220019
3-Indoleglyoxylic acid
98%
Synonym(s):
NSC 71954
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About This Item
Empirical Formula (Hill Notation):
C10H7NO3
CAS Number:
Molecular Weight:
189.17
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Assay
98%
form
solid
mp
217 °C (dec.) (lit.)
functional group
carboxylic acid
ketone
storage temp.
2-8°C
SMILES string
OC(=O)C(=O)c1c[nH]c2ccccc12
InChI
1S/C10H7NO3/c12-9(10(13)14)7-5-11-8-4-2-1-3-6(7)8/h1-5,11H,(H,13,14)
InChI key
DWLVFWDCSFTDOD-UHFFFAOYSA-N
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General description
Chemiluminescence (CL) intensity of 3-indoleglyoxylic acid has been measured.
Application
3-Indoleglyoxylic acid was used in the synthesis of oxazinin-1, -2 and -3.
- Reactant for synthesis of fenbufen and ethacrynic acid derivatives
- Reactant for preparation of glyoxyl analogs of indole phytoalexins as anticancer agents
- Reactant for synthesis of tertiary amides
- Reactant for preparation of fuconojirimycin derivatives as inhibitors of α-Fucosidases
- Reactant for total synthesis of oxazinin-3 from 3-indoleglyoxylic acid via an intramolecular addition/cyclization reactions
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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Synthetic studies towards oxazinins. An expedient first total synthesis and proof of the absolute stereochemistry of oxazinin-3.
Couladouros EA, et al.
Tetrahedron Letters, 45(41), 7779-7781 (2004)
J Bai et al.
Rapid communications in mass spectrometry : RCM, 10(7), 839-844 (1996-01-01)
Three structurally related compounds, 4-hydroxy-33-methoxyphenylpyruvic acid (HMPPA), indole-3 pyruvic acid (IPA), and indole-3-glyoxylic acid have been evaluated as matrix-assisted laser desorption/ionization (MALDI) matrices. HMPPA and IPA were found to be effective matrices for MALDI-MS analysis of proteins and peptides and
Manabu Nakazono et al.
Analytical sciences : the international journal of the Japan Society for Analytical Chemistry, 19(1), 123-127 (2003-02-01)
The chemiluminescence (CL) intensities of various indole derivatives substituted with a glyoxylyl group at the 3-position and a hydroxyl group at the 5-position of the indole ring were compared upon the addition of H2O2 in alkaline media. The CL intensities
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