Cas no 102735-84-2 (5-Chloro-1H-indazole-3-carbaldehyde)

5-Chloro-1H-indazole-3-carbaldehyde is a versatile heterocyclic building block widely used in organic synthesis and pharmaceutical research. The compound features a reactive aldehyde group at the 3-position of the indazole core, enabling diverse functionalization through condensation, nucleophilic addition, or cyclization reactions. The chloro substituent at the 5-position enhances its utility in further derivatization via cross-coupling or substitution reactions. This high-purity intermediate is particularly valuable in the development of biologically active molecules, including kinase inhibitors and other therapeutic agents. Its well-defined structure and stability under standard handling conditions make it a reliable choice for medicinal chemistry and material science applications.

5-Chloro-1H-indazole-3-carbaldehyde structure

102735-84-2 structure

Product Name:5-Chloro-1H-indazole-3-carbaldehyde

CAS No:102735-84-2

MF:C₈H₅ClN₂O

MW:180.59110045433

MDL:MFCD07781535

CID:62314

PubChem ID:22055864

Update Time:2025-05-26

5-Chloro-1H-indazole-3-carbaldehyde Chemical and Physical Properties

Names and Identifiers

- 5-Chloro-1H-indazole-3-carbaldehyde
- 5-CHLORO INDAZOLE-3-CARBOXALDEHYDE
- 5-chloro-2H-indazole-3-carbaldehyde
- 1H-Indazole-3-carboxaldehyde,5-chloro
- 5-CHLORO-3-(1H)INDAZOLE CARBOXALDEHYDE
- 5-Chloro-3-(1H)indazole
- 1H-Indazole-3-carboxaldehyde, 5-chloro-
- 5-Chloro-1H-indazole-3-carbaldehyde ,97%
- 1H-Indazole-3-carboxaldehyde,5-chloro-
- AK111418
- 5-Chloroindazole-3-carboxaldehyde
- PubChem7807
- XQELXOTYHCBYAI-UHFFFAOYSA-N
- FCH857313
- RP24193
- AB42684
- 5-chloro-2H-indazole-3-carboxaldehyde
- 5-chloranyl-2H-indazole-3-carbaldehyde
- 5-Chloroindazole-3-carbaldehyde
- AC-15051
- EN300-268712
- MFCD07781535
- AM20120490
- J-517227
- SY058264
- 102735-84-2
- DTXSID00622089
- DS-5220
- 5-CHLORO-1H-INDAZOLE-3-CARBOXALDEHYDE
- A800609
- SCHEMBL3541493
- AKOS006284428
- FT-0654004
- MDL： MFCD07781535
- Inchi： 1S/C8H5ClN2O/c9-5-1-2-7-6(3-5)8(4-12)11-10-7/h1-4H,(H,10,11)
- InChI Key： XQELXOTYHCBYAI-UHFFFAOYSA-N
- SMILES： ClC1C=CC2C(C=1)=C(C=O)NN=2

Computed Properties

Exact Mass: 180.00900
Monoisotopic Mass: 180.009
Isotope Atom Count: 0
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 2
Heavy Atom Count: 12
Rotatable Bond Count: 1
Complexity: 188
Covalently-Bonded Unit Count: 1
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count : 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Topological Polar Surface Area: 45.8
XLogP3: 2

Experimental Properties

Density: 1.521
Boiling Point: 391.7±22.0°C at 760 mmHg
Flash Point: 190.691 °C
Refractive Index: 1.748
PSA: 45.75000
LogP: 2.02880

5-Chloro-1H-indazole-3-carbaldehyde Security Information

Signal Word：Warning
Hazard Statement： H302
Warning Statement： P280-P305+P351+P338
Storage Condition：Inert atmosphere,2-8°C

5-Chloro-1H-indazole-3-carbaldehyde Customs Data

HS CODE：2933990090
Customs Data：

China Customs Code:
2933990090

Overview:

2933990090. Other heterocyclic compounds containing only nitrogen heteroatoms. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

Declaration elements:

Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

Summary:

2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

5-Chloro-1H-indazole-3-carbaldehyde Pricemore >>

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5-Chloro-1H-indazole-3-carbaldehyde Suppliers

Amadis Chemical Company Limited

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Audited Supplier

(CAS:102735-84-2)5-Chloro-1H-indazole-3-carbaldehyde

Order Number:A800609

Stock Status:in Stock

Quantity:5g

Purity:99%

Pricing Information Last Updated:Friday, 30 August 2024 04:36

Price ($):432.0

Email:[email protected]

Product Official Link

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Related Categories

Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzopyrazoles Indazoles

Additional information on 5-Chloro-1H-indazole-3-carbaldehyde

Research Brief on 5-Chloro-1H-indazole-3-carbaldehyde (CAS: 102735-84-2) in Chemical Biology and Pharmaceutical Applications

5-Chloro-1H-indazole-3-carbaldehyde (CAS: 102735-84-2) is a key intermediate in the synthesis of various biologically active compounds, particularly in the development of kinase inhibitors and anticancer agents. Recent studies have highlighted its versatility as a building block in medicinal chemistry, owing to its reactive aldehyde group and indazole core, which facilitate diverse chemical modifications. This research brief consolidates the latest findings on its applications, synthetic methodologies, and biological evaluations.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the use of 5-Chloro-1H-indazole-3-carbaldehyde in the design of novel Bruton's tyrosine kinase (BTK) inhibitors. The compound served as a precursor for the introduction of electrophilic warheads, enabling covalent binding to BTK's active site. The resulting inhibitors exhibited nanomolar potency in B-cell lymphoma models, with improved selectivity profiles compared to first-generation inhibitors like ibrutinib. This underscores its potential in targeted cancer therapies.

Advances in synthetic routes have also been reported. A green chemistry approach utilizing microwave-assisted synthesis (Organic Process Research & Development, 2024) reduced the reaction time of 5-Chloro-1H-indazole-3-carbaldehyde production by 60%, achieving yields >85% with minimal byproducts. This method emphasizes sustainability while maintaining scalability for industrial applications.

In neurodegenerative research, derivatives of 5-Chloro-1H-indazole-3-carbaldehyde have shown promise as tau protein aggregation inhibitors (ACS Chemical Neuroscience, 2023). Structure-activity relationship (SAR) studies revealed that chloro-substitution at the 5-position enhances blood-brain barrier permeability, making it a valuable scaffold for Alzheimer's disease drug candidates.

Ongoing clinical trials (Phase I/II) by several biopharmaceutical companies are investigating indazole-based compounds derived from this aldehyde for inflammatory diseases. Preliminary data suggest potent IL-17 pathway modulation, with potential applications in psoriasis and rheumatoid arthritis.

In conclusion, 5-Chloro-1H-indazole-3-carbaldehyde continues to be a pivotal structure in drug discovery, with emerging roles in oncology, CNS disorders, and immunology. Future research directions include exploring its utility in PROTAC design and as a fluorescent probe for cellular imaging.

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