2-Phenylindole

Synonym(s):NSC 15776;Stabilizer I

CAS NO.：948-65-2
Empirical Formula: C14H11N
Molecular Weight: 193.24
MDL number: MFCD00005608
EINECS: 213-436-3
SAFETY DATA SHEET (SDS)
Update Date: 2024-08-24 19:19:26

What is 2-Phenylindole?

Chemical properties

off-white to beige or slightly green powder

The Uses of 2-Phenylindole

Reactant for preparation of: • ;Oxopyrrolidine analogs via iodine-catalyzed Markovnikov addition1• ;Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators2• ;Organic light emitting diodes (OLEDs)3• ;Anti inflammatory agents4• ;Potential cyclooxygenase-1 (COX-1)/cyclooxygenase-2 (COX-2) inhibitors5• ;Agents for cancer and malaria therapy6• ;Antifungal and antibacterial agents7• ;Fluorescent probes8Reactant in:• ;Difluorohydroxylation reactions†• ;Mannich-type reactions†

The Uses of 2-Phenylindole

Phenylindole is a stabilizer in PVC-plastic products (α-phenylindole).

The Uses of 2-Phenylindole

Reactant for preparation of:

Oxopyrrolidine analogs via iodine-catalyzed Markovnikov addition
Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators
Organic light emitting diodes (OLEDs)
Anti inflammatory agents
Potential cyclooxygenase-1 (COX-1)/cyclooxygenase-2 (COX-2) inhibitors
Agents for cancer and malaria therapy
Antifungal and antibacterial agents
Fluorescent probes

Reactant in:

Difluorohydroxylation reactions?
Mannich-type reactions?

What are the applications of Application

2-Phenylindole is a reactant in difluorohydroxylation reactions

Preparation

2-phenylindole is prepared by condensing phenylhydrazine and acetophenone, and then closing the ring in the presence of zinc chloride. or it can be prepared by heating bromoacetophenone with excess aniline, or heating N-(2-methylphenyl)benzamide and sodium ethoxide at 360-380℃ in isolation from air.

Definition

ChEBI: 2-phenyl-1H-indole is a phenylindole.

Synthesis Reference(s)

Tetrahedron Letters, 33, p. 1459, 1992 DOI: 10.1016/S0040-4039(00)91646-0
Journal of Heterocyclic Chemistry, 29, p. 1085, 1992 DOI: 10.1002/jhet.5570290509

Properties of 2-Phenylindole

Melting point:	188-190 °C (lit.)
Boiling point:	250 °C/10 mmHg (lit.)
Density	1.1061 (rough estimate)
refractive index	1.5850 (estimate)
Flash point:	250°C/10mm
storage temp.	Sealed in dry,Room Temperature
solubility	almost transparency in Methanol
pka	16.80±0.30(Predicted)
form	Powder
color	Off-white to beige or slightly green
CAS DataBase Reference	948-65-2(CAS DataBase Reference)
NIST Chemistry Reference	1H-Indole, 2-phenyl-(948-65-2)
EPA Substance Registry System	1H-Indole, 2-phenyl- (948-65-2)

Safety information for 2-Phenylindole

Signal word	Danger
Pictogram(s)	Corrosion Corrosives GHS05 Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H318:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation H413:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes	P273:Avoid release to the environment. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water.