344-72-9

Basic information

• Product Name: 2-AMINO-4-TRIFLUOROMETHYL-THIAZOLE-5-CARBOXYLIC ACID ETHYL ESTER
• Synonyms: Ethyl-2-amino-4-trifluoromethylthiazolecarboxylate;5-Thiazolecarboxylicacid, 2-aMino-4-(trifluoroMethyl)-, ethyl ester;NSC 4465;2-amino-4-(trifluoromethyl)-5-thiazolecarboxylicacidethylester;2-amino-4-(trifluoromethyl)-5-thiazolecarboxylicaciethylester;BUTTPARK 11\03-53;ETHYL 2-AMINO-4-(TRIFLUOROMETHYL)-1,3-THIAZOLE-5-CARBOXYLATE;ETHYL 2-AMINO-4-(TRIFLUOROMETHYL)-5-THIAZOLECARBOXYLATE
• CAS NO: 344-72-9
• Molecular Formula: C₇H₇F₃N₂O₂S
• Molecular Weight: 240.2
• Product Categories: Amines;blocks;Carboxes;FluoroCompounds;Oxazoles
• Mol File: 344-72-9.mol
• Article Data: 19

Chemical Properties

• Melting Point: 170 °C
• Boiling Point: 81.4°C (rough estimate)
• Flash Point: 153.2 °C
• Appearance: /
• Density: 1.479
• Vapor Pressure: 0.000174mmHg at 25°C
• Refractive Index: 1.507
• PKA: 0.08±0.10(Predicted)
• CAS DataBase Reference: 2-AMINO-4-TRIFLUOROMETHYL-THIAZOLE-5-CARBOXYLIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-4-TRIFLUOROMETHYL-THIAZOLE-5-CARBOXYLIC ACID ETHYL ESTER(344-72-9)
• EPA Substance Registry System: 2-AMINO-4-TRIFLUOROMETHYL-THIAZOLE-5-CARBOXYLIC ACID ETHYL ESTER(344-72-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 344-72-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 28, p. 907, 1991 DOI: 10.1002/jhet.5570280412

Safety Profile

Poison by intravenous route.When heated to decomposition it emits toxic vapors ofNOx and SOx.

InChI:InChI=1/C7H7F3N2O2S/c1-2-14-5(13)3-4(7(8,9)10)12-6(11)15-3/h2H2,1H3,(H2,11,12)

Upstream product

• 363-58-6 ethyl 2-chloro-4,4,4-trifluoro-3-oxobutanoate 
• 372-31-6 ethyl 4,4,4-trifluoroacetoacetate 
• 17356-08-0 thiourea 
• 4544-43-8 Ethyl 2-Bromo-4,4,4-trifluoro-3-oxobutanoate 
• 141860-78-8 ethyl 3-amino-4,4,4-trifluorocrotonate 
• 65573-12-8 4-chloro-5H-1,2,3-dithiazole-5-one 

Downstream Products

• 72850-79-4 ethyl 2-bromo-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate 

Relevant articles and documents

Synthesis of 2-aminoethyl-5-carbethoxythiazoles utilizing a Michael-like addition strategy

Ethyl 4-(trifluoromethyl)-2-vinylthiazole-5-carboxylate was utilized as a precursor to ethyl 4-(trifluoromethyl)-2-(aminoethyl)thiazole-5-carboxylate analogs via Michael-like addition of various secondary amines. Reactions employed 1.2 equiv of amine, and the products were isolated by solvent removal and acid/base extraction. Use of primary amines was also investigated.

Synthesis and Fungicidal Activity of Novel 2-Heteroatomthiazole-based Carboxanilides

A new series of 2-heteroatomthiazole-based carboxanilides (8) are prepared by reacting 2-heteroatomthiazole-based carboxylic acid chlorides with 2,6-dibromo-4-(trifluoromethoxy)aniline. The structures of all the newly synthesized compounds were supported by spectroscopic data NMR, MS, and elemental analysis, etc. Bioassay showed that the compounds exhibited potent fungicidal activities against Rhizoctonia solani, etc. Particularly, N-(2,6-dibromo-4-(trifluoromethoxy)phenyl)-2-methoxy-4-(trifluoromethyl)thiazole-5-carboxamide (8a-2) showed fungicidal potency which was comparable to that of Thifluzamide, the only commercialized thiazole carboxanilide fungicides of succinate dehydrogenase inhibitor (SDHI).

Synthesis and Biological Activity of Ethyl 4-Alkyl-2-(2-(substituted phenoxy)acetamido)thiazole-5-carboxylate

(Chemical Equation Presented) A series of novel ethyl 4-(methyl or trifluoromethyl)-2-(2-(substituted phenoxy)acetamido)thiazole-5-carboxylates 7a, 7b, 7c, 7d, 7e and 8f, 8g, 8h, 8i, 8j, 8k, 8l, 8m, 8n, 8o, 8p, 8q, 8r were synthesized, and their structures were confirmed by IR, 1H-NMR, MS spectra and elemental analysis. The results of preliminary bioassays show that some of the title compounds exhibit moderate to good herbicidal activities. Compared with the fluorine free compounds 7a, 7b, and 7e, the compounds bearing fluorine 8g, 8j, and 8q showed higher herbicidal activities with 70-100% inhibition against Capsella bursa-pastoris, Amaranthus restroflexus, and Eclipta prostrata at the dosage of 150 g/ha, which indicated that the trifluoromethyl on the thiazole ring was beneficial for the herbicidal activity. Furthermore, compounds 8f, 8g, 8h, 8i, 8j, 8k, 8l, 8m, 8n, 8o, 8p, 8q, 8r were tested for fungicidal activity against Pseudoperonospora cubensis at 500 μg/mL. Compounds 8f and 8q showed the best fungicidal activity with more than 80% inhibition.