129-45-3

Usage

Uses

Used in Textile Industry:
1-(butylamino)anthraquinone is used as a blue colorant for dyeing and printing processes in textiles, providing long-lasting, vibrant color to fabrics due to its high color strength and lightfastness.
Used in Ink Industry:
1-(butylamino)anthraquinone is used as a pigment in the production of inks, offering a consistent and durable blue color for various printing applications, including digital, offset, and screen printing.
Used in Plastics Industry:
1-(butylamino)anthraquinone is used as a colorant in the manufacturing of colored plastics, imparting a stable and vibrant blue hue to the final product, suitable for a wide range of applications, from packaging materials to consumer goods.
Used in Commercial Product Manufacturing:
1-(butylamino)anthraquinone is used as a colorant in the production of various commercial products, such as paints, coatings, and cosmetics, due to its versatility and ability to provide a consistent, long-lasting color.

InChI:InChI=1/C18H17NO2/c1-2-3-11-19-15-10-6-9-14-16(15)18(21)13-8-5-4-7-12(13)17(14)20/h4-10,19H,2-3,11H2,1H3

Upstream product

• 82-44-0 1-chloroanthracene-9,10-dione 
• 111-92-2 dibutylamine 
• 109-73-9 N-butylamine 
• 81-62-9 1-amino-4-bromo-9,10-anthracenedione 
• 84-65-1 9,10-phenanthrenequinone 
• 109-65-9 1-bromo-butane 
• 82-45-1 1-amino-9,10-anthracenedione 
• 542-69-8 1-iodo-butane 
• 64-19-7 acetic acid 
• 123-72-8 butyraldehyde 
• 632-83-7 1-Bromoanthraquinone 
• 3485-80-1 1-iodo-9,10-anthraquinone 
• 82-34-8 1-nitroanthraquinone 
• 129-43-1 1-hydroxyanthraquinone 

Relevant academic research and scientific papers

Anthroneamine based chromofluorogenic probes for Hg2+ detection in aqueous solution

Anthroneamine derivatives 1-3 (H2O:DMSO; 9:1, HEPES buffer, pH 7.0 ± 0.1) undergo highly selective fluorescence quenching with Hg 2+. The observed linear fluorescence intensity change allows the quantitative detection of Hg2+ between 200 nM/40 ppb - 12 μM/2.4 ppm even in the presence of interfering metal ions viz. Na+, K +, Mg2+, Ca2+, Ba2+, Cr 3+, Fe2+, Co2+, Ni2+, Cu 2+, Zn2+, Ag+, Cd2+, Pb 2+. Probes 1-3 and their Hg2+ complexes also show the broad pH resistance for their practical applicability.

Facile synthesis of 1-butylamino- and 1,4-bis(butylamino)-2-alkyl-9,10-anthraquinone dyes for improved supercritical carbon dioxide dyeing

Supercritical carbon dioxide (scCO2) has recently been conquering both material sciences and process engineering owing to its intriguing properties like high diffusivity and tuneable (de)solubilizing performance. However, except for impregnation with biocidal preservatives, utilization of scCO2 for modification of wood including dyeing has been hitherto less explored. Therefore, we recently proposed a green wood dyeing approach that relies on the excellent carrier medium properties of CO2 for non-polar disperse dyes in supercritical conditions and their reversion when leaving the supercritical state. However, using a common disperse dye of the 9,10-anthraquinone family (Disperse Blue, DB-134) without the addition of co-solvent, only a moderate colour change was obtained for the interior of small wood cuboids (1 cm × 1 cm x 2 cm) even after extensive variation of scCO2 process conditions. Insufficient solubility of the dye in scCO2 was assumed to be a major hindrance for homogeneous wood dyeing. Therefore, we synthesized a variety of 1-n-butylamino- and 1,4-bis(n-butylamino)-9,10-anthraquinone derivatives carrying different alkyl moieties in 2-position, which was confirmed to improve scCO2 solubility. Instead of a previously reported seven-step synthesis affording moderate yields only (60% on average), we propose an alternate much simpler synthesis comprising of Marschalk alkylation (2-position) and a sequence of tosylation and n-alkylamination (1-position). The latter proved to pave way to a wide variety of colours and disperse dyes of improved solubility in scCO2. Moreover, all products were characterized by various techniques including liquid-state 1H and 13C NMR and X-ray crystallography. Complementing X-ray diffraction, quantum-mechanical simulations were performed to predict or confirm conformation and colour of selected compounds.

Sensitive fluorescent vesicles based on the supramolecular inclusion of β-cyclodextrins with N-alkylamino-L-anthraquinone

Self-assembly fluorescent vesicles were designed and prepared based on the supramolecular interaction of cyclodextrins and N-alkylamino-L-anthraquinone (n-AQ). As the guest molecules, n-AQs with alkyl lengths ranging from C 0 to C18 were synthesised by the direct reaction of alkylamine with L-nitroanthraquinone in N,N-dimethylformamide. Transmission electron microscopy (TEM), scanning electron microscopy, dynamic light scattering and epi fluorescence microscopy were employed to study the vesicle system in detail. The formation mechanism of the vesicles was suggested based on the results of TEM observation, UV spectrum, fluorescence spectrum, 1H NMR and simulation in the software Materials 4.3. The fluorescent vesicles show sensitive and multi-responsive properties to external stimuli. Based on these properties, we tried to use the vesicle as a new kind of fluorescence staining material for living cells. The vesicles can effectively stain the human breast cancer cells (MCF-7) and mice mononuclear macrophages (REW-264.7). This paper provides a better understanding in the design and preparation of drug delivery, biomaterials and intelligent materials.

Reactions of isomeric dinitronaphthalic-1,8-anhydrides with alkylamines

In the reaction products of 4,5-dinitronaphthalic-1,8-anhydride and of the 3,6-dinitro analogue with 1-butylamine only nitro groups in the former compound undergo reaction. 2,5-Dinitronaphthalic anhydride reacted partially. 4,5-Dibutylaminonaphthalic-N-butyl-1,8-imide was moderately fluorescent by comparison with 4-butylamino-N-butyl-1,8-imide, (FBYR). The ease of nucleophilic replacement of the nitro group in mononitro substituted rings increases with ring size and appears to be related to the stability of a Meisenheimer intermediate.

Solid-liquid phase transfer catalytic reaction of 1-aminoanthraquinone with alkyl halides: A case of N-alkylation

N-Alkylation of 1-aminoanthraquinone I has been carried out under mild condition of solid-liquid phase transfer catalysis using tetrabutyl ammonium bromide and dibenzo-(18)-crown-6 at room temperature in better yield.

Phase transfer catalysed N-monoalkylation of amino anthraquinones

1-Alkylaminoanthraquinones (2a-f) and 1,4-bisalkylaminoanthraquinones (4a-c) were prepared from aminoanthraquinones (1,3) by alkylation with alkyl sulphate/alkyl halide in presence of powdered sodium hydroxide, potassium carbonate and phase transfer catalyst.

Kinetics and product studies on Ullmann amination of 1-halogenoanthraquinones catalysed by copper(I)salts in acetonitrile solution

The kinetics and products of reactions of some primary amines (RNH2) with 1-halogenoanthraquininone (AQX) promoted by copper salts, particularly tetrakis(acetonitrile)copper(I) tetrafluoroborate, have been investigated in acetonitrile solution at 70 deg C.Provided that oxygen does not come into contact with solutions of the copper(I) salt and amine, the kinetics of the reactions have the simple form v = k, and the products consist almost entirely of the aminated anthraquinone, AQNHR, and dehalogenated material, AQH, their ratio being directly proportional to .The reaction rate is dependent on the identity of the departing halogen X, decreasing in the sequence I > Br > Cl, but the product ratio is little affected.N-Deuteration of the reactant amine gives rise to a small kinetic isotope effect, but the product ratio is unaffected.Conversely deutearation on the α-carbon atom of the amine has little kinetic effect but leads to a four-fold increase in the ratio of aminated to dehalogenated product.The observations are interpreted in terms of (i) formation of a copper(I)-amine complex, (II) activation of this species for attack on AQX by proton abstraction from an amine ligand by a free molecule (stepwise or concerted), and (iii) generation of an arylcopper(III) intermediate which is partitioned between formation of AQNHR by attack of an externel amine molecule and formation of AQH by an intramolecular process involving hydrogen transfer from the α-carbon atom in the amine ligand generated in (ii).Exposure of the initial copper(I)-amine complex to oxygen leads to a new complex, itself capable of reacting with AQX, which on prolonged incubation at 70 deg C in the presence of an excess of amine is transformed back to its original state.

Amide Ion Formation and N-Alkylation of Aminoanthraquinones in the presence of Potassium Hydroxide in Dimethyl Sulfoxide

Amide ions were formed by the deprotonation of the amino group of amino group of amino- and (monoalkylamino)anthroquinones in the presence of powdered potassium hydroxide in dimethyl sulfoxide (DMSO).Under a nitrogen atmosphere these amide ions changed to their radical anions.The amide ions of 1-aminoanthroquinones reacted with excess alkyl halides to yield 1-alkylaminoanthraquinones, while the N-alkylation of 2-aminoanthraquinones afforded 2-alkylaminoanthraquinones in good yields. 2-Aminobenzophenone underwent mono-N-alkylation, while 4-aminoazobenzene and p-nitroaniline underwent di-N-alkylation.It was also found that carbanion of DMSO easily attacked the carbonyl group of the (dialkylamino)anthraquinones.

Aromatic compounds and their manufacture

Compounds of Formula I or Formula II STR1 where A is an electron withdrawing group and B is a secondary or tertiary amino group or the group OD where D is H, aryl or an aliphatic group are made by reacting a corresponding compound of Formula Ia or Formula IIa STR2 in a solvent with a reagent selected from organic primary and secondary amines and compounds of the formula MOD where M is an alkali metal and A and D are as defined above. In this process the nitro group and the group B in Formula I and Ia are in the 2- or 4- position and the compounds of Formula I, Ia, II and IIa may optionally be further substituted. Preferably a primary or secondary amine is reacted with a compound of formula Ia, preferably using dimethylformamide as solvent. The process can result in the production of novel compounds, including (1) Compounds of Formula III wherein each group A is CO2 H or an alkali metal, amine or ammonium salt thereof or the two groups A together form a carboxylic anhydride group and B is in the 2- or 4-position and is OD, where D is hydrogen or an aliphatic group or is a secondary or tertiary amine group, (2) compounds of Formula IV STR3 where B is the group OD or the group NR2 R3 and wherein at least one of R1 and D or at least one of R1, R2 and R3 comprise a solubilizing group containing a primary amino, carboxylic, sulphonate or phosphate ester group in the form of an alkali metal, amine or ammonium salt or is a polyalkylene oxide group, the compounds optionally being further substituted.

REACTION OF 1-AMINOANTHRAQUINONE WITH BUTYRALDEHYDE AND VALERALDEHYDE

With butyraldehyde and valeraldehyde in the presence of acids through a series of intermediate stages 1-aminoanthraquinone gives N-monoalkyl derivatives and the corresponding aminals.In addition, derivatives of naphthoquinoline are formed through the intermediate stage of aliphatic N-(1-anthraquinonyl)-β-amino aldehydes, which can be isolated from the reaction mixture.