Basic information
- CAS
19012-03-4- Standard SMILES
Cn1cc(C=O)c2ccccc21- InChIKey
KXYBYRKRRGSZCX-UHFFFAOYSA-N- Molecular formula
- C10H9NO
- Average molar mass
- 159.18 g/mol
- Monoisotopic mass
- 159.06841391
Names & identifiers
- Preferred name
- 1-Methyl-1H-indole-3-carbaldehyde
- IUPAC
- 1-methylindole-3-carbaldehyde
- English name
- 1-Methylindole-3-carboxaldehyde
- Molecular formula
- C10H9NO
- Molecular weight
- 159.18
Names & synonyms
1-Methyl-1H-indole-3-carbaldehyde19012-03-41-Methylindole-3-carboxaldehyde1-methylindole-3-carbaldehyde1H-Indole-3-carboxaldehyde, 1-methyl-3-Formyl-1-methylindoleN-Methyl-3-formylindole1-Methyl-3-formylindoleN-Methyl-3-indolecarboxaldehydeN-Methylindole-3-carbaldehydeZ612E3VMZ5EINECS 242-750-3
Show more names
AKOS JY2082515RARECHEM AH BS 0121TIMTEC-BB SBB010057ASINEX-REAG BAS 12967420N-methyl-3-carboxaldehyde1 METHYLINDOLE-3-ALDEHYDE
NSC-83042AI3-51477DTXSID50172483NSC 83042RefChem:433863DTXCID2094974242-750-3MFCD00014570
Database identifiers
- CAS
19012-03-4- PubChem CID
- 87894
- DTXSID
DTXSID50172483- ChEMBL
CHEMBL210779- UNII
- Z612E3VMZ5
- EC Number
- 242-750-3
- Nikkaji
- J46.086I
Properties
Computed structural properties
- XLogP
- 1.7
- Topological polar surface area
- 22 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 1
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 181
Experimental & physicochemical properties
Solubility>23.9 [ug/mL] (The mean of the results at pH 7.4)
Physicochemical properties
- Melting point
- 70 · 70-72 °C (lit.)
- Boiling point
- 186 · 186-189 °C(Press: 3-4 Torr)
- Density
- 1.1 · 1.10±0.1 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- form
- Crystalline Powder and Chunks
- color
- Light yellow to orange or brown
- Water Solubility
- Insoluble in water.
- Sensitive
- Air Sensitive
- BRN
- 121302 · 121302
- InChI
- 1S/C10H9NO/c1-11-6-8(7-12)9-4-2-3-5-10(9)11/h2-7H,1H3
- InChIKey
- KXYBYRKRRGSZCX-UHFFFAOYSA-N
- SMILES
- Cn1cc(C=O)c2ccccc12
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (97.6%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, 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.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)；Eye Irrit. 2 (100%)；STOT SE 3 (97.6%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- hs_code
- 29339900
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-37/39
- hazard_class
- IRRITANT
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
Chemistry & industry
Applications
UsesReactant for preparation of nitroolefins and β-nitroalcohols via microwave- or ultrasound-assisted Henry reactions Reactant for synthesis of quinolinones via three-component Ugi reaction Reactant for synthesis of α-ketoamides as inhibitors of Dengue virus protease with antiviral activity in cell-culture Reactant for preparation of thiazolopyrimidinones as inhibitors of Bcl-2 proteins Reactant for preparation of vinylindoles via Peterson olefination or olefination with Nysted reagent Reactant for preparation of indolyl alkenes from microwave-enhanced Knoevenagel condensation as antibacterial agents.
Uses1-Methylindole-3-carboxaldehyde is used as a reactant for preparation of nitroolefins and β-nitroalcohols via microwave- or ultrasound-assisted Henry reactions, reactant for synthesis of quinolinones via three-component Ugi reaction, reactant for synthesis of α-ketoamides as inhibitors of Dengue virus protease with antiviral activity in cell-culture, reactant for preparation of thiazolopyrimidinones as inhibitors of Bcl-2 proteins, reactant for preparation of vinylindoles via Peterson olefination or olefination with Nysted reagent, reactant for preparation of indolyl alkenes from microwave-enhanced Knoevenagel condensation as antibacterial agents 1-Methylindole-3-carboxaldehyde may be used in the synthesis of (Z)-3-(1-methyl-1H-indol-3-yl)-2-(thiophen-3-yl)acrylonitrile, via base-catalyzed condensation with thiophene-3-acetonitrile. It was also used in the preparation of monomer, required for the synthesis of poly(3-vinyl-1-methylindole).
General Description1-Methylindole-3-carboxaldehyde is a heterocyclic indole aldehyde. 1-Methylindole-3-carboxaldehyde on condensation with 2-hydroxybenzohydrazide yields Schiff base.
Upstream & downstream products
Upstream raw materials
Related reactions
37 records
Compound notes
Loading…