693-95-8

Basic information

• Product Name: 4-Methylthiazole
• Synonyms: 4-methyl-thiazol;Thiazole, 4-methyl-;METHYLTHIAZOLE, 4-;FEMA NUMBER 3716;FEMA 3716;4-METHYLTHIAZOLE;4-METHYL-1,3-THIAZOLE;4-METHYLTHIAZOLE 98+%
• CAS NO: 693-95-8
• Molecular Formula: C₄H₅NS
• Molecular Weight: 99.1542
• EINECS: 211-764-1
• Product Categories: Thiazoles;thiazole Flavor;Building Blocks;Heterocyclic Building Blocks;Alphabetical Listings;Flavors and Fragrances;M-N
• Mol File: 693-95-8.mol
• Article Data: 16

Chemical Properties

• Melting Point: 134 °C
• Boiling Point: 133-134 °C(lit.)
• Flash Point: 90 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 1.09 g/mL at 25 °C(lit.)
• Vapor Pressure: 10mmHg at 25°C
• Refractive Index: n20/D 1.524(lit.)
• Storage Temp.: Flammables area
• PKA: pK1:3.16(+1) (25°C,μ=0.1)
• BRN: 105228
• CAS DataBase Reference: 4-Methylthiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methylthiazole(693-95-8)
• EPA Substance Registry System: 4-Methylthiazole(693-95-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 10-22-37/38-41
• Safety Statements: 16-26-39
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• RTECS: XJ5096000
• TSCA: T
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 693-95-8(Hazardous Substances Data)

Usage

Description

4-Methylthiazole has a nutty, green odor.

Chemical Properties

Different sources of media describe the Chemical Properties of 693-95-8 differently. You can refer to the following data:
1. 4-Methylthiazole has a nutty, green odo
2. CLEAR COLOURLESS TO SLIGHTLY YELLOW LIQUID

Occurrence

Reported found in cooked asparagus, roasted barley, cooked beef, cocoa, cooked pork, roasted coffee, roasted peanuts, boiled egg, malt, wort and cooked shrimp.

Uses

4-Methylthiazole was used in the synthesis of catalytic dendrophanes, as functional mimics of the thiamine-diphosphate-dependent enzyme pyruvate oxidase. It was used in small scale preparation of 3-butyl-4-methylthiazolium bromide.

Definition

ChEBI: A 1,3-thiazole substituted by a methyl group at position 4.

Taste threshold values

Taste characteristics at 10 ppm: green, vegetative and meaty with an alliaceous nuance

General Description

4-Methylthiazole forms complexes with cobalt(II), zinc(II), nickel(II) and copper(II) halides.

InChI:InChI=1/C4H5NS/c1-4-2-6-3-5-4/h2-3H,1H3

Synthetic route

4-methylthiazole-5-carboxylic acid (20485-41-0) → 4-Methylthiazole (693-95-8)

Conditions	Yield
With acetic acid In N,N-dimethyl-formamide at 105 - 110℃; for 8h; Reagent/catalyst; Temperature; Green chemistry;	95%
With acetic acid; silver carbonate In dimethyl sulfoxide at 120℃; for 16h;	100 %Spectr.

4-methylthiazole-2-thiol (5685-06-3) → 4-Methylthiazole (693-95-8)

Conditions	Yield
With hydrogenchloride; dihydrogen peroxide In water at 45℃; for 1.5h; Temperature;	78%
With hydrogenchloride; dihydrogen peroxide

4-methylthiazol-2-ylamine (1603-91-4) → 4-Methylthiazole (693-95-8)

Conditions	Yield
Stage #1: 4-methylthiazol-2-ylamine With sulfuric acid; sodium nitrite In water at -15 - -10℃; for 4h; Stage #2: With sodium hypophosphite In water at -10 - -5℃; for 6h; Temperature;	72%

methyl-1 ethylideneamine (6407-34-7, 19885-74-6) → 4-Methylthiazole (693-95-8)

Conditions	Yield
With sulfur dioxide; soda-lime; zirconium(IV) oxide at 450℃;	70%

4-methyl-3-thiazoline (52558-99-3) → 4-Methylthiazole (693-95-8)

Conditions	Yield
With ethanol; iron(III) chloride

4-methyl-2(3H)-thiazolone (32497-10-2) → 4-Methylthiazole (693-95-8)

Conditions	Yield
With zinc bei der Destillation;
bei der Zinkstaub-Destillation;

4-methylthiazole-2(3H)-thione (5685-06-3) → 4-Methylthiazole (693-95-8)

Conditions	Yield
With dihydrogen peroxide

4-methyl-1,3-thiazole-2-carboxylic acid (14542-16-6) → 4-Methylthiazole (693-95-8)

2-chloro-4-methyl-1,3-thiazole (26847-01-8) → 4-Methylthiazole (693-95-8)

Conditions	Yield
With acetic acid; zinc

2-hydrazinyl-4-methylthiazole hydrochloride (14397-08-1) → 4-Methylthiazole (693-95-8)

Conditions	Yield
With water; mercury(II) oxide
With hydrogenchloride; dihydrogen peroxide

formamide (77287-34-4, 77287-35-5, 60100-09-6) + chloroacetone (78-95-5) → 4-Methylthiazole (693-95-8)

Conditions	Yield
With tetraphosphorus decasulfide In benzene
With tetraphosphorus decasulfide

formamide (77287-34-4, 77287-35-5, 60100-09-6) + 1-bromoacetone (598-31-2) → 4-Methylthiazole (693-95-8)

Conditions	Yield
With 1,4-dioxane; tetraphosphorus decasulfide

ethanol (64-17-5) + thiocarboxamide (115-08-2) + chloroacetone (78-95-5) → 4-Methylthiazole (693-95-8)

thiocarboxamide (115-08-2) + chloroacetone (78-95-5) → 4-Methylthiazole (693-95-8)

Conditions	Yield
With ethanol

chloroacetone (78-95-5) → 4-Methylthiazole (693-95-8)

Conditions	Yield
With sodium hydrogensulfide; ethanol Erwaermen des Reaktionsprodukts mit Formamid und NaOH;

methyl-4 thiazole-I2 (57516-12-8) → 4-Methylthiazole (693-95-8)

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

4-methylisothiazole (693-90-3) → 4-Methylthiazole (693-95-8)

Conditions	Yield
In ethanol Ambient temperature; Irradiation;
With TEA In methanol for 0.5h; Irradiation;	32 % Chromat.

2-oxy-4-methyl-thiazole → 4-Methylthiazole (693-95-8)

Conditions	Yield
bei der Zinkstaub-Destillation;

4-methylthiazole-2(3H)-thione (5685-06-3) + dihydrogen peroxide (7722-84-1) → 4-Methylthiazole (693-95-8)

diazotized 2-amino-4-methyl-thiazole → 4-Methylthiazole (693-95-8)

Conditions	Yield
With ethanol

4-methyl-3-thiazoline (52558-99-3) + sulfur → 4-Methylthiazole (693-95-8)

Conditions	Yield
at 140℃;

formamide (77287-34-4, 77287-35-5, 60100-09-6) + chloroacetone (78-95-5) + P2S5 → 4-Methylthiazole (693-95-8)

formamide (77287-34-4, 77287-35-5, 60100-09-6) + toluene (108-88-3) + 1-bromoacetone (598-31-2) + P2S5 → 4-Methylthiazole (693-95-8)

thiocyanoacetone (3029-48-9) + zinc → 4-Methylthiazole (693-95-8)

cobalt phthalocyanine disulfonate + 4-methylthiazole-2-thiol (5685-06-3) → 4-Methylthiazole (693-95-8)

Conditions	Yield
With sodium hydroxide

trichloro(4-methylthiazole)gold(III) (132963-45-2) + lithium chloride → 4-Methylthiazole (693-95-8) + 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(4-methylthiazole)gold(III) (132963-45-2) + chloride (16887-00-6) → 4-Methylthiazole (693-95-8) + 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;

[platinum(II) (2,2':6,2''-terpyridine) (4-methylthiazole)] (perchlorate)2 + lithium chloride → 4-Methylthiazole (693-95-8) + [Pt(2,2':6',2''-terpyridine)Cl]ClO4 (166268-05-9)

Conditions	Yield
With methanesulfonic acid In methanol; N,N-dimethyl-formamide Kinetics; Pt-complex in DMF added to a methanolic soln. of chloride ion at 25°C in a thermostated cell in a spectrophotometer;

7-hydroxy-3-(4-methyl-1,3-thiazol-2-yl)-8-(pyrrolidin-1-ylmethyl)coumarin → 4-Methylthiazole (693-95-8) + carbon dioxide (124-38-9) + 3-methyl-4H-1,4-thiazine (1062446-56-3)

Conditions	Yield
With silica gel at 20 - 750℃; Kinetics;

4-Methylthiazole (693-95-8) + methyl iodide (74-88-4) → 3,4-dimethylthiazolinium iodide (24300-70-7)

Conditions	Yield
In tetrahydrofuran at 90℃; for 48h;	100%
In methanol; ethyl acetate at 20℃; for 36h;	61%

4-Methylthiazole (693-95-8) + 2-chloro-1-(4-morpholino)propan-1-one (54022-76-3) → 2-chloro-1-(4-methylthiazol-2-yl)propan-1-one (1375709-69-5)

Conditions	Yield
Stage #1: 4-Methylthiazole With n-butyllithium In diethyl ether; n-heptane; toluene at -78℃; for 0.5h; Stage #2: 2-chloro-1-(4-morpholino)propan-1-one In diethyl ether; hexane; toluene at -78 - 20℃; Stage #3: With water; sodium hydrogencarbonate In diethyl ether; hexane; toluene	100%

4-Methylthiazole (693-95-8) + pentafluorophenyl(tetrahydrothiophene)gold(I) → [Au(C6F5)(4-methylthiazole)]2

Conditions	Yield
In diethyl ether (Ar); addn. of ligand to a soln. of gold complex in Et2O, stirring for 1.5 h at room temp.; evapn., extn. with Et2O, filtration through anhyd. MgSO4, evapn., recrystn. by layering a soln. in Et2O with hexane; elem. anal.;	99%

4-Methylthiazole (693-95-8) + 1-bromo-4-methoxy-benzene (104-92-7) → 5-(4-methoxyphenyl)-4-methylthiazole

Conditions	Yield
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;	99%
With C23H20ClFeN3Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 140℃; for 10h; Reagent/catalyst; regioselective reaction;	79%
With palladium(II) trimethylacetate; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Schlenk technique; Inert atmosphere; regioselective reaction;	71%

4-Methylthiazole (693-95-8) + 4-bromobenzenecarbonitrile (623-00-7) → 4-(4-methyl-1,3-thiazol-5-yl)benzonitrile (122957-57-7)

Conditions	Yield
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 19h; Inert atmosphere;	99%
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 19h; Inert atmosphere;	99%
With potassium acetate; palladium diacetate at 150℃; for 19h; Inert atmosphere;	99%

4-Methylthiazole (693-95-8) + 1-Bromo-4-fluorobenzene (460-00-4) → 5-(4-fluorophenyl)-4-methylthiazole (623577-48-0)

Conditions	Yield
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;	99%
With C23H20ClFeN3Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 140℃; for 10h; Reagent/catalyst; regioselective reaction;	94%
With C34H48Cl2N2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 8h;	83%

4-Methylthiazole (693-95-8) + 3,4,6-tri-O-triisopropylsilyl-1-iodo-D-glucal (135145-81-2) → 2-((2R,3R,4R)-3,4-bis((triisopropylsilyl)oxy)-2-(((triisopropylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-6-yl)-4-methylthiazole

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; palladium diacetate; lithium tert-butoxide In 1,4-dioxane at 100℃; for 24h; Schlenk technique; Inert atmosphere; regioselective reaction;	99%

4-Methylthiazole (693-95-8) + 5-bromo-2-chloropyridine (53939-30-3) → 5-(6-chloropyridin-3-yl)-4-methylthiazole

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

4-Methylthiazole (693-95-8) + gold(III) tetrachloride trihydrate → trichloro(4-methylthiazole)gold(III) (132963-45-2)

Conditions	Yield
In methanol; water addn. of 4-methylthiazole in methanol to soln. of HAuCl4*3H2O in water, neutralised with equimolar NaHCO3;; filtration, washed (water, methanol), recrystd. (dichloromethane), elem. anal.;	98%

4-Methylthiazole (693-95-8) + bromochlorobenzene (106-39-8) → 5-(4-chlorophenyl)-4-methylthiazole (1127217-94-0)

Conditions	Yield
With C68H65Cl2N3Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; regioselective reaction;	98%
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;	94%
With C23H20ClFeN3Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 140℃; for 10h; Reagent/catalyst; regioselective reaction;	92%

4-Methylthiazole (693-95-8) + 1-benzyl-4-(3-chlorophenylamino)piperidine-4-carbonitrile (84254-99-9) → [1-benzyl-4-(4-methylthiazol-2-yl)-4-piperidinyl]-(3-chlorophenyl)amine (690273-75-7)

Conditions	Yield
Stage #1: 4-Methylthiazole With sec.-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.333333h; Stage #2: 1-benzyl-4-(3-chlorophenylamino)piperidine-4-carbonitrile In tetrahydrofuran; hexane at -78 - 0℃; for 0.5h; Stage #3: With water In tetrahydrofuran; hexane	98%

4-Methylthiazole (693-95-8) + 4-bromo-benzaldehyde (1122-91-4) → 4-(4-methylthiazol-5-yl)benzaldehyde (1330767-26-4)

Conditions	Yield
With C68H65Cl2N3Pd; 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;	97%
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;	92%

4-Methylthiazole (693-95-8) + bromobenzene (108-86-1) → 4-methyl-5-phenyl-1,3-thiazole (19968-61-7)

Conditions	Yield
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;	98%
With C22H18ClFeN3Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 140℃; for 10h; Reagent/catalyst; Solvent; Temperature; Time; regioselective reaction;	94%
With palladium diacetate; potassium carbonate; tricyclohexylphosphine tetrafluoroborate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 20h; Inert atmosphere;	73%
With palladium(II) trimethylacetate; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Schlenk technique; Inert atmosphere; regioselective reaction;	57%
With C42H42Cl2N2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 24h;

4-Methylthiazole (693-95-8) + 5-bromopyrimidine (4595-59-9) → 4-methyl-5-(pyrimidin-5-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;	98%
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;	87%
With C32H33Cl2NOPd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;	82%

4-Methylthiazole (693-95-8) + para-nitrophenyl bromide (586-78-7) → 4-methyl-5-(4-nitrophenyl)thiazole (25021-61-8)

Conditions	Yield
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;	98%
With C23H20ClFeN3Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 140℃; for 10h; Reagent/catalyst; regioselective reaction;	96%
With C34H48Cl2N2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 8h;	82%
With C42H42Cl2N2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 24h;
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 15h; Inert atmosphere;

4-Methylthiazole (693-95-8) + (S)-tert-butyl (1-(4-bromophenyl)ethyl)carbamate (847728-89-6) → tert-butyl N-[(1S)-1-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]ethyl]carbamate

Conditions	Yield
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 120℃; for 2h; Inert atmosphere;	98%
With palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 90℃; for 18h; Inert atmosphere;	82.3%
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 90℃; for 18h; Inert atmosphere;	82.3%

4-Methylthiazole (693-95-8) + 3,5-dibromopyridine (625-92-3) → 3,5-bis(4-methylthiazol-5-yl)pyridine

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;	98%
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;	97%

4-Methylthiazole (693-95-8) + 2-methoxy-5-bromopyridine (13472-85-0) → 5-(6-methoxypyridin-3-yl)-4-methylthiazole

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

4-Methylthiazole (693-95-8) + p-trifluoromethylphenyl bromide (402-43-7) → 4-methyl-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;	89%
With tris [tris(3,5-bis(trifluoromethyl)phenyl)phosphine]palladium(0); potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 140℃; for 3h; regioselective reaction;	78%
With palladium diacetate; potassium carbonate; tricyclohexylphosphine tetrafluoroborate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 20h; Inert atmosphere;	75%
With C42H42Cl2N2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 24h;

4-Methylthiazole (693-95-8) + tetrafluoroboric acid + trimethyl orthoformate (149-73-5) → 3,4-dimethylthiazol-3-ium tetrafluoroborate

Conditions	Yield
In water at 0 - 110℃; for 23h;	97%

4-Methylthiazole (693-95-8) + tetrafluoroboric acid + Tributyl orthoformate (588-43-2) → 3-butyl-4-methylthiazol-3-ium tetrafluoroborate

Conditions	Yield
In water at 0 - 140℃; for 30h;	97%

4-Methylthiazole (693-95-8) + 4-bromoisoquinoline (1532-97-4) → 5-(isoquinolin-4-yl)-4-methylthiazole

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

4-Methylthiazole (693-95-8) + 1-(carboxymethoxy)cyclopentadiene (25662-28-6) → methyl 5-(4-methylthiazol-5-yl)cyclopent-1-enecarboxylate

Conditions	Yield
Stage #1: 4-Methylthiazole With C37H24F2N6O2Pd In dichloromethane at 20℃; for 0.333333h; Stage #2: 1-(carboxymethoxy)cyclopentadiene With 1,1,1,3',3',3'-hexafluoro-propanol; silver(I) acetate; palladium diacetate; N-acetylglycine In dichloromethane at 80℃; for 30h; Sealed tube;	96%

4-Methylthiazole (693-95-8) + 4-bromoquinoline (3964-04-3) → 4-methyl-5-(quinolin-4-yl)thiazole

Conditions	Yield
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;	96%

4-Methylthiazole (693-95-8) + benzaldehyde (100-52-7) → 2-(α-hydroxybenzyl)-4-methylthiazole (54918-64-8)

Conditions	Yield
Stage #1: 4-Methylthiazole With n-butyllithium In tetrahydrofuran at -78℃; Stage #2: benzaldehyde In tetrahydrofuran at -78 - 20℃; for 1h;	95%
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane at -78℃; for 1h;	79%

4-Methylthiazole (693-95-8) → 4-methyl-thiazole-5-sulfonic acid (114389-49-0)

Conditions	Yield
With sulfur trioxide In 1,2-dichloro-ethane for 5h; Heating;	95%
With sulfuric acid; sulfur trioxide at 200℃;

4-Methylthiazole (693-95-8) → 4-methyl-5-chlorothiazole (125402-79-1)

Conditions	Yield
With N-chloro-succinimide; Perbenzoic acid In tetrachloromethane for 1h; Heating;	95%

4-Methylthiazole (693-95-8) + 3-Bromopyridine (626-55-1) → 3-(4-methylthiazol-5-yl)-pyridine

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;	95%
With C23H20ClFeN3Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 140℃; for 10h; Reagent/catalyst; regioselective reaction;	92%
With C32H33Cl2NOPd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;	90%

4-Methylthiazole (693-95-8) + 1-benzyl-4-(o-toluidino)piperidine-4-carbonitrile (972-17-8) → [1-benzyl-4-(4-methylthiazol-2-yl)-4-piperidinyl](2-methylphenyl)amine

Conditions	Yield
Stage #1: 4-Methylthiazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.333333h; Stage #2: 1-benzyl-4-(o-toluidino)piperidine-4-carbonitrile at -78 - 0℃; for 0.5h;	95%

Upstream product

• 14397-08-1 2-hydrazinyl-4-methylthiazole hydrochloride 
• 693-90-3 4-methylisothiazole 
• 1603-91-4 4-methylthiazol-2-ylamine 
• 313375-56-3 3-(4-methyl-1,3-thiazol-2-yl)-7-hydroxycoumarin 
• 5685-06-3 4-methylthiazole-2-thiol 
• 3029-48-9 thiocyanoacetone 
• 77287-34-4 formamide 
• 108-88-3 toluene 
• 598-31-2 1-bromoacetone 
• 78-95-5 chloroacetone 
• 52558-99-3 4-methyl-3-thiazoline 
• 5685-06-3 4-methylthiazole-2(3H)-thione 
• 7722-84-1 dihydrogen peroxide 
• 57516-12-8 methyl-4 thiazole-I₂ 

Downstream Products

• 111600-83-0 5-bromo-4-methyl-1,3-thiazole 
• 7036-04-6 1,3-thiazol-4-ylmethanol 
• 59020-78-9 2-(1-hydroxy-2-propenyl)-4-methylthiazole 
• 38117-54-3 cyclopentadienyl iron(II) dicarbonyl dimer 
• 690273-87-1 [1-(1-methyl-1-phenylethyl)-4-(4-methylthiazol-2-yl)-4-piperidinyl]-phenyl-amine 
• 690273-75-7 [1-benzyl-4-(4-methylthiazol-2-yl)-4-piperidinyl]-(3-chlorophenyl)amine 
• 13750-63-5 (4-methylthiazol-2-yl)-methanol 
• 1025699-19-7 4'-methyl-5-(4-methyl-thiazol-5-yl)-biphenyl-3-carboxylic acid (2-meth-oxy-1-methyl-ethyl)-amide 
• 102-54-5 ferrocene 
• 174824-73-8 2,2,2-trifluoro-1-(4-methyl-1,3-thiazol-2-yl)ethanone 
• 13750-68-0 4-methyl-thiazole-2-carbaldehyde 
• 113411-23-7 4-methylthiazole-2-sulfonamide 
• 321911-23-3 (5Z,7E)-(1S,3R)-1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-24-(4-methylthiazol-2-yl)-9,10-secochola-5,7,10⁽¹⁹⁾-trien-24-ol 
• 52829-53-5 4-bromomethyl-1,3-thiazole 

Relevant articles and documents

Decarboxylation method for heterocyclic carboxylic acid compounds

The invention relates to a decarboxylation method for heterocyclic carboxylic acid compounds. The method comprises the following steps: dissolving the heterocyclic carboxylic acid compounds in an aprotic polar solvent N,N-dimethylformamide, and performing decarboxylation at 85-150 DEG C with an organic acid as a catalyst. The method in the invention allows the yield of decarboxylation products obtained after a reaction to be higher than the yield of the products obtained through decarboxylation methods in the prior art, and does not need an expensive metal catalyst; and the solvent (DMF) in the present invention is more stable than DMSO, is not prone to decompose at a high temperature, and it can be recycled, so the cost is reduced. The method has the advantages of simple operation process, zero pollution, greenness, environmental protection and excellent application prospect.

A TPD-MS study of the interaction of coumarins and their heterocyclic derivatives with a surface of fumed silica and nanosized oxides CeO 2/SiO2, TiO2/SiO2, Al 2O3/SiO2

The interactions between coumarins and the surface of fumed SiO 2, CeO2/SiO2, TiO2/SiO2 and Al2O3/SiO2 were assessed by means of temperature-programed desorption mass spectrometry. The different stages of the thermolysis of coumarin were identified and an analysis of the underlying reactions was performed. The kinetic parameters of the involved reactions were thus obtained. The decomposition of thiazolyl-substituted coumarins was found to proceed through a 'thiazole-thiazine' ring expansion in the adsorbed state. A linear correlation between the sigma constants (Σσ) of the coumarin substituents and the activation energy of CO2 formation was obtained. Copyright

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

The kinetics of the forward and reverse steps of the reaction [Pt(terpy)Cl]+ + nu ? [Pt(terpy)(nu)]2+ + Cl- (terpy = 2,2′:6′,2″-terpyridine, nu = one of a number of thiazoles, oxazole, isoxazole, imidazole, pyrazole and 3,5-dimethylpyrazole, covering a wide range of basicities) have been studied in methanol at 25 °C. Both forward and reverse reactions obey the usual two-term rate law observed in square-planar substitution. The second-order rate constants for the forward reactions, k2f, show a slight dependence upon the basicity of the entering nu, while the steric hindrance due to the presence of one methyl group in the α position to the nitrogen markedly decreases the reactivity. The second-order rate constants for the reverse reactions, k2r, are very sensitive to the nature of the leaving group and a plot of log k2r against the pKa of the conjugate acids of the unhindered five-membered N-donors is linear with a slope of -0.51. The results are compared with data from the literature regarding a series of pyridines reacting with the [Pt(terpy)Cl]+ cation under the same experimental conditions. Both in the forward and in the reverse reaction, the reactivity depends not only upon the ligand basicity but also upon the nature of the nucleophile in the order: (thiazoles, oxazole, isoxazole, imidazole, pyrazoles) > pyridines for the entry of N-donors and on the contrary for the displacement by Cl-. Steric retardation, due to the presence of a methyl group in the α position to the nitrogen, is remarkably lower for five-membered N-donors if compared to pyridines both in the forward and in the reverse reaction.