3-Formyl-2-methylindole (HCID 73166)

Names & identifiers

Preferred name: 3-Formyl-2-methylindole
IUPAC: 2-methyl-1H-indole-3-carbaldehyde
English name: 2-Methylindole-3-carboxaldehyde
Molecular formula: C10H9NO
Molecular weight: 159.18

Names & synonyms

5416-80-82-Methyl-1H-indole-3-carbaldehyde2-Methylindole-3-carboxaldehyde3-Formyl-2-methylindole2-Methyl-3-formylindole1H-Indole-3-carboxaldehyde, 2-methyl-Indole-3-carboxaldehyde, 2-methyl-R0Y4EK4FX7EINECS 226-512-6NSC 11895NSC-118952-Methyl-1H-indole-3-carboxaldehyde

Show more names

AKOS 233-93AURORA KA-4266AKOS JY2083591AKOS BBS-00000868OTAVA-BB BB01274417362-Methyl-3-formyl-1H-indole

DTXSID1063853RefChem:502048DTXCID8041614Indole-3-carboxaldehyde, 2-methyl-(8CI)226-512-6MFCD000120772-methylindole-3-carbaldehydeNSC11895

Database identifiers

CAS: 5416-80-8
PubChem CID: 73166
DTXSID: DTXSID1063853
UNII: R0Y4EK4FX7
EC Number: 226-512-6
Nikkaji: J36.865B

Properties

Computed structural properties

XLogP: 1.9
Topological polar surface area: 32.9 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 1
Rotatable bonds: 1
Heavy atoms: 12
Formal charge: 0
Complexity: 181

Physicochemical properties

Melting point: 200 · 200-201 °C (lit.)
Boiling point: 344.3 · 344.3±22.0 °C(Predicted)
Density: 1.226 · 1.226±0.06 g/cm3(Predicted)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
solubility: soluble in Methanol
pka: 16.08 · 16.08±0.30(Predicted)
form: 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 · 5416-80-8(CAS DataBase Reference)
FDA UNII: 0 Y4EK4FX7 · R0Y4EK4FX7
EPA Substance Registry System: 1 H-Indole-3-carboxaldehyde, · 1H-Indole-3-carboxaldehyde, 2-methyl- (5416-80-8)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 261 · P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
target organs: Respiratory system
Hazard Codes: Xi,Xn
Risk Statements: 36 · 36/37/38-22
Safety Statements: 37 · 37/39-26
WGK Germany: 3 · 3
TSCA: TSCA listed
HazardClass: IRRITANT
HS Code: 29339900 · 29339900
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 4 OralEye · Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (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 information

Hazard Classes and CategoriesAcute Tox. 4 (92.9%)

Safety data

wgk: 3
tsca: TSCA listed
hs_code: 29339900
risk_code: 36/37/38-22
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi,Xn
safety_code: 37/39-26
hazard_class: IRRITANT
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H302-H315-H319-H335
Hazard Classifications: Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P270-P301+P312-P302+P352-P305+P351+P338

Chemistry & industry

Uses & manufacturing

General Manufacturing Information1H-Indole-3-carboxaldehyde, 2-methyl-: INACTIVE

Applications · 3 items

UsesReactant 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

UsesReactant 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 DescriptionOxidative activation of 2-methylindole-3-carboxaldehyde via N-heterocyclic carbene organocatalysis generates heterocyclic ortho-quinodimethane as a key intermediate.