105-55-5 Usage
Description
N,N'-Diethylthiourea, a thiourea derivative, is a white to buff-colored solid or powder. It is characterized by the presence of two ethyl substituents on each nitrogen atom, as defined by ChEBI. N,N'-Diethylthiourea is primarily used as a rubber chemical, particularly in the production of solid neoprene products.
Uses
1. Chemical Synthesis:
N,N'-Diethylthiourea is used as a reactant in the synthesis of various compounds for different applications:
a. It is used as a reactant to prepare 3,5-Diethyltetrahydro-4-thioxo-1,3,5-triazine-1(2H)-propanoic acid by condensation reaction with formaldehyde and β-alanine.
b. It is used in a one-pot reaction with dimethyl acetylenedicarboxylate in the presence of a triphenylphosphine catalyst to produce Methyl 3-ethyl-2-(ethylimino)-3,4-dihydro-4-oxo-2H-1,3-thiazine-6-carboxylate.
c. It is used in a cyclization reaction with 2-chloroacetic acid to form 2-(Ethylimino)-3-ethyl-thiazolidin-4-one.
d. It is used in a condensation reaction with maleimides via a Michael-type reaction to produce 3-Ethyl-2-(ethylimino)-4-oxo-5-thiazolidineacetamide.
2. Rubber Industry:
N,N'-Diethylthiourea is used as an accelerator for mercaptan-modified chloroprene rubber, enhancing the curing process and improving the rubber's properties.
3. Corrosion Inhibition:
In the metal pickling industry, N,N'-Diethylthiourea serves as a corrosion inhibitor, protecting metal surfaces from unwanted chemical reactions during the pickling process.
4. Antidegradant:
N,N'-Diethylthiourea is used as an antidegradant for various types of rubber, including natural, nitrile-butadiene, styrene-butadiene, and chloroprene rubbers. It helps to extend the lifespan of rubber products by preventing degradation caused by environmental factors such as heat, light, and oxygen.
Air & Water Reactions
N,N'-Diethylthiourea may be sensitive to exposure to air. . Slightly soluble in water.
Reactivity Profile
N,N'-Diethylthiourea is an amide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).
Health Hazard
ACUTE/CHRONIC HAZARDS: When heated to decomposition N,N'-Diethylthiourea emits toxic fumes.
Fire Hazard
Flash point data are not available for N,N'-Diethylthiourea, but N,N'-Diethylthiourea is probably combustible.
Flammability and Explosibility
Nonflammable
Contact allergens
Diethylthiourea, a thiourea derivative, is used mainly as a
rubber chemical, particularly in solid neoprene products.
Safety Profile
Poison by ingestion.
Moderately toxic by intraperitoneal route.
Questionable carcinogen with experimental
carcinogenic data. Mutation data reported.
When heated to decomposition it emits very
toxic fumes of NOx and SOx
Purification Methods
Crystallise it from *benzene. [Beilstein 4 H 118, 4 I 355, 4 II 610, 4 III 220, 4 IV 375.]
Check Digit Verification of cas no
The CAS Registry Mumber 105-55-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 5 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 105-55:
(5*1)+(4*0)+(3*5)+(2*5)+(1*5)=35
35 % 10 = 5
So 105-55-5 is a valid CAS Registry Number.
105-55-5Relevant articles and documents
The mechanisms of hydrolysis of alkyl N-alkylthioncarbamate esters at 100°C
Humeres, Eduardo,Sanchez, Maria De Nazare,Lobato, Conceicao M. L.,Debacher, Nito A.,De Souza, Eduardo P.
, p. 1483 - 1491 (2005)
The hydrolysis of ethyl N-ethylthioncarbamate (ETE) at 100°C was studied in the range of 7 mol/L HCl to 4 mol/L NaOH. The pH-rate profile showed that the hydrolysis occurred through specific acid catalysis at pH 6.5. The Hammett acidity plot and the excess acidity plot against X were linear. The Bunnett-Olsen plot gave a negative slope indicating that the conjugate acid was less hydrated than the neutral substrate. It was concluded that the acid hydrolysis occurred by an Al mechanism. The neutral species hydrolyzed with general base catalysis shown by the Bronsted plot with β = 0.48 ± 0.04. Water acted as a general base catalyst with (pseudo-)first-order rate constant, kN = 3.06 × 10-7 s-1. At pH > 6.5 the rate constants increased, reaching a plateau at high basicity. The basic hydrolysis rate constant of ethyl N,N-diethylthioncarbamate, which must react by a BAc2 mechanism, increased linearly at 1-3 mol/L NaOH with a second-order rate constant, k2 = 2.3 × 10-4 (mol/L)-1 s-1, which was 10 times slower than that expected for ETE. Experiments of ETE in 0.6 mol/L NaOH with an excess of ethylamine led to the formation of diethyl thiourea, presenting strong evidence that the basic hydrolysis occurred by the E1cb mechanism. In the rate-determining step, the E1cb mechanism involved the elimination of ethoxide ion from the thioncarbamate anion, producing an isothiocyanate intermediate that decomposed rapidly to form ethylamine, ethanol, and COS.
Green Process Development for the Synthesis of Aliphatic Symmetrical N,N ′-Disubstituted Thiourea Derivatives in Aqueous Medium
Jangale, Asha D.,Kumavat, Priyanka P.,Wagh, Yogesh B.,Tayade, Yogesh A.,Mahulikar, Pramod P.,Dalal, Dipak S.
supporting information, p. 376 - 385 (2015/10/29)
A highly efficient green process for the synthesis of N,N′-disubstituted aliphatic thiourea derivatives using primary aliphatic amines and carbon disulfide in an aqueous medium at room temperature via a nonisothiocyanate route is described. This protocol illustrates the rapid preparation of N,N′-disubstituted aliphatic thiourea derivatives in excellent yields with some advantages such as no catalyst and simple workup without any side product formation. Moreover, the new route is concise, does not require chromatography, and is adaptable to pilot-scale preparation. GRAPHICAL ABSTRACT.
α-Thioureidoalkylation of functionally substituted ureas: I. Tandem cyclization and esterification in reactions of N-(carboxyalkyl)ureas with 1,3-dialkyl-4,5-dihydroxy-4,5-diphenylimidazolidine-2-thiones in alcohols
Baranov,Gazieva,Nelyubina,Kravchenko,Makhova
experimental part, p. 1564 - 1571 (2012/03/10)
Acid-catalyzed reactions of N-(carboxyalkyl)ureas with 1,3-dialkyl-4,5- dihydroxy-4,5-diphenylimidazolidine- 2-thiones in methanol or propan-2-ol led to the formation of previously unknown ω-(4,6-dialkyl- 2-oxo-3a,6a-diphenyl- 5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)alkanoic acids and their methyl and isopropyl esters. The structure of some esters was proved by X-ray analysis. Methyl (4,6-diethyl-2-oxo-3a,6adiphenyl- 5-thioxooctahydroimidazo[4,5-d] imidazol-1-yl)acetate showed anxiolytic effect. Pleiades Publishing, Ltd., 2011.