15679-12-6

Usage

Uses

Used in Flavor and Fragrance Industry:
2-Ethyl-4-methyl thiazole is used as a flavoring agent for its musty, oily, nutty, and cocoa powdery aroma with a coffee top note. It is particularly suitable for enhancing the taste and aroma of various food products, such as roasted coffee, raspberry, and roasted pork, where it has been reported to be found naturally.
Used in Perfumery:
2-Ethyl-4-methyl thiazole is used as a fragrance ingredient for its unique combination of musty, oily, nutty, and cocoa powdery aroma with a coffee top note, casky, and whiskey-like nuances, along with a slight meaty savory nuance. It can be employed in the creation of various perfumes and colognes to provide a distinct and appealing scent profile.
Used in the Chemical Industry:
2-Ethyl-4-methyl thiazole can be used as a building block or intermediate in the synthesis of various chemicals and pharmaceuticals. Its unique chemical properties make it a valuable component in the development of new compounds with potential applications in various industries, including agriculture, pharmaceuticals, and materials science.

Preparation

By esterification of cis-3-hexenol with benzoic acid.

InChI:InChI=1/C6H9NS/c1-3-6-7-5(2)4-8-6/h4H,3H2,1-2H3

Synthetic route

2-ethenyl-4-methyl-1,3-thiazole (45534-10-9) → 2-ethyl-4-methyl-1,3-thiazole (15679-12-6)

Conditions	Yield
Hydrogenation;

2-ethyl-4-methyl-3-thiazoline (41803-21-8) → 2-ethyl-4-methyl-1,3-thiazole (15679-12-6)

Conditions	Yield
With ethanol; iron(III) chloride
With sulfur

1-(4-methyl-1,3-thiazol-2-yl)ethan-1-one (7533-07-5) → 2-ethyl-4-methyl-1,3-thiazole (15679-12-6)

thiopropanamide (631-58-3) + chloroacetone (78-95-5) → 2-ethyl-4-methyl-1,3-thiazole (15679-12-6)

Conditions	Yield
With ethanol

2,4-dimethylthiazole (541-58-2) + methyl p-toluene sulfonate (80-48-8) → 2-ethyl-4-methyl-1,3-thiazole (15679-12-6) + 2,4,5-trimethylthiazole (13623-11-5)

Conditions	Yield
(i) nBuLi, Et2O, (ii) /BRN= 609209/; Multistep reaction;

propionic acid (802294-64-0) + chloroacetone (78-95-5) → 2-ethyl-4-methyl-1,3-thiazole (15679-12-6)

Conditions	Yield
Stage #1: propionic acid With dmap; dacarbazine; Rink resin Acylation; amidation; Stage #2: With Lawessons reagent In tetrahydrofuran for 4h; thioamidation; Heating; Stage #3: chloroacetone In tetrahydrofuran for 16h; Cyclization; Heating;

methylhydroxyethyl thiazole (333385-00-5) → 2-ethyl-4-methyl-1,3-thiazole (15679-12-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: KOH / 200 °C 2: Hydrogenation View Scheme

2-ethyl-4-methyl-1,3-thiazole (15679-12-6) + 9-bromophenanthrene (573-17-1) → 2-ethyl-4-methyl-5-(phenanthren-9-yl)thiazole

Conditions	Yield
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere; Schlenk technique;	97%

2-ethyl-4-methyl-1,3-thiazole (15679-12-6) + 4'-Bromopropiophenone (10342-83-3) → 1-(4-(2-ethyl-4-methylthiazol-5-yl)phenyl)propan-1-one

Conditions	Yield
With palladium 10% on activated carbon; potassium acetate In i-Amyl alcohol at 150℃; for 16h; Solvent; Inert atmosphere; Green chemistry;	96%

2-ethyl-4-methyl-1,3-thiazole (15679-12-6) + 4-bromobenzenecarbonitrile (623-00-7) → 4-(2-ethyl-4-methylthiazol-5-yl)benzonitrile

Conditions	Yield
With palladium 10% on activated carbon; potassium acetate In i-Amyl alcohol at 150℃; for 16h; Solvent; Inert atmosphere; Green chemistry;	96%

2-ethyl-4-methyl-1,3-thiazole (15679-12-6) + 2-(4-bromophenyl)-5-n-butylfuran (1415426-34-4) → 5-[4-(5-n-butylfuran-2-yl)phenyl]-2-ethyl-4-methylthiazole

Conditions	Yield
With PdCl(C3H5)(1,4-bis(diphenylphosphino)butane); potassium acetate In N,N-dimethyl acetamide at 130℃; for 20h; Inert atmosphere;	95%
With PdCl(1,4-bis(diphenylphosphino)butane)(C3H5); potassium acetate In N,N-dimethyl acetamide at 130℃; for 20h; Inert atmosphere; Schlenk technique;	95%

2-ethyl-4-methyl-1,3-thiazole (15679-12-6) + 4-(4-bromophenyl)-4-(2,6,6-trimethylcyclohex-1-enyl)butan-2-one → 4-(4-(2-ethyl-4-methylthiazol-5-yl)phenyl)-4-(2,6,6-trimethylcyclohex-1-enyl)butan-2-one

Conditions	Yield
With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 130℃; for 20h; Inert atmosphere; Schlenk technique;	94%

2-ethyl-4-methyl-1,3-thiazole (15679-12-6) + C17H14BrN3O2 → C23H22N4O2S

Conditions	Yield
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere; regioselective reaction;	94%

2-ethyl-4-methyl-1,3-thiazole (15679-12-6) + 2-bromo-6-(trifluoromethyl)pyridine (189278-27-1) → 2-ethyl-4-methyl-5-(6-(trifluoromethyl)pyridin-2-yl)thiazole

Conditions	Yield
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Schlenk technique;	92%

2-ethyl-4-methyl-1,3-thiazole (15679-12-6) + 2,6-Dibromopyridine (626-05-1) → 2,6-bis(2-ethyl-4-methylthiazol-5-yl)pyridine

Conditions	Yield
With palladium diacetate; potassium trifluoroacetate In N,N-dimethyl acetamide at 150℃; for 5h; Reagent/catalyst; Time; Schlenk technique;	91%

2-ethyl-4-methyl-1,3-thiazole (15679-12-6) + ethyl 1-(4-bromophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate → C18H20N4O2S

Conditions	Yield
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere; regioselective reaction;	91%

2-ethyl-4-methyl-1,3-thiazole (15679-12-6) + 3-bromo-2-fluoro-4′-nitro-1,1′-biphenyl → 2-ethyl-5-(2-fluoro-4′-nitro-[1,1′-biphenyl]-3-yl)-4-methylthiazole

Conditions	Yield
With PdCl(1,4-bis(diphenylphosphino)butane)(C3H5); potassium acetate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere; Schlenk technique; Green chemistry; regioselective reaction;	91%

2-ethyl-4-methyl-1,3-thiazole (15679-12-6) + methyl phosphite (96-36-6, 868-85-9) → (2-ethyl-4-methyl-thiazol-5-yl)-phosphonic acid dimethyl ester

Conditions	Yield
With manganese triacetate In acetic acid at 80℃; for 3h;	90%

2-ethyl-4-methyl-1,3-thiazole (15679-12-6) + 2,7-dibromofluorene-9-one (14348-75-5) → 2,7-bis-(2-ethyl-4-methylthiazol-5-yl)fluoren-9-one

Conditions	Yield
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 120℃; for 17h; Reagent/catalyst; Temperature; Inert atmosphere;	90%

2-ethyl-4-methyl-1,3-thiazole (15679-12-6) + 2-(1-(2-bromobenzyl)-4-chloropyrazol-5-yl)benzonitrile → 2-(4-chloro-1-(2-(2-ethyl-4-methylthiazol-5-yl)benzyl)pyrazol-5-yl)benzonitrile

Conditions	Yield
With PdCl(1,4-bis(diphenylphosphino)butane)(C3H5); potassium acetate In N,N-dimethyl acetamide at 150℃; for 20h; Schlenk technique; Inert atmosphere;	90%

2-ethyl-4-methyl-1,3-thiazole (15679-12-6) + 3-(4-bromo-phenyl)-4-ethyl-3H-[1,2,3]triazole-5-carboxylic acid ethyl ester → C19H22N4O2S

Conditions	Yield
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere; regioselective reaction;	90%

2-ethyl-4-methyl-1,3-thiazole (15679-12-6) + ethyl 1-(2-bromophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate → C18H20N4O2S

Conditions	Yield
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere; regioselective reaction;	90%

2-ethyl-4-methyl-1,3-thiazole (15679-12-6) + 3′-bromo-2′-fluoro-[1,1′-biphenyl]-4-carbonitrile → 3′-(2-ethyl-4-methylthiazol-5-yl)-2′-fluoro-[1,1′-biphenyl]-4-carbonitrile

Conditions	Yield
With PdCl(1,4-bis(diphenylphosphino)butane)(C3H5); potassium acetate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere; Schlenk technique; Green chemistry; regioselective reaction;	90%

2-ethyl-4-methyl-1,3-thiazole (15679-12-6) + 1-(2-bromobenzyl)-4-chloro-5-(4-nitrophenyl)pyrazole → 5-(2-((4-chloro-5-(4-nitrophenyl)pyrazol-1-yl)methyl)phenyl)-2-ethyl-4-methylthiazole

Conditions	Yield
With PdCl(1,4-bis(diphenylphosphino)butane)(C3H5); potassium acetate In N,N-dimethyl acetamide at 150℃; for 20h; Schlenk technique; Inert atmosphere;	89%

2-ethyl-4-methyl-1,3-thiazole (15679-12-6) + 5-(2-bromophenyl)-1-methyltetrazole → 2-ethyl-4-methyl-5-(2-(1-methyltetrazol-5-yl)phenyl)thiazole

Conditions	Yield
With PdCl(1,4-bis(diphenylphosphino)butane)(C3H5); potassium pivalate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere; Schlenk technique;	89%
With PdCl(1,4-bis(diphenylphosphino)butane)(C3H5); potassium pivalate In N,N-dimethyl acetamide at 150℃; Inert atmosphere;

2-ethyl-4-methyl-1,3-thiazole (15679-12-6) + 2-(4’-bromophenyl)benzofuran → 5-(4-benzofuran-2-ylphenyl)-2-ethyl-4-methylthiazole (1622457-14-0)

Conditions	Yield
With PdCl(C3H5)(1,4-bis(diphenylphosphino)butane); potassium acetate In N,N-dimethyl acetamide at 130℃; for 20h; Inert atmosphere; Schlenk technique; regioselective reaction;	88%

2-ethyl-4-methyl-1,3-thiazole (15679-12-6) + 2-bromo-9H-fluorene (1133-80-8) → 2-ethyl-5-(fluoren-2-yl)-4-methylthiazole

Conditions	Yield
With PdCl(C3H5)(1,4-bis(diphenylphosphino)butane); potassium acetate In N,N-dimethyl acetamide at 150℃; for 17h; Concentration; Reagent/catalyst; Temperature; Inert atmosphere;	88%

2-ethyl-4-methyl-1,3-thiazole (15679-12-6) + 4-(4-bromophenyl)-4-phenylbutan-2-one (1005497-31-3) → 4-(4-(2-ethyl-4-methylthiazol-5-yl)phenyl)-4-phenylbutan-2-one

Conditions	Yield
With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 130℃; for 20h; Inert atmosphere; Schlenk technique;	88%

2-ethyl-4-methyl-1,3-thiazole (15679-12-6) + 2,6-Dibromopyridine (626-05-1) → 5-(6-bromopyridin-2-yl)-2-ethyl-4-methylthiazole

Conditions	Yield
With palladium diacetate; potassium trifluoroacetate In N,N-dimethyl acetamide at 150℃; for 5h; Reagent/catalyst; Temperature; Schlenk technique;	88%

2-ethyl-4-methyl-1,3-thiazole (15679-12-6) + 4-(2-bromopyridin-2-yl)morpholine → 6-thiazolyl-4-(pyridin-2-yl)morpholine

Conditions	Yield
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Schlenk technique;	88%

2-ethyl-4-methyl-1,3-thiazole (15679-12-6) + 5-(2-bromophenyl)-1-pivalyltetrazole → 5-(2-(1-pivalyltetrazol-5-yl)phenyl)-2-ethyl-4-methylthiazole

Conditions	Yield
With PdCl(1,4-bis(diphenylphosphino)butane)(C3H5); potassium pivalate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere; Schlenk technique;	88%
With PdCl(1,4-bis(diphenylphosphino)butane)(C3H5); potassium pivalate In N,N-dimethyl acetamide at 150℃; Inert atmosphere;

2-ethyl-4-methyl-1,3-thiazole (15679-12-6) + o-cyanobromobenzene (2042-37-7) → 2-(2-ethyl-4-methylthiazol-5-yl)benzonitrile (1109226-51-8)

Conditions	Yield
With PdCl(1,4-bis(diphenylphosphino)butane)(C3H5); potassium acetate In Diethyl carbonate at 140℃; for 24h; Inert atmosphere;	87%

2-ethyl-4-methyl-1,3-thiazole (15679-12-6) + 1-(3-bromo-phenyl)-5-methyl-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester → C18H20N4O2S

Conditions	Yield
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere; regioselective reaction;	87%

2-ethyl-4-methyl-1,3-thiazole (15679-12-6) + 1-(4-(5-bromoselenophen-2-yl)phenyl)ethan-1-one → 1-(4-(5-(2-ethyl-4-methylthiazol-5-yl)selenophen-2-yl)phenyl)ethan-1-one

Conditions	Yield
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere;	87%

2-ethyl-4-methyl-1,3-thiazole (15679-12-6) → 5-bromo-2-ethyl-4-methylthiazole

Conditions	Yield
With bromine In acetic acid at 20℃; for 2h;	85%

2-ethyl-4-methyl-1,3-thiazole (15679-12-6) + C17H14BrN3O2 → C23H22N4O2S

Conditions	Yield
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere; regioselective reaction;	85%

2-ethyl-4-methyl-1,3-thiazole (15679-12-6) + 4-(2-bromophenyl)-2-methyl-5-(quinolin-3-yl)thiazole → 2-ethyl-4-methyl-5-(2-(2-methyl-5-(quinolin-3-yl)thiazol-4-yl)-phenyl)thiazole

Conditions	Yield
With C31H33ClP2Pd; potassium acetate In N,N-dimethyl acetamide at 150℃; for 24h; Schlenk technique; Inert atmosphere;	85%

Upstream product

• 45534-10-9 2-ethenyl-4-methyl-1,3-thiazole 
• 41803-21-8 2-ethyl-4-methyl-3-thiazoline 
• 7533-07-5 1-(4-methyl-1,3-thiazol-2-yl)ethan-1-one 
• 631-58-3 thiopropanamide 
• 78-95-5 chloroacetone 
• 541-58-2 2,4-dimethylthiazole 
• 80-48-8 methyl p-toluene sulfonate 
• 333385-00-5 methylhydroxyethyl thiazole 
• 802294-64-0 propionic acid 

Downstream Products

• 7478-40-2 2-ethyl-3-(4-bromo-β-hydroxyimino-phenethyl)-4-methyl-thiazolium; bromide 
• 789-20-8 1-(3,7-dimethyl-6-phenyl-pyrrolo[2,1-b]thiazol-5-yl)-ethanone 
• 800-27-1 (3,7-dimethyl-6-phenyl-pyrrolo[2,1-b]thiazol-5-yl)-phenyl-methanone 
• 1005759-03-4 2-ethyl-4-methyl-5-phenylthiazole 
• 1109226-51-8 2-(2-ethyl-4-methylthiazol-5-yl)benzonitrile 
• 1109226-47-2 2-ethyl-5-[4-(trifluoromethyl)phenyl]-4-methylthiazole 
• 1109226-46-1 1-[4-(2-ethyl-4-methylthiazol-5-yl)phenyl]ethanone 
• 1286260-93-2 C₁₄H₁₅NOS 
• 1109226-48-3 2-ethyl-5-(4-fluorophenyl)-4-methylthiazole 
• 1426829-26-6 ethyl 4'-(2-ethyl-4-methylthiazol-5-yl)-2',3',5',6'-tetrafluorobiphenyl-4-carboxylate 
• 1426829-27-7 4'-(2-ethyl-4-methylthiazol-5-yl)-2',3',5',6'-tetrafluorobiphenyl-3-carbonitrile 
• 1426829-33-5 5-(4′-chloro-2,6-difluorobiphenyl-4-yl)-2-ethyl-4-methylthiazole 
• 1426829-17-5 2-ethyl-4-methyl-5-(2,3,5-trifluorophenyl)thiazole 
• 1426829-22-2 5-(3,5-difluorophenyl)-2-ethyl-4-methylthiazole 

Relevant academic research and scientific papers

Thiazole formation via traceless cleavage of Rink resin

The traceless cleavage of Rink amide resin to form thiazoles has been achieved using commercially available reagents. Conversion of Rink amide species to thioamides by use of Lawesson's reagent prepares the resin bound substrates for traceless cleavage. C

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Provided is a method of decreasing intraocular pressure or improving ocular accommodation in an animal, including a human, comprising administering an intraocular pressure decreasing amount or ocular accommodation improving amount of a compound of the formula I or IA, wherein J is oxygen, sulfur, or N—Rd.