38076-80-1

Basic information

• Product Name: 5-Chloro-2-hydroxynicotinic acid
• Synonyms: BUTTPARK 43\57-84;5-CHLORO-2-HYDROXYNICOTINIC ACID;5-CHLORO-2-HYDROXYPYRIDINE-3-CARBOXYLIC ACID;5-chloro-2-hydroxy-3-pyridinecarboxylic acid;clioqinol;5-Chloro-2-hydroxynicotinic acid 97+%;5-chloro-2-hydroxynicotinic;5-Chloro-2-hydroxypyridine-3-carboxylic acid, 3-Carboxy-5-chloro-2-hydroxypyridine
• CAS NO: 38076-80-1
• Molecular Formula: C₆H₄ClNO₃
• Molecular Weight: 173.55
• Product Categories: Pyridine
• Mol File: 38076-80-1.mol

Chemical Properties

• Melting Point: 260 °C
• Boiling Point: 343.8 °C at 760 mmHg
• Flash Point: 161.7 °C
• Appearance: Solid
• Density: 1.62 g/cm³
• Vapor Pressure: 1.23E-05mmHg at 25°C
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 5-Chloro-2-hydroxynicotinic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloro-2-hydroxynicotinic acid(38076-80-1)
• EPA Substance Registry System: 5-Chloro-2-hydroxynicotinic acid(38076-80-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-37/39-37
• HazardClass: IRRITANT
• Hazardous Substances Data: 38076-80-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthetic Communications, 19, p. 553, 1989 DOI: 10.1080/00397918908050699

InChI:InChI=1/C6H4ClNO3/c7-3-1-4(6(10)11)5(9)8-2-3/h1-2H,(H,8,9)(H,10,11)/p-1

Upstream product

• 609-71-2 2-hydroxy-3-carboxypyridine 
• 108-20-3 di-isopropyl ether 
• 5437-33-2 3,5-Dichloro-2-pyridinol 

Downstream Products

• 67754-03-4 methyl 2,5-dichloronicotinate 
• 148065-10-5 ethyl 5-chloro-2-chloronicotinate 
• 648421-99-2 5-chloro-3-[(3-methyl-1-piperidinyl)carbonyl]-2-pyridinol 
• 882679-04-1 methyl 5-chloro-1-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate 
• 157361-96-1 methyl-5-chloro-2-propylaminonicotinate 
• 78686-87-0 2,5-dichloronicotinoyl chloride 
• 59782-85-3 2,5-dichloronicotinic acid 

Relevant articles and documents

SUBSTITUTED NAPHTHYRIDINE DERIVATIVES AS INHIBITORS OF MACROPHAGE MIGRATION INHIBITORY FACTOR AND THEIR USE IN THE TREATMENT OF HUMAN DISEASES

Inhibitors of MIF having a naphthyridine backbone are provided which have utility in the treatment of a variety of disorders, including the treatment of pathological conditions associated with MIF activity. The inhibitors of MIF have the following structures: (Ia), (Ib), (Ic), (Id) including stereoisomers, prodrugs and pharmaceutically acceptable salts thereof, wherein n, R, R1, R2, X, Y and Z are as defined herein. Compositions containing an inhibitor of MIF in combination with a pharmaceutically acceptable carrier are also provided, as well as methods for use of the same.

2-(Alkylamino)nicotinic Acid and Analogs. Potent Angiotensin II Antagonists

A series of pyridines and other six-membered ring heterocycles connected to a biphenyltetrazole with a-CH2-NR'-link (1) were discovered to be potent angiotensin II antagonists.In the pyrimidine carboxylic acid series (W = CR, X = N, Y = CH, Z = COOH), compounds with an alkyl group (R') on the exocyclic nitrogen were much more potent than compounds with an alkyl group (R) on the heterocyclic ring.The corresponding pyridine, pyridazine, pyrazine, and 1,2,4-triazine carboxylic acids also showed potent in vitro angiotensin II antagonism.The pyridine (W, X, Y = CH, Z = COOH, R' = n-C3H7) demonstrated potent in vitro activity (pA2 = 10.10, rabbit aorta, and Ki = 0.61 nM, receptor binding in rat liver) as well as exceptional oral antihypertensive activity and bioavailability.Any nonacidic replacement for the carboxylic acid was detrimental for activity.

Process for the preparation of 5-chloro and 5-bromo-2-hydroxynicotinic acids

A process for the preparation of 5-halo-2-hydroxynicotinic acids having the formula: STR1 wherein X is chlorine or bromine, Y and Z are selected from hydrogen, loweralkyl or loweralkyl, is described wherein a corresponding 2-hydroxynicotinic acid is halogenated with alkali-metal hypohalite in a strongly alkaline solution pH 12 and above. Certain aspects of the isolation of the product are directed to avoiding replacement of the carboxy group with halogen.

HALOGENATION OF 2-HYDROXYNICOTINIC ACID

A convenient method to prepare 5-halo-2-hydroxynicotinic acid is described.