Basic information
- CAS
942-24-5- Standard SMILES
COC(=O)c1c[nH]c2ccccc12- InChIKey
QXAUTQFAWKKNLM-UHFFFAOYSA-N- Molecular formula
- C10H9NO2
- Average molar mass
- 175.18 g/mol
- Monoisotopic mass
- 175.06332853
Overview
Methyl indole-3-carboxylate is the methyl ester of indole-3-carboxylic acid. It has a role as a metabolite. It is a member of indoles and a methyl ester. It is functionally related to an indole-3-carboxylic acid.
Names & identifiers
- Preferred name
- Methyl indole-3-carboxylate
- IUPAC
- methyl 1H-indole-3-carboxylate
- English name
- Methyl indole-3-carboxylate
- Molecular formula
- C10H9NO2
- Molecular weight
- 175.18
Names & synonyms
Methyl indole-3-carboxylate942-24-5Methyl 1H-indole-3-carboxylateIndole-3-carboxylic Acid Methyl Ester3-carbomethoxyindole3-methoxycarbonylindoleCHEBI:65019DTXSID10343334RefChem:817800DTXCID70294414629-395-3Methyl 3-indolecarboxylate
Show more names
methyl indoline-3-carboxylate1H-INDOLE-3-CARBOXYLIC ACID METHYL ESTERRARECHEM AH BS 0112Oxiracetam Impurity 383-indole,Methyl forMate
1H-Indole-3-carboxylic acid, methyl estermethylindole-3-carboxylateMFCD00189407Indole-3-carboxylic acid, methyl esterCHEMBL2270066Methyl 1H-indole-3-carboxylate #METHYL INDOLE-3- CARBOXYLATEHY-79635
Database identifiers
- CAS
942-24-5- PubChem CID
- 589098
- DTXSID
DTXSID10343334- ChEMBL
CHEMBL2270066- ChEBI
CHEBI:65019
Properties
Computed structural properties
- XLogP
- 2.6
- Topological polar surface area
- 42.1 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 205
Physicochemical properties
- Melting point
- 149 · 149-152 °C (lit.)
- Boiling point
- 306.47 °C · 306.47°C (rough estimate)
- Density
- 1.1999 · 1.1999 (rough estimate)
- refractive index
- 1.506 · 1.5060 (estimate)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 15.42 · 15.42±0.30(Predicted)
- color
- Light Pink
- Water Solubility
- Slightly soluble methanol and dimethyl sulfoxide. Insoluble in water.
- BRN
- 142023 · 142023
- InChI
- InChI=1S/C10H9NO2/c1-13-10(12)8-6-11-9-5-3-2-4-7(8)9/h2-6,11H,1H3
- InChIKey
- QXAUTQFAWKKNLM-UHFFFAOYSA-N
- SMILES
- N1C2=C(C=CC=C2)C(C(OC)=O)=C1
- CAS DataBase Reference
- 942 · 942-24-5(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
This chemical does not meet GHS hazard criteria for 2.4% (1 of 42) of reports.
Warning
H315 (97.6%): Causes skin irritation [Warning Skin corrosion/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.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (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
- 26-36-37/39
- hazard_class
- IRRITANT
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H402
- Precautionary statements
- P501-P273-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
Chemistry & industry
Applications
UsesMethyl indole-3-carboxylate is a reagent in the preaparation of oncrasin-1 derivatives which is a novel inhibitor of the C-terminal domain of RNA polymerase II.
UsesReactant for preparation of:Nitric oxide synthase (nNOS) inhibitorSProtein kinase c alpha (PKCα) inhibitorsInhibitors of the C-terminal domain of RNA polymerase II as antitumor agentsKinase insert domain receptor (KDR) inhibitorsOrganocatalysts for the anti-Mannich reactionVery late antigen-4 (VLA-4) antagonistsInhibitors of Human 5-LipoxygenaseSerotonin 5-HT4 receptor antagonistsHyaluronidase inhibitorsReactant for:Enantioselective Meerwein-Eschenmoser Claisen rearrangement reactions
General DescriptionMethyl indole-3-carboxylate (3-Methoxycarbonylindole, 3-Carbomethoxyindole, Methyl indolyl-3-carboxylate) has been extracted from the marine Streptomyces sp. 060524. Its crystal structure indicates the presence of inter-molecular N-H…O hydrogen bond. It is also obtained during the isolation of sorazinones A and B from Sorangium cellulosum strain Soce895. It undergoes regioselective dibromination with bromine in acetic acid to afford methyl 5,6-dibromoindole-3-carboxylate.
Upstream & downstream products
Downstream products
Suppliers100 total
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
Related reactions
102 records
Compound notes
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