CAS 16732-73-3 6-methoxy-1H-indole-2-carboxylic acid (HCID 410327)

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Basic information

CAS: 16732-73-3
Standard SMILES: COc1ccc2cc(C(=O)O)[nH]c2c1
InChIKey: XNBGANWAZJWOHS-UHFFFAOYSA-N
Molecular formula: C10H9NO3
Average molar mass: 191.18 g/mol
Monoisotopic mass: 191.05824315

Names & identifiers

Preferred name: 6-methoxy-1H-indole-2-carboxylic acid
IUPAC: 6-methoxy-1H-indole-2-carboxylic acid
English name: 6-METHOXY-1H-INDOLE-2-CARBOXYLIC ACID
Molecular formula: C10H9NO3
Molecular weight: 191.18

Names & synonyms

6-Methoxy-1H-indole-2-carboxylic acidRefChem:543576692-318-716732-73-36-Methoxyindole-2-carboxylic acid1h-indole-2-carboxylic acid, 6-methoxy-MFCD015488236-Methoxy-1H-indole-2-carboxylic Acid; 6-Methoxy-1H-indole-2-carboxylic Acid; 6-Methoxyindole-2-carboxylic Acid; NSC 27988NSC27988BAS 06489245A1CO7Oprea1_070191

Show more names

NSC 27988AKOS JY20825596-Methoxindole-2-Carboxylic Acid6-Methoxy-1H-indole-2-carboxylic aci6-Methoxy-1H-indol-2-carboxylic acid6-Methoxyindole-2-carboxylicacid,95%Indole-2-carboxylic acid, 6-methoxy-6-Methoxyindole-2-carboxylic acid 95%

SCHEMBL335655SCHEMBL7880276SCHEMBL30189510DTXSID10328449HMS3446G14ALBB-006745BBL020243NSC-27988

Database identifiers

CAS: 16732-73-3

Properties

Computed structural properties

XLogP: 2.3
Topological polar surface area: 62.3 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 3
Rotatable bonds: 2
Heavy atoms: 14
Formal charge: 0
Complexity: 231

Physicochemical properties

Melting point: 198 · 198-203℃
Boiling point: 447.6 · 447.6±25.0 °C(Predicted)
Density: 1.381 · 1.381±0.06 g/cm3(Predicted)
storage temp.: Sealed in dry,Room Temperature
solubility: DMSO (Slightly)
pka: 4.54 · 4.54±0.30(Predicted)
form: Solid
color: Light Pink
InChI: 1S/C10H9NO3/c1-14-7-3-2-6-4-9(10(12)13)11-8(6)5-7/h2-5,11H,1H3,(H,12,13)
InChIKey: XNBGANWAZJWOHS-UHFFFAOYSA-N
SMILES: COc1ccc2cc([nH]c2c1)C(O)=O
CAS DataBase Reference: 16732 · 16732-73-3(CAS DataBase Reference)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): 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 44 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 (100%)

Safety data

wgk: 3
hs_code: 2933998090
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26
hazard_class: IRRITANT
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H315-H319-H335
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Chemistry & industry

Applications · 2 items

Uses• ;Reactant for demethylation reactions using ionic liquids under microwave irradiation1• ;Reactant for preparation of pyrazinoindoledione via Ugi reaction and microwave-assisted cyclization2• ;Reactant for preparation of isoquinolinecarboxamides and their derivatives as opioid receptor antagonists3• ;Synthetic intermediate for preparation of indole fatty alcohol derivatives4• ;Reactant for preparation of acylaminoalkylindoles as MT2-selective melatonin antagonists5

UsesReactant for demethylation reactions using ionic liquids under microwave irradiationReactant for preparation of pyrazinoindoledione via Ugi reaction and microwave-assisted cyclizationReactant for preparation of isoquinolinecarboxamides and their derivatives as opioid receptor antagonistsSynthetic intermediate for preparation of indole fatty alcohol derivativesReactant for preparation of acylaminoalkylindoles as MT2-selective melatonin antagonists