3973-08-8

Basic information

• Product Name: 4-Thiazolecarboxylic acid
• Synonyms: 4-Thiazolecarboxylic acid 3973-8-8;1,3-Thiazole-4-Carboxylic Acid 3973-8-8;1,3-thiazole-4-carboxylic acid(SALTDATA: FREE);4-Carboxy-1,3-thiazole;NSC 195467;4-Thiazolecarboxylic acid 97%;4-Thiazolecarboxylic Acid, 97+%;3973/8/8
• CAS NO: 3973-08-8
• Molecular Formula: C₄H₃NO₂S
• Molecular Weight: 129.14
• EINECS: 1533716-785-6
• Product Categories: Thiazoles;Sulphur Derivatives;Carboxylic Acids;Thiazoles, Isothiazoles &Benzothiazoles;Carboxylic Acids;Thiazoles, Isothiazoles & Benzothiazoles;Building Blocks;Heterocyclic Building Blocks;Heterocycles;Miscellaneous Reagents;Sulfur & Selenium Compounds;blocks;Carboxes
• Mol File: 3973-08-8.mol
• Article Data: 9

Chemical Properties

• Melting Point: 195-199 °C(lit.)
• Boiling Point: 319.2 °C at 760 mmHg
• Flash Point: 146.9 °C
• Appearance: /
• Density: 1.525 g/cm³
• Vapor Pressure: 0.000143mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.57±0.10(Predicted)
• CAS DataBase Reference: 4-Thiazolecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Thiazolecarboxylic acid(3973-08-8)
• EPA Substance Registry System: 4-Thiazolecarboxylic acid(3973-08-8)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 3973-08-8(Hazardous Substances Data)

Usage

Uses

4-Thiazolecarboxylic Acid (cas# 3973-08-8) is a compound useful in organic synthesis.

InChI:InChI=1/C4H3NO2S/c6-4(7)3-1-8-2-5-3/h1-2H,(H,6,7)/p-1

Synthetic route

4-thiazolecarboxylate methyl ester (59418-09-6) → Thiazole-4-carboxylic acid (3973-08-8)

Conditions	Yield
With sodium hydroxide for 1h; Reflux;	96.1%

ethyl Bromopyruvate (70-23-5) + thiourea (17356-08-0) → Thiazole-4-carboxylic acid (3973-08-8)

Conditions	Yield
Stage #1: ethyl Bromopyruvate; thiourea In water at 40℃; for 5h; Stage #2: With hydrogenchloride; sodium nitrite In water for 2h; Temperature; Concentration;	94%

4-Methylthiazole (693-95-8) → Thiazole-4-carboxylic acid (3973-08-8)

Conditions	Yield
at 30℃; for 16h; Pseudomonas putida ATCC 33015;	80%
With potassium permanganate In water at 55℃; for 22h; Reagent/catalyst; Temperature;	70.2%

bromopyruvic acid (1113-59-3) + formamide (77287-34-4, 77287-35-5, 60100-09-6) → Thiazole-4-carboxylic acid (3973-08-8)

Conditions	Yield
Stage #1: formamide With tetraphosphorus decasulfide In tetrahydrofuran at 30℃; for 3h; Stage #2: bromopyruvic acid In tetrahydrofuran at 40 - 50℃; for 3h;	22%

1,2,3,4-tetrahydroisoquinoline (635-46-1) + thiazole 2,5-dicarboxylic acid (22358-80-1) → Thiazole-4-carboxylic acid (3973-08-8)

Conditions	Yield
at 153.9℃; Rate constant; sowie bei 164.7.Decarboxylation;

ethyl 2-bromothiazole-4-carboxylate (100367-77-9) → Thiazole-4-carboxylic acid (3973-08-8)

Conditions	Yield
With potassium hydroxide anschliessend Hydrieren an Raney-Nickel;

2-propionyl-thiazole-4-carboxylic acid (89791-92-4) → Thiazole-4-carboxylic acid (3973-08-8)

Conditions	Yield
With sulfuric acid at 180℃;

2-propionyl-thiazole-4-carboxylic acid (89791-92-4) → Thiazole-4-carboxylic acid (3973-08-8) + thiazole-2,4-dicarboxylic acid (89379-29-3)

Conditions	Yield
With sodium hydroxide; potassium permanganate

thiazole-2,4-dicarboxylic acid (89379-29-3) → Thiazole-4-carboxylic acid (3973-08-8)

Conditions	Yield
at 140 - 144℃; Decarboxylation;

thiazole 2,5-dicarboxylic acid (22358-80-1) + acetic anhydride (108-24-7) → Thiazole-4-carboxylic acid (3973-08-8)

thiazole 2,5-dicarboxylic acid (22358-80-1) → Thiazole-4-carboxylic acid (3973-08-8)

Conditions	Yield
at 180℃;

[2,4']bithiazolyl-4-carboxylic acid hydrazide (7113-13-5) → Thiazole-4-carboxylic acid (3973-08-8)

Conditions	Yield
(i) NaNO2, aq. HCl, AcOH, (ii) Ac2O, (iii) aq. HCl; Multistep reaction;

hydrogenchloride (7647-01-0) + thiazole-2,4-dicarboxylic acid (89379-29-3) → Thiazole-4-carboxylic acid (3973-08-8)

Conditions	Yield
Decarboxylation;

thiocarboxamide (115-08-2) + bromopyruvic acid (1113-59-3) → Thiazole-4-carboxylic acid (3973-08-8)

Conditions	Yield
In tetrahydrofuran at 45 - 50℃; for 5.5h;	3.59 g

ethyl thiazole-4-carboxylate (14527-43-6) → Thiazole-4-carboxylic acid (3973-08-8)

Conditions	Yield
With sodium hydroxide

amoxicillin (26787-78-0) → Thiazole-4-carboxylic acid (3973-08-8) + 5,5-Dimethyl-4,5-dihydro-thiazole-4-carboxylic acid (740742-98-7) + formic acid (64-18-6) + glycolic Acid (79-14-1) + 1,5-pentanedioic acid (110-94-1) + Adipic acid (124-04-9) + tartronic acid (80-69-3) + glyceric acid (473-81-4) + oxamic acid (471-47-6) + succinic acid (110-15-6) + C5H8O6S (1378848-02-2) + pisolithin A (15573-67-8) + C9H10N2O4 + C9H12N2O5S + C8H10N2O6S + C9H14N2O7S + C9H12N2O6S + C8H10N2O4S + C10H12N2O7S + C15H21N3O4S + C15H18N2O4S + C14H21N3O3S + C8H12N2O4S + C8H10N2O5S + C6H10O7S + C6H7NO4S + C6H11NO3S + C6H9NO3S + oxalic acid (144-62-7) + acetic acid (64-19-7) + propionic acid (802294-64-0) + 2-oxo-propionic acid (127-17-3) + tartaric acid (87-69-4) + 6-aminopenicillanic acid (551-16-6) + benzoic acid (65-85-0) + Glyoxilic acid (298-12-4) + 2-hydroxy-3-(4-hydroxyphenyl)pyrazine + 2-butenedioic acid (6915-18-0) + butyric acid (107-92-6) + (4S)-2t-{(R)-[(R)-2-amino-2-(4-hydroxy-phenyl)-acetylamino]-carboxy-methyl}-5,5-dimethyl-thiazolidine-4r-carboxylic acid (57457-65-5) + 4-hydroxy-benzoic acid (99-96-7)

Conditions	Yield
With Ru/CNT; sodium hydroxide for 8h; Reagent/catalyst; Electrolysis;

...Expand

Thiazole-4-carboxylic acid (3973-08-8) → 1,3-thiazole-4-carbonyl chloride (3745-79-7)

Conditions	Yield
With thionyl chloride for 2h; Heating / reflux;	99%
With thionyl chloride for 2h; Reflux;	80.5%
With thionyl chloride

3,4-diaminopyridine (54-96-6) + Thiazole-4-carboxylic acid (3973-08-8) → 4-(1H-imidazo[4,5-c]pyridin-2-yl)thiazole (65911-26-4)

Conditions	Yield
With PPA at 180℃; for 2h;	98%

2,3-Diaminopyridine (452-58-4) + Thiazole-4-carboxylic acid (3973-08-8) → 4-(1H-imidazo[4,5-b]pyridin-2-yl)thiazole (1848-82-4)

Conditions	Yield
With PPA at 180℃; for 2h;	97%

Thiazole-4-carboxylic acid (3973-08-8) + ethanol (64-17-5) → ethyl thiazole-4-carboxylate (14527-43-6)

Conditions	Yield
With thionyl chloride at 80℃; Cooling with ice;	96%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 5h;	87.6%

Thiazole-4-carboxylic acid (3973-08-8) + tert-butyl alcohol (75-65-0) → tert-butyl 1,3-thiazole-4-carboxylate (1037746-91-0)

Conditions	Yield
Stage #1: Thiazole-4-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 50℃; for 1h; Stage #2: tert-butyl alcohol With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 60℃; for 48h;	94%
Stage #1: Thiazole-4-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 50℃; for 1h; Inert atmosphere; Stage #2: tert-butyl alcohol With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 60℃; for 48h; Inert atmosphere;	94%

Thiazole-4-carboxylic acid (3973-08-8) + tert-butyl alcohol (75-65-0) → thiazol-4-ylaminocarboxylic acid tert-butyl ester (1235406-42-4)

Conditions	Yield
With diphenyl phosphoryl azide; triethylamine at 0℃; Reflux;	94%
With diphenyl phosphoryl azide; triethylamine In tert-butyl alcohol for 16h; Inert atmosphere; Reflux;	94%
With diphenylphosphoranyl azide; triethylamine for 18h; Curtius Rearrangement; Reflux;	77.4%

Thiazole-4-carboxylic acid (3973-08-8) + tert-butyl (2-aminothiazol-4-yl)methylcarbamate (1146084-66-3) → tert-butyl(2-(thiazole-4-carboxamido)thiazol-4-yl)methylcarbamate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	94%

methyl 2-oxo-2-phenylacetate (15206-55-0) + Thiazole-4-carboxylic acid (3973-08-8) → 2-methoxy-2-oxo-1-phenylethyl thiazole-4-carboxylate

Conditions	Yield
With phenylsilane; 2,2,3,4,4-pentamethyl-1-(pyrrolidin-1-yl)phosphetane 1-oxide In 1,2-dichloro-ethane at 80℃; for 20h; Sealed tube; chemoselective reaction;	94%

Thiazole-4-carboxylic acid (3973-08-8) + 1,2-diamino-benzene (95-54-5) → thiabendazole (148-79-8)

Conditions	Yield
Stage #1: 1,2-diamino-benzene With polyphosphoric acid at 150℃; Inert atmosphere; Stage #2: Thiazole-4-carboxylic acid at 230℃; for 2h; Reagent/catalyst; Temperature; Inert atmosphere;	88%
With polyphosphoric acid for 3h; Reflux;

Thiazole-4-carboxylic acid (3973-08-8) + 2-(4-Fluorophenyl)ethanol (7589-27-7) → 4-fluorophenethyl thiazole-4-carboxylate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 5h;	87.6%

Thiazole-4-carboxylic acid (3973-08-8) + cyclohexanol (108-93-0) → cyclohexyl thiazole-4-carboxylate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 5h;	87.49%

Thiazole-4-carboxylic acid (3973-08-8) + (S)-allyl 2-(allyloxy)-4-(2-(allyloxy)-4-(4-(2-(4-aminobenzamido)-3-cyanopropanamido)benzamido)-3-methoxybenzamido)-3-methoxybenzoate → C47H43N7O11S

Conditions	Yield
Stage #1: Thiazole-4-carboxylic acid With 2,4,6-trimethyl-pyridine; bis(trichloromethyl) carbonate In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Stage #2: (S)-allyl 2-(allyloxy)-4-(2-(allyloxy)-4-(4-(2-(4-aminobenzamido)-3-cyanopropanamido)benzamido)-3-methoxybenzamido)-3-methoxybenzoate With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 12h;	86%

Thiazole-4-carboxylic acid (3973-08-8) + 2-phenyl-2H-pyrazolo[3,4-c]quinolin-4-ylamine (298201-68-0) → C20H13N5OS (1120368-16-2)

Conditions	Yield
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃;	85%

Thiazole-4-carboxylic acid (3973-08-8) + 17β-estradiol-3-t-butyldimethylsilyl ether (57441-02-8) → C28H39NO3SSi (1083177-79-0)

Conditions	Yield
With dmap; 2-methyl-6-nitrobenzoic anhydride; triethylamine In tetrahydrofuran at 20℃; for 1h;	84%

Thiazole-4-carboxylic acid (3973-08-8) + hexan-1-amine (111-26-2) → N-hexylthiazole-4-carboxamide

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 5h;	83.7%

Thiazole-4-carboxylic acid (3973-08-8) + cyclohexyl 2-amino-2-deoxy-1-thio-α-D-glucopyranoside (479255-66-8) → cyclohexyl 2-deoxy-2-(thiazole-4-carbonylamino)-1-thio-α-D-glucopyranoside

Conditions	Yield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 0 - 23℃; for 3h;	83%

Thiazole-4-carboxylic acid (3973-08-8) + 4-chloro-3-(oxazolo[4,5-b]pyridin-2-yl)benzenamine → N-(4-chloro-3-(oxazolo[4,5-b]pyridin-2-yl)phenyl)thiazole-4-carboxamide (1448806-17-4)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 45℃; Inert atmosphere;	83%

Thiazole-4-carboxylic acid (3973-08-8) + butan-1-ol (71-36-3) → butyl thiazole-4-carboxylate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 5h;	83%

Thiazole-4-carboxylic acid (3973-08-8) → thiazole-4-carbonitrile (1452-15-9)

Conditions	Yield
Stage #1: Thiazole-4-carboxylic acid With 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; ammonium chloride Stage #2: With triethylamine; trifluoroacetic anhydride at 0 - 20℃; for 6h;	83%

Thiazole-4-carboxylic acid (3973-08-8) + 2-(3-methoxyphenyl)-1-ethanamine (2039-67-0) → N-(3-methoxyphenethyl)thiazole-4-carboxamide

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 5h;	82.4%

Thiazole-4-carboxylic acid (3973-08-8) + N-{3-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]-4-methylphenyl}-3-(1-cyano-1-methylethyl)benzamide (1092395-11-3) → N-{6-[5-({[3-(1-cyano-1-methylethyl)phenyl]carbonyl}amino)-2-methylphenoxy][1,2,4]triazolo[1,5-a]pyridin-2-yl}-1,3-thiazole-4-carboxamide (1092393-75-3)

Conditions	Yield
Stage #1: Thiazole-4-carboxylic acid With oxalyl dichloride; N,N-dimethyl-formamide In tetrahydrofuran at 20℃; for 1h; Stage #2: N-{3-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]-4-methylphenyl}-3-(1-cyano-1-methylethyl)benzamide With pyridine at 20℃; for 16h;	82%

7-azabicyclo[4.1.0]heptane (286-18-0) + Thiazole-4-carboxylic acid (3973-08-8) → 7-azabicyclo[4.1.0]heptan-7-yl(thiazol-4-yl)methanone (1372857-68-5)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere;	82%

Thiazole-4-carboxylic acid (3973-08-8) + 4-[(2S',6S')-6'-(4-((6-aminohexyl)oxy)butyl)tetrahydropyran-2-yl]-1-[(2S'',6S'')-6''-(4-hydroxybutyltetrahydropyran-2-yl)methyl]-1H-1,2,3-triazole → N-(6-(4-((2S,6S)-6-((4-((2S,6S)-6-(4-(benzyloxy)butyl)tetrahydro-2H-pyran-2-yl)-1H-1,2,3-triazol-1-yl)methyl)tetrahydro-2H-pyran-2-yl)butoxy)hexyl)thiazole-4-carboxamide

Conditions	Yield
Stage #1: Thiazole-4-carboxylic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.166667h; Stage #2: 4-[(2S',6S')-6'-(4-((6-aminohexyl)oxy)butyl)tetrahydropyran-2-yl]-1-[(2S'',6S'')-6''-(4-hydroxybutyltetrahydropyran-2-yl)methyl]-1H-1,2,3-triazole In dichloromethane at 20℃;	82%

methanol (67-56-1) + Thiazole-4-carboxylic acid (3973-08-8) → 4-thiazolecarboxylate methyl ester (59418-09-6)

Conditions	Yield
With thionyl chloride at -15℃; Reflux; Inert atmosphere;	81%
With thionyl chloride at -15℃; Inert atmosphere; Reflux;	81%
With sulfuric acid
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 5h;

Thiazole-4-carboxylic acid (3973-08-8) + propan-1-ol-3-amine (156-87-6) → 3-hydroxypropyl thiazole-4-carboxylate

Conditions	Yield
With propane-1,3-diyl dinitrite In tetrahydrofuran at 100℃; under 12929 Torr; for 0.5h;	81%

Thiazole-4-carboxylic acid (3973-08-8) + diethyl 4-(6-hydroxyhexan-2-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate → diethyl 2,6-dimethyl-4-(6-((thiazole-4-carbonyl)oxy)hexan-2-yl)-1,4-dihydropyridine-3,5-dicarboxylate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2h;	80%

Thiazole-4-carboxylic acid (3973-08-8) → thiazole-4-carbonyl azide

Conditions	Yield
Stage #1: Thiazole-4-carboxylic acid With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at 0℃; for 0.25h; Stage #2: With sodium azide In tetrahydrofuran for 0.25h;	79%

Upstream product

• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 22358-80-1 thiazole-4,5-dicarboxylic acid 
• 100367-77-9 ethyl 2-bromothiazole-4-carboxylate 
• 89791-92-4 2-propionyl-thiazole-4-carboxylic acid 
• 693-95-8 4-Methylthiazole 
• 14527-43-6 ethyl thiazole-4-carboxylate 
• 59418-09-6 4-thiazolecarboxylate methyl ester 
• 26787-78-0 amoxicillin 
• 70-23-5 ethyl Bromopyruvate 
• 17356-08-0 thiourea 
• 1113-59-3 bromopyruvic acid 
• 77287-34-4 formamide 
• 115-08-2 thiocarboxamide 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 59418-09-6 4-thiazolecarboxylate methyl ester 
• 3745-79-7 1,3-thiazole-4-carbonyl chloride 
• 1064707-06-7 N-(4-fluorobenzyl)-5-hydroxy-1-methyl-2-{1-methyl-1-[(1,3-thiazol-5-ylcarbonyl)amino]ethyl}-6-oxo-1,6-dihydropyrimidine-4-carboxamide 
• 3575-09-5 1,3-thiazole-4-carboxamide 
• 30216-60-5 thiazole-4-carboxylic acid phenyl ester 
• 93336-05-1 thiazole-4-carbothioic acid anilide 
• 88218-99-9 N-phenylthiazole-4-carboxamide 
• 214759-95-2 N-methoxy-N-methyl-1H-indole-3-carboxamide 
• 1452-15-9 thiazole-4-carbonitrile 

Relevant articles and documents

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Method for preparing thiazole-4-formic acid

The invention discloses a method for preparing thiazole-4-formic acid. By the aid of the method, the problems of relatively high prices of raw materials used in old processes for thiabendazole which is one of important traditional pesticide and bactericide varieties and low yield of the thiabendazole can be solved. The method includes steps of generating thiazolidine-4-formic acid from L-cysteinehydrochloride, formaldehyde and pyridine; carrying out reaction on the thiazolidine-4-formic acid, methyl alcohol and HCl gas to generate thiazolidine-4-methyl formate; carrying out reaction on the thiazolidine-4-methyl formate, acetonitrile and MnO2 to generate thiazole-4-methyl formate; hydrolyzing the thiazole-4-methyl formate under the effect of sodium hydroxide to obtain the thiazole-4-formicacid which is a product. The method has the advantages of simple process synthetic route, mild reaction condition, low cost, environmental protection, safety, excellent application prospect, good social benefit and high economic benefit.

Preparation method for thiazol-4-formic acid

The invention discloses a preparation method for thiazol-4-formic acid. The method comprises the following steps: uniformly mixing ethyl bromopyruvate, thiourea and water, performing ring closure reaction, then adding concentrated hydrochloric acid for uniform mixing, adding dropwise an aqueous solution of sodium nitrite, performing stirring for 1.5 to 2.5h, performing filtering, and extracting a filter cake to obtain the thiazol-4-formic acid. The method is easy to operate, low in cost and suitable for industrial production, and the raw materials are cheap and are easily to obtain; water is used as a reaction solvent, and can be reutilized, so that the method is environment-friendly and pollution-free; the yield is high, and can reach 90 percent.