698-26-0

Basic information

• Product Name: 5-CHLORO (1H)INDAZOLE
• Synonyms: 1H-Indazole, 5-chloro-;5-chloro-1H-indazole(SALTDATA: FREE);5-CHLORO (1H)INDAZOLE;5-chloro-1h-indazol;5-CHLOROINDAZOLE
• CAS NO: 698-26-0
• Molecular Formula: C₇H₅ClN₂
• Molecular Weight: 152.58
• EINECS: 211-812-1
• Product Categories: pharmacetical
• Mol File: 698-26-0.mol

Chemical Properties

• Melting Point: 119-120 °C(Solv: water (7732-18-5))
• Boiling Point: 309.5 °C at 760 mmHg
• Flash Point: 169.9 °C
• Appearance: /
• Density: 1.425 g/cm³
• Vapor Pressure: 0.00116mmHg at 25°C
• Refractive Index: 1.703
• Storage Temp.: 2-8°C
• PKA: 12.81±0.40(Predicted)
• CAS DataBase Reference: 5-CHLORO (1H)INDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO (1H)INDAZOLE(698-26-0)
• EPA Substance Registry System: 5-CHLORO (1H)INDAZOLE(698-26-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• HazardClass: IRRITANT
• Hazardous Substances Data: 698-26-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Production:
5-Chloro (1H) indazole is used as a key intermediate in the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its presence in the production process is crucial for the creation of effective medications.
Used in Biochemical Research:
In the field of biochemistry, 5-chloro (1H) indazole is employed as a research compound, aiding scientists in understanding the molecular mechanisms and interactions of various biological processes. Its role in research is vital for advancing knowledge in this scientific domain.
Used in Drug Development:
5-Chloro (1H) indazole is utilized as a building block in the design and development of new drugs, with the potential to improve the efficacy and safety of existing medications. Its application in drug development is significant for the creation of innovative pharmaceutical solutions.
Used in Chemical Synthesis:
As a chemical compound, 5-chloro (1H) indazole is used in various chemical synthesis processes, allowing for the creation of a wide range of compounds with diverse applications. Its versatility in synthesis is essential for the production of various chemical products.

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

Upstream product

• 41475-06-3 tert-butyl (4-chloro-2-methylphenyl)azo sulfide 
• 95-69-2 4-chloro-2-methylbenzeneamine 
• 174265-12-4 2-bromo-5-chlorobenzaldehyde 
• 7758-89-6 copper(I) chloride 
• 19335-11-6 1H-indazol-5-ylamine 
• 13436-49-2 1-acetylindazole 
• 86991-00-6 5-chloro-1-p-nitrobenzylbenzindazole 
• 61495-07-6 N-(4-chloro-2-methylphenyl)benzamide 
• 64-19-7 acetic acid 
• 98083-43-3 1-Acetyl-5-chlorindazol 

Downstream Products

• 1334951-08-4 5-chloro-2-(4-methoxyphenyl)-2H-indazole 
• 1471251-93-0 (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-3-(pyridin-4-yl)-1H-indazol-5-yl)benzo[d]thiazol-6-yl)acetic acid 
• 351456-45-6 5-chloro-3-iodo-1H-indazole 
• 1339955-98-4 4-[5-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl]piperazin-1-carboxylic acid benzyl ester 

Relevant articles and documents

A novel copper-catalyzed, hydrazine-free synthesis of N-1 unsubstituted 1H-indazoles using stable guanylhydrazone salts as substrates

A CuI-catalyzed, hydrazine-free transformation of 2-(2-bromoarylidene)guanylhydrazone hydrochlorides using Cs2CO3 as a base and DMEDA as a ligand at 120 °C for 5 h delivers substituted 1H-indazoles with yields up to 75%. The C,N double bond configuration of the substrates was determined by NMR experiments and quantum chemical calculations. The reaction mechanism was studied using quantum chemical calculations.

Visible-Light-Mediated N-Desulfonylation of N-Heterocycles Using a Heteroleptic Copper(I) Complex as a Photocatalyst

A photoredox protocol that uses a heteroleptic Cu (I) complex, [Cu(dq)(BINAP)]BF4, has been developed for the photodeprotection of benzenesulfonyl-protected N-heterocycles. A range of substrates was examined, including indazoles, indoles, pyrazoles, and benzimidazole, featuring both electron-rich and electron-deficient substituents, giving good yields of the N-heterocycle products with broad functional group tolerance. This transformation was also found to be amenable to flow reaction conditions.

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.

Indazole compounds, pharmaceutical compositions, and methods for mediating or inhibiting cell proliferation

Indazole compounds that modulate and/or inhibit cell proliferation, such as the activity of protein kinases are described. These compounds and pharmaceutical compositions containing them are capable of mediating, e.g., kinases-dependent diseases to modulate and/or inhibit unwanted cell proliferation. The invention is also directed to the therapeutic or prophylactic use of pharmaceutical compositions containing such compounds, and to methods of treating cancer as well as other disease states associated with unwanted angiogenesis and/or cellular proliferation, such as diabetic retinopathy, neovascular glaucoma, rheumatoid arthritis, and psoriasis, by administering effective amounts of such compounds.

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.

Azoles. Part 14: On the behaviour of 5-chloro-2-nitroindazole against aliphatic and cyclic amines

The authors describe the synthesis of 5-chloro-1- (7) and 5-chloro-2-nitroindazole (5). 5 reacts with methyl, dimethyl and diethyl amine, pyrrolidine, piperidine and morpholine to form besides 5-chloro-3-nitroindazole (6) and 8 the corresponding 3-amino-5-chloroindazoles 9-12. The isomerization of 5 to 6 takes place under the influence of light and temperature too.

Phase Transfer Catalyzed Synthesis of Indazoles from o-Alkylbenzenediazonium Tetrafluoroborates

Reaction of o-methyl- and o-ethylbenzenediazonium tetrafluoroborates with two equivalents of potassium acetate and five mole percent of 18-crown-6 in ethanol-free chloroform produce indazoles in good to excellent yields.Indazoles bearing either electron-withdrawing or electron-donating substituents may be prepared.

CLEAVAGE REACTIONS USING BASIC HYDROGEN PEROXIDE. A METHOD FOR DEBLOCKING p-NITROBENZYL PROTECTED BASES AND PHENOLS

The hydrolysis of certain nitriles with basic hydrogen peroxide is accompanied by an oxidative cleavage reaction giving the lower homologue carboxylic acid.Under the same conditions, p-nitrobenzylated bases and phenols yield the corresponding N-H base or phenol respectively.

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.