3-Formyl-2-methylindole
2-METHYL-3-FORMYLINDOLE · 2-METHYL-1H-INDOLE-3-CARBALDEHYDE · NSC 11895 · AKOS 233-93 · AURORA KA-4266 · AKOS JY2083591 · AKOS BBS-00000868 · OTAVA-BB BB0127441736
Identifiers & Physical Properties
| CAS No. | 5416-80-8 |
|---|---|
| Molecular formula | C10H9NO |
| Average molar mass | 159.18 g/mol |
| Monoisotopic mass | 159.06841391 g/mol |
| SMILES | Cc1[nH]c2ccccc2c1C=O |
| InChIKey | CYZIVXOEJNAIBS-UHFFFAOYSA-N |
| PubChem CID | 73166 |
| EC No. | 226-512-6 |
| DTXSID | DTXSID1063853 |
Chemical & Physical Properties
| XLogP | 1.9 |
|---|---|
| Topological polar surface area | 32.9 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 1 |
| Heavy atoms | 12 |
| Formal charge | 0 |
| Complexity | 181 |
| Melting point | 200-201 °C (lit.) |
| Boiling point | 344.3±22.0 °C(Predicted) |
| Density | 1.226±0.06 g/cm3(Predicted) |
| Storage conditions | Keep in dark place,Sealed in dry,Room Temperature |
| Solubility | soluble in Methanol |
| pKa (acidity coefficient) | 16.08±0.30(Predicted) |
| Physical state | Powder |
| Color | Brown |
| InChI | 1S/C10H9NO/c1-7-9(6-12)8-4-2-3-5-10(8)11-7/h2-6,11H,1H3 |
| InChIKey | CYZIVXOEJNAIBS-UHFFFAOYSA-N |
| SMILES | Cc1[nH]c2ccccc2c1C=O |
| CAS DataBase Reference | 5416-80-8(CAS DataBase Reference) |
| FDA UNII | R0Y4EK4FX7 |
| EPA Substance Registry System | 1H-Indole-3-carboxaldehyde, 2-methyl- (5416-80-8) |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H302-H315-H319-H335 |
| GHS precautionary statements | P261-P264-P270-P301+P312-P302+P352-P305+P351+P338 |
| Target organs | Respiratory system |
| Hazard symbols | Xi,Xn |
| Risk statements (R) | 36/37/38-22 |
| Safety statements (S) | 37/39-26 |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| Hazard class | IRRITANTAcute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3 |
| Customs code | 29339900 |
| Storage class | 11 - Combustible Solids |
Safety & Regulations
| GHS classification | WarningH302 (92.9%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 42 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (92.9%) |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| Customs code | 29339900 |
| Risk statements (R) | 36/37/38-22 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi,Xn |
| Safety statements (S) | 37/39-26 |
| Hazard class | IRRITANTAcute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3 |
| Storage class | 11 - Combustible Solids |
| Target organs | Respiratory system |
| GHS hazard statements | H302-H315-H319-H335 |
| GHS precautionary statements | P261-P264-P270-P301+P312-P302+P352-P305+P351+P338 |
Applications & Uses
Uses
Reactant for preparation of:• ;Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators1• ;Fluorescent sensors (BODIPY)2• ;Antimicrobial agents against methicillin-resistant Staphylococcus aureus3• ;G protein-coupled receptor CRTh2 antagonists4• ;Inhibitors of PI3 kinase-α5• ;Antitubercular agents6• ;Anti-inflammatory agents7• ;Mycobacterium tuberculosis protein tyrosine phosphatase B8• ;Glucocorticoid receptor ligands9• ;Agents stimulating neurite outgrowth10
Uses
Reactant for preparation of:Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulatorsFluorescent sensors (BODIPY)Antimicrobial agents against methicillin-resistant Staphylococcus aureusG protein-coupled receptor CRTh2 antagonistsInhibitors of PI3 kinase-αAntitubercular agentsAnti-inflammatory agentsMycobacterium tuberculosis protein tyrosine phosphatase BGlucocorticoid receptor ligandsAgents stimulating neurite outgrowth
General Description
Oxidative activation of 2-methylindole-3-carboxaldehyde via N-heterocyclic carbene organocatalysis generates heterocyclic ortho-quinodimethane as a key intermediate.