18764-68-6

Basic information

• Product Name: 1,1-bis(1-methylethyl)-3-phenylthiourea
• CAS NO: 18764-68-6
• Molecular Formula: C₁₃H₂₀N₂S
• Molecular Weight: 236.3763
• Mol File: 18764-68-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 310.9°C at 760 mmHg
• Flash Point: 141.8°C
• Density: 1.069g/cm³
• Vapor Pressure: 0.000583mmHg at 25°C
• Refractive Index: 1.59
• CAS DataBase Reference: 1,1-bis(1-methylethyl)-3-phenylthiourea(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-bis(1-methylethyl)-3-phenylthiourea(18764-68-6)
• EPA Substance Registry System: 1,1-bis(1-methylethyl)-3-phenylthiourea(18764-68-6)

Safety Data

• Hazardous Substances Data: 18764-68-6(Hazardous Substances Data)

Usage

General Description

1,1-bis(1-methylethyl)-3-phenylthiourea, also known as APTU, is an organic compound that belongs to the class of thioureas. It is commonly used as a catalyst in the polymerization of urea-formaldehyde resins, and as an accelerator for the vulcanization of rubber. APTU has also shown potential as an antioxidant and a corrosion inhibitor in various industrial applications. It is a white crystalline solid that is sparingly soluble in water but more soluble in organic solvents such as acetone and chloroform. APTU is considered to be relatively non-toxic, with low acute oral toxicity reported in animal studies. However, it is important to handle this compound with care and follow proper safety protocols when working with it in a laboratory or industrial setting.

Upstream product

• 103-72-0 phenyl isothiocyanate 
• 108-18-9 diisopropylamine 

Downstream Products

• 1329430-12-7 N,N-diisopropyl-N'-phenyl-2-phenylsulfanyl-benzamidine 
• 1461-81-0 N,N-diisopropyl-N'-phenylurea 
• 78363-43-6 Cu[C₆H₅NC(S)N(CH(CH₃)2)2]2 

Relevant articles and documents

2-Picolylamino(diphenylphosphinoselenoic)amide supported zinc complexes: Efficient catalyst for insertion of N–H bond into carbodiimides, isocyanates, and isothiocyanate

We report here the hydroamination of heterocumulenes such as carbodiimides, isocyanates, and isothiocyanates by zinc complexes supported by the ligand 2-picolylamino-(diphenylphosphinoselenoic)amide [{(Ph2P-(?Se)}2NCH2(C5H4N)] (1). A series of zinc complexes [κ2-{(Ph2P-(?Se)}2NCH2(C5H4N)ZnX2] [(X?Cl (2), Br (3a), I (4)] were prepared from ligand 1 and the corresponding zinc dihalide in a 1:1 molar ratio at 60°C in a chloroform solvent. The reaction of ligand 1 and ZnBr2 in methanol yielded another zinc complex [κ2-{(Ph2P-(?Se)}2NCH2(C5H4N)ZnBr2(CH3OH)] (3b). The molecular structures of compounds 3a, 3b, and 4 were established through single-crystal X-ray diffraction analyses. The solid-state structures of all the complexes revealed a κ2- chelation through pyridine nitrogen and selenium atoms of ligand 1 to the zinc ion. Complex 2 proved to be a competent pre-catalyst for the addition of the amine N–H bond to carbodiimides, isocyanates, and isothiocyanates. The reaction scope was expanded to reactions of aliphatic and aromatic amines with phenylisocyanate and phenylisothiocyanate in toluene solvents, which proceeded rapidly at room temperature with 5 mol% catalyst loading to yield (up to 99%) the corresponding derivatives of urea and thio-urea. However, a temperature of 90°C was needed for the hydroamination of N,N′ dicyclohexylcarbodiimide. We also report the most plausible mechanism of the hydroamination reaction.

Hydroamination of carbodiimides, isocyanates, and isothiocyanates by a bis(phosphinoselenoic amide) supported titanium(IV) complex

The hydroamination of heterocumulenes such as carbodiimides, isocyanates, and isothiocyanates by a bis(phosphinoselenoic amide) supported titanium(iv) complex as a precatalyst is reported here. The titanium(iv) complex [{Ph2P(Se)NCH2CH2NPPh2(Se)}Ti(NMe2)2] (1) was synthesised by the reaction of tetrakis-(dimethylamido)titanium(iv) [Ti(NMe2)4] with [{Ph2P(Se)NHCH2CH2NHPPh2(Se)}] in toluene at ambient temperature. Titanium complex 1 proved to be a competent pre-catalyst for the addition of an amine N-H bond to carbodiimides, isocyanates, and isothiocyanates. The reaction scope was expanded to reactions of aliphatic and aromatic amines with phenylisocyanates and phenylisothiocyanates in toluene solvents proceeding rapidly at room temperature with 5 mol% catalyst loadings to yield the corresponding urea and thio-urea derivatives up to 99%. However, ambient temperature was needed for hydroamination of 1,3-dicyclohexylcarbodiimide. The amine addition reactions with isocyanates showed first order kinetics with respect to catalyst 1 as well as substrates. The most plausible mechanism for the hydroamination reaction was established by isolating 1,1-dimethylphenyl urea as a side product.

Structural requirement of phenylthiourea analogs for their inhibitory activity of melanogenesis and tyrosinase

Effect of a series of 1-phenylthioureas 1a-k and 1,3-disubstituted thioureas 2a-k were evaluated against melanin formation in melanoma B16 cell line and mushroom tyrosinase. Inhibitory activity of tyrosinase of 1-phenylthioureas 1a-k is parallel to their melanogenic inhibition. Thus, the melanogenic inhibition in melanoma B16 cells of 1-phenylthioureas could be the result of inhibition of tyrosinase. However, 1,3-diaryl or 1-phenyl-3- alkylthioureas, 2a-k, appears as melanogenic inhibitor without inhibition of tyrosinase. The molecular docking study of 1e and 2b to binding pocket of tyrosinase provided convincing explanation regarding the necessity of direct connection of planar phenyl to thiourea unit without N′-substitution of phenylthioureas 1 as tyrosinase inhibitor and 2 as non-tyrosinase inhibitor.