37435-12-4

Basic information

• Product Name: 7-CHLORO-1H-INDAZOLE
• Synonyms: 7-CHLOROINDAZOLE;1H-Indazole, 7-chloro-;7-CHLORO-1H-INDAZOLE
• CAS NO: 37435-12-4
• Molecular Formula: C₇H₅ClN₂
• Molecular Weight: 152.58
• Mol File: 37435-12-4.mol

Chemical Properties

• Melting Point: 135-137
• Boiling Point: 309.536 °C at 760 mmHg
• Flash Point: 169.922 °C
• Appearance: /
• Density: 1.425 g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.703
• Storage Temp.: 2-8°C
• PKA: 11.93±0.40(Predicted)
• CAS DataBase Reference: 7-CHLORO-1H-INDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-CHLORO-1H-INDAZOLE(37435-12-4)
• EPA Substance Registry System: 7-CHLORO-1H-INDAZOLE(37435-12-4)

Safety Data

• Hazard Codes: Xi,T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN2811
• HazardClass: IRRITANT
• Hazardous Substances Data: 37435-12-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron, 50, p. 3529, 1994 DOI: 10.1016/S0040-4020(01)87030-7

InChI:InChI=1/C7H5ClN2/c8-6-3-1-2-5-4-9-10-7(5)6/h1-4H,(H,9,10)

Upstream product

• 90272-86-9 1-acetyl-7-chloro-1H-indazole 
• 85070-48-0 2-fluoro-3-chlorobenzaldehyde 
• 87-63-8 2-chloro-6-methylaniline 
• 1927-94-2 3-chlorosalicylaldehyde 

Downstream Products

• 1361332-05-9 7-chloro-3-(4-methoxyphenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole 
• 1361332-09-3 4-(7-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-3-yl)benzonitrile 
• 885522-00-9 7-chloro-3-iodo-1H-indazole 

Relevant articles and documents

INDOLE COMPOUNDS AS ANDROGEN RECEPTOR MODULATORS

Provided herein are compounds of formula (V) that bind to BF3 of an androgen receptor (AR), which can modulate the AR for the treatment of Kennedy's disease.

Synthesis, antifungal activity and qsar of novel pyrazole amides as succinate dehydrogenase inhibitors

We design and synthesize a series of novel pyrazole amides based on the commercialized fungicides and our previous work. The antifungal activity was tested in vitro by mycelial growth inhibition assay. The results show that all the compounds are of antifungal activities against the tested fungi at different levels. Among them, N-(2-(7-bromo-5-chloro-1H-indazol-1-yl)phenyl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide (Vk) exhibited higher antifungal activity than boscalid against two fungi. Molecular docking study revealed that the carbonyl oxygen atom of Vk forms two hydrogen bonds toward the hydroxyl hydrogens of TYR58 and TRP173.

4-Substituted indazoles as new inhibitors of neuronal nitric oxide synthase

A series of halo-1-H-indazoles has been synthesized and evaluated for its inhibitory activity on neuronal nitric oxide synthase. Introduction of bromine at the C4 position of the indazole ring system provided a compound almost as potent as the reference compound, that is, 7-nitroindazole (7-NI). The importance of position 4 is further demonstrated by the synthesis and pharmacological evaluation of the 4-nitroindazole which was also a potent inhibitor of NOS activity. These compounds also exhibited in vivo NOS inhibitory activity, as attested by potent antinociceptive effects following systemic administration.

An efficient synthesis of 1-H indazoles

The reaction of substituted salicyaldehydes with hydrazine hydrochloride under different conditions gave the corresponding 1-H indazoles. However, the reaction of benzaldehydes with hydrazine hydrate under the same conditions yielded only hydrazones.

New practical synthesis of indazoles via condensation of o-fluorobenzaldehydes and their O-methyloximes with hydrazine

The reaction of o-fluorobenzaldehydes and their O-methyloximes with hydrazine has been developed as a new practical synthesis of indazoles. Utilization of the methyloxime derivatives of benzaldehydes (in the form of the major E-isomers) in this condensation effectively eliminated a competitive Wolf-Kishner reduction to fluorotoluenes, which was observed in the direct preparations of indazoles from aldehydes. Reaction of Z-isomers of methyloximes with hydrazine resulted in the formation of 3-aminoindazoles via a benzonitrile intermediate.

A Novel Approach to 1H-Indazoles via Arylazosulfides

Treatment of variously substituted (o-alkylaryl)azosulfides 1a-n with potassium tert-butoxide in DMSO at room temperature smoothly furnishes 1H-indazoles 2a-n.

Aromatic Diazonium Salts, X. - A One-Pot Procedure for the Jacobson Synthesis of Indazole

Procedures are described for a one-pot synthesis of 1H-indazole and substituted indazoles 3 in good yield (Table 1) from o-toluidines 2, alkyl nitrite or nitrous oxides, potassium acetate, and acetic anhydride in benzene.The spectroscopic properties of substituted indazoles (Tables 2-4) are discussed. - 4-Phenylcinnoline (18) is prepared by the same procedure from o-(α-methylenebenzyl)aniline.