2-(1H-indol-3-yl)-2-oxoacetyl chloride

• ChemBase ID: 106722
• Molecular Formular: C10H6ClNO2
• Molecular Mass: 207.61314
• Monoisotopic Mass: 207.00870612
• SMILES: ClC(=O)C(=O)c1c[nH]c2c1cccc2
• Canonical SMILES: ClC(=O)C(=O)c1c[nH]c2c1cccc2
• InChI: InChI=1S/C10H6ClNO2/c11-10(14)9(13)7-5-12-8-4-2-1-3-6(7)8/h1-5,12H
• InChIKey: FPEGGKCNMYDNMW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(1H-indol-3-yl)-2-oxoacetyl chloride
• IUPAC Traditional name: 2-(1H-indol-3-yl)-2-oxoacetyl chloride
• Synonyms: α-Oxoindole-3-acetyl chloride; 2-(3-Indolyl)-2-oxoacetyl chloride; NSC 128332; 3-Indoleglyoxylyl chloride; 3-INDOLYLGLYOXALYL CHLORIDE; alpha-Oxoindoleacetyl chloride; Indole-3-glyoxylyl chloride; (1H-Indol-3-yl)oxoacetyl Chloride; 3-Indoleglyoxylyl Chloride; α-Oxo-1H-indole-3-acetyl Chloride; Indole-3-glyoxyloyl Chloride; 吲哚-3-乙醛酰氯

Database IDs

• CAS Number: 22980-09-2
• EC Number: 245-362-2
• MDL Number: MFCD00015460
• Beilstein Number: 147693
• PubChem SID: 162087699; 24873804
• PubChem CID: 89952

CALCULATED PROPERTIES

• Acid pKa: 12.2072525
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.122579
• LogD (pH = 7.4): 2.1225727
• Log P: 2.122579
• Molar Refractivity: 53.2007 cm^3
• Polarizability: 21.205353 Å^3
• Polar Surface Area: 49.93 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 138 °C (dec.)(lit.); ca 130°C dec.

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C); Toxic (T)
• UN Number: 1759; UN2923
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 23-34; 34
• Safety Statements: 26-27-36/37/39-45; 4-9-20-26-36/37/39-45-60
• TSCA Listed: 否
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H330-H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P304+P340-P305+P351+P338-P320-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 1759 8/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: 98%; 98+%
• Empirical Formula (Hill Notation): C10H6ClNO2

DETAILS

MP Biomedicals - 05201179

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 515205

Packaging
5 g in glass bottle
Application

• Reactant for preparation of dual IGF-1R/SRC inhibitors1
• Reactant for preparation of indolylglyoxylamides as a new class of antileishmanial agents2
• Reactant for preparation of glyoxyl analogs of indole phytoalexins as anticancer agents3
• Reactant for diastereoselective synthesis of heptacyclic core of dragmacidin E4
• Reactant for preparation of benzoylmethylpyrrolopyridinylethanedione as HIV-1 inhibitor5
• Reactant for preparation of fascaplysin-inspired diindolyls as selective inhibitors of CDK4/cyclin D16

Toronto Research Chemicals - I627080

An indole derivative used in the preparation of reagents for chemiluminescent enzyme immunoassay. It is an impurity in the manufacture of tryptamines and related compounds.

REFERENCES

• Nakazono, M. et al.: Anal. Sci., 19, 123 (2003)
• Cowie, J.S. et al.: J. Forensic Sci., 27, 527 (2003)