56503-96-9

Basic information

• Product Name: 4-(1-Naphthalenyl)-2-thiazolamine
• Synonyms: 2-amino-4-(1-naphthyl)-thiazol;2-amino-4-alpha-naphthylthiazole;4-(1-naphthalenyl)-2-thiazolamin;AKOS B000323;AKOS BBS-00000643;4-Naphthalen-1-yl-1,3-thiazol-2-amine;4-(NAPHTHALEN-1-YL)THIAZOL-2-AMINE;4-NAPHTHALEN-1-YL-THIAZOL-2-YL-AMINE
• CAS NO: 56503-96-9
• Molecular Formula: C₁₃H₁₀N₂S
• Molecular Weight: 226.3
• EINECS: -0
• Mol File: 56503-96-9.mol
• Article Data: 10

Chemical Properties

• Melting Point: 155-158°C
• Boiling Point: 428.4 °C at 760 mmHg
• Flash Point: 212.9 °C
• Appearance: crystalline powder
• Density: 1.301 g/cm³
• Vapor Pressure: 1.53E-07mmHg at 25°C
• Refractive Index: 1.73
• PKA: 4.58±0.10(Predicted)
• BRN: 164858
• CAS DataBase Reference: 4-(1-Naphthalenyl)-2-thiazolamine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(1-Naphthalenyl)-2-thiazolamine(56503-96-9)
• EPA Substance Registry System: 4-(1-Naphthalenyl)-2-thiazolamine(56503-96-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RTECS: XJ1990000
• HazardClass: IRRITANT
• Hazardous Substances Data: 56503-96-9(Hazardous Substances Data)

Usage

Description

4-(1-Naphthalenyl)-2-thiazolamine, also known as 2-Amino-4-(1-naphthyl)thiazole, is an organic compound with a unique chemical structure that features a naphthalene ring and a thiazolamine group. It is known for its potential applications in the pharmaceutical and chemical industries due to its versatile chemical properties.

Uses

Used in Pharmaceutical Industry:
4-(1-Naphthalenyl)-2-thiazolamine is used as a reagent for the synthesis of 2-substituted ethenesulfonic acid ester derivatives, which serve as Protein Tyrosine Phosphatase 1B (PTP1B) inhibitors. These inhibitors play a crucial role in regulating various cellular processes and have potential therapeutic applications in treating type 2 diabetes and obesity.
Additionally, 4-(1-Naphthalenyl)-2-thiazolamine is used as a reagent in the preparation of pirinixic acid derivatives. These derivatives act as dual 5-lipoxygenase and microsomal prostaglandin E2 synthase-1 inhibitors, which are essential in the treatment of inflammation and various types of cancer. By targeting these specific enzymes, pirinixic acid derivatives can help alleviate inflammation and potentially slow down the progression of cancer.

InChI:InChI=1/C13H10N2S/c14-13-15-12(8-16-13)11-7-3-5-9-4-1-2-6-10(9)11/h1-8H,(H2,14,15)

Upstream product

• 879-18-5 naphthalene-1-carbonic acid chloride 
• 17356-08-0 thiourea 
• 352517-78-3 1-(α-tosyloxy)acetonaphthone 
• 333-20-0 potassium thioacyanate 
• 941-98-0 1'-naphthacetophenone 
• 703-55-9 1-naphthylmagnesiumbromide 
• 13686-51-6 2-bromoaceto-1-naphthone 

Downstream Products

• 79652-49-6 7-[(4-Naphthalen-1-yl-thiazol-2-ylamino)-phenyl-methyl]-quinolin-8-ol 
• 6125-40-2 4--2-(α-diaethylamino-acetamino)-thiazol 
• 6664-58-0 4--2-<α-(N-methyl-anilino-acetamino)-thiazol 
• 6674-32-4 N-ethyl-N-phenyl-glycine 4-naphthalen-1-yl-thiazol-2-ylamide 
• 6121-98-8 N-benzyl-N-phenyl-glycine 4-naphthalen-1-yl-thiazol-2-ylamide 
• 99757-14-9 Chloro-acetic acid 4-{[(E)-4-naphthalen-1-yl-thiazol-2-ylimino]-methyl}-phenyl ester 
• 89405-39-0 2-Methoxy-4-{[(E)-4-naphthalen-1-yl-thiazol-2-ylimino]-methyl}-phenol 
• 99756-63-5 4-{[(E)-4-Naphthalen-1-yl-thiazol-2-ylimino]-methyl}-phenol 
• 56503-91-4 3-(4-naphthalen-1-yl-thiazol-2-ylamino)-1-phenyl-propan-1-one 
• 4582-52-9 2-Acetamido-4-α-naphthyl-5-morpholinomethyl-thiazole 
• 109693-28-9 4-(2-amino-4-[1]naphthyl-thiazol-5-ylazo)-benzenesulfonic acid amide 
• 103327-94-2 4,4'-di-[1]naphthyl-5,5'-benzylidene-bis-thiazol-2-ylamine 
• 313393-87-2 N-[4-(1-Naphthyl)thiazol-2-yl]-(2-chloro-5-nitrophenyl)carboxamide 

Relevant articles and documents

Synthesis of 2-aminothiazoles via rhodium-catalyzed carbenoid insertion/annulation of sulfoxonium ylides with thioureas

Sulfoxonium ylides as carbene precursors couple smoothly with thioureas in the presence of 5 mol% of rhodium(II) acetate dimmer via carbenoid insertion to afford the corresponding 2-aminothiazoles with high chemoselectivity, providing a facile and efficient approach to access a variety of 2-aminothiazole derivatives with good functional groups tolerance.

4 - substituted -2 - amino thiazole compound preparation method

The invention discloses a preparation method of a 4-substituted-2-aminothiazole compound. The method comprises the following step: olefin azide shown by the formula I reacts with potassium thiocyanate under the catalysis of palladium acetate to obtain the 4-substituted-2-aminothiazole compound, wherein the molar ratio of the olefin azide compound to potassium thiocyanate to palladium acetate is 20:(59-61):1, the reaction temperature is 75-85 DEG C, and the reaction time is 11-13 hours; and in the formula I, R1 is phenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 4-methylphenyl, 4-ethyoxy-3-bromophenyl, 3-nitrophenyl, 4-methoxyacylphenyl, 1-naphthyl, phenylaminomethyl or trans-4-(3-phenylallyloxymethyl).

Selective Access to 4-Substituted 2-Aminothiazoles and 4-Substituted 5-Thiocyano-2-aminothiazoles from Vinyl Azides and Potassium Thiocyanate Switched by Palladium and Iron Catalysts

A highly selective construction of 4-substituted 2-aminothiazoles and 4-substituted 5-thiocyano-2-aminothiazoles, respectively, catalyzed by palladium(II) acetate and promoted by iron(III) bromide from vinyl azides and potassium thiocyanate has been developed. Use of readily available starting materials, high selectivity, as well as mild reaction conditions make this practical method particularly attractive.