4,5-Dimethylthiazole

Base Information

• Chemical Name: 4,5-Dimethylthiazole
• CAS No.: 3581-91-7
• Molecular Formula: C5H7NS
• Molecular Weight: 113.183
• Hs Code.: 29349990
• European Community (EC) Number: 222-703-3
• UNII: U3RP5I088G
• DSSTox Substance ID: DTXSID40189348
• Nikkaji Number: J45.577F
• Wikidata: Q27290649
• Metabolomics Workbench ID: 45825
• Mol file: 3581-91-7.mol

Synonyms:4,5-DIMETHYLTHIAZOLE;3581-91-7;4,5-Dimethyl-1,3-thiazole;Thiazole, 4,5-dimethyl-;4,5-dimethyl thiazole;4,5-dimethyl-thiazole;FEMA No. 3274;EINECS 222-703-3;MFCD00005336;BRN 0105694;UNII-U3RP5I088G;U3RP5I088G;4-27-00-00986 (Beilstein Handbook Reference);FMOC-D-LYS-OHHCL;4,5-Dimethylthiazole, 97%;SCHEMBL104484;FEMA 3274;4,5-Dimethyl-1,3-thiazole #;DTXSID40189348;CHEBI:193947;AMY23262;4,5-Dimethylthiazole, >=97%, FG;AKOS005207225;4,5-DIMETHYL THIAZOLE [FHFI];CS-W011256;(trichloromethyl)-Phosphonous dichloride;BP-10468;CS-17342;LS-150975;BB 0263152;D2142;FT-0617208;EN300-50400;A822988;Q-100428;Q27290649;Z600503292

Chemical Property of 4,5-Dimethylthiazole

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Vapor Pressure: 3.46mmHg at 25°C
• Melting Point: 83-84 °C
• Refractive Index: n20/D 1.521(lit.)
• Boiling Point: 158.1 °C at 760 mmHg
• PKA: pK1:3.73 (25°C,μ=0.1)
• Flash Point: 51.1 °C
• PSA: 41.13000
• Density: 1.081 g/cm³
• LogP: 1.75990
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 113.02992040
• Heavy Atom Count: 7
• Complexity: 65.1

Purity/Quality:

99% ^*data from raw suppliers

4,5-Dimethylthiazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi, F
• Hazard Codes: Xn,Xi,F
• Statements: 10-22-37/38-41-36/37/38
• Safety Statements: 16-26-39-37/39-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(SC=N1)C
• Chemical Composition and Structure: 4,5-Dimethylthiazole is a thiazole derivative with two methyl groups attached to the 4th and 5th positions of the thiazole ring.
• Uses and Mechanism of Action: Anticancer Activity:; Novel derivatives synthesized and tested for anticancer activity against various cancer cell lines which showed potential anticancer effects.^[1]; ; Catalyst in Chemical Reactions:; 4,5-Dimethylthiazole can be used in the synthesis of N-heterocyclic carbene palladium complexes for Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions.^[2] Utilized in the direct arylation of azoles as a catalyst for C-H bond arylation reactions.^[3]
• Physical and Chemical Properties: Exhibits torsional splittings arising from two inequivalent methyl internal rotations.; Low hindering barriers to internal rotation compared to monomethyl-substituted thiazole derivatives.; Displays nitrogen quadrupole hyperfine structures.
• References: [1] Design and Efficient Synthesis of Novel 4,5-Dimethylthiazole-Hydrazone Derivatives and their Anticancer Activity; DOI 10.2174/1570180817999201022192937; [2] N-heterocyclic carbene palladium complexes with different N-coordinated ligands: Comparison of their catalytic activities in Suzuki-Miyaura and Mizoroki-Heck reactions; DOI 10.1016/j.poly.2019.114271; [3] 4,5-Dihydro-imidazol-2-ylidene-linked palladium complexes as catalysts for the direct C?H bond arylation of azoles; DOI 10.1002/aoc.6551

Technology Process of 4,5-Dimethylthiazole

There total 20 articles about 4,5-Dimethylthiazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

4,5-dimethyl-1,3-thiazole-2-amine (2289-75-0) → 4,5-Dimethylthiazole (3581-91-7)

Guidance literature:

With tetrahydrofuran; oxygen; nitrogen(II) oxide; for 2h; Ambient temperature;

DOI:10.1248/cpb.45.1547

Reference yield: 41.0%

formamide (77287-34-4,77287-35-5,60100-09-6) + 3-bromo-butanone (814-75-5) → 4,5-Dimethylthiazole (3581-91-7)

Guidance literature:

With phosphorous (V) sulfide; In benzene; for 48h;

DOI:10.1039/P29810001538

Reference yield:

L-Cysteine (52-90-4) + [1-13C]ascorbic acid (178101-88-7) → 2,5-dihydro-thiophene (1708-32-3) + thiophene (188290-36-0,8014-23-1,25233-34-5) + 2-Methylthiophene (554-14-3) + 4,5-Dimethylthiazole (3581-91-7) + 4,5-Dihydro-2-methylthiophen-3-(2H)-on (74015-70-6,13679-85-1) + 2,4,5-trimethylthiazole (13623-11-5) + 2-Acetylthiophene (88-15-3,97511-16-5) + 2-Acetylthiazole (24295-03-2,260998-74-1) + 2-acetyl-3-methylthiophene (13679-72-6) + 3-(vinylthio)thiophene (867253-51-8)

Guidance literature:

at 140 ℃; for 2h; pH=8; aq. phosphate buffer; Sealed vessel;

DOI:10.1016/j.foodchem.2011.11.111

upstream raw materials:

4,5-dimethyl-3H-thiazole-2-thione

4,5-dimethylthiazole-2-carboxylic acid

4,5-dimethyl-oxazole

2-hydrazino-4,5-dimethyl-thiazole; hydrochloride

Downstream raw materials:

3-benzyl-4,5-dimethylthiazol-3-ium chloride

4,5-dimethyl-1,3-thiazole 3-oxide

(2-bromo-3,5-dimethoxyphenyl)(4,5-dimethylthiazol-2-yl)methanol

2-(1-methoxy-1-phenylmethyl)-4,5-dimethylthiazole

Refernces

• 1、 Pitteri, Bruno,Bortoluzzi, Marco. "Reactivity of neutral nitrogen donors in square-planar d8 metal complexes: The system chloro(2,2′:6′,2″-terpyridine)platinum(II) cation with five-membered N-donor heterocycles in methanol". . p. 2698 - 2704. Retrieved 2008/10/09.
• 2、 -. "Method for treating glaucoma IIB". . . Retrieved 2008/06/13.