5-Benzyloxyindole
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Basic information
- CAS
1215-59-4- Standard SMILES
c1ccc(COc2ccc3[nH]ccc3c2)cc1- InChIKey
JCQLPDZCNSVBMS-UHFFFAOYSA-N- Molecular formula
- C15H13NO
- Average molar mass
- 223.27 g/mol
- Monoisotopic mass
- 223.09971404
Names & identifiers
- Preferred name
- 5-Benzyloxyindole
- IUPAC
- 5-phenylmethoxy-1H-indole
- English name
- 5-Benzyloxyindole
- Molecular formula
- C15H13NO
- Molecular weight
- 223.27
Names & synonyms
5-Benzyloxyindole1215-59-45-(Benzyloxy)-1H-indole1H-Indole, 5-(phenylmethoxy)-Benzyloxy-5 indoleINDOLE, 5-BENZYLOXY-Indole, 5-(benzyloxy)-5-(phenylmethoxy)indoleBenzyloxy-5 indole [French]5-(Phenylmethoxy)-1H-indoleNSC 62895UNII-YCI4Z02E1C
Show more names
bredreck`s5-Benzyindole5-benzyloxy-indolBENZYLOXYINDOLE(5-)TIMTEC-BB SBB0033315-BENZYLOXY-1H-INDOLE5-Benzyloxyindole,95%
EINECS 214-930-1YCI4Z02E1CBRN 0173532NSC-62895DTXSID801532855-21-03-00019 (Beilstein Handbook Reference)BENZYL 1H-INDOL-5-YL ETHERRefChem:102057
Database identifiers
- CAS
1215-59-4- PubChem CID
- 14624
- DTXSID
DTXSID80153285- ChEMBL
CHEMBL1288719- UNII
- YCI4Z02E1C
- EC Number
- 214-930-1
- Nikkaji
- J40.604J
Properties
Computed structural propertiesFilling in
- XLogP
- 3.6
- Topological polar surface area
- 25 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 3
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 237
Physicochemical properties
- Melting point
- 100 · 100-104 °C (lit.)
- Boiling point
- 364.56 °C · 364.56°C (rough estimate)
- Density
- 1.0707 · 1.0707 (rough estimate)
- refractive index
- 1.55 · 1.5500 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- ethanol: may be hazy yellow
- form
- powder
- pka
- 16.63 · 16.63±0.30(Predicted)
- color
- white to light yellow
- BRN
- 173532 · 173532
- InChI
- InChI=1S/C15H13NO/c1-2-4-12(5-3-1)11-17-14-6-7-15-13(10-14)8-9-16-15/h1-10,16H,11H2
- InChIKey
- JCQLPDZCNSVBMS-UHFFFAOYSA-N
- SMILES
- N1C2=C(C=C(OCC3=CC=CC=C3)C=C2)C=C1
- CAS DataBase Reference
- 1215 · 1215-59-4(CAS DataBase Reference)
- FDA UNII
- 4 Z02E1C · YCI4Z02E1C
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
Danger
H228 (10%): Flammable solid [Danger Flammable solids]
P210, P240, P241, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 10 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesFlam. Sol. 1 (10%)
Safety data
- F
- 8-10
- wgk
- 3
- rtecs
- NL4850000
- hs_code
- 2933990099
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- Xi
- safety_code
- 26-24/25-22
- hazard_class
- IRRITANT
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H333-H335-H361
- Precautionary statements
- P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P201-P261-P305+P351+P338-P405-P501a
Chemistry & industry
Applications
UsesReactant in regio- and stereoselective morpholine-catalyzed direct C-3 alkenylation with α,β-unsaturated aldehydes Reactant in selective debenzylation of protective groups using SiliaCat-palladium under mild reaction conditions Reactant in metal-free Friedel-Crafts alkylation reactions Reactant in preparation of protein kinase (PKC) inhibitors Reactant in preparation of indole/quinoline carbothioic acid amide derivatives.
UsesReactant in regio- and stereoselective morpholine-catalyzed direct C-3 alkenylation with α,β-unsaturated aldehydesReactant in selective debenzylation of protective groups using SiliaCat-palladium under mild reaction conditionsReactant in metal-free Friedel-Crafts alkylation reactionsReactant in preparation of protein kinase (PKC) inhibitorsReactant in preparation of indole/quinoline carbothioic acid amide derivatives
Uses5-Benzyloxyindole is used as reagent/reactant in regioselective preparation of CF3-β-tryptamine derivatives via base-free thermal ring-opening reaction of N-nosyl-2-CF3-aziridine with indoles.
Upstream & downstream products
Upstream raw materials
Related reactions
104 records
Compound notes
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