29199-09-5

Usage

Uses

Used in Organic Synthesis:
3',6'-BIS(DIETHYLAMINO)-2-(4-NITROPHENYL)SPIRO[ISOINDOLE-1,9'-XANTHENE]-3-ONE is used as a key intermediate in organic synthesis for the development of novel compounds with specific properties and functions. Its unique structure and functional groups make it a versatile building block for the creation of advanced materials and pharmaceuticals.
Used in Fluorescence Imaging:
In the field of biochemistry and molecular biology, 3',6'-BIS(DIETHYLAMINO)-2-(4-NITROPHENYL)SPIRO[ISOINDOLE-1,9'-XANTHENE]-3-ONE is utilized as a fluorescent probe for imaging and detecting specific biomolecules or cellular processes. Its fluorescence properties allow for the visualization and tracking of biological events with high sensitivity and specificity.
Used as a Dye in the Textile Industry:
3',6'-BIS(DIETHYLAMINO)-2-(4-NITROPHENYL)SPIRO[ISOINDOLE-1,9'-XANTHENE]-3-ONE is employed as a dye in the textile industry due to its vibrant color and stability. Its unique structure and functional groups provide excellent colorfastness and resistance to fading, making it suitable for various applications in fabric dyeing and printing.
Used in Advanced Materials Research:
In the field of materials science, 3',6'-BIS(DIETHYLAMINO)-2-(4-NITROPHENYL)SPIRO[ISOINDOLE-1,9'-XANTHENE]-3-ONE is used as a component in the development of advanced materials with specific properties, such as optoelectronic devices, sensors, and energy storage systems. Its highly conjugated structure and functional groups contribute to the unique characteristics and performance of these materials.

Synthetic route

rhodamine B (81-88-9) + 4-nitro-aniline (100-01-6) → 3',6'-bis-diethylamino-2-(4-nitro-phenyl)-spiro[isoindoline-1,9'-xanthen]-3-one (29199-09-5)

Conditions	Yield
With trichlorophosphate In 1,2-dichloro-ethane at 0 - 85℃; for 5.25h; Inert atmosphere;	83%
With trichlorophosphate In acetonitrile at 90℃; for 12h; Inert atmosphere;	79%

C34H34AlN6O10(1+) → 3',6'-bis-diethylamino-2-(4-nitro-phenyl)-spiro[isoindoline-1,9'-xanthen]-3-one (29199-09-5)

Conditions	Yield
With ethylenediaminetetraacetic acid In water; acetonitrile pH=7.2;

methanol (67-56-1) + 3',6'-bis-diethylamino-2-(4-nitro-phenyl)-spiro[isoindoline-1,9'-xanthen]-3-one (29199-09-5) → C35H38N4O2

Conditions	Yield
With potassium tert-butylate at 130℃; for 48h; Sealed tube;	97%
With C24H32N3P; palladium diacetate; potassium hydroxide at 110℃; for 5h; Inert atmosphere;	63%

methanol (67-56-1) + 3',6'-bis-diethylamino-2-(4-nitro-phenyl)-spiro[isoindoline-1,9'-xanthen]-3-one (29199-09-5) → C36H40N4O2

Conditions	Yield
With aluminum (III) chloride; water In acetonitrile at 20℃; Irradiation;	73%

3',6'-bis-diethylamino-2-(4-nitro-phenyl)-spiro[isoindoline-1,9'-xanthen]-3-one (29199-09-5) → C34H35N4O4(1+)*Cl(1-)

Conditions	Yield
With hydrogenchloride In ethanol; water Kinetics;

aluminum(III) nitrate nonahydrate + 3',6'-bis-diethylamino-2-(4-nitro-phenyl)-spiro[isoindoline-1,9'-xanthen]-3-one (29199-09-5) → C34H34AlN6O10(1+)

Conditions	Yield
In water; acetonitrile pH=7.2;

aluminum (III) chloride (7446-70-0, 7784-13-6) + 3',6'-bis-diethylamino-2-(4-nitro-phenyl)-spiro[isoindoline-1,9'-xanthen]-3-one (29199-09-5) → C34H34N4O4*Al(3+)

Conditions	Yield
In water; acetonitrile pH=7.2;

potassium alum + 3',6'-bis-diethylamino-2-(4-nitro-phenyl)-spiro[isoindoline-1,9'-xanthen]-3-one (29199-09-5) → C34H34N4O4*Al(3+)

Conditions	Yield
In water; acetonitrile pH=7.2;

3',6'-bis-diethylamino-2-(4-nitro-phenyl)-spiro[isoindoline-1,9'-xanthen]-3-one (29199-09-5) → C36H38N4O3

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium tert-butylate / 48 h / 130 °C / Sealed tube 2: phenylsilane / acetonitrile / 6 h / 20 °C / 760.05 Torr / Inert atmosphere; Schlenk technique View Scheme

Upstream product

• 81-88-9 rhodamine B 
• 100-01-6 4-nitro-aniline 

Relevant academic research and scientific papers

Selective sensing of Al3+ ions by nitrophenyl induced coordination: Imaging in zebrafish brain tissue

A p-nitrophenyl based rhodamine probe (NPRB) has been designed and synthesized for the selective, real-time detection of Al(iii) in aqueous medium with a lower micromolar range detection limit at physiological pH. All the spectroscopic and theoretical analyses validated the proposed 1 : 1 complexation between NPRB and Al3+ along with an 80-fold enhancement in fluorescence intensity. Using the "turn on" response of the probe, binding of NPRB to Al3+ in the brain tissue of adult male zebrafish (D. rerio) has been visualized through fluorescence microscopy.

Substituent effects on the turn-on kinetics of rhodamine-based fluorescent pH probes

Fluorescent turn-on probes based on a rhodamine spirolactam (RSL) structure have recently become a popular means of detecting pH, metal ions, and other analytes of interest. RSLs are colorless and non-fluorescent until the target analyte induces opening of the spirocyclic ring system, revealing the fully conjugated and highly fluorescent rhodamine dye. Among RSLs opened by acid, we have observed wide variation in the kinetics of the fluorescence turn-on process such that some probes would not be usable in situations where a rapid reading is desired or the pH fluctuates temporally. Herein we present a systematic investigation of the fluorescence turn-on kinetics of RSLs to probe the hypothesis that the reaction rates are influenced by the electronic properties of the spirolactam ring system. A series of 8 aniline-derived RSLs with para substituents ranging from electron-donating to electron-withdrawing was prepared from rhodamine B. The fluorescence turn-on rates are observed to increase by a factor of four as the substituent is tuned from methoxy to nitro. This effect is explained in terms of the destabilization of the reaction intermediate by the substituent. As the reaction rates increase across the series, a concomitant increase in fluorescence intensity is also observed. This result is attributed to an increase in the concentration of the fluorescent form of the dye and is consistent with the expected equilibrium properties of this system. These findings are applied to the design of a faster-reacting and more intensely fluorescent RSL pH probe.