Indole-3-carboxaldehyde

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Indole-3-carboxaldehyde are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Indole-3-carboxaldehyde?

The molecule Indole-3-carboxaldehyde presents a molecular formula of C9H7NO and its IUPAC name is 1H-indole-3-carbaldehyde.

Indole-3-carboxaldehyde, also known as 3-indolealdehyde or 3-formylindole, is a white, crystalline solid with a pungent, musty odor..

Indole-3-carboxaldehyde is an intermediate in the synthesis of a variety of compounds, including fragrances, dyes, and pharmaceuticals. It is also used as a reagent in chemical reactions, such as the preparation of indoles, a class of compounds that are widely distributed in nature and have a variety of biological activities..

One of the most important properties of indole-3-carboxaldehyde is its ability to act as a ligand, or chemical bond donor, in coordination chemistry. It forms complexes with metals, such as copper and palladium, which are used in catalytic reactions. Indole-3-carboxaldehyde is also a starting material for the synthesis of indole-3-carboxylic acid, a compound that has a wide range of applications, including the production of plasticizers and detergents..

Indole-3-carboxaldehyde is a highly reactive compound and should be handled with caution. It can cause skin irritation and is toxic if ingested or inhaled. It should be stored in a cool, dry place, away from heat and ignition sources..

Summary

From all the above, this molecule is a chemical compound with a wide range of uses in the synthesis of compounds and as a ligand in coordination chemistry. It is a highly reactive compound that should be handled with caution..

3D structure

Cartesian coordinates

Geometry of Indole-3-carboxaldehyde in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Indole-3-carboxaldehyde OLNJUISKUQQNIM-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Indole-3-carboxaldehyde

 

Molecule descriptors

 
IUPAC name1H-indole-3-carbaldehyde
InChI codeInChI=1S/C9H7NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-6,10H
InChI KeyOLNJUISKUQQNIM-UHFFFAOYSA-N
SMILESc1ccc2c(c1)c(c[nH]2)C=O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • .beta.-Indolylaldehyde
  • 1228547-52-1
  • 1H-Indole-3-carbaldehyde
  • 1H-Indole-3-carboxaldehde
  • 1H-Indole-3-carboxaldehyde
  • 1H-indole-3-aldehyde
  • 1H-indole-3-carbaldehyd
  • 1H-indole-3-carbaldehyde1H-Indole-3-carboxaldehyde487-89-8246045-99-8.beta.-IndolylaldehydeIndole-3-carbaldehydeIndole-3-carboxaldehyde57210_FLUKA129445_ALDRICHZINC00087959SBB004120BAS 07339836C084933
  • 3-Formyl-1H-indole
  • 3-Formylindol
  • 3-Formylindole
  • 3-Indolealdehyde
  • 3-Indolecarbaldehyde
  • 3-Indolecarboxaldehyde
  • 3-formyl indole
  • 3-formyl-indole
  • 3-indole aldehyde
  • 3-indolemethanal
  • 3-indolylformaldehyde
  • 487-89-8
  • 4877-89-8
  • 7FN04C32UO
  • 87I898
  • A-Indolylaldehyde
  • A827605
  • A871878
  • A897853
  • AB00443651-03
  • AC-23425
  • ACT03589
  • AG-205/01412034
  • AI3-52407
  • AM1029
  • BB 0242392
  • BCP00081
  • BDBM50182880
  • BRN 0114117
  • C08493
  • CS-W007376
  • CU-00000000108-1
  • DB-011568
  • F0918-0115
  • FT-0615872
  • FT-0652575
  • FT-0670335
  • HY-W007376
  • I-2200
  • I0027
  • I3CA
  • I3CHO
  • INDOLE-3-CARBOXALDEHYDE
  • INDOLE-3-CARBOXYALDEHYDE
  • Indol-3-aldehyde
  • Indol-3-carbaldehyd
  • Indol-3-carbaldehyde
  • Indol-3-carboxaldehyde
  • Indole-3-aldehyde
  • Indole-3-carbaldehyde
  • Indole-3-carboxaldehyde
  • Indole-3-carboxaldehyde (3-Formylindole)
  • MFCD00005622
  • NCGC00161738-01
  • NCGC00161738-02
  • NSC 10118
  • NSC-10118
  • NSC10118
  • OLNJUISKUQQNIM-UHFFFAOYSA-
  • PS-5323
  • Q27103575
  • SB14957
  • STK387546
  • b-Indolylaldehyde
  • beta-Indolylaldehyde
  • bmse000645
  • h-indole-3-carboxaldehyde
  • indole 3-carboxaldehyde
  • indole-3-carboaldehyde
  • indole-3-carboxy-aldehyde
  • indolyl-3-aldehyde

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC87959
  • UNII-7FN04C32UO
  • AKOS000119898
  • DTXSID5060069
  • CHEMBL147741
  • CHEBI:28238
  • EINECS 207-665-8
  • SCHEMBL56373

Physico-Chemical properties

IUPAC name1H-indole-3-carbaldehyde
Molecular formulaC9H7NO
Molecular weight145.16
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity43.7
LogP1.7
Topological polar surface area32.9

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.