2154-67-8

Basic information

• Product Name: 2,2,5,5-TETRAMETHYL-3-PYRROLIN-1-OXYL-3-CARBOXYLIC ACID
• Synonyms: 3-CARBOXYL-1-OXY-2,2,5,5-TETRAMETHYLPYRROLINE;3-CARBOXYL-2,2,5,5-TETRAMETHYL-3-PYRROLIN-1-YLOXY;3-CARBOXY-2,2,5,5-TETRAMETHYL-3-PYRROLIN-1-YLOXY;2,5-DIHYDRO-1-OXY-2,2,5,5-TETRAMETHYLPYRROLE-3-CARBOXYLIC ACID;2,2,5,5-TETRAMETHYL-3-PYRROLIN-1-OXYL-3-CARBOXYLIC ACID;1-OXY-2,2,5,5-TETRAMETHYL-3-PYRROLINE-3-CARBOXYLIC ACID;3-carboxy-2,5-dihydro-2,2,5,5-tetramethyl-1h-pyrrol-1-ylox;3-carboxy-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-yloxy
• CAS NO: 2154-67-8
• Molecular Formula: C₉H₁₄NO₃
• Molecular Weight: 184.21
• EINECS: 218-447-7
• Product Categories: Spin Labeling Compounds
• Mol File: 2154-67-8.mol
• Article Data: 7

Chemical Properties

• Melting Point: 202 °C
• Boiling Point: 318.16°C (rough estimate)
• Flash Point: 142.2°C
• Appearance: Yellow/Crystalline Powder
• Density: 1.1776 (rough estimate)
• Vapor Pressure: 0.000123mmHg at 25°C
• Refractive Index: 1.4760 (estimate)
• Storage Temp.: -20°C Freezer
• CAS DataBase Reference: 2,2,5,5-TETRAMETHYL-3-PYRROLIN-1-OXYL-3-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,5,5-TETRAMETHYL-3-PYRROLIN-1-OXYL-3-CARBOXYLIC ACID(2154-67-8)
• EPA Substance Registry System: 2,2,5,5-TETRAMETHYL-3-PYRROLIN-1-OXYL-3-CARBOXYLIC ACID(2154-67-8)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 2154-67-8(Hazardous Substances Data)

Usage

Chemical Properties

yellow crystalline powder

Uses

A highly reactive spin-label.

InChI:InChI=1/C9H15NO3/c1-8(2)5-6(7(11)12)9(3,4)10(8)13/h5,13H,1-4H3,(H,11,12)/p-1

Upstream product

• 19187-50-9 3-{[(ethoxycarbonyl)oxy]carbonyl}-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-yloxy 
• 71051-83-7 3-formyl-2,2,5,5-tetramethyl-pyrroline-1-oxyl 
• 46147-14-2 3-carbamoyl-2,2,5,5-tetramethyl-3-pyrrolin-1-oxyl 
• 76194-00-8 2,2,5,5-tetramethyl-2,5-dihydro-pyrrole-3-carboxylic acid 

Downstream Products

• 69588-78-9 C₁₅H₁₃Cl₅NO₃ 
• 55738-75-5 (2,5-dihydro-2,2,5,5-tetramethyl-1-oxyl-1H-pyrrol-3-yl)methanol 
• 1391158-77-2 C₂₇H₃₂NO₇ 
• 1582289-16-4 p-methoxyphenyl O-{6-O-(DPRO-3-carbonyl)}-β-D-glucoside 
• 2154-32-7 methyl 1-oxyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-3-carboxylate radical 

Relevant articles and documents

Synthesis of new pyrrolidine nitroxide epoxides as versatile paramagnetic building blocks

Pyrrolidine nitroxide epoxides were synthesized by oxidation of the corresponding alkene, diene and α,β-unsaturated aldehyde with m-CPBA or H2O2 to provide new spin labels and paramagnetic synthons.

A CONVENIENT HIGH YIELD SYNTHESIS OF NITROXIDES

Appropriate secondary amines are readily converted to nitroxides by dimethyldioxirane in a rapid, convenient, and essentially quantitative process.

Synthesis and structure of products of hydroxylamine acylation with 3-carboxy-2,2,5,5-tetramethylpyrrolinoxyl derivatives

The reaction of NH2OH with the derivatives of 2,2,5,5-tetramethylpyrrolin-1-oxyl-3-carboxylic acid in all events led to the formation of a mixture of the corresponding nitroxylhydroxamic acid with a stable O-acylhydroxylamine. The ratio between

Synthesis of nitroxide containing polyenes: two chemically modified retinals and their interaction with bacterioopsin

The synthesis and spectroscopic characterization of two retinal analogues is described, the paramagnetic 3-pyrrolin-1-yloxy analogue 1 and its diamagnetic equivalent, the 3-pyrroline analogue 2.Various aspects of the synthesis of the aminoxy group containing polyenes are discussed.Upon interaction with bacterioopsin, both 1 and 2 are incorporated in the protein and form a system with λmax 459 nm.Neither of the two bacteriorhodopsin analogues is photoactive.ESR spectroscopy data of the system containing 1 show that the ring part of the chromophore in the protein is rigidly fixed in orientation.