137144-20-8

Basic information

• Product Name: 1-Propanone, 2,2-dimethyl-1-(9H-xanthen-9-yl)-
• CAS NO: 137144-20-8
• Molecular Formula: C18H18O2
• Molecular Weight: 266.34
• Mol File: 137144-20-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-Propanone, 2,2-dimethyl-1-(9H-xanthen-9-yl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Propanone, 2,2-dimethyl-1-(9H-xanthen-9-yl)-(137144-20-8)
• EPA Substance Registry System: 1-Propanone, 2,2-dimethyl-1-(9H-xanthen-9-yl)-(137144-20-8)

Safety Data

• Hazardous Substances Data: 137144-20-8(Hazardous Substances Data)

Usage

Chemical structure

1-Propanone, 2,2-dimethyl-1-(9H-xanthen-9-yl)with a thiocynate group (-N=C=S).

Molecular weight

315.39 g/mol.

Appearance

Yellow crystalline powder.

Solubility

Soluble in water, dimethyl sulfoxide (DMSO), and alcohol.

Excitation wavelength

490-495 nm.

Emission wavelength

520-530 nm.

Quantum yield

High quantum yield, which contributes to its strong fluorescence.

Photostability

High photostability, allowing it to resist photobleaching under certain conditions.

Derivative of fluorescein

FITC is a synthetic compound derived from the parent compound, fluorescein.

Fluorescent labeling reagent

It is used to label various biological molecules, such as antibodies, proteins, and nucleic acids, for detection in assays and experiments.

Applications

Widely used in fluorescence microscopy, flow cytometry, and immunofluorescent staining.

Compatibility

FITC can be conjugated to a variety of biological molecules, making it versatile for different research and diagnostic purposes.

Upstream product

• 26454-53-5 9H-xanthene-9-carbonyl chloride 
• 594-19-4 tert.-butyl lithium 

Relevant articles and documents

Substituted xanthenylidene enols. The importance of β-Ar-C=C conjugation in the stabilization of aryl-substituted enols

9-Xanthenecarboxaldehyde (7a) and methyl (7b), mesityl (7c), 2,4,6-triisopropylphenyl (Tip) (7d), and tert-butyl (7e) 9-xanthenyl ketones were prepared and found to be ketonic in CDCl3. In DMSO-d6,7a, 7c, 7d, and diphenylacetaldehyde 16 are in rapid equilibrium with the enols 15a, 15c, 15d, and 17, respectively. Keto ? enol equilibrium constants, Kenol, were measured in DMSO-d6 at various temperatures. The values at 294 K are 7a (101) > 16 (5.06) > 7d (1.1) > 7c (0.48). The ΔH° values are -2.0 to -4.4 kcal mol-1, and the ΔS° values are -9.1 to -11.8 cal mol-1 K-1. From the decrease of δ(OH) values on increasing the temperature, the association constants, Kassoc, of the enols with DMSO-d6 and the derived ΔHassoc and ΔSassoc values were obtained. The qualitative rates of formation of the enol acetates in DMSO-pyridine/Ac2O follow the Kenol values. X-ray diffraction data for 7b, 7c, and 18c - the acetate of 15c - gave the Ar - C=C and Mes - CO dihedral angles and showed that the xanthenyl moiety had a butterfly conformation. Several triarylethanones PhCH(Ar1)COAr2 (Ar1 = Ph, Ar2 = Mes, Tip; Ar1 = Ar2 = Mes) also isomerize in DMSO-d6 to the ketone-enol mixtures. The increase of Kenol by planarization of the β-aryl groups is reflected by the Kenol(7a)/Kenol(16) ratio of 20 at 294 K. Lower ratios for the α-aryl derivatives are Kenol(15c)/Kenol(Ph2CHCOMes) = 2 and 13.2 for the α-Tip analogues. These ratios were discussed in terms of ArC=C and ArC=O conjugation in the enols and ketones. β,β-Dimesityl substitution increased Kenol more than did β,β-diphenyl substitution due to steric effects. α-Alkyl substitution decreased Kenol strongly due to the higher stability of the ketones. The Kenol(DMSO-d6)/Kenol(H2O) ratio was 46 for 16 at 294 K. This first such ratio measured for a simple enol is ascribed to higher hydrogen bond acceptance by the DMSO-d6. Solvation of the enol is an important contributor to Kenol. The thermodynamic parameters resemble those for the nonsimple stable enol of acetylacetone rather than for the simple but much less stable enol, H2C=C(OH)Me.