Indole-3-carboxaldehyde

Synonym(s):3-Formylindole;Indole-3-carbaldehyde;3-Indolylformaldehyde;Indol-3-aldehyde;β-Indolylaldehyde

CAS NO.：487-89-8
Empirical Formula: C9H7NO
Molecular Weight: 145.16
MDL number: MFCD00005622
EINECS: 207-665-8
SAFETY DATA SHEET (SDS)
Update Date: 2024-11-20 17:10:30

What is Indole-3-carboxaldehyde?

Chemical properties

?Indole-3-aldehyde [487-89-8], C9H7NO, Mr 145.16, mp 194 ℃, forms colorless crystals. It is readily soluble in ethanol and slightly soluble in cold water. It can be produced by Vilsmeier reaction of indole with formylmethylaniline or with dimethylformamide and phosphorus oxychloride. Indole-3-aldehyde can be used to make D,L-tryptophan and cyanine dyes.

The Uses of Indole-3-carboxaldehyde

Indole-3-carboxaldehyde is a biochemical used to prepare analogs of the indole phytoalexin cyclobrassinin with NR1R2 group. It was also used as the starting material for the synthesis of higher order indoles including isoindolo[2,1-a]indoles, aplysinopsins, and 4-substituted-tetrahydrobenz[cd]indoles.

What are the applications of Application

Indole-3-carboxaldehyde is A biochemical used to prepare analogs of the indole phytoalexin cyclobrassinin with NR1R2 group.

Definition

ChEBI: A heteroarenecarbaldehyde that is indole in which the hydrogen at position 3 has been replaced by a formyl group.

Synthesis Reference(s)

Journal of the American Chemical Society, 68, p. 1156, 1946 DOI: 10.1021/ja01211a006
The Journal of Organic Chemistry, 60, p. 7272, 1995 DOI: 10.1021/jo00127a036
Organic Syntheses, Coll. Vol. 4, p. 539, 1963

General Description

Indole-3-carboxaldehyde can undergo Schiff bases condensation to form multifunctional silica nano-vehicles and magnetic nanoparticles.

Properties of Indole-3-carboxaldehyde

Melting point:	193-198 °C(lit.)
Boiling point:	264.27°C (rough estimate)
Density	1.1555 (rough estimate)
refractive index	1.4500 (estimate)
Flash point:	240 °C
storage temp.	Store below +30°C.
solubility	DMSO (Slightly), Methanol (Slightly)
pka	15.50±0.30(Predicted)
form	Crystalline Powder
color	Off-white to beige-brown
Water Solubility	Insoluble in water.
Sensitive	Air Sensitive
BRN	114117
Stability:	Hygroscopic
CAS DataBase Reference	487-89-8(CAS DataBase Reference)
NIST Chemistry Reference	3-Indole aldehyde(487-89-8)
EPA Substance Registry System	1H-Indole-3-carboxaldehyde (487-89-8)

Safety information for Indole-3-carboxaldehyde

Signal word	Danger
Pictogram(s)	Corrosion Corrosives GHS05 Exclamation Mark Irritant GHS07
GHS Hazard Statements	H302:Acute toxicity,oral H314:Skin corrosion/irritation
Precautionary Statement Codes	P260:Do not breathe dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P280:Wear protective gloves/protective clothing/eye protection/face protection. P363:Wash contaminated clothing before reuse. P301+P330+P331:IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. P405:Store locked up.