.90±0.50(Predicted)
• Water Solubility: 48.8μg/L at 20℃
• CAS DataBase Reference: Diisobutylthiuram disulfide(CAS DataBase Reference)
• NIST Chemistry Reference: Diisobutylthiuram disulfide(3064-73-1)
• EPA Substance Registry System: Diisobutylthiuram disulfide(3064-73-1)

Safety Data

• Hazardous Substances Data: 3064-73-1(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 3064-73-1 differently. You can refer to the following data:
1. Isobutyl Thiuram Disulfide is an effective curing agent for acrylonitrile-butadiene rubber (NBR) only in the presence of ZnO and stearic acid as curing activators.Also, it is derived from Diisobutylamine (D446538), which is a reagent used in organic synthesis including the preparation of bx7 inhibitors which may be useful in the treatment of certain cancers.
2. Isobutyl Thiuram Disulfide is an effective curing agent for acrylonitrile-butadiene rubber (NBR) only in the presence of ZnO and stearic acid as curing activators.Also, it is derived from Diisobutylamine (D446538), which is a reagent used in organic synthesis including the preparation of bx7 inhibitors which may be useful in the treatment of certain cancers.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C18H36N2S4/c1-13(2)9-19(10-14(3)4)17(21)23-24-18(22)20(11-15(5)6)12-16(7)8/h13-16H,9-12H2,1-8H3

Synthetic route

carbon disulfide (75-15-0) + diisobutylamine (110-96-3) → tetra(isobutyl)thiuram disulfide (3064-73-1)

Conditions	Yield
With oxygen In isopropyl alcohol at 50℃; under 1275.13 Torr; for 1h; Autoclave;	98.3%
Stage #1: carbon disulfide; diisobutylamine In ethanol at 10 - 50℃; for 1h; Stage #2: With iodine In ethanol	93%
With triethylamine In ethanol at 20℃; for 14h; Green chemistry;	73%
With oxygen; eosin Y disodium salt In methanol under 3750.38 Torr; for 0.333333h; Solvent; Flow reactor; Irradiation; Green chemistry;	46%
With methanol; potassium hydroxide; iodine

sodium diisobutyl dithiocarbamate → tetra(isobutyl)thiuram disulfide (3064-73-1)

Conditions	Yield
With hydrogenchloride; methanol; sodium nitrite at 5 - 12℃;

diisobutylamine (110-96-3) → tetra(isobutyl)thiuram disulfide (3064-73-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: water / 0.5 h / 20 °C 2: dihydrogen peroxide / 6 h / 50 °C View Scheme

Diisobutyl dithiocarbamate (7283-77-4) → tetra(isobutyl)thiuram disulfide (3064-73-1)

Conditions	Yield
With dihydrogen peroxide at 50℃; for 6h; Temperature;

diisobutylcarbodithioic acid sodium salt (2219-18-3) → tetra(isobutyl)thiuram disulfide (3064-73-1)

Conditions	Yield
With sulfuric acid; dihydrogen peroxide

tetra(isobutyl)thiuram disulfide (3064-73-1) → diisobutylcarbamic acid chloride (38952-42-0)

Conditions	Yield
Stage #1: tetra(isobutyl)thiuram disulfide With chlorine In dichloromethane at 24 - 26℃; for 7.58333h; Cooling with ice; Stage #2: With water; sodium hydrogencarbonate In dichloromethane Cooling with ice;	87%

tetraselenidotungstate ion + tetra(isobutyl)thiuram disulfide (3064-73-1) → WSe2{N(CH2CH(CH3)2)2C(S)S}3 (139957-26-9)

Conditions	Yield
In acetonitrile room temp.; recrystn. (CH2Cl2-hexane);	79%

tetraethylammonium tetrathioperrhenate + tetra(isobutyl)thiuram disulfide (3064-73-1) → Re2(μ-S)2(S2CN(CH2CH(CH3)2)2)4

Conditions	Yield
In [(2)H6]acetone byproducts: S2CN(i-Bu)2(1-); Ar-atmosphere; treatment of Re-complex with 2.6 equivs. of disulfide (room temp., overnight, pptn.); filtration, washing (ether); elem. anal.; product contaminated with S;	50%
In acetonitrile byproducts: sulfur; elem. anal.;

Mo2S4{(C4H9)2NCS2}2 + tetra(isobutyl)thiuram disulfide (3064-73-1) → Mo4S4{(C4H9)2NCS2}6

Conditions	Yield
With NaBH4 In N,N-dimethyl-formamide soln. of the Mo-complex and the disulfide combined with a soln. of NaBH4, refluxed for 1 h; chromd. on silica gel with CH2Cl2/hexane (3:1);	35%

tetra(isobutyl)thiuram disulfide (3064-73-1) + Mo3S13(2-)*2H3N*2H(1+) + sodium iodide (7681-82-5) → I(1-)*C27H54Mo3N3S13(1+)

Conditions	Yield
Stage #1: tetra(isobutyl)thiuram disulfide; Mo3S13(2-)*2H3N*2H(1+) In N,N-dimethyl-formamide for 0.5h; Stage #2: sodium iodide In ethanol; N,N-dimethyl-formamide at 50℃; for 12h;	30%

tetra(isobutyl)thiuram disulfide (3064-73-1) → diisobutyl-thiocarbamoyl chloride (35026-87-0)

Conditions	Yield
With chlorine

{AgSCSN(i-C4H9)2} + tetra(isobutyl)thiuram disulfide (3064-73-1) → {Ag(SCSN(i-C4H9)2)2} (126020-78-8)

Conditions	Yield
In chloroform instantaneous react.;
In benzene instantaneous react.;

tetra(isobutyl)thiuram disulfide (3064-73-1) + {AgSCSN(i-C4H9)2} → Ag((i-C4H9)2NCSS)2

tetra(isobutyl)thiuram disulfide (3064-73-1) + tris(tricaprylylmethylammonium)tetrathiovanadate → [V2(μ-S2)2(S2CN(isobutyl)2)4]

Conditions	Yield
In N,N-dimethyl-formamide; toluene byproducts: S(x)(2-); under inert atmosphere; solid tetraisobutylthiuram disulfide added to asoln. of V-compound and stirred for 1 h; chromy.; evapd.; recrystd. from toluene/hexane; elem. anal.;

Upstream product

• 75-15-0 carbon disulfide 
• 110-96-3 diisobutylamine 
• 2219-18-3 diisobutylcarbodithioic acid sodium salt 
• 7283-77-4 Diisobutyl dithiocarbamate 

Downstream Products

• 38952-42-0 diisobutylcarbamic acid chloride 

Relevant articles and documents

Continuous-flow step-economical synthesis of thiuram disulfidesviavisible-light photocatalytic aerobic oxidation

A continuous-flow photocatalytic synthesis of the industrially important thiuram disulfides has been developed, utilizing O2as the oxidant and Eosin Y as the photoredox catalyst. This highly atom- and step-economical method features much reduced reaction time as well as excellent product yield and purity, making it a sustainable and potentially scalable process for industrial production.

A disulphide diisobutylcarbamoylmethyl thiuram method for the preparation of (by machine translation)

The invention discloses a method for the preparation of diisobutyl thiuram sulfide, its steps are: the two isobutyl amine into solvent, then dropping to the carbon disulfide, reaction after the dipping 0.5-1h, shall be diisobutylcarbamoylmethyl dithio Carbamic reaction liquid; the step (1) the diisobutylcarbamoylmethyl dithiocarbamate is slowly dripped into the reaction solution in a hydrogen peroxide solution, oxidizing reaction temperature rise after the dipping, filtering the reaction liquid after the reaction, the obtained precipitate washing, drying, be disulphide diisobutylcarbamoylmethyl thiuram disulfide. The preparation process of the invention is simple, by controlling the solvent, drop conditions, such as acceleration and dropping sequence, no longer add strong acid and strong alkali, reduce the production cost, reduces the potential safety hazard, less pollution, energy saving and environmental protection, the resulting product quality is good, high yield, the policy requirements of the green chemical States. (by machine translation)

Development of an improved method for conversion of thiuram disulfides into N,N-dialkylcarbamoyl halides and derivatives

A convenient procedure for preparing N,N-disubstituted carbamoyl halides is reported. It consists of two steps: (1) reaction of carbon disulfide and a secondary amine in the presence of a polar organic solvent and oxygen to produce the corresponding tetraalkyl thiuram disulfides and (2) reaction of tetraalkyl thiuram disulfide with a halide in the presence of an aprotic organic solvent to produce the corresponding N,N-disubstituted carbamoyl halide. Copyright Taylor & Francis Group, LLC.