436151-85-8

Basic information

• Product Name: 4-(2-AMINO-THIAZOL-4-YL)-BENZONITRILE
• Synonyms: BUTTPARK 41\03-40;4-(2-AMINO-1,3-THIAZOL-4-YL)BENZONITRILE;4-(2-AMINO-THIAZOL-4-YL)-BENZONITRILE;4-(4-CYANOPHENYL)-2-AMINOTHIAZOLE;AKOS BBR-001638;IFLAB-BB F1386-0385;4-(2-amino-4-thiazoyl)benzotrile;2-Amino-4-(4-cyanophenyl)-1,3-thiazole
• CAS NO: 436151-85-8
• Molecular Formula: C₁₀H₇N₃S
• Molecular Weight: 201.25
• Mol File: 436151-85-8.mol

Chemical Properties

• Boiling Point: 440.7 °C at 760 mmHg
• Flash Point: 220.3 °C
• Appearance: /
• Density: 1.37 g/cm³
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: 4-(2-AMINO-THIAZOL-4-YL)-BENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-AMINO-THIAZOL-4-YL)-BENZONITRILE(436151-85-8)
• EPA Substance Registry System: 4-(2-AMINO-THIAZOL-4-YL)-BENZONITRILE(436151-85-8)

Safety Data

• Hazardous Substances Data: 436151-85-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
4-(2-AMINO-THIAZOL-4-YL)-BENZONITRILE is used as a building block for the development of various pharmaceutical compounds due to its potential biological activities and its role in the synthesis of therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, 4-(2-AMINO-THIAZOL-4-YL)-BENZONITRILE is utilized as a key intermediate for creating a range of organic compounds, highlighting its importance in chemical reactions and the formation of new molecules.
Used in Chemical Production:
4-(2-AMINO-THIAZOL-4-YL)-BENZONITRILE is used as a component in the production of dyes and other chemical products, indicating its versatility and applicability in industrial chemical processes.
Used in Therapeutic Applications:
4-(2-AMINO-THIAZOL-4-YL)-BENZONITRILE is being investigated for its potential therapeutic applications in the treatment of various diseases, showcasing its promise as a candidate for medicinal development.

Upstream product

• 25309-65-3 4-ethylbenzonitrile 
• 1443-80-7 4-cyanophenyl methyl ketone 
• 3435-51-6 4-ethenylbenzonitrile 
• 17356-08-0 thiourea 
• 20099-89-2 4-Cyanophenacyl bromide 

Downstream Products

• 928649-72-3 4-[2-(3-methyl-butylamino)-thiazol-4-yl]-benzonitrile 
• 1070792-19-6 N-[4-(4-cyanophenyl)thiazol-2-yl]-4-diethylaminosulfonylbenzamide 
• 1070792-20-9 N-[4-(4-cyanophenyl)thiazol-2-yl]-3-(4-dipropylaminosulfonylphenyl)-propionamide 
• 1070794-74-9 N-[4-(4-methoxyphenyl)thiazol-2-yl]-2-(1-octylsulfonylpiperidin-4-yl)acetamide 
• 928650-02-6 4-(2-aminothiazol-4-yl)-N-(tert-butoxycarbonyl)-benzylamine 

Relevant articles and documents

Solid state thiazole-based fluorophores: Promising materials for white organic light emitting devices

A facile and more efficient solvent-free mechanochemical synthetic route has been developed for the synthesis of a series of solid state white light emissive thiazole-based donor-acceptor (D-A) type fluorophores, 2-(3-pyridyl)/2-aminothiazoles from ω-bromomethylketones and pyridine-3-carbothioamide/thiourea in the presence of silica-supported HClO4 as a reusable solid Br?nsted acid catalyst at RT. The photophysical and electrochemical properties of these compounds have been derived. Most of the studied D-A type solid thiazole-based fluorophores emitted white light and it can be tuned from warm - ideal - cold white light by introduction of a variety of substituents at 4th position of 2-(3-pyridyl)/2-aminothiazoles. Further, HOMO and LUMO energy levels of the titled compounds are found to be in the range ?5.52 eV to ?5.72 eV and ?1.84 eV to ?2.45 eV, respectively. The lifetimes of these levels of thiazole-based fluorophores have been determined through luminescence decay curves and are found to be in the range of 7.7–11 μs. The photophysical and electrochemical properties of the synthesized thiazole-based fluorophores indicate that the compounds could be promising materials for white organic light emitting devices.

COMPOUNDS AND USES THEREOF

The present disclosure features compounds useful for the treatment of BAF complex-related disorders.

2-Amino-4-arylthiazoles through One-Pot Transformation of Alkylarenes with NBS and Thioureas

Treatment of alkylarenes with N-bromosuccinimide in a mixture of ethyl acetate and water at 60 °C, a mixture of acetonitrile and water at 80 °C, or a mixture of diethyl carbonate and water under irradiation with a tungsten lamp, followed by a reaction with thioureas or arenethioamides provided the corresponding 2-amino- 4-arylthiazoles or 2,4-diarylthiazoles in good to moderate yields, respectively, in one pot. The present reaction is an efficient one-pot transformation method of alkylarenes into 2-amino-4-arylthiazoles and 2,4-diarylthiazoles directly under mild and transition-metal-free conditions.

COMPOUNDS AND USES THEREOF

The present disclosure features compounds useful for the treatment of BAF complex-related disorders.

SUBSTITUTED PROPANAMIDES AS INHIBITORS OF NUCLEASES

The invention provides compounds represented by the structural formula (1): wherein R1, R2, R3, R4, R5, R6 are as defined in the claims. The compounds are inhibitors of nucleases, and are useful in particular in a method of treatment and/or prevention of proliferative diseases, neurodegenerative diseases, and other genomic instability associated diseases.

Development of 2-amino-4-phenylthiazole analogues to disrupt myeloid differentiation factor 88 and prevent inflammatory responses in acute lung injury

Myeloid differentiation primary response protein 88 (MyD88), an essential adapter protein used by toll-like receptors (TLR), is a promising target molecule for the treatment of respiratory inflammatory diseases. Previous studies explored the activities of novel 2-amino-4-phenylthiazole analogue (6) in inflammation-induced cancer, and identified the analogue as an inhibitor of MyD88 toll/interleukin-1 receptor (TIR) homology domain dimerization. Here, we describe the synthesis of 47 new analogues by modifying different sites on this lead compound and assessed their anti-inflammatory activities in lipopolysaccharide-induced mouse primary peritoneal macrophages (MPMs). The most promising compound, 15d, was found to effectively interact with MyD88 protein and prevented formation of the MyD88 homodimeric complex. Furthermore, 15d showed in vivo anti-inflammatory activity in LPS-caused model of acute lung injury. This work provides new candidates as MyD88 inhibitors to combat inflammation diseases.

N,O π-Conjugated 4-Substituted 1,3-Thiazole BF2 Complexes: Synthesis and Photophysical Properties

A series of 1,3-thiazole-based organoboron complexes has been designed and synthesized by acylation of 2-amino 4-subsituted 1,3-thiazoles with (4-dimethylamino)benzoyl chloride and the subsequent BF2 complexation reaction. The influence of substituents in position 4 of the thiazole ring on photophysical properties of the complexes has been investigated. Synthesized thiazolo[3,2-c][1,3,5,2]oxadiazaborinines mainly showed intensive fluorescence in solutions. Complex with a 4,5-unsubstituted thiazole unit demonstrated an aggregation induced emission (AIE) effect and a very high fluorescent quantum yield (94%) in the solid state because of the inhibition of π-π/π-n interactions in the molecular packing.

Synthesis of 2-aminothiazoles from styrene derivatives mediated by 1,3-dibromo-5,5-dimethylhydrantoin (DBH)

An efficient procedure for the synthesis of 2-aminothiazoles via DBH-mediated oxidative cyclization of styrenes and thioureas is reported. Various alkenes were successfully transformed to the corresponding 2-aminothiazoles in yields of 10–81% via a two-step one-pot manner using DBH as both the bromine source and oxidant. The method can be readily carried out in gram-scale and successfully applied to the synthesis of anti-inflammatory drug fanetizole using styrene as starting material.

Preparation of 3,4-Substituted-5-Aminopyrazoles and 4-Substituted-2-Aminothiazoles

3,4-Substituted-5-aminopyrazoles and 4-substituted-2-aminothiazoles are frequently used intermediates in medicinal chemistry and drug discovery projects. We report an expedient flexible synthesis of 3,4-substituted-5-aminopyrazoles (35 examples), based on palladium-mediated α-arylation of β-ketonitriles with aryl bromides. A library of 4-substituted-2-aminothiazoles (21 examples) was assembled by a sequence employing Suzuki coupling of newly prepared, properly protected pinacol ester and MIDA ester of 4-boronic acid-2-aminothiazole with (hetero)aryl halides.

MNPs@SiO2-Pr-AP: A new catalyst for the synthesis of 2-amino-4-aryl thiazole derivatives

A simple and efficient synthesis of 2-amino-4-aryl thiazole derivatives was carried out through the reaction of substituted acetophenones and thiourea using three different types of catalytic systems including N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide [TBBDA], poly(N,N′-dibromo-N-ethylbenzene-1,3-disulfonamide) [PBBS] and a combination of TBBDA and nano-magnetic catalyst supported with functionalized 4-amino-pyridine silica (MNPs@SiO2-Pr-AP). The results showed that the use of TBBDA along with the MNPs@SiO2-Pr-AP gains the highest yields of the products in the shortest reaction time.