Indole-4-carboxaldehyde

HCID 333703CAS 1074-86-8
Substructure searchFind similar structures

Basic information

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Indole-4-carbaldehyde is a heteroarenecarbaldehyde that is indole in which the hydrogen at position 4 has been replaced by a formyl group.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 properties

XLogP
2.2
Topological polar surface area
32.9 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
1
Heavy atoms
11

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)

Safety & regulation

GHS classification

GHS Classification · 4 items

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
29333990
risk_code
22-36-43
Signal word
Warning
Symbol(GHS)
GHS07

Chemistry & industry

Applications · 3 items

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

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
温州共赢化学有限公司+86-0086-577-64498589 +86-15355981851 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]

Additional notes

DefinitionChEBI: 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.

Related reactions

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Linked notes

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