Conditions | Yield |
---|---|
Stage #1: 2-bromo-1,3-thiazole With n-butyllithium In tetrahydrofuran Stage #2: carbon dioxide | 73% |
Stage #1: 2-bromo-1,3-thiazole With n-butyllithium In diethyl ether; hexane at -78℃; for 0.166667h; Stage #2: carbon dioxide In diethyl ether; hexane at -78℃; for 1.16667h; | 64% |
1,3-thiazole
carbon dioxide
A
thiazole-5-carboxylic acid
B
1,3-thiazole-2-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: carbon dioxide With AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene); potassium hydroxide In tetrahydrofuran at 20℃; under 1125.11 Torr; for 0.25h; Stage #2: 1,3-thiazole In tetrahydrofuran at 20℃; under 1125.11 Torr; for 12h; Stage #3: With hydrogenchloride In tetrahydrofuran; water regioselective reaction; | A 27% B 61% |
Conditions | Yield |
---|---|
With n-butyllithium; carbon dioxide | A 57% B n/a |
thiazole-2-carboxylic acid ethyl ester
1,3-thiazole-2-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: thiazole-2-carboxylic acid ethyl ester With potassium hydroxide; ethanol; water at 20℃; for 2h; Stage #2: With hydrogenchloride; water In ethanol | 25% |
With potassium hydroxide | |
Stage #1: thiazole-2-carboxylic acid ethyl ester With potassium hydroxide; ethanol at 120℃; for 0.5h; Stage #2: With hydrogenchloride; water In ethanol pH=4.0; | |
Stage #1: thiazole-2-carboxylic acid ethyl ester With potassium hydroxide; ethanol at 120℃; for 0.5h; Stage #2: With hydrogenchloride In ethanol; water pH=4.0; | |
Stage #1: thiazole-2-carboxylic acid ethyl ester With potassium hydroxide; ethanol; water at 20℃; for 2h; Stage #2: With hydrogenchloride; water |
1,3-thiazole
1,3-thiazole-2-carboxylic acid
Conditions | Yield |
---|---|
With diethyl ether; phenyllithium anschliessend Behandeln mit CO2; |
2-bromo-1,3-thiazole
1,3-thiazole-2-carboxylic acid
Conditions | Yield |
---|---|
With n-butyllithium; diethyl ether anschliessend mit CO2; |
thiocarboxamide
1,3-thiazole-2-carboxylic acid
Conditions | Yield |
---|---|
beim anschliessenden Verseifen; reagirt analog mit 2-Chlor-acetessigsaeure-aethylester, 3-Chlor-laevulinsaeure-aethylester,; |
C4H2NO2S(1-)*Li(1+)
1,3-thiazole-2-carboxylic acid
Conditions | Yield |
---|---|
With sulfuric acid; water |
Conditions | Yield |
---|---|
Stage #1: 1,3-thiazole With n-butyllithium In tetrahydrofuran at -60℃; for 0.166667h; Stage #2: carbon dioxide In tetrahydrofuran | |
Stage #1: 1,3-thiazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: carbon dioxide In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Inert atmosphere; | 12 g |
1,3-thiazole-2-carboxylic acid
6-aminohexanoic acid phenylamide
Conditions | Yield |
---|---|
With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; | 94% |
Conditions | Yield |
---|---|
With PS-PPh3; trichloroacetonitrile In acetonitrile at 150℃; for 0.25h; microwave irradiation; | 94% |
1,3-thiazole-2-carboxylic acid
1-(3-amino-2,6-difluoro-phenyl)-ethanone
thiazole-2-carboxylic acid (3-acetyl-2,4-difluoro-phenyl)-amide
Conditions | Yield |
---|---|
With triethylamine; HATU In tetrahydrofuran | 92% |
1,3-thiazole-2-carboxylic acid
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃; | 92% |
1,3-thiazole-2-carboxylic acid
ethyl potassium malonate
3-oxo-3-thiazol-2-yl-propionic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: 1,3-thiazole-2-carboxylic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 0 - 20℃; for 4h; Stage #2: ethyl potassium malonate With magnesium chloride In tetrahydrofuran at 50 - 75℃; for 20h; | 91% |
1,3-thiazole-2-carboxylic acid
Conditions | Yield |
---|---|
With 2-chloro-1-methyl-pyridinium iodide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 0.5h; Inert atmosphere; | 91% |
1,3-thiazole-2-carboxylic acid
1-(1-benzhydrylazetidin-3-yl)piperazine
(4-(1-benzhydrylazetidin-3-yl)piperazin-1-yl)(thiazol-2-yl)methanone
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane for 48h; | 90% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane for 48h; Inert atmosphere; | 90% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In water; N,N-dimethyl-formamide at 20℃; for 16h; | 78% |
1,3-thiazole-2-carboxylic acid
2-Fluoroaniline
Conditions | Yield |
---|---|
With pyridine; trichlorophosphate In dichloromethane at 20℃; Cooling with ice; | 79% |
With pyridine; trichlorophosphate In dichloromethane at 20℃; Cooling with ice; | 79% |
1,3-thiazole-2-carboxylic acid
4-chlorobenzoic acid hydrazide
Conditions | Yield |
---|---|
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In N,N-dimethyl-formamide at 20℃; | 73% |
1,3-thiazole-2-carboxylic acid
Conditions | Yield |
---|---|
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; | 71% |
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 10 - 35℃; | 170 mg |
1,3-thiazole-2-carboxylic acid
N,O-dimethylhydroxylamine*hydrochloride
thiazole-2-carboxylic acid methoxy-methyl-amide
Conditions | Yield |
---|---|
Stage #1: 1,3-thiazole-2-carboxylic acid With 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In tetrahydrofuran at 0℃; for 0.25h; Stage #2: With 4-methyl-morpholine In tetrahydrofuran at 20℃; for 1.5h; Stage #3: N,O-dimethylhydroxylamine*hydrochloride In tetrahydrofuran at 0 - 20℃; | 70% |
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide |
1,3-thiazole-2-carboxylic acid
N-(2'-chloro-5'-aminobenzoyl)-4-(p-fluorobenzy)-piperidine hydrochloride
Conditions | Yield |
---|---|
Stage #1: 1,3-thiazole-2-carboxylic acid With N-ethyl-N,N-diisopropylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate In acetonitrile for 0.25h; Stage #2: N-(2'-chloro-5'-aminobenzoyl)-4-(p-fluorobenzy)-piperidine hydrochloride With N-ethyl-N,N-diisopropylamine In acetonitrile for 2.25h; | 69% |
1,3-thiazole-2-carboxylic acid
potassium tert-butylate
Conditions | Yield |
---|---|
Stage #1: 1,3-thiazole-2-carboxylic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 23℃; for 5h; Stage #2: potassium tert-butylate In dichloromethane; N,N-dimethyl-formamide at 23℃; for 1h; Temperature; | 67% |
Stage #1: 1,3-thiazole-2-carboxylic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 23℃; for 5h; Stage #2: potassium tert-butylate In dichloromethane at 23℃; for 1h; | 67% |
1,3-thiazole-2-carboxylic acid
Demethylmifepristone
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 16h; Inert atmosphere; | 66% |
N2-phenyl-5-amino-3-methyl-2,4-thiophenecarboxamide
1,3-thiazole-2-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: 1,3-thiazole-2-carboxylic acid With N-ethyl-N,N-diisopropylamine; ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: N2-phenyl-5-amino-3-methyl-2,4-thiophenecarboxamide In N,N-dimethyl-formamide at 20℃; | 66% |
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 90℃; for 0.5h; Microwave irradiation; | 61% |
1,3-thiazole-2-carboxylic acid
ethyl 5-methyl-3-oxo-2-(thiazole-2-carboxamido)hexanoate
Conditions | Yield |
---|---|
With pyridine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0℃; Molecular sieve; | 60% |
With pyridine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0℃; Molecular sieve; | 60% |
1,3-thiazole-2-carboxylic acid
Conditions | Yield |
---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In dichloromethane at 0 - 20℃; for 16h; | 60% |
1,3-thiazole-2-carboxylic acid
4-methylthiosemicarbazide
Conditions | Yield |
---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate; N,N-dimethyl-formamide at 20℃; Cooling with ice; | 59% |
Stage #1: 1,3-thiazole-2-carboxylic acid; 4-methylthiosemicarbazide With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate; N,N-dimethyl-formamide at 20℃; for 12h; Stage #2: With sodium hydroxide for 0.666667h; Reflux; | |
Stage #1: 1,3-thiazole-2-carboxylic acid; 4-methylthiosemicarbazide With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate; N,N-dimethyl-formamide at 0 - 20℃; Stage #2: With sodium hydroxide In ethyl acetate; N,N-dimethyl-formamide at 70℃; |
1,3-thiazole-2-carboxylic acid
ethyl 5-methyl-3-oxo-2-(thiazole-2-carboxamido)hexanoate
Conditions | Yield |
---|---|
Stage #1: C9H17NO3*2ClH With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide for 0.166667h; Stage #2: 1,3-thiazole-2-carboxylic acid With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; | 59% |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h; | 57% |
1,3-thiazole-2-carboxylic acid
(S)-3-[3-(4-fluoro-phenyl)-[1,2,4]oxadiazol-5-yl]-piperidine
Conditions | Yield |
---|---|
With 1-hydroxy-7-aza-benzotriazole; PS-DCC; N-ethyl-N,N-diisopropylamine In dichloromethane | 55% |
1,3-thiazole-2-carboxylic acid
water
zinc(II) acetate dihydrate
bis(κ2-N,O-thiazole-2-carboxylate)diaquazinc(II)
Conditions | Yield |
---|---|
In water High Pressure; metal:thiazole=2:1 molar ratio, heated at 90°C for 24 h; slowly cooled overnight, crysts. washed (ethanol), dried (N2 stream, room temp.); elem. anal., single cryst. XRD, TGA; | 55% |
1,3-thiazole-2-carboxylic acid
2-phenyl-1,3-benzothiazol-5-amine
Conditions | Yield |
---|---|
Stage #1: 1,3-thiazole-2-carboxylic acid With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In tetrahydrofuran at 20℃; for 1.5h; Stage #2: 2-phenyl-1,3-benzothiazol-5-amine In tetrahydrofuran | 55% |
Stage #1: 1,3-thiazole-2-carboxylic acid With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In tetrahydrofuran at 20℃; for 1.5h; Stage #2: 2-phenyl-1,3-benzothiazol-5-amine In tetrahydrofuran | 55% |
1,3-thiazole-2-carboxylic acid
N1-(1,2,3,4-tetrahydroacridin-9-yl)hexane-1,6-diamine
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 12h; | 55% |
IUPAC Name: 1,3-Thiazole-2-carboxylic acid
Synonyms of Thiazole-2-carboxylic acid (CAS NO.14190-59-1): 1,3-Thiazole-2-carboxylic acid ; 2-Thiazolecarboxylic acid,thiazole-2-carboxylic acid
CAS NO: 14190-59-1
Molecular Formula: C4H3NO2S
Molecular Weight: 129.1371
Molecular Structure:
Melting Point: 91.6-93°C
ProductCategories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts ; Thiazole series ; Carboxylic Acids ; Thiazoles, Isothiazoles &Benzothiazoles ; Carboxylic Acids ; Thiazoles, Isothiazoles & Benzothiazoles
Polar Surface Area: 67.43 Å2
Index of Refraction: 1.617
Molar Refractivity: 29.65 cm3
Molar Volume: 84.6 cm3
Surface Tension: 72 dyne/cm
Density of Thiazole-2-carboxylic acid (CAS NO.14190-59-1): 1.525 g/cm3
Flash Point: 141.6 °C
Enthalpy of Vaporization: 58.22 kJ/mol
Boiling Point: 310.6 °C at 760 mmHg
Vapour Pressure: 0.000256 mmHg at 25°C
Risk Statements of Thiazole-2-carboxylic acid (CAS NO.14190-59-1): 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements 26-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
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