61830-21-5

Basic information

• Product Name: Ethyl 2-amino-5-bromothiazole-4-carboxylate
• Synonyms: 4-THIAZOLECARBOXYLIC ACID, 2-AMINO-5-BROMO-, ETHYL ESTER;2-AMINO-5-BROMOTHIAZOLE-4-CARBOXYLIC ACID ETHYL ESTER;Ethyl 2-amino-5-bromothiazole-4-carboxylate;Ethyl 2-Amino-5-bromothiazole-4-carboxylicacid;ethyl 2-amino-5-bromo-1,3-thiazole-4-carboxylate;Ethyl 2-amino-5-bromo-4-thiazolecarboxylate;Ethyl 2-amino-5-bromothiazole-4-carboxy;2-Amino-5-bromo-4-(ethoxycarbonyl)-1,3-thiazole
• CAS NO: 61830-21-5
• Molecular Formula: C₆H₇BrN₂O₂S
• Molecular Weight: 251.1
• Product Categories: Sulphur Derivatives;Esters;Thiazoles, Isothiazoles &Benzothiazoles;Thiazoles;Thiazoles, Isothiazoles & Benzothiazoles
• Mol File: 61830-21-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 115-117 °C
• Boiling Point: 357 °C at 760 mmHg
• Flash Point: 169.7 °C
• Appearance: /
• Density: 1.731 g/cm³
• Vapor Pressure: 2.82E-05mmHg at 25°C
• Refractive Index: 1.621
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 0.88±0.10(Predicted)
• CAS DataBase Reference: Ethyl 2-amino-5-bromothiazole-4-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 2-amino-5-bromothiazole-4-carboxylate(61830-21-5)
• EPA Substance Registry System: Ethyl 2-amino-5-bromothiazole-4-carboxylate(61830-21-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 61830-21-5(Hazardous Substances Data)

Usage

General Description

Ethyl 2-amino-5-bromothiazole-4-carboxylate is a chemical compound with the molecular formula C7H8BrN2O2S. It is a derivative of thiazole, a heterocyclic compound containing a five-membered ring with sulfur and nitrogen atoms. Ethyl 2-amino-5-bromothiazole-4-carboxylate is used in organic synthesis and pharmaceutical research, as it has the potential to be a building block for the synthesis of various biologically active molecules. Its structure contains an ethyl group, an amino group, a bromine atom, and a carboxylic ester group, making it a versatile intermediate for the production of pharmaceuticals and other organic compounds. Its potential biological properties and applications make it a valuable compound for chemical and pharmaceutical research.

InChI:InChI=1/C6H7BrN2O2S/c1-2-11-5(10)3-4(7)12-6(8)9-3/h2H2,1H3,(H2,8,9)

Upstream product

• 5398-36-7 2-aminothiazole-4-carboxylate 
• 70-23-5 ethyl Bromopyruvate 

Downstream Products

• 103878-58-6 5-bromo-1,3-thiazole-4-carboxylic acid 
• 61830-23-7 ethyl 5‐bromo‐1,3‐thiazole‐4‐carboxylate 
• 175603-81-3 2-Amino-5-phenylsulfanyl-thiazole-4-carboxylic acid ethyl ester 
• 208264-60-2 2,5-dibromo-1,3-thiazole-4-carboxylic acid ethyl ester 
• 1125409-85-9 5-bromo-2-chloro-thiazole-4-carboxylic acid ethyl ester 
• 61830-24-8 5-(4-methoxy-benzylsulfanyl)-thiazole-4-carboxylic acid ethyl ester 
• 172933-16-3 ethyl 5-bromo-2-(4,4-difluorobut-3-enylthio)thiazole-4-carboxylate 
• 1443205-13-7 C₂₁H₁₈N₄O₃S₂ 
• 1443205-14-8 C₂₂H₂₀N₄O₃S₂ 
• 1443205-15-9 C₂₀H₁₅ClN₄O₃S₂ 
• 1443205-16-0 C₂₁H₁₇ClN₄O₃S₂ 
• 1443205-17-1 C₂₂H₂₀N₄O₅S₂ 
• 1443205-18-2 C₂₃H₂₂N₄O₅S₂ 
• 1279863-32-9 ethyl 5-bromo-2-((tert-butoxycarbonyl)amino)thiazole-4-carboxylate 

Relevant articles and documents

Synthesis, biological evaluation and molecular docking studies of thiazole-based pyrrolidinones and isoindolinediones as anticonvulsant agents

A series of new 1-(thiazol-2-yl)pyrrolidin-2-one 5a-m and 2-(thiazol-2-yl)isoindoline-1,3-dione 6a-n derivatives were synthesized and evaluated for anticonvulsant activity. The activity was established in three seizure models: PTZ, picrotoxin and MES. Selected compounds were elected for neurotoxicity by the rotarod test. The most active compound of the series was 1-(4-(naphthalen-2-yl)thiazol-2-yl)pyrrolidin-2-one (5g), showing a PTZ effect dose (ED50) value of 18.4 mg/kg in mice. The median toxic dose (TD50) was 170.2 mg/kg, which provided a protection index (PI = TD50/ED50) of 9.2. A computational study was also carried out, including prediction of pharmacokinetic properties and docking studies. The structural assignments of the newly synthesized compounds were elucidated on the basis of spectroscopic data and single-crystal X-ray crystallography. Graphical Abstract: A series of new thiazole-based pyrrolidinones 5a-m and isoindolinediones 6a-l were synthesized and tested as anticonvulsant. The most active compound was 1-(4-(naphthalen-2-yl)thiazol-2-yl)pyrrolidin-2-one (5g), showing ED50 value 18.4 mg/kg.[Figure not available: see fulltext.]

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A compound having the formula R--S(O)n CH2 CH2 CH=CF2, wherein R is a phenyl group or a heterocyclic group selected from furyl, thienyl, isoxazolyl, isothiazolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-oxadiazolyl, 1,3,4-thidiazolyl, tetrazolyl, pyridyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,3,4-triazinyl, and 1,3,5-triazinyl groups, said phenyl or heterocyclic group being optionally substituted by optionally substituted alkyl, optionally substituted alkenyl, alkynyl, cycloalkyl, alkylcycloalkyl, alkoxy, alkenyloxy, alkynyloxy, hydroxyalkyl, alkoxyalkyl, optionally substituted aryl, optionally substituted arylalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted aryloxyalkyl, optionally substituted heteroaryloxy, optionally substituted heteroarylalkoxy, optionally substituted heteroaryloxyalkyl, haloalkyl, haloalkenyl, haloalkynyl, haloalkoxy, haloalkenyloxy, haloalkynyloxy, halogen, hydroxy, cyano, nitro, --NR7R8, --NR7COR8, --NR7CSR8, --NR7SO2R8, --N(SO2R7)(SO2R8), --COR7, --CONR7R8, -alkylCONR7R8, --CR7NR8, --COOR7, --OCOR7, --SR7, --SOR7, --SO2R7, -alkylSR7, -alkylSOR7, -alkylSO2R7, --OSO2R7, --SO2NR7R8, --CSNR7R8, --SiR7R8R9, --OCH2CO2R7, --OCH2CH2CO2R7, --CONR7SO2R8, -alkylCONR7SO2R8, --NHCONR7R8, --NHCSNR7R8, or an adjacent pair of R1, R2, R3, R4, R5 and R6 when taken together form a fused 5- or 6-membered carbocyclic or heterocyclic ring; R7, R8 and R9 are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, alkynyl, optionally substituted aryl or optionally substituted arylalkyl, haloalkyl, haloalkenyl, haloalkynyl, halogen or hydroxy.