945493-49-2

Basic information

• Product Name: 1H-Indole-1-carboxylic acid, 2-borono-5-(dimethylamino)-, 1-(1,1-dimethylethyl) ester
• Synonyms: 1H-Indole-1-carboxylic acid, 2-borono-5-(dimethylamino)-, 1-(1,1-dimethylethyl) ester;(1-(tert-butoxycarbonyl)-5-(dimethylamino)-1H-indol-2-yl)boronic acid;KQJRUICWEPXFIJ-UHFFFAOYSA-N
• CAS NO: 945493-49-2
• Molecular Formula: C15H21BN2O4
• Molecular Weight: 304.15
• Mol File: 945493-49-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 488.7°C at 760 mmHg
• Flash Point: 249.4°C
• Appearance: /
• Density: 1.15g/cm³
• Vapor Pressure: 2.3E-10mmHg at 25°C
• Refractive Index: 1.542
• CAS DataBase Reference: 1H-Indole-1-carboxylic acid, 2-borono-5-(dimethylamino)-, 1-(1,1-dimethylethyl) ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-1-carboxylic acid, 2-borono-5-(dimethylamino)-, 1-(1,1-dimethylethyl) ester(945493-49-2)
• EPA Substance Registry System: 1H-Indole-1-carboxylic acid, 2-borono-5-(dimethylamino)-, 1-(1,1-dimethylethyl) ester(945493-49-2)

Safety Data

• Hazardous Substances Data: 945493-49-2(Hazardous Substances Data)

Usage

Molecular structure

The molecule consists of an indole ring system with a carboxylic acid group at position 1, a boron atom at position 2, a dimethylamino group at position 5, and a tert-butyl ester group at position 1.

Functional groups

The molecule contains a carboxylic acid group, a boronic acid group, a dimethylamino group, and a tert-butyl ester group.

Reactivity

The boronic acid group in the molecule can react with certain reagents to form stable complexes, and the molecule is commonly used in the Suzuki-Miyaura coupling reaction for the formation of carbon-carbon bonds.

Stability

The tert-butyl ester group in the molecule provides stability and ease of handling.

Use in organic synthesis and medicinal chemistry

The molecule is an important reagent in the development of new drugs and materials due to its reactivity and stability.

InChI:InChI=1/C15H21BN2O4/c1-15(2,3)22-14(19)18-12-7-6-11(17(4)5)8-10(12)9-13(18)16(20)21/h6-9,20-21H,1-5H3

Upstream product

• 6843-23-8 5-(N,N-dimethylamino)indole 
• 945493-67-4 N-Boc-5-(dimethylamino)indole 
• 24424-99-5 di-tert-butyl dicarbonate 

Relevant articles and documents

Fluorescent pyrimidopyrimidoindole nucleosides: Control of photophysical characterizations by substituent effects

(Chemical Equation Presented) 10-(2-Deoxy-β-D-ribofuranosyl) pyrimido[4′,5′:4,5]pyrimido[1,6-a]indole-6,9(7H)-dione (dC PPI) and its derivatives were synthesized via the Suzuki-Miyaura coupling reaction of 5-iododeoxycytidine with 5-substituted N-Boc-indole-2- borates and characterized by UV-vis and fluorescence spectroscopy. The new fluorescent nucleosides showed rather large Stokes shifts (116-139 nm) in an aqueous buffer. The fluorescent intensities were dependent on the nature of the substituents on the indole rings. The electron-withdrawing groups increased the fluorescent intensity while the electron-donating groups having lone pairs decreased it. Among the substituted dCPPI derivatives tested, the trimethylammonium derivative of dCPPI was found to emit the brightest fluorescent light. The solvatochromism of dCPPI and its derivatives was also studied. Some of the dCPPI derivatives showed interesting solvent-dependent fluorescence enhancement and could be useful as new fluorescent structural probes for nucleic acids. The Lippert-Mataga analyses of the Stokes shift were also carried out to obtain estimated values of the dipole moment of the excited states of some of the derivatives.