15679-12-6

Basic information

• Product Name: 2-Ethyl-4-methyl thiazole
• Synonyms: FEMA 3680;FEMA NUMBER 3680;ETHYL-4-METHYLTHIAZOLE, 2-;2-ETHYL-4-METHYLTHIAZOLE;4-METHYL-2-ETHYLTHIAZOLE;2-Ethyl-4-methyl-1,3-thiazole;2-ethyl-4-methyl-thiazol;Thiazole, 2-ethyl-4-methyl-
• CAS NO: 15679-12-6
• Molecular Formula: C₆H₉NS
• Molecular Weight: 127.21
• EINECS: 239-757-9
• Product Categories: Industrial/Fine Chemicals;Heterocyclic Compounds;Thiazoles;thiazole Flavor;Alphabetical Listings;E-F;Flavors and Fragrances;Building Blocks;C3 to C7;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 15679-12-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 161-162 °C(lit.)
• Flash Point: 130 °F
• Appearance: clear colorless or pale yellow to light brown liquid
• Density: 1.026 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.71mmHg at 25°C
• Refractive Index: n20/D 1.505(lit.)
• Storage Temp.: 2-8°C
• PKA: 3.67±0.10(Predicted)
• CAS DataBase Reference: 2-Ethyl-4-methyl thiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Ethyl-4-methyl thiazole(15679-12-6)
• EPA Substance Registry System: 2-Ethyl-4-methyl thiazole(15679-12-6)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-26-36
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 15679-12-6(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 15679-12-6 differently. You can refer to the following data:
1. clear colorless or pale yellow to
2. 2-Ethyl-4-methylthiazole has a nutty, green odor

Occurrence

Reported found in roasted coffee, raspberry and roasted pork.

Preparation

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

Aroma threshold values

Detection: 100 ppb. Aroma characteristics at 0.1%: musty, oily, nutty, cocoa powdery with a coffee top note, casky and whiskey-like, with a slight meaty savory nuance.

Taste threshold values

Taste characteristics at 0.10–0.50 ppm: oily, woody, musty cocoa powdery with a coffee bean nuance

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

Downstream Products

• 7478-40-2 2-ethyl-3-(4-bromo-β-hydroxyimino-phenethyl)-4-methyl-thiazolium; bromide 
• 1005759-03-4 2-ethyl-4-methyl-5-phenylthiazole 
• 786-96-9 6-(4-methoxy-phenyl)-3,7-dimethyl-pyrrolo[2,1-b]thiazole 
• 781-60-2 3,7-dimethyl-6-phenyl-pyrrolo[2,1-b]thiazole 
• 1092504-61-4 C₁₃H₁₃NO₂S 

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