Indole-4-carboxaldehyde
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Basic information
- CAS
1074-86-8- Standard SMILES
O=Cc1cccc2[nH]ccc12- InChIKey
JFDDFGLNZWNJTK-UHFFFAOYSA-N- Molecular formula
- C9H7NO
- Average molar mass
- 145.16 g/mol
- Monoisotopic mass
- 145.05276384
Overview
Indole-4-carbaldehyde is a heteroarenecarbaldehyde that is indole in which the hydrogen at position 4 has been replaced by a formyl group. It has a role as an algal metabolite. It is a member of indoles and a heteroarenecarbaldehyde.
Names & identifiers
- Preferred name
- Indole-4-carboxaldehyde
- IUPAC
- 1H-indole-4-carbaldehyde
- English name
- Indole-4-carboxaldehyde
- Molecular formula
- C9H7NO
- Molecular weight
- 145.16
Names & synonyms
Indole-4-carboxaldehyde1074-86-81H-Indole-4-carbaldehydeindole-4-carbaldehydeCHEBI:143235DTXSID40318838RefChem:148200DTXCID30269961625-162-5JFDDFGLNZWNJTK-UHFFFAOYSA-N4-Formylindole1H-Indole-4-carboxaldehyde
Show more names
4-FLUOROINDOLENSC 337264e-4-carboxaLRARECHEM AH BS 0110
4-Indole-carboxaldehydeMFCD016322214-Indolecarbaldehyde4-Formyl-1H-indole1H-indol-4-carbaldehyde4-formylindolINDOLE-4-ALDEHYDENSC337264
Database identifiers
- CAS
1074-86-8- PubChem CID
- 333703
- DTXSID
DTXSID40318838- ChEBI
CHEBI:143235- EC Number
- 625-162-5
- Nikkaji
- J1.412.229J
Properties
Computed structural propertiesFilling in
- XLogP
- 2.2
- Topological polar surface area
- 32.9 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 1
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 158
Physicochemical properties
- Melting point
- 139 · 139-143 °C(lit.)
- Boiling point
- 339.1 · 339.1±15.0 °C(Predicted)
- Density
- 1.278 · 1.278±0.06 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- 10 mg/ml; · DMF: 10 mg/ml; DMSO: 3 mg/ml; Ethanol: 10 mg/ml; Ethanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
- pka
- 15.84 · 15.84±0.30(Predicted)
- form
- powder to crystal
- color
- Light yellow to Brown
- Water Solubility
- Soluble in ethanol and acetone. Insoluble in water.
- Sensitive
- Air Sensitive
- InChI
- InChI=1S/C9H7NO/c11-6-7-2-1-3-9-8(7)4-5-10-9/h1-6,10H
- InChIKey
- JFDDFGLNZWNJTK-UHFFFAOYSA-N
- SMILES
- N1C2=C(C(C=O)=CC=C2)C=C1
- CAS DataBase Reference
- 1074 · 1074-86-8(CAS DataBase Reference)
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
Warning
H302 (86%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 50 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (86%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 3
- hs_code
- 2933399090
- risk_code
- 22-36-43
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,Xi
- hazard_note
- Irritant/Keep Cold
- safety_code
- 26-36/37
- hazard_class
- IRRITANT
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H317-H319
- Hazard Classifications
- Acute Tox. 4 OralEye Irrit. 2Skin Sens. 1
- Precautionary statements
- P280-P301+P312+P330-P302+P352-P305+P351+P338
Chemistry & industry
Applications
Uses4-Indolecarbaldehyde is a synthetic intermediate used for pharmaceutical synthesis. Also used as reactant in Biginelli reaction, synthesis of aurora kinase A inhibitors, preparation of antitumor agents, intermolecular Friedel-Crafts acylation, preparation of inhibitors of cell division in E. coli and synthesis of Hantzsch pyridine-containing Schiff bases.
UsesIndole-4-carboxaldehyde is usually used as reactant in Biginelli reaction,preparation of antitumor agents,intramolecular Friedel-Crafts acylation,preparation of inhibitors of cell division in E. Coli,synthesis of Hantzsch pyridine-containing Schiff bases.
General DescriptionIndole-4-carboxaldehyde participates in the synthesis of arcyriacyanin A. Synthesis of 4-indole-4-carboxaldehyde has been reported. Intramolecular Friedel-Crafts (FC) acylation of indole-4-carboxaldehyde has been reported.
Upstream & downstream products
Upstream raw materials
Related reactions
158 records
Compound notes
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