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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.

Photorelease of Pyridines Using a Metal-Free Photoremovable Protecting Group

Dong, Zaizai,Fang, Xiaohong,Kou, Xiaolong,Tan, Weihong,Tang, Xiao-Jun,Wu, Yayun,Zhang, Zhen,Zhao, Rong,Zhou, Wei

supporting information, p. 18386 - 18389 (2020/08/24)

The photorelease of bioactive molecules has emerged as a valuable tool in biochemistry. Nevertheless, many important bioactive molecules, such as pyridine derivatives, cannot benefit from currently available organic photoremovable protecting groups (PPGs). We found that the inefficient photorelease of pyridines is attributed to intramolecular photoinduced electron transfer (PET) from PPGs to pyridinium ions. To alleviate PET, we rationally designed a strategy to drive the excited state of PPG from S1 to T1 with a heavy atom, and synthesized a new PPG by substitution of the H atom at the 3-position of 7-dietheylamino-coumarin-4-methyl (DEACM) with Br or I. This resulted in an improved photolytic efficiency of the pyridinium ion by hundreds-fold in aqueous solution. The PPG can be applied to various pyridine derivatives. The successful photorelease of a microtubule inhibitor, indibulin, in living cells was demonstrated for the potential application of this strategy in biochemical research.

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

Phototransposition Chemistry of Methylisothiazoles and Methylthiazoles

Pavlik, James W.,Pandit, Chennagiri R.,Samuel, Christopher J.,Day, A. Colin

, p. 3407 - 3410 (2007/10/02)

Methylisothiazoles undergo phototransition in neutral solution to methylthiazoles by a single permutation process.Methylisothiazole -> methylisothiazole transpositions, previously reported to occur, were not detected in these reactions.In trifluoroacetic acid solvent, protonated methylisothiazoles and methylthiazoles phototranspose by P4 and P5 permutation pathways, respectively, resulting in a unique phototransposition cycle.

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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