15679-19-3

Basic information

• Product Name: 2-Ethoxythiazole
• Synonyms: 2-ethoxy-thiazol;FEMA 3340;FEMA NUMBER 3340;2-ETHOXYTHIAZOLE;2-ETHOXYTHIAZOLE 99+%;2-ETHOXY THIAZOLE FEMA NO.3340;Thiazole, 2-ethoxy-;2-EHTOXYTHIAZOLE
• CAS NO: 15679-19-3
• Molecular Formula: C₅H₇NOS
• Molecular Weight: 129.18
• EINECS: 239-760-5
• Product Categories: thiazole Flavor;Alphabetical Listings;E-F;Flavors and Fragrances
• Mol File: 15679-19-3.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 157-160 °C(lit.)
• Flash Point: 129 °F
• Appearance: Colorless to light yellow liquid
• Density: 1.133 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.2mmHg at 25°C
• Refractive Index: n20/D 1.504(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.32±0.10(Predicted)
• CAS DataBase Reference: 2-Ethoxythiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Ethoxythiazole(15679-19-3)
• EPA Substance Registry System: 2-Ethoxythiazole(15679-19-3)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-26
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 15679-19-3(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 15679-19-3 differently. You can refer to the following data:
1. Colorless to light yellow liqui
2. 2-Ethoxythiazole has a strong, burnt, nutty, roasted meat-like odor.

Preparation

2-Bromothiazole is treated with sodium alkoxides to give 2-alkoxythiaxole

Aroma threshold values

Aroma characteristics at 2.0%: musty, vegetative, green, phenolic, nutty, coffee and brothy

Taste threshold values

Taste characteristics at 2.0 ppm: musty, vegetative, brothy, nutty and coffee with a slight rubbery nuance.

InChI:InChI=1/C5H7NOS/c1-2-7-5-6-3-4-8-5/h3-4H,2H2,1H3

Synthetic route

2-bromo-1,3-thiazole (3034-53-5) + sodium ethanolate (141-52-6) → 2-ethoxythiazole (15679-19-3)

Conditions	Yield
In ethanol Heating;	90%
In methanol for 20h; Heating;

O-ethyl thiocarbamate (625-57-0) → 2-ethoxythiazole (15679-19-3)

2-ethoxythiazole (15679-19-3) → 5-bromo-2-ethoxythiazole (1086382-60-6)

Conditions	Yield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 3h;	91%

2-ethoxythiazole (15679-19-3) + methyl phosphite (96-36-6, 868-85-9) → (2-ethoxy-thiazol-5-yl)-phosphonic acid dimethyl ester

Conditions	Yield
With manganese triacetate In acetic acid at 80℃; for 3h;	89%

2-ethoxythiazole (15679-19-3) + N-ethoxycarbonyl-4-piperidone (29976-53-2) → ethyl 4-(2-ethoxy-1,3-thiazol-5-yl)-4-hydroxypiperidine-1-carboxylate (850221-28-2)

Conditions	Yield
Stage #1: 2-ethoxythiazole With n-butyllithium In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: N-ethoxycarbonyl-4-piperidone In tetrahydrofuran at 0 - 25℃; for 4h;	69%

2-ethoxythiazole (15679-19-3) + C22H23NO3 → C25H24N2O3S

Conditions	Yield
With trifluoroacetic acid In dichloromethane for 4h; Reflux; stereoselective reaction;	68%

2-ethoxythiazole (15679-19-3) → C5H6ClNO3S2 (1432129-33-3)

Conditions	Yield
Stage #1: 2-ethoxythiazole With sec.-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: With sulfur dioxide In tetrahydrofuran; hexane at 20℃; for 3h; Stage #3: With N-chloro-succinimide In tetrahydrofuran; hexane at 20℃; for 1h;	65%

2-ethoxythiazole (15679-19-3) → 3H-thiazol-2-one (6039-97-0) + 4,5-dihydro-3H,3'H-[4,5']bithiazolyl-2,2'-dione (90109-73-2)

Conditions	Yield
With hydrogenchloride

2-ethoxythiazole (15679-19-3) → 3H-thiazol-2-one (6039-97-0) + ethene (74-85-1)

Conditions	Yield
at 314.2 - 405.7℃; Kinetics;

Upstream product

• 3034-52-4 2-chlorothiazole 
• 64-17-5 ethanol 
• 3034-53-5 2-bromo-1,3-thiazole 
• 141-52-6 sodium ethanolate 
• 625-57-0 O-ethyl thiocarbamate 

Downstream Products

• 1086382-60-6 5-bromo-2-ethoxythiazole 
• 6039-97-0 3H-thiazol-2-one 
• 74-85-1 ethene 
• 90109-73-2 4,5-dihydro-3H,3'H-[4,5']bithiazolyl-2,2'-dione 

Relevant articles and documents

Cs2CO3-Promoted C?O Coupling Protocol Enables Solventless (Hetero)aryl Ether Synthesis under Air Atmosphere

In this work, a Cs2CO3-promoted synthetic approach was identified for (hetero)aryl ether synthesis via the C?O coupling of various (hetero)aryl chlorides and alcohols/phenol. To our delight, the reactions could be carried out under transition-metal-free and solvent-free conditions. Moreover, analytical-grade reagents and air atmosphere were readily tolerated. To showcase the practical usefulness of the present protocol, the assembly of a bioactive molecule was facilely realized and the gram-scale production of selected ether products was also efficiently accomplished. In addition, density functional theory (DFT) studies, along with a few mechanistic experiments, were conducted to elucidate a proposed reaction pathway and rationalize the pivotal role of Cs2CO3 in promoting this process. Hopefully, this work could provide useful information for researchers who are engaging in C?O cross-coupling reactions.