Indole-5-carboxaldehyde - ≥98% , CAS No.1196-69-6

CAS: 1196-69-6 Cat. No.: I115574 Molecular Weight: 145.16 Beilstein Registry Number: 21(5)8,267 EC Number: 627-955-1

GRADE & PURITY ≥98%

Synonyms

DTXSID20343325 | 1h-indole-5-carboxaldehyde | FT-0633462 | 1H-Indole-5-carbaldehyde | SY014625 | ADZUEEUKBYCSEY-UHFFFAOYSA- | NCGC00188180-02 | SCHEMBL97208 | F0001-0322 | Z254198328 | 1,5-Naphthalenetrisulfonic acid, 8,8'-[ureylenebis[m-phenylenecarbonyl

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

Indole-5-carboxaldehyde is used as a reactant in preparation of curcumin derivatives as anti-proliferative & anti-inflammatory agents; and in synthesis of para-para stilbenophanes by McMurry coupling. It is also used as a reactant in stereoselective synthesis of dibenzylideneacetone derivatives as β-amyloid imaging probes and in structure-based drug design of aurora kinase A inhibitors.

Specifications

Synonyms

DTXSID20343325 | 1h-indole-5-carboxaldehyde | FT-0633462 | 1H-Indole-5-carbaldehyde | SY014625 | ADZUEEUKBYCSEY-UHFFFAOYSA- | NCGC00188180-02 | SCHEMBL97208 | F0001-0322 | Z254198328 | 1, 5-Naphthalenetrisulfonic acid, 8, 8'-[ureylenebis[m-phenylenecarbonyl

Specifications & Purity

≥98%

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504759398
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504759398
• Canonical Smiles: C1=CC2=C(C=CN2)C=C1C=O
• IUPAC Name: 1H-indole-5-carbaldehyde
• InChIKey: ADZUEEUKBYCSEY-UHFFFAOYSA-N
• INCHI: 1S/C9H7NO/c11-6-7-1-2-9-8(5-7)3-4-10-9/h1-6,10H
• Isomeric SMILES: C1=CC2=C(C=CN2)C=C1C=O
• WGK Germany: 3
• Molecular Weight: 145.16
• Beilstein: 21(5)8,267
• Reaxy-Rn: 1524963
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1524963&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Indoles and derivatives
      • Subclass Indoles

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Indoles and derivatives
• Subclass: Indoles
• Intermediate Tree Nodes: Not available
• Direct Parent: Indoles
• Alternative Parents: Aryl-aldehydes Benzenoids Pyrroles Heteroaromatic compounds Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Indole - Aryl-aldehyde - Benzenoid - Heteroaromatic compound - Pyrrole - Azacycle - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Aldehyde - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as indoles. These are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

CYP2A6 Tchem Cytochrome P450 2A6 (2 Activities)

Discover Target: CYP2A6

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CYP2A6 Tchem Cytochrome P450 2A6 (2861 Activities)

Discover Target: CYP2A6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: air sensitive
• Melt Point(°C): 100-103°C
• Molecular Weight: 145.160 g/mol
• XLogP3: 1.800
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 145.053 Da
• Monoisotopic Mass: 145.053 Da
• Topological Polar Surface Area: 32.900 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 158.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Xianhong Wang, Jiuying Cui, Qinghua Gong, Lu Zheng, Dandan Liu, Guangming Nie.  (2024)  A multiple signal amplification electrochemiluminescence sensor for Hg2+ detection based on Ce2Sn2O7/poly(5-formylindole) nanocomposites.  TALANTA,      [PMID:39561617] [10.1016/j.talanta.2024.127227]

2. Junde Zhang, Yanmei Cheng, Chunhui Du, Guangming Nie.  (2025)  Co single-atom doped V2O5-x coupled with poly(5-formylindole) for high-performance electrochromic supercapacitor.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2025.167766]