541-58-2

Basic information

• Product Name: 2,4-Dimethylthiazole
• Synonyms: 2,4-METHYLTHIAZOLE;2,4-DIMETHYL-1,3-THIAZOLE;2,4-DIMETHYLTHIAZOLE;2,4-dimethyl-thiazol;2 4-DIMETHYLTHIAZOLE 95+%;2,4-Dimethylthiazole,97%;dimethylthiazole,2,4-dimethylthiazole;Thiazole, 2,4-dimethyl-
• CAS NO: 541-58-2
• Molecular Formula: C₅H₇NS
• Molecular Weight: 113.18
• EINECS: 208-786-9
• Product Categories: Organics;Thiazoles;thiazole Flavor;Building Blocks;Heterocyclic Building Blocks;Alphabetical Listings;C-D;Flavors and Fragrances;NULL
• Mol File: 541-58-2.mol
• Article Data: 6

Chemical Properties

• Melting Point: 272 °C
• Boiling Point: 144-146 °C719 mm Hg(lit.)
• Flash Point: 109 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 1.056 g/mL at 25 °C(lit.)
• Vapor Pressure: 4.28mmHg at 25°C
• Refractive Index: n20/D 1.509(lit.)
• Storage Temp.: −20°C
• PKA: pK1:3.98 (25°C,μ=0.1)
• Water Solubility: Slightly soluble in water
• BRN: 106414
• CAS DataBase Reference: 2,4-Dimethylthiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dimethylthiazole(541-58-2)
• EPA Substance Registry System: 2,4-Dimethylthiazole(541-58-2)

Safety Data

• Hazard Codes: Xi,F
• Statements: 10-36/37/38
• Safety Statements: 16-26-36-37/39
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• RTECS: XJ4375000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 541-58-2(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liqui

Uses

2,4-Dimethylthiazole is a substance used in the preparation of insects repellant. It also functions as an anesthetic for aquatic animals. 2,4-Dimethylthiazole is a flavor component of peanut oils.

InChI:InChI=1/C5H7NS/c1-4-3-7-5(2)6-4/h3H,1-2H3

Synthetic route

thioacetamide (62-55-5) + chloroacetone (78-95-5) → 2,4-dimethylthiazole (541-58-2)

Conditions	Yield
In benzene for 1h; Heating;	97%

thioacetamide (62-55-5) + 1-bromoacetone (598-31-2) → 2,4-dimethylthiazole (541-58-2)

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 1h; Hantzsch Thiazole Synthesis; Sealed tube;	75%

2,4-dimethyloxazole (7208-05-1) → 2,4-dimethylthiazole (541-58-2)

Conditions	Yield
With aluminum oxide; hydrogen sulfide at 375℃;

α-(2-methyl-4-thiazolyl)acetic acid (13797-62-1) → 2,4-dimethylthiazole (541-58-2) + methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5)

Conditions	Yield
bei der trocknen Destillation;

4-chloromethyl-2-methylthiazole hydrochloride (77470-53-2) → 2,4-dimethylthiazole (541-58-2)

Conditions	Yield
With acetic acid; zinc

acetamide (60-35-5) + chloroacetone (78-95-5) → 2,4-dimethylthiazole (541-58-2)

Conditions	Yield
With sodium hydroxide; sodium hydrogensulfide; ethanol
With diphosphorus pentasulfide; benzene
With diphosphorus pentasulfide

2,4-dimethyl-4,5-dihydro-1,3-thiazole (6114-40-5) → 2,4-dimethylthiazole (541-58-2)

Conditions	Yield
With dihydrogen peroxide

4-Methylthiazole (693-95-8) + dimethyl sulfate (77-78-1) → 2,4-dimethylthiazole (541-58-2)

Conditions	Yield
(i) BuLi, Et2O, (ii) /BRN= 635994/; Multistep reaction;

1-iminoethylthiopropanone hydrobromide (76133-03-4) → 2,4-dimethylthiazole (541-58-2)

Conditions	Yield
With sodium carbonate In acetic acid at 40 - 50℃;	12.6 g

2,4-Dimethyl-thiazole; compound with iodine (57516-14-0) → 2,4-dimethylthiazole (541-58-2)

Conditions	Yield
In tetrachloromethane at 24.9℃; Equilibrium constant; investigated by electronic absorption spectra;

2.4-dimethyl-thiazole-carboxylic acid-(5) → 2,4-dimethylthiazole (541-58-2)

Conditions	Yield
With calcium oxide

<2-methyl-thiazolyl-(4)>-acetic acid → 2,4-dimethylthiazole (541-58-2)

Conditions	Yield
bei der trocknen Destillation;

thioacetimidic acid acetonyl ester → 2,4-dimethylthiazole (541-58-2)

Conditions	Yield
at 130 - 140℃;

thioacetamide (62-55-5) + α-chloro-acetone → 2,4-dimethylthiazole (541-58-2)

hydrogenchloride (7647-01-0) + acetonitrile (75-05-8) + 1-mercaptopropan-2-one (24653-75-6) → 2,4-dimethylthiazole (541-58-2)

Conditions	Yield
at 135℃;

acetic acid-(α,β-dibromo-isopropyl ester) (854667-12-2) + water (7732-18-5) + thioacetamide (62-55-5) → 2,4-dimethylthiazole (541-58-2)

Conditions	Yield
at 100℃; reagiert analog mit Thioharnstoff;

trichloro(2,4-dimethylthiazole)gold(III) (132963-53-2) + lithium chloride → 2,4-dimethylthiazole (541-58-2) + lithium tetrachloroaurate (3145-91-3)

Conditions	Yield
In methanol; dichloromethane; water Kinetics; addn. of Au-complex in dichloromethane to LiCl+HClO4 in methanol:water (95:5 v/v) at 25 °C; detected by UV;

trichloro(2,4-dimethylthiazole)gold(III) (132963-53-2) + chloride (16887-00-6) → 2,4-dimethylthiazole (541-58-2) + tetrachloroaurate(III)(1-)

Conditions	Yield
In methanol; dichloromethane; water Kinetics; addn. of Au-complex in dichloromethane to LiCl+HClO4 in methanol:water (95:5 v/v) at 25 °C; detected by UV;

2,4-dimethylthiazole (541-58-2) + 4-bromoquinoline (3964-04-3) → 2,4-dimethyl-5-(quinolin-4-yl)thiazole

Conditions	Yield
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;	99%

2,4-dimethylthiazole (541-58-2) + para-bromoacetophenone (99-90-1) → (4-(2,4-dimethylthiazol-5-yl)phenyl)ethanone

Conditions	Yield
With [Pd(IPr*IMe)An(3-Cl-pyridinyl)Cl2]; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; regioselective reaction;	98%
With C34H48Cl2N2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 8h;	81%

2-bromothiophene (1003-09-4) + 2,4-dimethylthiazole (541-58-2) → 2,4-dimethyl-5-(thiophen-2-yl)thiazole

Conditions	Yield
With C68H65Cl2N3Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; Reagent/catalyst; regioselective reaction;	98%

2,4-dimethylthiazole (541-58-2) + 2-methoxy-5-bromopyridine (13472-85-0) → 5-(6-methoxypyridin-3-yl)-2,4-dimethylthiazole

Conditions	Yield
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;	98%

2,4-dimethylthiazole (541-58-2) → 5-bromo-2,4-dimethyl-1,3-thiazole (28599-52-2)

Conditions	Yield
With bromine; calcium carbonate In dichloromethane for 3h;	97%
Stage #1: 2,4-dimethylthiazole With bromine; acetic acid at 0℃; Stage #2: With sodium carbonate In water pH=>= 9;	83%
With carbon disulfide; bromine at 0℃;	80%

2,4-dimethylthiazole (541-58-2) + gold(III) tetrachloride trihydrate → trichloro(2,4-dimethylthiazole)gold(III) (132963-53-2)

Conditions	Yield
In methanol; water addn. of 2,4-dimethylthiazole in methanol to soln. of HAuCl4*3H2O in water, neutralised with equimolar NaHCO3;; filtration, washed (water, methanol), recrystd. (dichloromethane), elem. anal.;;	97%

2,4-dimethylthiazole (541-58-2) + 4-bromo-benzaldehyde (1122-91-4) → 4-(2, 4-dimethylthiazol-5-yl)benzaldehyde

Conditions	Yield
With C34H48Cl2N2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 8h;	97%
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;	96%
With C42H42Cl2N2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 24h;

2,4-dimethylthiazole (541-58-2) + bromobenzene (108-86-1) → 2,4-dimethyl-5-phenylthiazole (19968-55-9)

Conditions	Yield
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;	97%
With C34H48Cl2N2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 8h;	85%
With [Pd(IPr*IMe)An(3-Cl-pyridinyl)Cl2]; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; regioselective reaction;	55%
With C42H42Cl2N2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 24h;

2,4-dimethylthiazole (541-58-2) + 4-bromoisoquinoline (1532-97-4) → 5-(isoquinolin-4-yl)-2,4-dimethylthiazole

Conditions	Yield
With {N,N-(1,2-diphenylethane-1,2-diylidene)bis(2-benzhydryl-4,6-dimthylaniline)}dichloropalladium; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; Catalytic behavior;	97%
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;	94%
With C34H48Cl2N2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 8h;	72%

2,4-dimethylthiazole (541-58-2) + p-trifluoromethylphenyl bromide (402-43-7) → 2,4-dimethyl-5-(4-(trifluoromethyl)phenyl)thiazole

Conditions	Yield
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;	97%
With C34H48Cl2N2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 8h;	93%

2,4-dimethylthiazole (541-58-2) + 5-bromo-2-methylpyridine (3430-13-5) → 2,4-dimethyl-5-(6-methylpyridin-3-yl)thiazole

Conditions	Yield
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;	97%

2,4-dimethylthiazole (541-58-2) + ethyl bromoacetate (105-36-2) → 3-(carboethoxymethyl)-2,4-dimethylthiazolium bromide (33446-11-6)

Conditions	Yield
at 50℃; for 6h;	96%
In acetonitrile Heating;

3-Bromopyridine (626-55-1) + 2,4-dimethylthiazole (541-58-2) → 2,4-dimethyl-5-(pyridin-3-yl)thiazole (1267180-21-1)

Conditions	Yield
With {N,N-(1,2-diphenylethane-1,2-diylidene)bis(2-benzhydryl-4,6-dimthylaniline)}dichloropalladium; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; Catalytic behavior;	96%
With C68H65Cl2N3Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; regioselective reaction;	95%
With palladium diacetate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 180℃; for 0.166667h; Reagent/catalyst; Temperature; Time; Solvent; Sealed tube; Microwave irradiation;	83%
With C34H48Cl2N2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 8h;	65%

2,4-dimethylthiazole (541-58-2) + 3-bromoquinoline (5332-24-1) → 2,4-dimethyl-5-(quinolin-3-yl)thiazole (1516952-56-9)

Conditions	Yield
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;	96%
With palladium diacetate; caesium carbonate; lithium chloride In N,N-dimethyl-formamide at 150℃; for 24h; Reagent/catalyst; Temperature; Time; Solvent; Sealed tube;	82%

2,4-dimethylthiazole (541-58-2) + 4-bromobenzenecarbonitrile (623-00-7) → 4-(2,4-dimethylthiazol-5-yl)benzonitrile (122957-56-6)

Conditions	Yield
With C34H48Cl2N2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 8h;	96%
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;	95%
With C42H42Cl2N2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 24h;

2,4-dimethylthiazole (541-58-2) + 3,6-bis(trifluoromethyl)bromobenzene (328-70-1) → C13H9F6NS

Conditions	Yield
With C34H48Cl2N2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 8h;	96%

2,4-dimethylthiazole (541-58-2) + methyl iodide (74-88-4) → 2,3,4-trimethylthiazol-3-ium iodide (5787-82-6)

Conditions	Yield
In acetone for 24h; Heating;	95%

2,4-dimethylthiazole (541-58-2) + 4-methoxycarbonylphenyl bromide (619-42-1) → methyl 4-(2, 4-dimethylthiazol-5-yl)benzoate

Conditions	Yield
With C34H48Cl2N2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 8h;	95%
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;	93%
With [Pd(IPr*IMe)An(3-Cl-pyridinyl)Cl2]; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; regioselective reaction;	88%
With C42H42Cl2N2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 24h;

2,4-dimethylthiazole (541-58-2) + 5-bromo-2-fluoropyridine (766-11-0) → 5-(6-fluoropyridin-3-yl)-2,4-dimethylthiazole

Conditions	Yield
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;	95%

2,4-dimethylthiazole (541-58-2) + 4-(bromoacetyl)toluene (619-41-0) → 2,4-Dimethyl-3-(2-oxo-2-p-tolyl-ethyl)-thiazol-3-ium; perchlorate

Conditions	Yield
With sodium perchlorate 1.) toluene, reflux, 0.5-1h, room temperature, 12h, 2.) water;	94%

2,4-dimethylthiazole (541-58-2) + 1-bromo-2-methylnaphtalene (2586-62-1) → 2, 4-dimethyl-5-(2-methylnaphthalen-1-yl)thiazole

Conditions	Yield
With {N,N-(1,2-diphenylethane-1,2-diylidene)bis(2-benzhydryl-4,6-dimthylaniline)}dichloropalladium; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; Catalytic behavior;	94%
With [Pd(IPr*IMe)An(3-Cl-pyridinyl)Cl2]; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; regioselective reaction;	58%

2,4-dimethylthiazole (541-58-2) + triphenylphosphonium bromide (62546-56-9) → C32H30NOPS(2+)*2ClO4(1-)

Conditions	Yield
With sodium perchlorate 1.) nitromethane, reflux, 1h, room temperature, 12h, 2.) water;	93%

2,4-dimethylthiazole (541-58-2) + 4-chlorobenzoylmethyl bromide (536-38-9) → 3-[2-(4-Chloro-phenyl)-2-oxo-ethyl]-2,4-dimethyl-thiazol-3-ium; perchlorate

Conditions	Yield
With sodium perchlorate 1.) toluene, reflux, 0.5-1h, room temperature, 12h, 2.) water;	92%

2,4-dimethylthiazole (541-58-2) + methyl phosphite (96-36-6, 868-85-9) → 2,4-dimethyl-5-dimethylphosphonothiazole

Conditions	Yield
With manganese triacetate In acetic acid at 80℃; for 3h;	92%

2,4-dimethylthiazole (541-58-2) + 1-Bromonaphthalene (90-11-9) → 2,4-dimethyl-5-(naphthalen-1-yl)thiazole

Conditions	Yield
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;	92%
With C34H48Cl2N2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 8h;	91%
With [Pd(IPr*IMe)An(3-Cl-pyridinyl)Cl2]; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; regioselective reaction;	87%

2,4-dimethylthiazole (541-58-2) + α-bromoacetophenone (70-11-1) → 2,4-dimethyl-3-phenacylthiazol-3-ium perchlorate

Conditions	Yield
With sodium perchlorate 1.) toluene, reflux, 0.5h, room temperature, 12h, 2.) water;	91%

2,4-dimethylthiazole (541-58-2) → 2,4-dimethylthiazole N,S,S-trioxide + 2,4-dimethylthiazole N-oxide (76133-04-5)

Conditions	Yield
With HOF* CH3CN In dichloromethane at 20℃; for 0.333333h;	A 5% B 91%

2,4-dimethylthiazole (541-58-2) + 1-Bromo-4-fluorobenzene (460-00-4) → 5-(4-fluorophenyl)-2,4-dimethylthiazole

Conditions	Yield
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;	91%
With C34H48Cl2N2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 8h;	79%

2,4-dimethylthiazole (541-58-2) + 4-Nitrophenacyl bromide (99-81-0) → 2,4-Dimethyl-3-[2-(4-nitro-phenyl)-2-oxo-ethyl]-thiazol-3-ium; perchlorate

Conditions	Yield
With sodium perchlorate 1.) toluene, reflux, 0.5-1h, room temperature, 12h, 2.) water;	90%

Upstream product

• 7208-05-1 2,4-dimethyloxazole 
• 60-35-5 acetamide 
• 78-95-5 chloroacetone 
• 854667-12-2 acetic acid-(α,β-dibromo-isopropyl ester) 
• 7732-18-5 water 
• 62-55-5 thioacetamide 
• 132963-53-2 trichloro(2,4-dimethylthiazole)gold(III) 
• 598-31-2 1-bromoacetone 
• 16887-00-6 chloride 
• 7647-01-0 hydrogenchloride 
• 75-05-8 acetonitrile 
• 24653-75-6 1-mercaptopropan-2-one 
• 57516-14-0 2,4-Dimethyl-thiazole; compound with iodine 
• 76133-03-4 1-iminoethylthiopropanone hydrobromide 

Downstream Products

• 121357-04-8 2-(2-methylthiazol-4-yl)ethanol 
• 6273-13-8 3-(2-cyclohexyl-ethyl)-2,4-dimethyl-thiazolium; bromide 
• 17091-45-1 3-Benzyl-2,4-dimethyl-thiazolium 
• 18298-61-8 4-methyl-2-(4-nitro-trans-styryl)-thiazole 
• 24622-44-4 (E)-4-methyl-2-styrylthiazole 
• 6274-04-0 2,4-dimethyl-3-phenacylthiazolium bromide 
• 29238-74-2 N,N-dimethyl-4-[trans-2-(4-methyl-thiazol-2-yl)-vinyl]-aniline 
• 16183-05-4 2,3,4-trimethyl-thiazolium; toluene-4-sulfonate 
• 5787-82-6 2,3,4-trimethylthiazol-3-ium iodide 
• 76133-04-5 2,4-dimethylthiazole-3-oxide 
• 28599-52-2 5-bromo-2,4-dimethyl-1,3-thiazole 
• 20751-81-9 2,4-Dimethyl-5-nitro-thiazol 
• 19961-27-4 N-isopropylethylamine 

Relevant articles and documents

Synthesis of trisubstituted thiazoles by ligand-free palladium-catalyzed direct 5-arylation of 2,4-disubstituted thiazoles under conventional and microwave-assisted heating

Trisubstituted thiazoles were synthesized with excellent yields using ligand-free, palladium-catalyzed, direct 5-arylation of 2,4-disubstituted thiazole and conventional or microwave-assisted heating. The palladium-catalyzed reaction yields were significantly influenced by LiCl additive, solvent, and heating method. The reaction times were reduced dramatically by employing microwave radiation instead of conventional heating. The synthetic methods can be applied to diverse 2,4,5-trisubstituted thiazoles by varying the aryl bromide and disubstituted thiazole reactants.

Isolation and Reaction of New Aromatic Dications. 4-Thioniapyridinium Dications: 2-Aryl-(or 2-Alkyl-)4-methyl-3-oxo-2H-1,4-thiazin-2-ylium Tetrafluoroborates

2-Hydroxy-4-methyl-2-aryl(or -2-tert-butyl)-2H-1,4-thiazin-3-ones (5) generate carbocations 6 in trifluoroacetic acid solution at room temperature.These ions are sufficiently stable to be observed spectroscopically in this solution.Reaction of 6 with some nucleophiles are described.Stable crystalline tetrafluoroborates of 6 were isolated.From 1H NMR, 13C NMR, and UV-vis spectral data it was concluded that these cations are aromatic in nature and should be depicted as 9 and called 4-thioniapyridinium dications.

Spectral studies on the interaction of iodine with thiazoles

The electron donor-acceptor molecular complexes between thiazole and some of its derivatives and iodine in several solvents have been investigated spectrophotometrically at different temperatures.Spectral characteristics, equilibrium constants, K, extinction coefficients, ε, and thermodynamic functions of formation, ΔH0, ΔG0, and ΔS0 have been determined.It was found that the data fit satisfactorily the 1:1 stoichiometric equilibrium: D + I2 = DI2 "outer complex".The EDA complexes obtained are of "n - ?*" type in which the nitrogen atom of thiazole is the donor center.Moreover, the effect of solvents on the K values is discussed in terms of the solute-solute and solute-solvent competing equilibria.