7620-46-4

Usage

InChI:InChI=1/C14H8N2S/c17-9-15-14-10-5-1-3-7-12(10)16-13-8-4-2-6-11(13)14/h1-8H

Upstream product

• 1207-69-8 9-Chloroacridine 
• 333-20-0 potassium thioacyanate 
• 1701-93-5 silver thiocyanate 
• 110166-26-2 aminacrine 
• 578-95-0 10H-acridin-9-one 

Downstream Products

• 26687-12-7 N'-phenyl-N-(acridyl-9) thiocarbamide 
• 42940-66-9 3-(acridin-9-yl)-1-benzylthiourea 
• 95256-52-3 9-Isothiocyanato-10-methylacridinium-trifluormethansulfonat 
• 720669-56-7 3-(acridin-9-yl)-1-cyclohexyl-1-ethylthiourea 
• 720669-61-4 3-(acridin-9-yl)-1-cyclohexyl-1-isopropylthiourea 
• 1048370-05-3 4-(9,10-dihydroacridin-9-ylidene)-1-benzoylthiosemicarbazide 

Relevant academic research and scientific papers

FLUORESCENCE REAGENTS FOR LABELLING OF BIOMOLECULES. PART I. SYNTHESIS AND SPECTRAL CHARACTERIZATION OF 2- AND 4-SUBSTITUTED 9-ISOTHIOCYANATOACRIDINES

9-Isothiocyanatoacridines VIII-XIV were prepared from the corresponding 9-chloroacridines I - VII.The IR, 1H NMR, 13C NMR and fluorescence spectra of the products are given.The 13C NMR chemical shifts of the C-9 ipso carbon atom exhibit a trend that is in accord with the Hammett constants of substituents bonded to the C-2 carbon.Effect of these substituents on the chemical shift of C-NCS was only small.The dependence of hydrolysis of isothiocyanates VIII - XIV on pH of the medium was studied.It was found that 9-isothiocyanatoacridines do not undergo hydrolysis at pH 7 - 10.The relative fluorescence intensities (F/F0) of compounds VIII - XIV at pH 7.4 have been determined in comparison with that of 9-aminoacridine.No direct dependence between the fluorescence intensity and the polar character of substituents has been found.

Reaction of Thiocarbonyl Fluoride Generated from Difluorocarbene with Amines

The reaction of thiocarbonyl fluoride, generated from difluorocarbene, with various amines under mild conditions is described. Secondary amines, primary amines, and o-phenylenediamines are converted to thiocarbamoyl fluorides, isothiocyanates, and difluoromethylthiolated heterocycles, respectively. Thiocarbamoyl fluorides were further transformed into trifluoromethylated amines by using a one-pot process. Thiocarbonyl fluoride is generated in situ and is rapidly fully converted in one pot under mild conditions; therefore, no special safety precautions are needed.

Dipole moments of 2-and 4-substituted 9-isothiocyanatoacridines

Dipole moments of a series of 2-and 4-substituted 9-isothiocyanatoacridines were determined and compared with the values calculated by vector addition using bond and group dipole moments. The results are discussed from the viewpoint of geometrical and conformational structures of the compounds investigated.

Reaction of O-alkyl-N-substituted iminothiocarbonates with bromoacetyl bromide. A general method for the synthesis of 3-substituted 1,3-thiazolidine-2,4-diones

Reaction of sodium salts of O-methyl-N-substituted iminothiocaibonates with bromoacetyl bromide represents a new general method for preparation of 3-substituted 1,3-thiazolidine-2,4-diones in good yields and high purity. The structure of the synthesized products has been confirmed by 1H NMR, 13C NMR, IR and mass spectroscopy as well as by independent synthesis.

FLUORESCENCE REAGENTS FOR LABELLING OF BIOMOLECULES. PART III. STUDY OF THE REACTIONS OF 2- AND 4-SUBSTITUTED 9-ISOTHIOCYANATOACRIDINES WITH GLYCINE

Kinetics of nucleophilic addition reaction of 2- and 4-substituted 9-isothiocyanatoacridines I-VII with glycine in buffered aqueous dimethylformamide has been studied.The addition products, N-(9-acridinylthiocarbamoyl)glycines VIII-XIV, were characterized by IR, UV, 1H NMR, mass and fluorescence spectra.Derivatives VIII, X and XII exhibited higher fluorescence intensity than the starting isothiocyanates; the highest fluorescence was found for the unsubstituted conpound X.The reaction mechanism is discussed on the basis of properties of the reaction products and kinetic characteristics.

KINETICS OF REACTIONS OF 9-ISOTHIOCYANATOACRIDINE WITH AROMATIC AND ALIPHATIC AMINES AND FLUORESCENCE PROPERTIES OF THE 1-ACRIDIN-9-YL-3-ALKYL(ARYL)THIOUREAS OBTAINED

Kinetics of nucleophilic addition reaction of 9-isothiocyanatoacridine with seventeen aliphatic and aromatic amines in organic solvents has been studied by the VIS spectroscopic method. 9-Isothiocyanatoacridine reacted by about two orders of magnitude faster than phenyl isothiocyanate.The reaction rates of aliphatic amines were markedly affected by steric effects.Excepting 1-acridin-9-yl-3-butylthiourea (IIIo), the products obtained exhibited weaker fluorescence than the starting 9-isothiocyanatoacridine.

Dication Ethers, 3. Substitution Reactions on Bis(acridinium) Ethers and 9-Trifloxyacridinium Salts by Halides, Pseudohalides and Sulfur Nucleophiles

9-Trifloxyacridinium salts 3a, b and 9,9'-oxy-bis(acridinium) salts 4a, b which are easily obtained from the 9-acridones 2a, b react readily with halides, pseudohalides and sulfur nucleophiles to give 9-substituted acridinium ions.This reaction represents an efficient alternative to the commonly used transformation of 9-chloroacridinium into other substituted acridinium salts; the two-step conversion of the carbonyl compound into a (pseudo)halide-substituted carbenium ion or into a thione may be generally applicable to ketones which can be transformed either into trifloxy carbenium ions or into dication ethers. - Keywords: Bis(acridinium) Ethers, 9-Substituted Acridinium Ions