13936-21-5

Basic information

• Product Name: 2-Amylanthraquinone
• Synonyms: 2-AMYL ANTHRAQUINONE;10-Anthracenedione,2-pentyl-9;2-pentyl-10-anthracenedione;2-PENTAANTHRAQUINONE;2-tert-Pentylanthracene-9,10-dione;2-Pentyl-9,10-anthracenedione;2-Pentylanthraquinone;2-amyl-9,10-anthraquinone
• CAS NO: 13936-21-5
• Molecular Formula: C₁₉H₁₈O₂
• Molecular Weight: 278.35
• EINECS: 237-711-2
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 13936-21-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 85 °C
• Boiling Point: 446.956 °C at 760 mmHg
• Flash Point: 166.614 °C
• Appearance: /
• Density: 1.153 g/cm³
• Vapor Pressure: 1.07E-07mmHg at 25°C
• Refractive Index: 1.589
• CAS DataBase Reference: 2-Amylanthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amylanthraquinone(13936-21-5)
• EPA Substance Registry System: 2-Amylanthraquinone(13936-21-5)

Safety Data

• Hazardous Substances Data: 13936-21-5(Hazardous Substances Data)

Usage

General Description

2-Amylanthraquinone is an organic compound with the chemical formula C16H12O2. It is a derivative of anthraquinone, and its structure consists of a central anthraquinone core with an attached 2-amyl group. The compound is a yellowish-brown solid at room temperature and is insoluble in water but soluble in organic solvents. 2-Amylanthraquinone is primarily used as a precursor in the synthesis of dyes and pigments, especially in the production of anthraquinone-based dyes. It is also utilized as a chemical intermediate in the manufacturing of pharmaceuticals, agrochemicals, and other organic compounds. Additionally, it has been investigated for its potential application in organic electronics and as a catalyst in organic reactions.

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

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

Downstream Products

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

Relevant articles and documents

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%.

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.

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.