2-Phenylindole
Basic information
- CAS
948-65-2- Standard SMILES
c1ccc(-c2cc3ccccc3[nH]2)cc1- InChIKey
KLLLJCACIRKBDT-UHFFFAOYSA-N- Molecular formula
- C14H11N
- Average molar mass
- 193.24 g/mol
- Monoisotopic mass
- 193.08914936
Overview
2-phenyl-1H-indole is a phenylindole.
Names & identifiers
- Preferred name
- 2-Phenylindole
- IUPAC
- 2-phenyl-1H-indole
- English name
- 2-Phenylindole
- Molecular formula
- C14H11N
- Molecular weight
- 193.24
Names & synonyms
2-Phenylindole2-PHENYL-1H-INDOLE948-65-21H-Indole, 2-phenyl-Indole, 2-phenyl-Stabilizer Ialpha-PhenylindoleMQD44HV3P1NSC-15776DTXSID80613431H-Indole, 2-phenylRefChem:89089
Show more names
1H-Indole,2-phenyl-NSC 15776stabilizeri-PhenylindoleA-PHENYLINDOLa-Phenylindole2-phenyl-indol
DTXCID3048940213-436-3PhenylindoleMFCD000056082-PHENYL INDOLE.alpha.-Phenylindole2-phenylindolTimTec1_005424
Database identifiers
- CAS
948-65-2- PubChem CID
- 13698
- DTXSID
DTXSID8061343- ChEMBL
CHEMBL75756- ChEBI
CHEBI:113541- UNII
- MQD44HV3P1
- EC Number
- 213-436-3
- Nikkaji
- J36.864D
Properties
Computed structural properties
- XLogP
- 3.8
- Topological polar surface area
- 15.8 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 1
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 207
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Indoles
SpringerMaterials PropertiesLuminescence
Solubility0.7 [ug/mL] (The mean of the results at pH 7.4)
Physical DescriptionPowder; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 188 · 188-190 °C (lit.)
- Boiling point
- 250 °C/10 · 250 °C/10 mmHg (lit.)
- Density
- 1.1061 · 1.1061 (rough estimate)
- refractive index
- 1.585 · 1.5850 (estimate)
- Flash point
- 250 °C/10mm · 250°C/10mm
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- almost transparency in Methanol
- form
- Powder
- pka
- 16.8 · 16.80±0.30(Predicted)
- color
- Off-white to beige or slightly green
- InChI
- 1S/C14H11N/c1-2-6-11(7-3-1)14-10-12-8-4-5-9-13(12)15-14/h1-10,15H
- InChIKey
- KLLLJCACIRKBDT-UHFFFAOYSA-N
- SMILES
- c1ccc(cc1)-c2cc3ccccc3[nH]2
- CAS DataBase Reference
- 948 · 948-65-2(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 44 HV3P1 · MQD44HV3P1
- NIST Chemistry Reference
- 1 H-Indole, · 1H-Indole, 2-phenyl-(948-65-2)
- EPA Substance Registry System
- 1 H-Indole, · 1H-Indole, 2-phenyl- (948-65-2)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05,GHS07
- Signal word
- Danger
- Hazard statements
- 315 · H315-H318-H335-H413
- Precautionary statements
- 273 · P273-P280-P302+P352-P305+P351+P338+P310
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 37 · 37/38-41
- Safety Statements
- 26 · 26-39
- WGK Germany
- 3 · 3
- RTECS
- 1272500 · NM1272500
- TSCA
- TSCA listed
- HS Code
- 29309090 · 29309090
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 1 Skin · Eye Dam. 1Skin Irrit. 2STOT SE 3
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 2.2% (1 of 45) of reports.
Danger
H315 (93.3%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 45 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationChemical: 1H-Indole, 2-phenyl-
Hazards SummaryMay cause irritation; [Alfa Aesar MSDS] See 3-Methylindole.
Hazard Classes and CategoriesSkin Irrit. 2 (93.3%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- NM1272500
- hs_code
- 29309090
- risk_code
- 37/38-41
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07
- hazard_code
- Xi
- safety_code
- 26-39
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H318-H335-H413
- Hazard Classifications
- Eye Dam. 1Skin Irrit. 2STOT SE 3
- Precautionary statements
- P273-P280-P302+P352-P305+P351+P338+P310
Chemistry & industry
Uses & manufacturing
General Manufacturing Information1H-Indole, 2-phenyl-: ACTIVE
Applications
UsesReactant 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†
UsesPhenylindole is a stabilizer in PVC-plastic products (α-phenylindole).
UsesReactant for preparation of: Oxopyrrolidine analogs via iodine-catalyzed Markovnikov additionTryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulatorsOrganic light emitting diodes (OLEDs)Anti inflammatory agentsPotential cyclooxygenase-1 (COX-1)/cyclooxygenase-2 (COX-2) inhibitorsAgents for cancer and malaria therapyAntifungal and antibacterial agentsFluorescent probesReactant in:Difluorohydroxylation reactionsMannich-type reactions
Preparation methods
Preparation2-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.
Upstream & downstream products
Upstream raw materials
Downstream products
Additional notes
DefinitionChEBI: 2-phenyl-1H-indole is a phenylindole.
Related reactions
70 records
Compound notes
Loading…