Basic information
- CAS
16136-58-6- Standard SMILES
Cn1c(C(=O)O)cc2ccccc21- InChIKey
MAHAMBLNIDMREX-UHFFFAOYSA-N- Molecular formula
- C10H9NO2
- Average molar mass
- 175.18 g/mol
- Monoisotopic mass
- 175.06332853
Names & identifiers
- Preferred name
- 1H-Indole-2-carboxylic acid, 1-methyl-
- IUPAC
- 1-methylindole-2-carboxylic acid
- English name
- 1-Methylindole-2-carboxylic acid
- Molecular formula
- C10H9NO2
- Molecular weight
- 175.18
Names & synonyms
1-Methyl-1H-indole-2-carboxylic acid16136-58-61H-INDOLE-2-CARBOXYLIC ACID, 1-METHYL-1-Methyl-2-indolecarboxylic acidBRN 0007274DTXSID601671235-22-03-00015 (Beilstein Handbook Reference)NSC 68357RefChem:438712DTXCID8089614625-083-61-Methylindole-2-carboxylic acid
Show more names
N-Methylindole-2-carboxylic acid1-Me-ICAAKOS JY2082906RARECHEM AL BE 08642-Carboxy-1-methyl-1H-indole1-methyl-2-indolecarboxylicacidN-METHYL-2-INDOLECARBOXYLIC ACID
MFCD00005801Indole-2-carboxylic acid, 1-methyl-ChemDiv3_011259CHEMBL36834CS-W0077401-Methylindole-2-carboxylic acid, 98%AC-22708EU-0015870
Database identifiers
- CAS
16136-58-6- PubChem CID
- 27695
- DTXSID
DTXSID60167123- ChEMBL
CHEMBL36834- EC Number
- 625-083-6
- Nikkaji
- J102.515E
Properties
Computed structural properties
- XLogP
- 2
- Topological polar surface area
- 42.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 217
Physicochemical properties
- Melting point
- 212 · 212-213 °C (dec.) (lit.)
- Boiling point
- 389 · 389.0±15.0 °C(Predicted)
- Density
- 1.24 · 1.24±0.1 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- pka
- 4.19 · 4.19±0.30(Predicted)
- form
- Crystalline Powder
- color
- Beige
- InChI
- 1S/C10H9NO2/c1-11-8-5-3-2-4-7(8)6-9(11)10(12)13/h2-6H,1H3,(H,12,13)
- InChIKey
- MAHAMBLNIDMREX-UHFFFAOYSA-N
- SMILES
- Cn1c(cc2ccccc12)C(O)=O
- CAS DataBase Reference
- 16136 · 16136-58-6(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- NIST Chemistry Reference
- 1 · 1-Methylindole-2-carboxylic acid(16136-58-6)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (95.2%): 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 (95.2%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 3
- rtecs
- NL6012400
- hs_code
- 29339980
- risk_code
- 22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,Xi
- safety_code
- 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-P305+P351+P338
Chemistry & industry
Applications
Uses• ;Reactant for preparation of keto-indoles as novel indoleamine 2,3-dioxygenase (IDO) inhibitors1• ;Reactant for synthesis of fenbufen and ethacrynic acid derivatives as potential antitumor agents via amide coupling reactions2• ;Reactant for diastereoselective synthesis of vinylated heterocycles via ruthenium-catalyzed oxidative vinylation with alkenes3• ;Reactant for synthesis of 2,3-dihalo indoles via hypervalent iodine mediated decarboxylative halogenation4• ;Reactant for preparation of α-ketoamides as cathepsin S inhibitors with potential applications ag
UsesReactant for preparation of keto-indoles as novel indoleamine 2,3-dioxygenase (IDO) inhibitorsReactant for synthesis of fenbufen and ethacrynic acid derivatives as potential antitumor agents via amide coupling reactionsReactant for diastereoselective synthesis of vinylated heterocycles via ruthenium-catalyzed oxidative vinylation with alkenesReactant for synthesis of 2,3-dihalo indoles via hypervalent iodine mediated decarboxylative halogenationReactant for preparation of α-ketoamides as cathepsin S inhibitors with potential applications against tumor invasion and angiogenesisReactant for preparation of anthranilic acid mimics as bacterial translation inhibitors
General Description1-Methylindole-2-carboxylic acid reacts with thionyl chloride to yield sulfinyl chlorides.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
106 records
Compound notes
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