671-24-9

Basic information

• Product Name: 5-(2-bromoethyl)-4-methylthiazole
• Synonyms: 5-(2-bromoethyl)-4-methylthiazole
• CAS NO: 671-24-9
• Molecular Formula: C₆H₈BrNS
• Molecular Weight: 206.10342
• Mol File: 671-24-9.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-(2-bromoethyl)-4-methylthiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(2-bromoethyl)-4-methylthiazole(671-24-9)
• EPA Substance Registry System: 5-(2-bromoethyl)-4-methylthiazole(671-24-9)

Safety Data

• Hazardous Substances Data: 671-24-9(Hazardous Substances Data)

Upstream product

• 874509-37-2 2-(2-bromo-4-methyl-thiazol-5-yl)-ethanol 
• 59-43-8 vitamin B₁ 
• 115-08-2 thiocarboxamide 
• 63141-05-9 3,5-Dibromo-2-pentanone 
• 75908-63-3 2-bromo-5-(2-bromo-ethyl)-4-methyl-thiazole 
• 137-00-8 5-hydroxyethyl-4-methylthiazole 

Downstream Products

• 1759-28-0 4-methyl-5-vinylthiazole 
• 1417745-60-8 5-(2-azidoethyl)-3-benzyl-4-methylthiazol-3-ium bromide 
• 120072-28-8 N-(2-Fluoro-phenyl)-N-{4-(4-methyl-thiazol-2-yl)-1-[2-(4-methyl-thiazol-5-yl)-ethyl]-piperidin-4-yl}-propionamide 
• 120656-98-6 N-(2-Fluoro-phenyl)-N-{1-[2-(4-methyl-thiazol-5-yl)-ethyl]-4-phenyl-piperidin-4-yl}-propionamide 
• 137-00-8 5-hydroxyethyl-4-methylthiazole 
• 100393-85-9 1-(4-methyl-thiazol-5-yl)-2-salicyloyloxy-ethane 

Relevant articles and documents

Breslow Intermediates (Amino Enols) and Their Keto Tautomers: First Gas-Phase Characterization by IR Ion Spectroscopy

Breslow intermediates (BIs) are the crucial nucleophilic amino enol intermediates formed from electrophilic aldehydes in the course of N-heterocyclic carbene (NHC)-catalyzed umpolung reactions. Both in organocatalytic and enzymatic umpolung, the question whether the Breslow intermediate exists as the nucleophilic enol or in the form of its electrophilic keto tautomer is of utmost importance for its reactivity and function. Herein, the preparation of charge-tagged Breslow intermediates/keto tautomers derived from three different types of NHCs (imidazolidin-2-ylidenes, 1,2,4-triazolin-5-ylidenes, thiazolin-2-ylidenes) and aldehydes is reported. An ammonium charge tag is introduced through the aldehyde unit or the NHC. ESI-MS IR ion spectroscopy allowed the unambiguous conclusion that in the gas phase, the imidazolidin-2-ylidene-derived BI indeed exists as a diamino enol, while both 1,2,4-triazolin-5-ylidenes and thiazolin-2-ylidenes give the keto tautomer. This result coincides with the tautomeric states observed for the BIs in solution (NMR) and in the crystalline state (XRD), and is in line with our earlier calculations on the energetics of BI keto–enol equilibria.

New bis-thiazolium analogues as potential antimalarial agents: Design, synthesis, and biological evaluation

Bis-thiazolium salts are able to inhibit phosphatidylcholine biosynthesis in Plasmodium and to block parasite proliferation in the low nanomolar range. However, due to their physicochemical properties (i.e., permanent cationic charges, the flexibility, and lipophilic character of the alkyl chain), the oral bioavailability of these compounds is low. New series of bis-thiazolium-based drugs have been designed to overcome this drawback. They feature linker rigidification via the introduction of aromatic rings and/or a decrease in the overall lipophilicity through the introduction of heteroatoms. On the basis of the structure-activity relationships, a few of the promising compounds (9, 10, and 11) were found to exhibit potent antimalarial in vitro and in vivo activities (EC50 50 ip 0.7 mg/kg).

Photochemical reactivity of aromatic and heteroaromatic nitroderivatives in the presence of arylalkenes

The irradiation of styrene in the presence of nitroarenes in acetonitrile gives the corresponding nitrones in high yields. However, when 4-methyl-5-ethenylthiazole is used as arylalkene the starting material is converted to a pyrrole analogous of thianthrene. On the contrary, when 1,1-diphenylethylene is used, the main product observed is benzophenone. Nitrones are obtained only as minor products. An unusual coupling product, where a substitution reaction has occurred on the carbon bearing the nitro group, is also obtained. trans-Stilbene is unreactive under the same photochemical conditions, and it gives in low yields only benzaldehyde. Finally, indene gives, when aromatic nitro derivatives are used, only oxidation products, while, when heteroaromatic nitro derivatives are used, only substitution products on the nitro group are observed. The above described reactivity can be explained by using the results of AM1 semiempirical calculations on the frontier orbitals of the reagents. Both the nature of the LSOMO of the nitroarenes and the dipole moments of the reagents can account for the observed reactivity. The nitrone obtained in the photochemical reaction between styrene and nitrobenzene is used as starting material in a 1,3-dipolar cycloaddition reaction with styrene.