38205-60-6

Basic information

• Product Name: 5-Acetyl-2,4-dimethylthiazole
• Synonyms: TIMTEC-BB SBB006624;5-ACETYL-2,4-DIMETHYLTHIAZOLE;2,4-DIMETHYL-5-THIAZOYL METHYL KETONE;2,4-DIMETHYL-5-ACETYLTHIAZOLE;1-(2,4-DIMETHYL-1,3-THIAZOL-5-YL)ETHAN-1-ONE;FEMA 3267;FEMA NUMBER 3267;1-(2,4-Dimethyl-1,3-thiazol-5-yl)ethanone
• CAS NO: 38205-60-6
• Molecular Formula: C₇H₉NOS
• Molecular Weight: 155.22
• EINECS: 253-826-0
• Product Categories: Alphabetical Listings;C-D;Flavors and Fragrances;Building Blocks;Heterocyclic Building Blocks;Thiazoles
• Mol File: 38205-60-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 228-230 °C(lit.)
• Flash Point: 220 °F
• Appearance: colorless to light yellow liquid
• Density: 1.15 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0712mmHg at 25°C
• Refractive Index: n20/D 1.543(lit.)
• Storage Temp.: 2-8°C
• PKA: 1.97±0.10(Predicted)
• BRN: 120560
• CAS DataBase Reference: 5-Acetyl-2,4-dimethylthiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Acetyl-2,4-dimethylthiazole(38205-60-6)
• EPA Substance Registry System: 5-Acetyl-2,4-dimethylthiazole(38205-60-6)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-43-22
• Safety Statements: 26-37/39-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 38205-60-6(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 38205-60-6 differently. You can refer to the following data:
1. Colorless to light yellow liqui
2. 2,4-Dimethyl-5-acetylthiazole is a heterocyclic thiazole that has an odor of roasted nut or sulfur, as in boiled meat.

Taste threshold values

Taste characteristics at 10 ppm: nutty, roasted, meaty and savory with woody and coffee nuances.

General Description

Conversion of 5-acetyl-2,4-dimethylthiazoleoxime by SeO2 via deoximation to 5-acetyl-2,4-dimethylthiazole has been reported.

InChI:InChI=1/C7H9NOS/c1-4-7(5(2)9)10-6(3)8-4/h1-3H3

Upstream product

• 64-17-5 ethanol 
• 62-55-5 thioacetamide 
• 1694-29-7 3-chloropentane-2,4-dione 
• 60-35-5 acetamide 
• 40236-03-1 1-(2,4-dimethylthiazol-5-yl)ethan-1-one oxime 
• 7660-21-1 3-chloroacetyl acetone 
• 3043-28-5 3-bromopentane-2,4-dione 
• 89775-33-7 1-(2,4-dimethyl-thiazol-5-yl)-ethanol 

Downstream Products

• 245748-84-9 4-[3-(2,4-dimethyl-1,3-thiazol-5-yl)-5-(trifluoromethyl)-1H-pyrazol-1-yl]aniline 
• 1415233-14-5 3-(2',4'-Dimethyl-[4,5']bithiazolyl-2-ylamino)-benzamide 
• 1415233-70-3 N-(5-fluoro-2-methoxyphenyl)-2',4',5-trimethyl-[4,5'-bithiazol]-2-amine.HBr 
• 364736-03-8 [2-(2,4-dimethyl-thiazole-5-carbonyl)-1,3-dioxo-indan-4-yl]-carbamic acid phenyl ester 
• 364333-82-4 {4-(2,4-dimethyl-thiazol-5-yl)-pyrimidin-2-yl}-(3-nitro-phenyl)-amine 
• 364334-88-3 N-[4-(2,4-dimethyl-thiazol-5-yl)pyrimidin-2-yl]-N′,N′-dimethylbenzene-1,4-diamine 

Relevant articles and documents

Thiazolyl-pyrazole derivatives as potential antimycobacterial agents

Mycobacterium tuberculosis (Mtb) is an obligate aerobe that is capable of long-term persistence under conditions of low oxygen tension. A series of thiazolyl-pyrazole derivatives (6a–f, 7a–f, 8c, 8e) were screened for antimycobacterial activity against dormant M. tuberculosis H37Ra (D-MTB) and M. bovis BCG (D-BCG). Nine thiazolyl-pyrazole analogs, 6c, 6e, 7a, 7b, 7c, 7e, 7f, 8c and 8e exhibited promissing minimum inhibitory concentration (MIC) values (0.20–28.25 μg/mL) against D-MTB and D-BCG strains of Mtb. Importantly, six compounds (7a, 7b, 7e, 7f, 8c and 8e) exhibited excellent antimycobacterial activity and low cytotoxicity at the maximum evaluated concentration of >250 μg/mL. Finally, the promising antimycobacterial activity and lower cytotoxicity profile suggested that, these compounds could be further subjected for optimization and development as a lead, which could have the potential to treat tuberculosis.

Discovery of N-Phenyl-4-(thiazol-5-yl)pyrimidin-2-amine aurora kinase inhibitors

Through cell-based screening of our kinase-directed compound collection, we discovered that a subset of N-phenyl-4-(thiazol-5-yl)pyrimidin-2-amines were potent cytotoxic agents against cancer cell lines, suppressed mitotic histone H3 phosphorylation, and caused aberrant mitotic phenotypes. It was subsequently established that these compounds were in fact potent inhibitors of aurora A and B kinases. It was shown that potency and selectivity of aurora kinase inhibition correlated with the presence of a substituent at the aniline para-position in these compounds. The anticancer effects of lead compound 4-methyl-5-(2-(4- morpholinophenylamino)pyrimidin-4-yl)thiazol-2-amine (18; Ki values of 8.0 and 9.2 nM for aurora A and B, respectively) were shown to emanate from cell death following mitotic failure and increased polyploidy as a consequence of cellular inhibition of aurora A and B kinases. Preliminary in vivo assessment showed that compound 18 was orally bioavailable and possessed anticancer activity. Compound 18 (CYC116) is currently undergoing phase I clinical evaluation in cancer patients.

Selective regeneration of carbonyl compounds from aldoximes and ketoximes, catalyzed by FeCl3 and SeO2

An oxidative deblocking procedure of aldoximes using FeCl3 and ketoximes using SeO2 in aprotic solvent is reported. Reaction yields are competitive as compared to previous methods. Reactions are easy to work and conditions are mild. Some important features of FeCl3 are mentioned.