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ETHYL 2-METHYLTHIAZOLE-4-CARBOXYLATE is an organic compound with the chemical formula C6H9NO2S. It is a light yellow to brown powder and is primarily known for its role in the synthesis of various compounds. ETHYL 2-METHYLTHIAZOLE-4-CARBOXYLATE has gained significant attention due to its potential applications in the pharmaceutical industry, particularly in the development of antituberculosis agents.

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  • 6436-59-5 Structure
  • Basic information

    1. Product Name: ETHYL 2-METHYLTHIAZOLE-4-CARBOXYLATE
    2. Synonyms: BUTTPARK 29\06-83;ETHYL 2-METHYLTHIAZOL-4-CARBOXYLATE;ETHYL 2-METHYLTHIAZOLE-4-CARBOXYLATE;ETHYL 2-METHYL-1,3-THIAZOLE-4-CARBOXYLATE;2-methylthiazole-4-carboxylic acid ethyl ester;methyl 2-methylthiazole-4-carboxylate;Ethyl 2-methyl-1,3-thiazole-4-carboxylate ,98%;ETHYL 2-METHYLTHIAZO
    3. CAS NO:6436-59-5
    4. Molecular Formula: C7H9NO2S
    5. Molecular Weight: 171.22
    6. EINECS: N/A
    7. Product Categories: Building Blocks;C3 to C7;Chemical Synthesis;Heterocyclic Building Blocks;Thiazoles
    8. Mol File: 6436-59-5.mol
  • Chemical Properties

    1. Melting Point: 54-56°C
    2. Boiling Point: 242.1 °C at 760 mmHg
    3. Flash Point: 100.2 °C
    4. Appearance: /
    5. Density: 1.198 g/cm3
    6. Vapor Pressure: 0.035mmHg at 25°C
    7. Refractive Index: 1.528
    8. Storage Temp.: Refrigerated.
    9. Solubility: N/A
    10. PKA: 1.10±0.10(Predicted)
    11. CAS DataBase Reference: ETHYL 2-METHYLTHIAZOLE-4-CARBOXYLATE(CAS DataBase Reference)
    12. NIST Chemistry Reference: ETHYL 2-METHYLTHIAZOLE-4-CARBOXYLATE(6436-59-5)
    13. EPA Substance Registry System: ETHYL 2-METHYLTHIAZOLE-4-CARBOXYLATE(6436-59-5)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26-37-24/25
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: IRRITANT
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 6436-59-5(Hazardous Substances Data)

6436-59-5 Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 2-METHYLTHIAZOLE-4-CARBOXYLATE is used as a reactant for the synthesis of 2,4,5-trisubstituted thiazoles. These thiazoles are known for their antituberculosis properties and are effective against drug-resistant tuberculosis. The development of new antituberculosis agents is crucial due to the increasing prevalence of drug-resistant strains, making ETHYL 2-METHYLTHIAZOLE-4-CARBOXYLATE a valuable compound in the fight against this global health issue.

Check Digit Verification of cas no

The CAS Registry Mumber 6436-59-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,4,3 and 6 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 6436-59:
(6*6)+(5*4)+(4*3)+(3*6)+(2*5)+(1*9)=105
105 % 10 = 5
So 6436-59-5 is a valid CAS Registry Number.
InChI:InChI=1/C7H9NO2S/c1-3-10-7(9)6-4-11-5(2)8-6/h4H,3H2,1-2H3

6436-59-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A12050)  Ethyl 2-methylthiazole-4-carboxylate, 98%   

  • 6436-59-5

  • 1g

  • 183.0CNY

  • Detail
  • Alfa Aesar

  • (A12050)  Ethyl 2-methylthiazole-4-carboxylate, 98%   

  • 6436-59-5

  • 5g

  • 734.0CNY

  • Detail
  • Alfa Aesar

  • (A12050)  Ethyl 2-methylthiazole-4-carboxylate, 98%   

  • 6436-59-5

  • 25g

  • 2931.0CNY

  • Detail
  • Aldrich

  • (716308)  Ethyl2-methylthiazole-4-carboxylate  97%

  • 6436-59-5

  • 716308-1G

  • 451.62CNY

  • Detail
  • Aldrich

  • (716308)  Ethyl2-methylthiazole-4-carboxylate  97%

  • 6436-59-5

  • 716308-5G

  • 1,375.92CNY

  • Detail

6436-59-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name Ethyl 2-methylthiazole-4-carboxylate

1.2 Other means of identification

Product number -
Other names ETHYL 2-METHYLTHIAZOLE-4-CARBOXYLATE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:6436-59-5 SDS

6436-59-5Relevant articles and documents

Asymmetric aldol reaction of thiazole-carbaldehydes: Regio- And stereoselective synthesis of tubuvalin analogues

Paladhi, Sushovan,Das, Joydeb,Samanta, Mousumi,Dash, Jyotirmayee

, p. 3370 - 3376 (2014)

The first organocatalytic enantioselective approach to precursors of tubuvaline (pre-Tuv) is presented employing a prolinamide-catalyzed aldol reaction of easily accessible thiazole-carbaldehyde with methyl isopropyl ketone "on water" in excellent yield as well as regio- and enantioselectivities. The analogues of pre-Tuv were achieved using an l-proline-catalyzed direct asymmetric aldol reaction of substituted thiazole-carbaldehydes with acetone. A direct and flexible approach to the tubavaline (Tuv) core of tubusylins has been established employing the reductive amination of the pre-Tuv species. The key aldol reaction should greatly expand the potential of this strategy to the synthesis of natural product tubulysins and a range of analogues.

Design, synthesis, and antitumor activity evaluation of pretubulysin analogs

Xu, Xiangrong,Fan, Meixia,Qi, Junhui,Yao, Lei

, p. 341 - 351 (2021/06/14)

Pretubulysin, a biosynthetic precursor of the tubulysins, shows potent biological activity in a variety of tumor cell lines. Although there are several total synthesis routes to tubulysin and pretubulysin reported, the commercialization still has been hampered due to the complexity of the structure. To find structurally simpler pretubulysin analogs, a series of 2-(3-(methylamino)propyl)thiazole-4-carboxamides are designed and synthesized, and their anticancer activities are screened using MCF-7 (breast cancer), and NCI-H157 (lung cancer) cell lines. Taxol (IC50?=?0.01?μM) and pretubulysin are used as the control. Compounds 8c (IC50?=?0.05?μM, MCF-7; 0.09?μM, NCI-H157) and 8h (IC50?=?0.01?μM, MCF-7; 0.02?μM, NCI-H157) exhibited certain antitumor activities comparable to those of Taxol. The urea analogs of pretubulysin might represent a promising scaffold for the further development of novel antitumor drugs.

New BI and TRI-Thiazole copper (II) complexes in the search of new cytotoxic drugs against breast cancer cells

Alvarez, Natalia,Velluti, Francesca,Guidali, Florencia,Serra, Gloria,Gabriela Kramer,Ellena, Javier,Facchin, Gianella,Scarone, Laura,Torre, María H.

, (2020/04/07)

New thiazolyl derivatives (BT and TT) and their copper (II) complexes [Cu2Cl2(BT)2] (Cu-BT) and [Cu4ClO2(TT)2]PF6?3.5H2O (Cu-TT) were synthesized and characterized by elemental analysis, 1H NMR and 13C NMR, HRMS, X-ray diffraction, IR and UV–Vis spectroscopies. The crystal structure of Cu-BT shows the formation of a dinuclear complex where each copper(II) center is bonded to two thiazol N atoms, from different BT ligands, one deprotonated amide N atom, an O atom from the ester terminal groups and a chlorine atom. The structure found for Cu-TT is a positively charged tetranuclear moiety containing two deprotonated TT ligands, a chlorine anion, two hydroxide anions acting as bridges between the copper centers and a water molecule. The cytotoxic activity of both copper complexes was evaluated on metastatic breast cancer cell lines, characterized for its rapidly dividing behavior. Both, Cu-BT and Cu-TT, show higher cytotoxic activity against these tumor cells than free BT and TT and also than cisplatin. In addition, we found that both complexes interact with DNA. Consistently, they also show cytotoxicity against a rapidly dividing non-tumor cell line, although with higher IC50, being such interaction and selectivity an indicator of the possible coexistence of more than one mechanism of action.

Synthesis and biological evaluation of 2,4,5-trisubstituted thiazoles as antituberculosis agents effective against drug-resistant tuberculosis

Karale, Uttam B.,Krishna, Vagolu Siva,Krishna, E. Vamshi,Choudhari, Amit S.,Shukla, Manjulika,Gaikwad, Vikas R.,Mahizhaveni,Chopra, Sidharth,Misra, Sunil,Sarkar, Dhiman,Sriram, Dharmarajan,Dusthackeer, V.N. Azger,Rode, Haridas B.

, p. 315 - 328 (2019/06/14)

The dormant and resistant form of Mycobacterium tuberculosis presents a challenge in developing new anti-tubercular drugs. Herein, we report the synthesis and evaluation of trisubstituted thiazoles as antituberculosis agents. The SAR study has identified a requirement of hydrophobic substituent at C2, ester functionality at C4, and various groups with hydrogen bond acceptor character at C5 of thiazole scaffold. This has led to the identification of 13h and 13p as lead compounds. These compounds inhibited the dormant Mycobacterium tuberculosis H37Ra strain and M. tuberculosis H37Rv selectively. Importantly, 13h and 13p were non-toxic to CHO cells. The 13p showed activity against multidrug-resistant tuberculosis isolates.

Development of a practical and scalable route for the preparation of the deacetoxytubuvaline (dTuv) fragment of pretubulysin and analogs

Brindisi, Margherita,Maramai, Samuele,Grillo, Alessandro,Brogi, Simone,Butini, Stefania,Novellino, Ettore,Campiani, Giuseppe,Gemma, Sandra

supporting information, p. 920 - 923 (2016/02/05)

We present herein a novel and convenient route for the scaling-up of the dTuv fragment of pretubulysin. The newly conceived chemical path involves a practical and efficient one-step procedure for the preparation of a key thiazole intermediate, followed by high-yielding Wittig olefination/reduction steps. The optimized route, starting from the inexpensive and non-toxic l-cysteine, encompasses five synthetic steps and only two chromatographic purifications, thus displaying a dramatically increased overall yield. The versatility of the proposed approach also provides new hints for the exploration of pretubulysin derivatives bearing diverse heterocyclic portions.

Solvent-free synthesis of bacillamide analogues as novel cytotoxic and anti-inflammatory agents

Kumar, Sunil,Aggarwal, Ranjana,Kumar, Virender,Sadana, Rachna,Patel, Bhumi,Kaushik, Pawan,Kaushik, Dhirender

, p. 718 - 726 (2016/08/15)

Synthesis of fourteen analogues of bacillamide, a bioactive tryptamide alkaloid of marine origin, has been accomplished through a highly efficient convergent route. The present solvent-free protocol involves the formation of thiazole ring in the initial step followed by amide coupling between substituted ethyl 2-alkyl/aryl/heteroaryl/amino/aminoarylthiazole-4-carboxylates and tryptamine in presence of 2-hydroxy-4,6-dimethylpyrimidine, a solid phase catalyst to yield N-[2-(1H-indol-3-yl)ethyl]-2-alkyl/aryl/heteroaryl/amino/aminoarylthiazole-4-carboxamides as bacillamide analogues having structural variation at position-2 of thiazole ring. Bacillamide and its analogues were evaluated for their cytotoxic activity against three cancer cell lines (HCT-116, MDA-MD-231 and JURKAT cell lines) using colorimetric cell proliferation assay. Compounds 17a and 17b exhibited potent anti-cell proliferation activity with IC50values in the range of ~3.0?μM and ~0.1–0.6?μM, respectively against these cell lines. Preliminary mechanism of action studies indicates that these compounds initiate caspase dependent apoptosis. Also, compounds 16d, 16f, 17a and 17d exhibited excellent anti-inflammatory activity comparable to well-known NSAID indomethacin and better to bacillamide, when evaluated using carrageenan induced rat hind paw oedema method.

Exploration and Optimization of an Efficient One-pot Sequential Synthesis of Di/tri-substituted Thiazoles from α-Bromoketones, Thioacids Salt, and Ammonium Acetate

Venkateswararao, Eeda,Jalani, Hitesh B.,Manoj,, Manickam,Jung, Sang-Hun

supporting information, p. 1449 - 1456 (2016/09/24)

Exploration of scope of an optimized one-pot sequential procedure for preparing of 2,4-di- and 2,4,5-tri-substituted thiazoles has been accomplished. The synthesis was performed by the initial formation of a β-keto-thioester intermediate from nucleophilic substitution of α-bromoketones with thioacid potassium salts, followed by treatment with ammonium acetate and one equivalent of acetic acid in toluene to form imine intermediate eventually leading to cyclization yielding thiazoles. This procedure should be highlighted with a flexible way to control the substitution pattern around thiazole ring by choosing appropriately substituted α-bromoketones even containing acid labile functionality and thioacid potassium salts, and thus its applicability is very wide.

Synthesis of substituted esters of imidazoles, oxazoles, thiazoles, and diethyl pyrazine-2,5-dicarboxylate from a common acyclic precursor employing C-formylation strategy

Khose, Goraksha,Shinde, Shailesh,Panmand, Anil,Kulkarni, Ravibhushan,Munot, Yogesh,Bandyopadhyay, Anish,Barawkar, Dinesh,Patil, Santoshkumar N.

supporting information, p. 2671 - 2674 (2014/05/06)

A novel synthetic route to substituted esters of imidazoles, oxazoles, thiazoles, and diethyl pyrazine-2,5-dicarboxylates via C-formylation of glycine ethyl ester hydrochloride is reported. This methodology is simple, robust, and gives good yields of different heterocyclic esters in one or two steps from a common acyclic precursor and is amenable to large scale synthesis.

An efficient total synthesis of (-)-epothilone B

Wang, Jie,Sun, Bing-Feng,Cui, Kai,Lin, Guo-Qiang

supporting information, p. 6354 - 6357 (2013/02/23)

An efficient total synthesis of (-)-epothilone B has been achieved in ca. 8% yield over 11 steps from 9 (or 10 steps from 7/8), which features a bissiloxane-tethered ring closing metathesis reaction to approach the trisubstituted (Z) double bond and forms a new basis for further development of an industrial process for epothilone B and ixabepilone.

An efficient synthesis of 2,4′-bi-1,3-oxa(thia)zoles as scaffolds for bioactive products

Pena,Scarone,Manta,Serra

experimental part, p. 703 - 709 (2012/02/01)

A rapid and efficient methodology to prepare 2,4′-bi-1,3-azoles as scaffolds for biologically active marine natural products is described. Hantzsch reaction and oxidative cyclodehydration of β-hydroxy amides or thioamides were used to construct the azole rings. The obtained biheterocycles displayed no cytotoxicity on HCT-15 cell line.

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