13920-91-7

Basic information

• Product Name: 2-(ethylthio)aniline
• Synonyms: 2-(ethylthio)aniline;UKRORGSYN-BB BBV-090017;2-(ethylthio)aniline(SALTDATA: FREE);2-(Ethylsulfanyl)aniline
• CAS NO: 13920-91-7
• Molecular Formula: C₈H₁₁NS
• Molecular Weight: 153.24
• Mol File: 13920-91-7.mol

Chemical Properties

• Boiling Point: 251.521°C at 760 mmHg
• Flash Point: 105.916°C
• Appearance: /
• Density: 1.093g/cm³
• Vapor Pressure: 0.02mmHg at 25°C
• Refractive Index: 1.595
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 2-(ethylthio)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(ethylthio)aniline(13920-91-7)
• EPA Substance Registry System: 2-(ethylthio)aniline(13920-91-7)

Safety Data

• Hazardous Substances Data: 13920-91-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(ethylthio)aniline is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new medicinal compounds.
Used in Dye and Pigment Production:
2-(ethylthio)aniline is used as a precursor in the production of dyes and pigments, leveraging its chemical structure to create a range of colorants for various applications.
Used in Manufacturing Industry:
As a versatile intermediate, 2-(ethylthio)aniline is used in the manufacturing industry for the synthesis of different organic compounds, highlighting its importance in chemical production processes.
It is important to handle and store 2-(ethylthio)aniline with proper care due to its potential hazards, ensuring safety in its applications across industries.

InChI:InChI=1/C8H11NS/c1-2-10-8-6-4-3-5-7(8)9/h3-6H,2,9H2,1H3

Upstream product

• 1222062-60-3 2-[(2-ethylsulfanylphenylamino)methylene]malonic acid diethyl ester 
• 108429-47-6 1-azido-2-ethylsulfanylbenzene 
• 6325-92-4 2-(benzylsulfanyl)aniline 
• 1408300-21-9 2-amino-S-cinnamylthiophenol 
• 77053-20-4 2-(2-propen-1-ylsulfanyl)aniline 
• 137-07-5 2-amino-benzenethiol 
• 105-53-3 diethyl malonate 
• 1141-88-4 2-Aminophenyl disulfide 
• 14290-92-7 2-(ethylthio)-2-methyl-propane 
• 622-37-7 Phenyl azide 
• 4110-50-3 ethyl propyl sulfide 
• 352-93-2 diethyl sulphide 
• 624-89-5 Ethyl methyl sulfide 
• 34009-61-5 diethyl 2-methyl-2-phenylmalonate 

Downstream Products

• 40818-92-6 1-(2-ethylmercapto-phenyl)-piperazine 
• 96207-56-6 o-iodophenyl ethyl sulfide 
• 5325-20-2 2H-1,4-benzothiazin-3-one 
• 1258874-62-2 C₁₃H₁₆N₂O₂S 
• 1431440-02-6 2-(ethylthio)-N-((pyridine-2-yl)methylene)benzenamine 
• 1000069-65-7 N-[2-(ethylsulfinyl)phenyl]-N-methyl-1H-indole-2-carboxamide 
• 1000069-63-5 N-[2-(ethylthio)phenyl]-N-methyl-1H-indole-2-carboxamide 
• 65605-24-5 2-methylaminophenyl ethyl sulphide 
• 1000069-56-6 N-[2-(ethylthio)phenyl]-1H-indole-2-carboxamide 
• 1000069-79-3 N-[2-(ethylthio)phenyl]-1H-indole-3-carboxamide 
• 102968-95-6 2-ethylthio-N,N-diallylaniline 
• 102968-90-1 2-ethylthio-N-allylaniline 
• 93681-53-9 N-(2-(ethylthio)phenyl)benzamide 
• 108429-47-6 1-azido-2-ethylsulfanylbenzene 

Relevant articles and documents

Novel sulfinyl anilino pyrimidine derivative and application thereof in preparation of antitumor drugs

The invention relates to the field of medicines. A novel sulfinyl anilino pyrimidine derivative is disclosed, and the structural formula of the novel sulfinyl anilino pyrimidine derivative is as shown in the specification. Compared with an existing L858R/T790M inhibitor and EGFR / ALK double-target-target reference substance, the aniline-based pyrimidine derivative containing the sulfoxide group has better antitumor H 1975 activity compared with ALK the prior art BaF3 inhibitor and the EGFR/ALK double ALK-target reference substance. As proved by human liver microsomal experiments, the aniline-based pyrimidine derivatives containing the sulfoxide group in the invention are compared with the existing anisyl-containing anilino pyrimidine derivatives. There is a great increase in stability.

Synthesis and evaluation of novel 2,4-diaminopyrimidines bearing a sulfoxide moiety as anaplastic lymphoma kinase (ALK) inhibition agents

Anaplastic lymphoma kinase (ALK) targeted therapies have demonstrated remarkable efficacy in ALK-positive lung adenocarcinomas. Here we synthesized and evaluated sixteen new 2,4-diaminopyrimidines bearing a sulfoxide moiety as anaplastic lymphoma kinase (ALK) inhibitors. The optimal compound 9e exhibited excellent antiproliferative activity against non-small cell lung cancer NCI-H2228 cells, which is better than that of Brigatinib and similar to Ceritinib. Mechanism study revealed that the optimal compound 9e decreased the mitochondrial membrane potential and arrested NCI-H2228 cells in the G0/G1 phase, finally resulting in cellular apoptosis. It is interesting that 9e could effectively inhibit the migration of NCI-H2228 cells and may be a promising leading compound for chemotherapy of metastatic cancer.

Di- tert-butyl Peroxide-Mediated Radical C(sp2/sp3)-S Bond Cleavage and Group-Transfer Cyclization

A novel strategy of cascade radical C(sp2/sp3)-S bond cleavage and group-transfer cyclization is disclosed. Triggered by alkyl radicals, varieties of 2-isocyanoaryl thioethers containing aliphatic, aryl, and heteroaromatic groups can be cleaved and precisely reinstalled to give benzothiazole derivatives. Mechanistic studies reveal that the cascade reaction undertakes an intermolecular pathway, and the inner radical sources (R radicals) exhibit high priority over those of methyl radical origin from di-tert-butyl peroxide.

1,2,3-TRIAZOLE DERIVATIVE AND INSECTICIDE AND ACARICIDE CONTAINING SAID DERIVATIVE AS ACTIVE INGREDIENT

The present invention provides a 1,2,3-triazole derivative and an insecticide or acaricide containing the 1,2,3-triazole derivative as an active ingredient.

Structures, redox behavior, antibacterial activity and correlation with electronic structure of the complexes of nickel triad with 3-(2-(alkylthio) phenylazo)-2,4-pentanedione

3-(2-(Alkylthio)phenylazo)-2,4-pentanedione (HL), an O, N, S donor ligand, is used for the synthesis of Ni(II), Pd(II) and Pt(II) complexes. The spectroscopic (IR, UV-Vis, and NMR) data determine the structure. The single crystal X-ray diffraction measurement of [Ni(L)2] and [Pt(L)Cl] has confirmed the structures. Coulometric oxidation of [Ni(L)2] and EPR spectra thereof show formation of Ni(III) state. DFT computation has calculated the electronic configuration and has explained the spectral and redox properties of the complexes. The compounds are screened for their in vitro anti-bacterial activity using Gram-positive and Gram-negative bacteria (Bacillus subtilis UC564, Escherichia coli TG1, Staphylococcus aureus Bang25, Pseudomonas aeruginosa C/1/7, Salmonella typhi NCTC62, Salmonella paratyphi NCTC A2, Shigella dysenteriae 8NCTC599/52, Streptococcus faecalis S2, Vibrio cholerae DN7 and Mricococcus luteus AGD1). The minimum inhibitory concentration is determined for the compounds. The effect of the structure of the investigated compounds on the antibacterial activity is discussed.

2,2-Bis(ethoxycarbonyl)vinyl (BECV) as a versatile amine protecting group for selective functional-group transformations

A 2,2-Bis(ethoxycarbonyl) vinyl- (BECV) group was used for the selective protection of amines at room temperature in the presence of potentially interfering functional groups such as OH, SH, COOH as well as other NH 2 groups. Several functional group transformations such as esterification, O-alkylation, O-acylation, N-alkylation, N-acylation, S-alkylation can selectively be carried out in the presence of the BECV group. The selective deprotection of the BECV group was achieved in a short time using ethylenediamine at room temperature while several other functional groups such as benzoate, aliphatic esters, amides and ethers remain intact. The BECV group shows orthogonal stability against the common protecting groups such as Fmoc, Cbz and Boc.

Copper(II) complexes of thioarylazo-pentanedione: Structures, magnetism, redox properties and correlation with DFT calculations

Copper(II) complexes of 3-((2-(alkylthio)phenylazo)-2,4-pentanedione, tridentate O, N, S donor ligands, are described in this work. Chloride bridged copper(II) polymers (1) and thiocyanato bridged copper(II) dimmers (2) are characterized by a single crystal X-ray diffraction study. The complexes show antiferromagnetic interactions, with J = -0.5 ± 0.1 cm-1 (1a) and -25.8 ± 0.5 cm-1 (2b), which implies stronger coupling in the -SCN-bridging compound. The spectra, redox and magnetism are explained by DFT studies.

Imidazoline derivatives as alpha-1A adrenoceptor ligands

Compound of formula (I) or a pharmaceutically acceptable salt or solvate thereof are disclosed. Such compounds are useful in the treatment of Alpha-1A mediated diseases or conditions such as urinary incontinence.

KF-alumina immobilized in ionic liquids: A novel heterogeneous base for heterocyclization of alkylsulfanylphenylamines into 1,4-benzothiazine

A rapid and convenient synthetic methodology for the cyclocondensative transformation of various alkylsulfanylphenylamines with bromoacetyl bromide by supporting on KF-alumina in ionic liquids [bmim] [Br] and [bmim][BF 4] has been developed to obtain 3-oxo-1,4-benzothiazine in good yields. The product is easily obtained by extraction with ethyl acetate and concentrating under vacuum. Easy recovery of ionic liquid and use in consecutive reactions is also reported.

2-(Anilinomethyl)imidazolines as α1 adrenergic receptor agonists: The discovery of α10 subtype selective 2′-alkylsulfonyl-substituted analogues

A series of 2′-alkylthio-2-(anilinomethyl)imidazolines were prepared to examine the effect of the alkyl group size, sulfur oxidation state, and phenyl ring substitution on ligand binding and agonism of α-adrenergic receptor subtypes α1a, α1b, α1d, α2a, and α2c. Binding at all receptor subtypes decreased for compounds in the sulfone oxidation state as compared to their sulfide analogues. While sulfides were generally potent, nonselective agonists, sulfones exhibited α1a subtype selectivity in a cell-based functional assay. Sulfone (32) was 250-7000-fold selective for α1a vs all other subtypes.