4-(4-Pyridinyl)thiazole-2-thiol supplier

Name
4-(4-Pyridinyl)thiazole-2-thiol
EINECS 616-441-2
CAS No. 77168-63-9
Article Data6
CAS DataBase
Density 1.356 g/cm³
Solubility
Melting Point
Formula C₈H₆N₂S₂
Boiling Point 356.135 °C at 760 mmHg
Molecular Weight 194.281
Flash Point 169.184 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2-mercapto-4-(4-pyridyl)thiazole;4-(pyridin-4-yl)-1,3-thiazole-2-thiol;4-(4-Pyridinyl)thiazole-2-thiol;4-(4-pyridyl)thiazole-2-thiol;[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol;4-(4-pyridyl)-1,3-thiazole-2-thiol;2-mercapto-4-(pyridine-4-yl)thiazole;
PSA 92.82000
LogP 2.49380

Synthetic route

: 4-(pyridin-4-yl)thiazole-2(3H)-thione

: 77168-63-9
[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

Conditions

Conditions	Yield
With acetic acid for 5h; Reflux;	85.2%

: 6221-13-2
4-(bromoacetyl)pyridine

: 513-74-6
ammonium dithiocarbamate

: 77168-63-9
[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

Conditions

Conditions	Yield
at 0 - 25℃; for 5h;	82.6%
In ethanol; water at 0℃; Reflux;

: 1122-54-9
methyl (4-pyridyl) ketone

: 77168-63-9
[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: bromine / tetrachloromethane / 2 h / -5 - 78 °C 2: ethanol / 5 h / 20 °C 3: acetic acid / 5 h / Reflux View Scheme

: 63821-56-7
benzhydryl 3-chloro-7β-(α-phenylacetamido)-3-cephem-4-carboxylate

: 77168-63-9
[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

: diphenylmethyl 7-phenylacetamido-3-[4-(1-methyl-4-pyridyl)-2-thiazolylthio]-3-cephem-4-carboxylate hydrochloride

Conditions

Conditions	Yield
With tert.-butylhydroperoxide In tetrachloromethane at 88℃; for 0.5h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere; Darkness;	97.1%

: 7β-phenylacetamido-3-(4-methylbenzenesulfonyloxy)-3-dimethylcephem-4-carboxylic acid

: 77168-63-9
[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

: 7β-phenylacetamido-3-[4-(1-methyl-4-pyridyl)thiazol-2-yl]-3-cephem-4-carboxylicacid diphenylmethyl ester

Conditions

Conditions	Yield
Stage #1: [4-(4-pyridyl)-1,3-thiazol-2-yl]thiol With sodium methylate In tetrahydrofuran at 20℃; for 0.5h; Large scale; Stage #2: 7β-phenylacetamido-3-(4-methylbenzenesulfonyloxy)-3-dimethylcephem-4-carboxylic acid In tetrahydrofuran for 4h; Reagent/catalyst; Solvent; Large scale;	90%

: 92096-37-2
benzhydryl (6R,7R)-7β-[(phenylacetyl)amino]-3-[(methylsulfonyl)oxy]-3-cephem-4-carboxylate

: 77168-63-9
[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

A: (6R,7R)-8-Oxo-7-phenylacetylamino-3-(4-pyridin-4-yl-thiazol-2-ylsulfanyl)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid benzhydryl ester

B: 400827-68-1
4-(2-{[(6R,7R)-2-[(diphenylmethoxy)carbonyl]-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]sulfanyl}-1,3-thiazol-4-yl)pyridine

Conditions

Conditions	Yield
With sodium methylate In tetrahydrofuran; methanol at -5℃; for 2h; Title compound not separated from byproducts;	A n/a B 81%

...Expand

: 123054-30-8
(7R)-7-[(phenylacetyl)amino]-3-trifluoromethanesulfonyloxy-3-cephem-4-carboxylate, 4-methoxybenzyl ester

: 77168-63-9
[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

: 189345-50-4
p-methoxybenzyl 7β-phenylacetamido-3-[4-(4-pyridyl)-1,3-thiazol-2-yl]thio-3-cephem-4-carboxylate

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 2h;	79%

: 35179-02-3
8-methyl-8-azabicyclo[3.2.1]octan-3-ylethanesulfonate

: 77168-63-9
[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

: 2-((8-methyl-8-azabicyclo[3.2.1]octan-3-yl)thio)-4-(pyridin-4-yl)thiazole

Conditions

Conditions	Yield
With sodium carbonate In tetrahydrofuran Reflux;	39%

: 77168-63-9
[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

: (6R,7S)-7-{2-[(Z)-2-Fluoro-ethoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-8-oxo-3-trifluoromethanesulfonyloxy-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

: (6R,7S)-7-{2-[(Z)-2-Fluoro-ethoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-8-oxo-3-(4-pyridin-4-yl-thiazol-2-ylsulfanyl)-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran Ambient temperature;

: 77168-63-9
[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

: 161692-28-0
(4R,5R,6S,8R)-p-nitrobenzyl-3-(diphenylphosphoryloxy)-4-methyl-6-(1-(trimethylsilyloxy)ethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

: 161681-62-5
(4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-7-oxo-3-(4-pyridin-4-yl-thiazol-2-ylsulfanyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran; toluene at 5℃; for 18h;

: 77168-63-9
[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

: 189345-52-6
7β-amino-3-[4-(1-methyl-4-pyridinio)-1,3-thiazol-2-yl]thio-3-cephem-4-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 79 percent / sodium hydride / tetrahydrofuran / 2 h / 20 °C 2.1: dimethylformamide / 16 h / 20 °C 3.1: phosphorus pentachloride; pyridine / CH2Cl2 / 1 h / 5 °C 3.2: MeOH / CH2Cl2 / 0.5 h / -20 °C 4.1: 8.28 g / TFA; anisole / CH2Cl2 / 1 h / 20 °C View Scheme

: 77168-63-9
[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

: 7β-amino-3-[4-(1-methyl-4-pyridinio)-1,3-thiazol-2-yl]thio-3-cephem-4-carboxylate dihydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 81 percent / sodium methoxide / methanol; tetrahydrofuran / 2 h / -5 °C 2.1: 97 percent / dimethylformamide / 8 h / 20 °C 3.1: phosphorus pentachloride; pyridine / CH2Cl2 / 1 h / 5 °C 3.2: 93 percent / iso-butanole / CH2Cl2 / 3 h / 20 °C 4.1: 76 percent / conc. HCl / acetonitrile; H2O / 0.5 h / 20 °C View Scheme

: 77168-63-9
[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

: C21H18N8O5S4

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 79 percent / sodium hydride / tetrahydrofuran / 2 h / 20 °C 2.1: dimethylformamide / 16 h / 20 °C 3.1: phosphorus pentachloride; pyridine / CH2Cl2 / 1 h / 5 °C 3.2: MeOH / CH2Cl2 / 0.5 h / -20 °C 4.1: 8.28 g / TFA; anisole / CH2Cl2 / 1 h / 20 °C 5.1: 38 percent / NaHCO3 / tetrahydrofuran; H2O / 5 °C View Scheme

: 77168-63-9
[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

: (6R,7R)-7-[[2(Z)-ethoxyimino-[5-amino-1,2,4-thiadiazol-3-yl]acetyl]amino]-3-[[4-(1-methyl-pyridinium-4-yl)thiazol-2-yl]sulfanyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-2-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 79 percent / sodium hydride / tetrahydrofuran / 2 h / 20 °C 2.1: dimethylformamide / 16 h / 20 °C 3.1: phosphorus pentachloride; pyridine / CH2Cl2 / 1 h / 5 °C 3.2: MeOH / CH2Cl2 / 0.5 h / -20 °C 4.1: 8.28 g / TFA; anisole / CH2Cl2 / 1 h / 20 °C 5.1: 62 percent / NaHCO3 / tetrahydrofuran; H2O / 0.5 h / 5 °C View Scheme

: 77168-63-9
[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

: C23H22N8O5S4

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 79 percent / sodium hydride / tetrahydrofuran / 2 h / 20 °C 2.1: dimethylformamide / 16 h / 20 °C 3.1: phosphorus pentachloride; pyridine / CH2Cl2 / 1 h / 5 °C 3.2: MeOH / CH2Cl2 / 0.5 h / -20 °C 4.1: 8.28 g / TFA; anisole / CH2Cl2 / 1 h / 20 °C 5.1: 41 percent / NaHCO3 / tetrahydrofuran; H2O / 5 °C View Scheme

: 77168-63-9
[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

: C21H17FN8O5S4

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 79 percent / sodium hydride / tetrahydrofuran / 2 h / 20 °C 2.1: dimethylformamide / 16 h / 20 °C 3.1: phosphorus pentachloride; pyridine / CH2Cl2 / 1 h / 5 °C 3.2: MeOH / CH2Cl2 / 0.5 h / -20 °C 4.1: 8.28 g / TFA; anisole / CH2Cl2 / 1 h / 20 °C 5.1: 23 percent / NaHCO3 / tetrahydrofuran; H2O / 5 °C View Scheme

: 77168-63-9
[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

: C25H24N8O5S4

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 79 percent / sodium hydride / tetrahydrofuran / 2 h / 20 °C 2.1: dimethylformamide / 16 h / 20 °C 3.1: phosphorus pentachloride; pyridine / CH2Cl2 / 1 h / 5 °C 3.2: MeOH / CH2Cl2 / 0.5 h / -20 °C 4.1: 8.28 g / TFA; anisole / CH2Cl2 / 1 h / 20 °C 5.1: 38 percent / NaHCO3 / tetrahydrofuran; H2O / 5 °C View Scheme

: 77168-63-9
[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

: (6R,7R)-7-{(2Z)-2-(ethoxyimino)-2-[5-(phosphonoamino)-1,2,4-thiadiazol-3-yl]acetylamino}-3-{[4-(1-methyl-4-pyridin-1-iumyl)-1,3-thiazol-2-yl]sulfanyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 81 percent / sodium methoxide / methanol; tetrahydrofuran / 2 h / -5 °C 2.1: 97 percent / dimethylformamide / 8 h / 20 °C 3.1: phosphorus pentachloride; pyridine / CH2Cl2 / 1 h / 5 °C 3.2: 93 percent / iso-butanole / CH2Cl2 / 3 h / 20 °C 4.1: 76 percent / conc. HCl / acetonitrile; H2O / 0.5 h / 20 °C 5.1: 77 percent / sodium acetate / H2O / 1 h / 20 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: 81 percent / sodium methoxide / methanol; tetrahydrofuran / 2 h / -5 °C
2.1: 97 percent / dimethylformamide / 8 h / 20 °C
3.1: phosphorus pentachloride; pyridine / CH2Cl2 / 1 h / 5 °C
3.2: 93 percent / iso-butanole / CH2Cl2 / 3 h / 20 °C
4.1: 76 percent / conc. HCl / acetonitrile; H2O / 0.5 h / 20 °C
5.1: 77 percent / sodium acetate / H2O / 1 h / 20 °C
View Scheme

: 77168-63-9
[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

: 4-{2-[(6R,7R)-7-Amino-2-(4-methoxy-benzyloxycarbonyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylsulfanyl]-thiazol-4-yl}-1-methyl-pyridinium; chloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 79 percent / sodium hydride / tetrahydrofuran / 2 h / 20 °C 2.1: dimethylformamide / 16 h / 20 °C 3.1: phosphorus pentachloride; pyridine / CH2Cl2 / 1 h / 5 °C 3.2: MeOH / CH2Cl2 / 0.5 h / -20 °C View Scheme

: 77168-63-9
[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

: benzhydryl 7β-amino-3-[4-(1-methyl-4-pyridinio)-1,3-thiazol-2-yl]thio-3-cephem-4-carboxylate chloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 81 percent / sodium methoxide / methanol; tetrahydrofuran / 2 h / -5 °C 2.1: 97 percent / dimethylformamide / 8 h / 20 °C 3.1: phosphorus pentachloride; pyridine / CH2Cl2 / 1 h / 5 °C 3.2: 93 percent / iso-butanole / CH2Cl2 / 3 h / 20 °C View Scheme

: 77168-63-9
[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

: 4-{2-[(6R,7R)-2-(4-Methoxy-benzyloxycarbonyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylsulfanyl]-thiazol-4-yl}-1-methyl-pyridinium; iodide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 79 percent / sodium hydride / tetrahydrofuran / 2 h / 20 °C 2: dimethylformamide / 16 h / 20 °C View Scheme

: 77168-63-9
[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

: benzhydryl 7β-[(phenylacetyl)amino]-3-[4-(1-methyl-4-pyridinio)-2-thiazolythio]-3-cephem-4-carboxylate iodide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / sodium methoxide / methanol; tetrahydrofuran / 2 h / -5 °C 2: 97 percent / dimethylformamide / 8 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: N,N,N',N'-tetramethylguanidine / 2.5 h / 0 °C 2: tetrahydrofuran / 20 °C 3: dmap; sodium hydrogencarbonate / acetonitrile / 16 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: tert.-butylhydroperoxide / tetrachloromethane / 0.5 h / 88 °C / Inert atmosphere; Darkness 2: tetrahydrofuran / 20 °C View Scheme
Multi-step reaction with 2 steps 1: tert.-butylhydroperoxide / tetrachloromethane / 0.5 h / 88 °C / Inert atmosphere; Darkness 2: tetrahydrofuran / 20 °C View Scheme
Multi-step reaction with 2 steps 1: tert.-butylhydroperoxide / tetrachloromethane / 0.5 h / 88 °C / Inert atmosphere; Darkness 2: N,N-dimethyl-formamide / 20 °C View Scheme

: 77168-63-9
[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

: (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-7-oxo-3-(4-pyridin-4-yl-thiazol-2-ylsulfanyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NaH / toluene; tetrahydrofuran / 18 h / 5 °C 2: H2, 0.05 M MOPS buffer / 10percent Pd/C / tetrahydrofuran / 1 h / Ambient temperature View Scheme

: 77168-63-9
[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

: (4R,5S,6S,8R)-3-[4-(1-aminocarbonylmethyl-pyridinio-4-yl)thiazol-2-ylthio]-4-methyl-6-(1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NaH / toluene; tetrahydrofuran / 18 h / 5 °C 2: 2.) H2, 0.1 M potassium phosphate buffer / 2.) 10percent Pd/C / 1.) acetone, THF, reflux, 7 h, 2.) THF, RT, 3 h View Scheme

: 77168-63-9
[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

: (6R,7S)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-2-fluoro-ethoxyimino]-acetylamino}-8-oxo-3-(4-pyridin-4-yl-thiazol-2-ylsulfanyl)-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NaH / tetrahydrofuran / Ambient temperature 2: triethylsilane, formic acid / 1 h View Scheme

: 77168-63-9
[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

: 161692-29-1
4-(4-pyridyl)-1,3-thiazole-2-thiol sodium salt

Conditions

Conditions	Yield
With sodium hydroxide
With sodium methylate; phosphorus pentaoxide In methanol
With sodium methylate In tetrahydrofuran; methanol at 20 - 25℃;

sodium methylate-methanol: sodium methylate-methanol

: benzhydryl 7β-[(phenylacetyl)amino]-3-[(methylsulfonyl)oxy]-3-cephem-4-carboxylate

: 77168-63-9
[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

: benzhydryl 7β-[(phenylacetyl)amino]-3-[4-pyridyl-2-thiazolylthio]-3-cephem-4-carboxylate

Conditions

Conditions	Yield
With acetic acid In tetrahydrofuran; methanol; water

...Expand

: 77168-63-9
[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

: benzhydryl 7β-[(phenylacetyl)amino]-3-[4-(1-methyl-4-pyridinio)-2-thiazolylthio]-3-cephem-4-carboxylate tetrafluoroborate

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: N,N,N',N'-tetramethylguanidine / 2.5 h / 0 °C 2: tetrahydrofuran / 20 °C 3: sodium hydrogencarbonate / methanol / 4 h / 0 °C / pH 7.6 - 8.0 4: tetrafluoroboric acid / acetonitrile; tert-butyl methyl ether / 1 h / 20 °C 5: sodium hydrogencarbonate / acetonitrile / 17 h / 20 °C View Scheme

: 77168-63-9
[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

: 1427207-51-9
benzhydryl 7β-[(phenylacetyl)amino]-3-[4-(1-methyl-4-pyridinio)-2-thiazolylthio]-3-cephem-4-carboxylate trifluoromethane sulfonate

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: N,N,N',N'-tetramethylguanidine / 2.5 h / 0 °C 2: tetrahydrofuran / 20 °C 3: sodium hydrogencarbonate / methanol / 4 h / 0 °C / pH 7.6 - 8.0 4: acetonitrile; tert-butyl methyl ether / 1 h / 20 °C 5: sodium hydrogencarbonate / acetonitrile / 22.5 h / 20 °C View Scheme

4-(4-Pyridinyl)thiazole-2-thiol Chemical Properties

Molecular Structure:

Molecular Formula: C₈H₆N₂S₂
Molecular Weight: 194.2766
IUPAC Name: 4-Pyridin-4-yl-3H-1,3-thiazole-2-thione
Synonyms of 4-(4-Pyridinyl)thiazole-2-thiol (CAS NO.77168-63-9): 2-Mercapto-4-(pyridine-4-yL) tniazoLe
CAS NO: 77168-63-9
Index of Refraction: 1.671
Molar Refractivity: 53.587 cm³
Molar Volume: 143.256 cm³
Surface Tension: 61.142 dyne/cm
Density: 1.356 g/cm³
Flash Point: 169.184 °C
Enthalpy of Vaporization: 57.765 kJ/mol
Boiling Point of 4-(4-Pyridinyl)thiazole-2-thiol (CAS NO.77168-63-9): 356.135 °C at 760 mmHg

Product Name

4-(4-Pyridinyl)thiazole-2-thiol

Synthetic route

4-(4-Pyridinyl)thiazole-2-thiol Chemical Properties

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