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3581-87-1

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3581-87-1 Usage

Uses

2-Methylthiazole is a derivative of thiazole, an anti-tubercular agent.

Check Digit Verification of cas no

The CAS Registry Mumber 3581-87-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,5,8 and 1 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 3581-87:
(6*3)+(5*5)+(4*8)+(3*1)+(2*8)+(1*7)=101
101 % 10 = 1
So 3581-87-1 is a valid CAS Registry Number.
InChI:InChI=1/C4H5NS/c1-4-5-2-3-6-4/h2-3H,1H3

3581-87-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Methylthiazole

1.2 Other means of identification

Product number -
Other names AURORA KA-6469

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:3581-87-1 SDS

3581-87-1Synthetic route

2-bromo-1,3-thiazole
3034-53-5

2-bromo-1,3-thiazole

[3-(dimethylamino)propyl]dimethylindium

[3-(dimethylamino)propyl]dimethylindium

2-methylthiazole
3581-87-1

2-methylthiazole

Conditions
ConditionsYield
bis-triphenylphosphine-palladium(II) chloride In benzene at 80℃; for 19h;94%
2-(methanesulfonyl)thiazole
69749-91-3

2-(methanesulfonyl)thiazole

methyl iodide
74-88-4

methyl iodide

2-methylthiazole
3581-87-1

2-methylthiazole

Conditions
ConditionsYield
Stage #1: methyl iodide With magnesium In tetrahydrofuran at 10 - 30℃; for 2h; Inert atmosphere;
Stage #2: 2-(methanesulfonyl)thiazole In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere;
86%
2-bromo-1,3-thiazole
3034-53-5

2-bromo-1,3-thiazole

bis(μ-[2-(dimethylamino)ethanolato-N,O:O]tetramethyldiindium

bis(μ-[2-(dimethylamino)ethanolato-N,O:O]tetramethyldiindium

2-methylthiazole
3581-87-1

2-methylthiazole

Conditions
ConditionsYield
bis-triphenylphosphine-palladium(II) chloride In benzene at 80℃; for 24h;84%
2-methyl-4,5-dihydro-thiazole
2346-00-1

2-methyl-4,5-dihydro-thiazole

2-methylthiazole
3581-87-1

2-methylthiazole

Conditions
ConditionsYield
With sulfur at 100 - 110℃;
2-methyl-2,5-dihydro-thiazole
66867-06-9

2-methyl-2,5-dihydro-thiazole

2-methylthiazole
3581-87-1

2-methylthiazole

Conditions
ConditionsYield
With ethanol; iron(III) chloride
2-chloroethanal
107-20-0

2-chloroethanal

thioacetamide
62-55-5

thioacetamide

2-methylthiazole
3581-87-1

2-methylthiazole

1,2-dichloro-2-ethoxyethane
623-46-1

1,2-dichloro-2-ethoxyethane

thioacetamide
62-55-5

thioacetamide

2-methylthiazole
3581-87-1

2-methylthiazole

Conditions
ConditionsYield
With ethanol
monochloroacetaldehyde hydrate
15873-56-0

monochloroacetaldehyde hydrate

thioacetamide
62-55-5

thioacetamide

2-methylthiazole
3581-87-1

2-methylthiazole

Conditions
ConditionsYield
With acetic anhydride; benzene
2-bromo-1,3-thiazole
3034-53-5

2-bromo-1,3-thiazole

dimethyl sulfate
77-78-1

dimethyl sulfate

2-methylthiazole
3581-87-1

2-methylthiazole

Conditions
ConditionsYield
(i) nBuLi, Et2O, (ii) /BRN= 635994/; Multistep reaction;
N-thiazol-2-ylmethyl-aniline; hydrochloride

N-thiazol-2-ylmethyl-aniline; hydrochloride

2-methylthiazole
3581-87-1

2-methylthiazole

Conditions
ConditionsYield
With hydrogenchloride (electrolysis);
3-methylisothiazole
693-92-5

3-methylisothiazole

2-methylthiazole
3581-87-1

2-methylthiazole

Conditions
ConditionsYield
In ethanol Ambient temperature; Irradiation;
In ethanol Mechanism; Ambient temperature; Irradiation; other substrates, other solvents;
3-((7-(diethylamino)-3-iodo-2-oxo-2H-chromen-4-yl)methyl)-2-methylthiazol-3-ium bromide

3-((7-(diethylamino)-3-iodo-2-oxo-2H-chromen-4-yl)methyl)-2-methylthiazol-3-ium bromide

2-methylthiazole
3581-87-1

2-methylthiazole

Conditions
ConditionsYield
In dimethyl sulfoxide pH=7.4; Quantum yield; Solvent; Irradiation;
2-methylthiazole
3581-87-1

2-methylthiazole

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

4-(2-methyl-1,3-thiazol-5-yl)benzaldehyde

4-(2-methyl-1,3-thiazol-5-yl)benzaldehyde

Conditions
ConditionsYield
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;100%
2-methylthiazole
3581-87-1

2-methylthiazole

tributyltin chloride
1461-22-9

tributyltin chloride

C13H25NSSn

C13H25NSSn

Conditions
ConditionsYield
Stage #1: 2-methylthiazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: tributyltin chloride In tetrahydrofuran; hexane at -78℃; for 1h;
99.2%
2-methylthiazole
3581-87-1

2-methylthiazole

1-Bromonaphthalene
90-11-9

1-Bromonaphthalene

2-methyl-5-(naphthalen-1-yl)thiazole
107559-03-5

2-methyl-5-(naphthalen-1-yl)thiazole

Conditions
ConditionsYield
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;90%
With C34H48Cl2N2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 8h;62%
2-methylthiazole
3581-87-1

2-methylthiazole

4-bromoquinoline
3964-04-3

4-bromoquinoline

2-methyl-5-(quinolin-4-yl)thiazole

2-methyl-5-(quinolin-4-yl)thiazole

Conditions
ConditionsYield
With C68H64Cl3N3Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; Reagent/catalyst; regioselective reaction;94%
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;80%
2-methylthiazole
3581-87-1

2-methylthiazole

ethyl acrylate
140-88-5

ethyl acrylate

(E)-ethyl 3-(2-methylthiazol-5-yl)acrylate
1392148-94-5

(E)-ethyl 3-(2-methylthiazol-5-yl)acrylate

Conditions
ConditionsYield
Stage #1: 2-methylthiazole With C37H24F2N6O2Pd In dichloromethane at 20℃; for 0.333333h;
Stage #2: ethyl acrylate With 1,1,1,3',3',3'-hexafluoro-propanol; silver(I) acetate; palladium diacetate; N-acetylglycine In dichloromethane at 80℃; for 30h; Sealed tube;
92%
2-methylthiazole
3581-87-1

2-methylthiazole

benzoyl chloride
98-88-4

benzoyl chloride

benzoic acid 1-phenyl-2-thiazol-2-ylvinyl ester
1256960-61-8

benzoic acid 1-phenyl-2-thiazol-2-ylvinyl ester

Conditions
ConditionsYield
With triethylamine In acetonitrile for 7h; Inert atmosphere; Reflux;89%
With triethylamine In acetonitrile at 20℃; for 7h; Inert atmosphere; Reflux;88.8%
With triethylamine In acetonitrile at 20℃; Inert atmosphere; Reflux;76%
2-methylthiazole
3581-87-1

2-methylthiazole

4-methoxycarbonylphenyl bromide
619-42-1

4-methoxycarbonylphenyl bromide

methyl 4-(2-methyl-1,3-thiazol-5-yl)benzoate

methyl 4-(2-methyl-1,3-thiazol-5-yl)benzoate

Conditions
ConditionsYield
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;88%
With C34H48Cl2N2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 8h;70%
methyl cyclohex-1-ene-1-carboxylate
18448-47-0

methyl cyclohex-1-ene-1-carboxylate

2-methylthiazole
3581-87-1

2-methylthiazole

methyl 6-(2-methylthiazol-5-yl)cyclohex-1-enecarboxylate

methyl 6-(2-methylthiazol-5-yl)cyclohex-1-enecarboxylate

Conditions
ConditionsYield
Stage #1: 2-methylthiazole With C37H24F2N6O2Pd In dichloromethane at 20℃; for 0.333333h;
Stage #2: methyl cyclohex-1-ene-1-carboxylate With 1,1,1,3',3',3'-hexafluoro-propanol; silver(I) acetate; palladium diacetate; N-acetylglycine In dichloromethane at 80℃; for 30h; Sealed tube;
88%
2-methoxy-5-bromopyridine
13472-85-0

2-methoxy-5-bromopyridine

2-methylthiazole
3581-87-1

2-methylthiazole

5-(6-methoxypyridin-3-yl)-2-methylthiazole

5-(6-methoxypyridin-3-yl)-2-methylthiazole

Conditions
ConditionsYield
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;88%
2-methylthiazole
3581-87-1

2-methylthiazole

tributyltin chloride
1461-22-9

tributyltin chloride

2-methyl-5-(tributylstannyl)thiazole
223418-75-5

2-methyl-5-(tributylstannyl)thiazole

Conditions
ConditionsYield
Stage #1: 2-methylthiazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: tributyltin chloride In tetrahydrofuran; hexane at -78 - 20℃; for 2h;
85%
Stage #1: 2-methylthiazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: tributyltin chloride In tetrahydrofuran; hexane at -78 - 20℃; for 2h;
85%
Stage #1: 2-methylthiazole With n-butyllithium In tetrahydrofuran at -78℃; for 1h;
Stage #2: tributyltin chloride In tetrahydrofuran at -78 - 20℃;
Stage #3: With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃;
72%
3-bromoquinoline
5332-24-1

3-bromoquinoline

2-methylthiazole
3581-87-1

2-methylthiazole

2-methyl-5-(quinolin-3-yl)thiazole

2-methyl-5-(quinolin-3-yl)thiazole

Conditions
ConditionsYield
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;83%
2-methylthiazole
3581-87-1

2-methylthiazole

mesitylenesulfonylhydroxylamine
36016-40-7

mesitylenesulfonylhydroxylamine

3-amino-2-methyl-thiazolium; 2,4,6-trimethyl-benzenesulfonate
52197-75-8

3-amino-2-methyl-thiazolium; 2,4,6-trimethyl-benzenesulfonate

Conditions
ConditionsYield
In ethyl acetate; toluene for 2h; Cooling with ice;81%
In dichloromethane for 0.166667h; Ambient temperature;62%
2-methylthiazole
3581-87-1

2-methylthiazole

acrylic acid n-butyl ester
141-32-2

acrylic acid n-butyl ester

(E)-butyl 3-(2-methylthiazol-5-yl)acrylate
1236376-59-2

(E)-butyl 3-(2-methylthiazol-5-yl)acrylate

Conditions
ConditionsYield
With silver(I) acetate; palladium diacetate; propionic acid at 120℃; for 8h; Inert atmosphere;80%
With 5-Nitro-1,10-phenanthroline; copper diacetate; palladium diacetate; caesium carbonate; dimethyl sulfoxide In tert-Amyl alcohol at 100℃; for 12h; Inert atmosphere; regioselective reaction;46%
2-methylthiazole
3581-87-1

2-methylthiazole

methyl 2-(4-bromo-2-chlorophenyl)acetate
849934-94-7

methyl 2-(4-bromo-2-chlorophenyl)acetate

methyl 2-(2-chloro-4-(2-methylthiazol-5-yl)phenyl)acetate
1428761-21-0

methyl 2-(2-chloro-4-(2-methylthiazol-5-yl)phenyl)acetate

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium acetate at 100℃; for 15h; Inert atmosphere;80%
With tetrakis(triphenylphosphine) palladium(0); potassium acetate In 1,2-dimethoxyethane at 100℃; for 15h; Inert atmosphere;80%
2-methylthiazole
3581-87-1

2-methylthiazole

2-Dibromomethylthiazole
134271-22-0

2-Dibromomethylthiazole

Conditions
ConditionsYield
With N-Bromosuccinimide In tetrachloromethane for 1.75h; Heating; Irradiation;79%
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 80℃; for 16h;
bromochlorobenzene
106-39-8

bromochlorobenzene

2-methylthiazole
3581-87-1

2-methylthiazole

5-(4-chlorophenyl)-2-methylthiazole
25594-97-2

5-(4-chlorophenyl)-2-methylthiazole

Conditions
ConditionsYield
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;79%
2-methylthiazole
3581-87-1

2-methylthiazole

p-trifluoromethylphenyl bromide
402-43-7

p-trifluoromethylphenyl bromide

2-methyl-5-(4-(trifluoromethyl)phenyl)thiazole
945860-92-4

2-methyl-5-(4-(trifluoromethyl)phenyl)thiazole

Conditions
ConditionsYield
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;78%
With C34H48Cl2N2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 8h;69%
2-methylthiazole
3581-87-1

2-methylthiazole

benzaldehyde
100-52-7

benzaldehyde

1-Phenyl-2-thiazol-2-yl-ethanol

1-Phenyl-2-thiazol-2-yl-ethanol

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; B-(trifluoromethanesulfonyloxy)-9-borabicyclo[3.3.1]nonane In dichloromethane for 17h; Ambient temperature;77%
With diisopropylamine; 9-BBN triflate 1.) -78 deg C, 2.) RT, 17 h; Yield given. Multistep reaction;
diethyl sulfate
64-67-5

diethyl sulfate

2-methylthiazole
3581-87-1

2-methylthiazole

3-ethyl-2-methylthiazolium ethosulfate

3-ethyl-2-methylthiazolium ethosulfate

Conditions
ConditionsYield
In xylene at 90℃; for 0.5h;76%
2-methylthiazole
3581-87-1

2-methylthiazole

1,4-dibromo-2,5-difluorobenzene
327-51-5

1,4-dibromo-2,5-difluorobenzene

1,4-bis(2-methylthiazol-5-yl)-2,5-difluorobenzene

1,4-bis(2-methylthiazol-5-yl)-2,5-difluorobenzene

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; tricyclohexylphosphine; Trimethylacetic acid In N,N-dimethyl acetamide; toluene at 100℃; for 24h; Inert atmosphere;75%
5-bromo-2-fluoropyridine
766-11-0

5-bromo-2-fluoropyridine

2-methylthiazole
3581-87-1

2-methylthiazole

5-(6-fluoropyridin-3-yl)-2-methylthiazole

5-(6-fluoropyridin-3-yl)-2-methylthiazole

Conditions
ConditionsYield
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;75%
bromobenzene
108-86-1

bromobenzene

2-methylthiazole
3581-87-1

2-methylthiazole

2-methyl-5-phenylthiazole
19968-60-6

2-methyl-5-phenylthiazole

Conditions
ConditionsYield
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;74%
2-methylthiazole
3581-87-1

2-methylthiazole

3,6-bis(trifluoromethyl)bromobenzene
328-70-1

3,6-bis(trifluoromethyl)bromobenzene

C12H7F6NS

C12H7F6NS

Conditions
ConditionsYield
With C34H48Cl2N2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 8h;73%
triethylsilane
617-86-7

triethylsilane

2-methylthiazole
3581-87-1

2-methylthiazole

2-[(triethylsilyl)methyl]thiazole

2-[(triethylsilyl)methyl]thiazole

Conditions
ConditionsYield
With 3,5-Lutidine; chlorohydrido(2,6-bis(di-tert-butylphosphinito)phen-1-yl)iridium(III); sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; cyclopentene at 130℃; for 20h; Schlenk technique; Inert atmosphere; regioselective reaction;73%
With 3,5-Lutidine; norborn-2-ene; dodecacarbonyltetrairidium In neat (no solvent) at 160℃; for 40h; Schlenk technique; Inert atmosphere; regioselective reaction;53%
5-bromo-2-methylpyridine
3430-13-5

5-bromo-2-methylpyridine

2-methylthiazole
3581-87-1

2-methylthiazole

2-methyl-5-(6-methylpyridin-3-yl)thiazole

2-methyl-5-(6-methylpyridin-3-yl)thiazole

Conditions
ConditionsYield
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;73%
2-methylthiazole
3581-87-1

2-methylthiazole

1,3-Diiodopropane
627-31-6

1,3-Diiodopropane

3-(3-iodopropyl)-2-methylthiazol-3-ium

3-(3-iodopropyl)-2-methylthiazol-3-ium

Conditions
ConditionsYield
In acetonitrile for 5h; Reflux;71%
2-methylthiazole
3581-87-1

2-methylthiazole

ethyl bromoacetate
105-36-2

ethyl bromoacetate

3-(2-ethoxy-2-oxoethyl)-2-methylthiazol-3-ium bromide

3-(2-ethoxy-2-oxoethyl)-2-methylthiazol-3-ium bromide

Conditions
ConditionsYield
for 16h; Reflux;70%

3581-87-1Relevant articles and documents

Preparation method of 2-alkyl substituted thiazole compound

-

Paragraph 0047-0050, (2021/06/06)

The invention discloses a preparation method of a 2-alkyl substituted thiazole compound, which comprises the following steps: oxidizing 2-alkyl thiothiazole into 2-alkyl sulfonyl thiazole, mixing the 2-alkyl sulfonyl thiazole with a Grignard reagent, reacting the mixture at 0-5 DEG C, heating the mixture to room temperature to continue the reaction; then adding an acid solution and continuously reacting the components at room temperature to obtain a 2-alkyl substituted thiazole compound, wherein the structural formula of the 2-alkyl thiothiazole is that a Grignard reagent of the 2-alkyl sulfonyl thiazole is RCH2MgX, R1 is selected from C1-C4 alkyl groups, R is selected from H and C1-C4 alkyl groups, and X is halogen. According to the present invention, the use of the expensive palladium catalyst and the ligand is avoided, the use of the poor safety butyl lithium reagent is avoided, the ultra-low temperature of-78 DEG C is not required, the cheap and easily available 2-alkylthiothiazole is adopted as the starting material, the 2-alkyl substituted thiazole compound can be prepared under the milder condition, and the method is suitable for the industrial production.

Palladium catalyzed cross-methylation of bromoheterocycles with intramolecularly stabilized dimethyl indium reagents

Jaber, Nimer,Schumann, Herbert,Blum, Jochanan

, p. 565 - 567 (2007/10/03)

Although the intramolecularly stabilized [(3- dimethylamino)propyl]dimethylaluminum (1a) fails to undergo palladium-catalyzed cross-coupling with bromopyridines and with bromofuran derivatives, the analogous gallium and indium reagent lb and 1c smoothly c

Pharmaceutical compositions and methods of inhibiting gastric acid secretion

-

, (2008/06/13)

Pharmaceutical compositions and methods of inhibiting gastric acid secretion by administering N-alkenyl and N-alkynyl thioamides.

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