2489-77-2

Basic information

• Product Name: TRIMETHYLTHIOUREA
• Synonyms: 1,1,3-trimethyl-2-thio-ure;1,1,3-Trimethyl-2-thiourea;1,1,3-trimethyl-2-thiourea[qr];1,1,3-Trimethylthiourea;1,1,3-trimethylthiourea[qr];1,3,3-Trimethylthiourea;1,3,3-trimethylthiourea[qr];n,n,n’-trimethylthiourea[qr]
• CAS NO: 2489-77-2
• Molecular Formula: C₄H₁₀N₂S
• Molecular Weight: 118.2
• EINECS: 219-644-0
• Mol File: 2489-77-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 84°C
• Boiling Point: 221.2°C
• Flash Point: 33.8°C
• Appearance: /solid
• Density: 1.027 (estimate)
• Vapor Pressure: 8.9mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• PKA: 15.29±0.70(Predicted)
• CAS DataBase Reference: TRIMETHYLTHIOUREA(CAS DataBase Reference)
• NIST Chemistry Reference: TRIMETHYLTHIOUREA(2489-77-2)
• EPA Substance Registry System: TRIMETHYLTHIOUREA(2489-77-2)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RTECS: YU4900000
• Hazardous Substances Data: 2489-77-2(Hazardous Substances Data)

Usage

Description

Trimethylthiourea, also known as 1,1,3-trimethylthiourea, is a thiourea derivative that exists as prisms or an off-white powder. It is a compound with potential applications in various industries due to its unique chemical properties. Patients sensitized to ethylbutyl thiourea may also react to trimethylthiourea.

Uses

Used in Chemical Synthesis:
Trimethylthiourea is used as a synthetic compound for the production of various isothiouronium compounds. Its unique structure allows it to serve as a building block for the creation of different chemical entities, which can be utilized in a range of applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, trimethylthiourea is used as an intermediate in the synthesis of various drugs. Its ability to form isothiouronium compounds makes it a valuable component in the development of new medications with potential therapeutic benefits.
Used in Research and Development:
Trimethylthiourea is also used in research and development settings, where it can be employed to study the properties and reactions of thiourea derivatives. This can lead to the discovery of new compounds and applications, further expanding the utility of trimethylthiourea in various fields.
Used in Analytical Chemistry:
Trimethylthiourea can be used as a reagent in analytical chemistry for the detection and quantification of certain elements or compounds. Its unique chemical properties make it a useful tool for researchers and analysts working in this field.

Air & Water Reactions

Very slightly soluble in water.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition TRIMETHYLTHIOUREA emits toxic fumes of nitrogen oxides and sulfur oxides.

Fire Hazard

Flash point data for TRIMETHYLTHIOUREA are not available; however, TRIMETHYLTHIOUREA is probably combustible.

Contact allergens

Trimethylthiourea is a thiourea derivative used, for example, for polychloroprene (neoprene) rubber vul- canization. Patients sensitized to ethylbutyl thiourea can also react to trimethylthiourea.

Safety Profile

Poison by ingestion. Questionable carcinogen with experimental carcinogenic data. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and SOx. See also ISOTHIOUREA.

InChI:InChI=1/C4H10N2S/c1-5-4(7)6(2)3/h1-3H3,(H,5,7)

Upstream product

• 13037-11-1 S-methyl N-methyl dithiocarbamate 
• 124-40-3 dimethyl amine 
• 52664-26-3 Methyldithiocarbamidsaeure-ethylester 
• 556-61-6 methyl thioisocyanate 
• 5815-08-7 tert-Butoxybis(dimethylamino)methane 
• 79645-01-5 N₁,N₃-dimethyl-N₁-nitrosothiourea 
• 74-89-5 methylamine 
• 75-04-7 ethylamine 
• 16420-13-6 N,N-Dimethylthiocarbamoyl chloride 
• 69859-15-0 1,1,3-trimethyl-3-(trimethylsilyl)thiourea 

Downstream Products

• 61713-37-9 tetramethyl-isothiourea 
• 632-14-4 1,1,3-trimethylurea 
• 463-58-1 carbon oxide sulfide 
• 124-40-3 dimethyl amine 
• 74-89-5 methylamine 
• 71535-33-6 N¹,N¹,N²-trimethyl-2,5-diphenyl-Δ²-1,3,4-thiadiazoline-4-carboxamidine 
• 36029-54-6 1,1,3-Trimethyl-2-phenyl-isothiourea 
• 16816-82-3 1,1,3-Trimethyl-2-(p-toluolsulfonyl)-guanidin 
• 100-61-8 N-methylaniline 
• 16887-00-6 chloride 
• 14808-79-8 Sulfate 

Relevant articles and documents

Latent Nucleophilic Carbenes

Using DFT and ab initio calculations, we demonstrate that noncyclic formamidines can undergo thermal rearrangement into their isomeric aminocarbenes under rather mild conditions. We synthesized the silylformamidine, for which the lowest activation energy in this process was predicted. Experimental studies proved it to serve as a very reactive nucleophilic carbene. The reactions with acetylenes, benzenes, and trifluoromethane proceeded via insertion into sp, sp2, and spCH bonds. The carbene also reacted with the functional groups, such as CHO, COR, and CN at double or triple bonds, displaying high mobility of the trimethylsilyl group. The obtained silylformamidine can be considered as a latent nucleophilic carbene. It can be prepared in bulk quantities, stored, and used when the need arises. Calculation results predict similar behavior for some other silylated formamidines and related compounds.

Quantitative solid-state reactions of amines with carbonyl compounds and isothiocyanates

A series of solid-state reactions is reported of gaseous or solid amines with aldehydes to give imines, with solid anhydrides to give diamides (therefrom imides) or amidic carboxylic salts or imides, with solid imides to give diamides, with solid lactones or carbonates to give functionalized carbamic esters, with polycarbonates to give degradative aminolysis, and with solid isothiocyanates to give thioureas. Diamides give imides by solid-state thermolysis or acid catalysis. Various double, two-step, 3-cascade, and sequential reactions are reported in the solid state without melting. The yields are quantitative in 53 reported reaction examples and no workup (except for washings in four cases) is required in the 100% yield reactions. Three initially solid-state reactions but with liquid product were not quantitative. An upscaling to the kg scale shows promise of the technique for large scale applications. Supermicroscopic analyses with AFM elucidate the solid-state mechanism by virtue of far-reaching anisotropic molecular movements in three-step processes. Gas-solid aminolyses of polycarbonates are also studied with AFM. The implications to sustainable chemistry are discussed. (C) 2000 Elsevier Science Ltd.

Pesticidal compositions containing phosphoric esters and divalent sulphur compounds

Pesticidal composition comprising: a pesticidal, phosphoric ester the molecule of which has at least one alkyl group of 1 to 3 carbon atoms, 0.05 to 10% of an agent stabilizing the said ester against decomposition by protonisation, together with adjuvants characterized in that the stabilizing agent comprises at least one sulphur compound containing per molecule at least one divalent sulphur atom of which one valence is bonded to an atom chosen from sulphur, carbon, nitrogen, hydrogen, and metals capable of giving a salt, the other valence being bonded to an atom chosen from hydrogen, the carbon atom already noted, a second carbon atom, the nitrogen atom already noted, a second nitrogen atom, the metal atom already noted in the case of a metal of valence greater than one, a second atom of metal and oxygen when the first valence is not attached to an atom of hydrogen, the proportion of sulphur calculated with reference to the weight of the sulphur compound being between 5 and 99%. Process for stabilizing a phosphoric ester of which the molecule possesses at least one alkyl group containing 1 to 3 carbon atoms characterized in that there is added to the phosphoric ester or to a mixture which contains it, 0.05 to 10% calculated on the weight of the phosphoric acid ester of an agent capable of stabilizing the said phosphoric ester against protonisation and comprising at least one sulphur compound such as that defined thereupon.