13936-21-5

Usage

Uses

Used in Dye and Pigment Synthesis:
2-Amylanthraquinone is used as a precursor in the synthesis of dyes and pigments, particularly for the production of anthraquinone-based dyes. Its unique structure contributes to the color properties of the resulting dyes, making it a valuable component in this industry.
Used in Pharmaceutical Manufacturing:
As a chemical intermediate, 2-Amylanthraquinone plays a crucial role in the manufacturing of pharmaceuticals. Its chemical properties allow it to be incorporated into the synthesis of various medicinal compounds, contributing to the development of new drugs and therapies.
Used in Agrochemical Production:
In the agrochemical industry, 2-Amylanthraquinone is utilized as a chemical intermediate for the production of various agrochemicals. Its involvement in the synthesis process helps create effective products for agricultural applications, such as pesticides and fertilizers.
Used in Organic Electronics:
2-Amylanthraquinone has been investigated for its potential application in organic electronics. Its properties make it a candidate for use in the development of organic electronic devices, such as organic light-emitting diodes (OLEDs) and organic solar cells, due to its ability to support charge transport and light emission.
Used as a Catalyst in Organic Reactions:
Furthermore, 2-Amylanthraquinone has been explored for its use as a catalyst in organic reactions. Its ability to facilitate chemical transformations makes it a valuable tool in the synthesis of various organic compounds, contributing to the advancement of organic chemistry.

InChI:InChI=1/C19H18O2/c1-4-19(2,3)12-9-10-15-16(11-12)18(21)14-8-6-5-7-13(14)17(15)20/h5-11H,4H2,1-3H3

Synthetic route

2-(4-pentylbenzoyl)benzene carboxylic acid (13936-26-0) → 2-amyl-anthraquinone (13936-21-5)

Conditions	Yield
Stage #1: 2-(4-pentylbenzoyl)benzene carboxylic acid With oxalyl bromide at 90℃; for 0.5h; Stage #2: With zinc(II) chloride at 80℃; for 0.5h;	90%
With oleum at 80℃; for 4.5h;
Multi-step reaction with 2 steps 1: thionyl chloride / 2 h / 50 °C 2: trifluorormethanesulfonic acid; aluminum (III) chloride / 1,2-dichloro-ethane / 2.5 h / 55 °C View Scheme
With ammonium molybdate at 140℃; for 3h; Friedel-Crafts Acylation;

phthalic anhydride (85-44-9) + pentylbenzene (538-68-1) → 2-amyl-anthraquinone (13936-21-5)

Conditions	Yield
With bifunctional sulfonic acid-based HZSM-5 molecular sieve solid acid catalyst In tetrahydrofuran at 30℃; for 8h;	72%

C19H19ClO2 → 2-amyl-anthraquinone (13936-21-5)

Conditions	Yield
With aluminum (III) chloride; trifluorormethanesulfonic acid In 1,2-dichloro-ethane at 55℃; for 2.5h;

2-pentylanthracene → 2-amyl-anthraquinone (13936-21-5)

Conditions	Yield
With hydrogenchloride; dihydrogen peroxide In methanol; water at 65℃; for 2h; Flow reactor;
With hydrogenchloride; dihydrogen peroxide In methanol; water at 65℃; for 2h; Flow reactor;

2-amyl-anthraquinone (13936-21-5) + para-methylphenylmagnesium bromide (4294-57-9) → C33H34O2 (1589553-74-1)

Conditions	Yield
With magnesium In tetrahydrofuran for 7h; Reflux;

2-amyl-anthraquinone (13936-21-5) + phenylmagnesium bromide (100-58-3) → C31H32O2

Conditions	Yield
With magnesium In tetrahydrofuran for 7h; Reflux;

2-amyl-anthraquinone (13936-21-5) + (4-n-hexylphenyl)magnesium bromide → C43H56O2

Conditions	Yield
With magnesium In tetrahydrofuran for 7h; Reflux;

2-amyl-anthraquinone (13936-21-5) → 2-pentyl-9,10-bis(4-methylphenyl)anthracene (1589553-85-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: magnesium / tetrahydrofuran / 7 h / Reflux 2: potassium iodide; sodium dihydrogen phosphate; acetic acid / 3 h / Reflux View Scheme

2-amyl-anthraquinone (13936-21-5) → 2-amylanthrahydroquinone

Conditions	Yield
With hydrogen; dihydrogen peroxide at 44.84℃; under 3000.3 Torr; Catalytic behavior; Autoclave;

2-amyl-anthraquinone (13936-21-5) → 2-amyl-5,6,7,8-tetrahydroanthraquinone

Conditions	Yield
With hydrogen In 1,3,5-trimethyl-benzene at 60℃; under 2250.23 Torr;

Upstream product

• 13936-26-0 2-(4-pentylbenzoyl)benzene carboxylic acid 
• 85-44-9 phthalic anhydride 
• 538-68-1 pentylbenzene 

Downstream Products

• 1589553-74-1 C₃₃H₃₄O₂ 
• 1589553-85-4 2-pentyl-9,10-bis(4-methylphenyl)anthracene 

Relevant academic research and scientific papers

Preparation method of 2-alkyl anthraquinone

The invention relates to the field of preparation of 2-alkyl anthraquinone, and particularly discloses a preparation method of the 2-alkyl anthraquinone. The method comprises the following steps: (1)preparing a reaction product containing alkyl anthracene from anthracene; (2) separating the reaction product containing THE alkyl anthracene obtained in the step (1), wherein the separation method comprises carrying out melt crystallization to separate the anthracene and carrying out distillation to separate the 2-alkyl anthracene; and (3) preparing the 2-alkyl anthraquinone from the 2-alkyl anthracene obtained in the step (2). The method provided by the invention opens up a new direction for green preparation of the 2-alkyl anthraquinone, the method can significantly reduce the separation operation difficulty of a high-boiling-point high-melting-point mixture system, the separation efficiency is high, the product purity is 99.5%, and the yield is 94.23%.

Method for obtaining 2-alkyl anthracene through anthracene alkylation and preparing 2-alkyl anthraquinone through reaction

The invention relates to the field of preparation of 2-alkyl anthraquinone. The invention relates to a method for obtaining 2-alkyl anthracene through anthracene alkylation and preparing 2-alkyl anthraquinone through reaction. The method comprises the following steps: (1) under alkylation conditions and in the presence of an alkylation reaction solvent and a catalyst, anthracene and an alkylationreagent are contacted for alkylation reaction, a reaction product containing alkyl anthracene is prepared, and the alkylation reaction solvent is a combination of a solvent A with a dielectric constant of 1-10 at 20 DEG C and a solvent B with a dielectric constant of more than 10 and less than or equal to 50 at 20 DEG C; (2)the reaction product containing the alkyl anthracene is subjected to meltcrystallization to separate the anthracene and distillation to separate the 2-alkyl anthracene; and (3) the 2-alkyl anthraquinone is prepared from the 2-alkyl anthracene. The method provided by the invention opens up a new direction for green preparation of 2-alkyl anthraquinone.

Green synthesis method for preparing 2-alkylanthraquinone from phthalic anhydride in one step

The invention relates to the technical field of green synthesis of organic matters. The invention relates to a synthetic method, in particular to a green synthetic method for preparing 2-alkylanthraquinone from phthalic anhydride in one step. According to the method, phthalic anhydride and alkylbenzene are used as raw materials, difunctional sulfonic acid type solid acid based on an HZSM-5 molecular sieve is used as a catalyst, phthalic anhydride and alkylbenzene are catalyzed to be subjected to a Friedel-Crafts acylation reaction and a dehydration cyclization reaction at the same time under the action of the catalyst, so that the 2-alkyl anthraquinone is prepared in one step, wherein the bifunctional sulfonic acid type solid acid based on the HZSM-5 molecular sieve is a sulfonic acid typeHZSM-5 molecular sieve obtained by carrying out sulfonation treatment on the HZSM-5 molecular sieve. According to the synthesis method of the 2-alkyl anthraquinone, the bifunctional (with strong Bronsted acidity and Lewis acidity) sulfonic acid type solid acid based on the HZSM-5 molecular sieve is used as the catalyst to replace AlCl3 and fuming sulfuric acid, so that generation of a large amount of waste residues, waste gas and wastewater is avoided, and green production is realized.

Synthetic method of 2-alkylanthraquinone

The invention provides a synthetic method of 2-alkylanthraquinone, comprising the steps of subjecting the raw material 2-(4'-alkylbenzoyl)benzoic acid to acryl halogenation under the action of an acryl halogenation reagent to obtain an intermediate; subjecting the intermediate of step I to intracellular Friedel-Crafts alkylation under the catalysis of Lewis acid; dissolving the product of step IIwith a solvent, filtering, and purifying. The synthetic method of 2-alkylanthraquinone has high reaction speed, high conversion rate and few side reactions, the reagent for reaction is low in price and easy to obtain, post-reaction treatment is simple, and few three wastes are produced.

Method for preparing 2-alkyl anthraquinone by taking solid super acids as catalysts

The invention provides a method for preparing 2-alkyl anthraquinone by taking solid super acids as catalysts. The 2-alkyl anthraquinone (alkyl is straight or branched alkyl with the number of carbon atoms of 1-6) is obtained by adopting the solid super acids like perfluorinated sulfonic acid resin and heteropoly acid as the catalysts, taking 2-(4'-alkyl benzoyl) benzoic acid as a raw material andperforming acylated dewatering closed loop through Friedel-Crafts reaction. The method provided by the invention is characterized in that traditional smoking sulfuric acid catalysts are replaced by the solid super acids, so that the environment is friendly, and no waste acid is discharged; the operation process is simple, and the solid catalysts are easy to recover; therefore, the method is a green pollution-free new process.

A 2 - alkyl anthraquinone synthetic method (by machine translation)

The invention provides a 2 - alkyl anthraquinone synthetic method, the 2 - alkyl anthraquinone synthetic method comprises the following steps: the 2 - (4' - alkyl benzoyl) benzoic acid in the presence of a solvent through the acyl acyl; under the action of the promoter, using anhydrous aluminum ring to carry out the dehydrochlorination; reactant through hydrolysis, liquid separation, pressure reducing desolventizing, drying, to obtain 2 - alkyl anthraquinone. The beneficial effect of the present invention is: not the use of fuming sulfuric acid, mild reaction conditions, acid-free, simple process operation, the product quality is stable, and the yield of the product than the existing production process to improve the 5 - 10%. (by machine translation)

Non-symmetric 9,10-diphenylanthracene-based deep-blue emitters with enhanced charge transport properties

Realization of efficient deep-blue anthracene-based emitters with superior film-forming and charge transport properties is challenging. A series of non-symmetric 9,10-diphenylanthracenes (DPA) with phenyl and pentyl moieties at the 2nd position and alkyl groups at para positions of the 9,10-phenyls were synthesized and investigated. The non-symmetric substitution at the 2nd position enabled to improve film forming properties as compared to those of the unsubstituted DPA and resulted in glass transition temperatures of up to 92 °C. Small-sized and poorly conjugated substituents allowed to preserve emission in the deep blue range (-3-1 × 10 -2 cm2 V-1 s-1) in the solution-processed amorphous films of the DPA compounds.