13096-96-3

Basic information

• Product Name: 4-CHLORO (1H)INDAZOLE
• Synonyms: 4-CHLORO (1H)INDAZOLE;4-CHLORO-1H-INDAZOLE, 95+%;4-CHLOROINDAZOLE;1H-Indazole, 4-chloro-;4-chloro-1H-indazole(SALTDATA: FREE);4-chloro-3a,7a-dihydro-1H-indazol
• CAS NO: 13096-96-3
• Molecular Formula: C₇H₅ClN₂
• Molecular Weight: 152.58
• Product Categories: blocks;IndolesOxindoles;Halides;Fused Ring Systems
• Mol File: 13096-96-3.mol

Chemical Properties

• Melting Point: 155-157
• Boiling Point: 309.5 °C at 760 mmHg
• Flash Point: 169.9 °C
• Appearance: /Solid
• Density: 1.425 g/cm³
• Vapor Pressure: 0.00116mmHg at 25°C
• Refractive Index: 1.703
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 4-CHLORO (1H)INDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO (1H)INDAZOLE(13096-96-3)
• EPA Substance Registry System: 4-CHLORO (1H)INDAZOLE(13096-96-3)

Safety Data

• Hazard Codes: Xi,T
• Statements: 25-36
• Safety Statements: 45-26
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 13096-96-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro (1H)indazole is used as a key intermediate in the synthesis of pharmaceutical drugs for its potential antitumor and anti-inflammatory properties. It contributes to the development of new medications that can address various health conditions by modulating biological pathways associated with inflammation and tumor growth.
Used in Agrochemical Industry:
In the agrochemical sector, 4-chloro (1H)indazole is utilized as a precursor in the production of agrochemicals, potentially enhancing crop protection and yield through its incorporation into compounds that target pests and diseases.
Used in Research and Development:
4-Chloro (1H)indazole is employed as a starting material in research and development for the synthesis of novel compounds with potential therapeutic applications. Its unique structure and properties make it a valuable component in the creation of innovative chemical entities that could lead to breakthroughs in medicine and other fields.

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

Upstream product

• 40447-04-9 N-(3-chloro-2-methylphenyl)benzamide 
• 145439-15-2 N-acetyl-4-chloro-1H-indazole 
• 87-60-5 3-chloro-2-methylbenzenamine 
• 7782-77-6 cis-nitrous acid 
• 64-19-7 acetic acid 
• 387-45-1 2-chloro-6-fluorobenzaldehyde 
• 7463-35-6 N-(3-chloro-2-methylphenyl)acetamide 

Downstream Products

• 145439-15-2 N-acetyl-4-chloro-1H-indazole 
• 956388-05-9 1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole 
• 1146955-35-2 2-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole 
• 1137278-45-5 4-chloro-1-(tetrahydro-2H-pyran-2-yl)-2H-indazole 
• 1146955-34-1 4-chloro-2-(tetrahydro-2H-pyran-2-yl)-2H-indazole 
• 885521-40-4 3-bromo-4-chloro-1H-indazole 
• 1339955-95-1 4-[4-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl]piperazin-1-carboxylic acid benzyl ester 
• 932041-14-0 methyl 4-chloro-1H-indazole-3-carboxylate 

Relevant articles and documents

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.

Application of C-H Functionalization in the Development of a Concise and Convergent Route to the Phosphatidylinositol-3-kinase Delta Inhibitor Nemiralisib

This paper describes the development of an improved and scalable method for the manufacture of nemiralisib, a phosphatidylinositol-3-kinase delta inhibitor. Incorporation of three consecutive catalytic reactions, including a palladium-catalyzed C-H functionalization and an iridium-catalyzed borylation, significantly simplified and shortened the synthetic sequence. The revised route was successfully implemented in a pilot plant on a multikilogram scale to deliver >100 kg of product.

CHEMICAL COMPOUNDS

The invention is directed to certain novel compounds. Specifically, the invention is directed to compounds of formula (I): and salts thereof. The compounds of the invention are inhibitors of kinase activity, in particular PI3-kinase activity.

PROCESSES TO MAKE INDAZOLE DERIVATIVES

The present invention provides novel processes for preparing compounds of formula (IV) and salts thereof, novel intermediates,and a novel salt and polymorph thereof.

ALKYNYL ALCOHOLS AND METHODS OF USE

The invention relates to compounds of Formula (0): wherein Q, A1-A8, R4 and R5 and each has the meaning as described herein. Compounds of Formula (0) and pharmaceutical compositions thereof are useful in the treatment of diseases and disorders in which undesired or over- activation of NF-kB signaling is observed.

DIOXINO-AND OXAZIN-[2,3-D]PYRIMIDINE PI3K INHIBITOR COMPOUNDS AND METHODS OF USE

Dioxino-and oxazin-[2,3-d]pyrimidine PI3K inhibitor compounds of Formula I with anti-cancer activity, anti-in-flammatory activity, or immunoregulatory properties, and more specifically with PI3 kinase modulating or inhibitory activity are de-scribed. Methods are described for using the tricyclic PI3K inhibitor compounds of Formula I for in vitro, in situ, and in vivo diagnosis or treatment of mammalian cells, organisms, or associated pathological conditions.

A practical synthesis of a PI3K inhibitor under noncryogenic conditions via functionalization of a lithium triarylmagnesiate intermediate

We report a practical synthesis of PI3K inhibitor GDC-0941. The synthesis was achieved using a convergent approach starting from a thienopyrimidine intermediate through a sequence of formylation and reductive amination followed by Suzuki-Miyaura cross-coupling. Metalation of the thienopyrimidine intermediate involving the intermediacy of triarylmagnesiates allowed formylation under noncryogenic conditions to produce the corresponding aldehyde. We also investigated aminoalkylation via a benzotriazolyl-piperazine substrate as an alternative to the reductive amination route. We evaluated both palladium and nickel catalyzed processes for the borylation and Suzuki-Miyaura cross-coupling. Final deprotection and salt formation afforded the API.

TRICYCLIC PI3K INHIBITOR COMPOUNDS AND METHODS OF USE

Tricyclic PI3k inhibitor compounds of Formula I with anti-cancer activity, anti- inflammatory activity, or immunoregulatory properties, and more specifically with PI3 kinase modulating or inhibitory activity are described. Methods are described for using the tricyclic PI3K inhibitor compounds of Formula I for in vitro, in situ, and in vivo diagnosis or treatment of mammalian cells, organisms, or associated pathological conditions. Formula I compounds include stereoisomers, geometric isomers, tautomers, and pharmaceutically acceptable salts thereof. The dashed lines indicate an optional double bond, and at least one dashed line is a double bond. The substituents are as described.

NOVEL ANTIVIRAL COMPOUNDS

The present invention relates to a compound of formula I: or a pharmaceutically acceptable salt thereof, wherein the symbols are as defined in the specification; a pharmaceutical composition comprising the same, a method for treating or preventing a viral infection such as HIV using the same.

THIAZOLOPYRIMIDINE PI3K INHIBITOR COMPOUNDS AND METHODS OF USE

Compounds of Formulas (Ia and Ib), and including stereoisomers, geometric isomers, tautomers, solvates, metabolites and pharmaceutically acceptable salts thereof, are useful for inhibiting lipid kinases including PI3K, and for treating disorders such as cancer mediated by lipid kinases. Methods of using compounds of formula Ia and Ib for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed