Production Method 1

81-64-1

Reaction Conditions

1.1 Reagents: Sulfuric acid ,  Fuming sulfuric acid ,  Boric acid (H3BO3) ;  rt; 5 h, 205 °C
1.2 Reagents: Water ;  cooled; 30 min, 85 °C

Reference

Combined spectral experiment and theoretical calculation to study the interaction of 1,4-dihydroxyanthraquinone for metal ions in solution

Yin, Caixia; et al, Spectrochimica Acta, 2013, 115, 772-777

Production Method 2

81-64-1

Reaction Conditions

1.1 Reagents: Sulfuric acid ,  Oxygen

Reference

Oxidative coupling of furans and naphthoquinones: a potential route to anthracyclinones

Bridson, John N.; et al, Journal of the Chemical Society, 1980, (9), 413-14

Production Method 3

1709-63-3

81-64-1

Reaction Conditions

1.1 Catalysts: Ethylenediamine

Reference

A novel ring-closure reaction between 1,4-dihydroxyanthraquinone and diamines promoted by copper ions

Takei, Toshio; et al, Bulletin of the Chemical Society of Japan, 1981, 54(9), 2735-8

Production Method 4

79207-97-9

81-64-1

Reaction Conditions

1.1 Reagents: Cesium carbonate Catalysts: Tetrabutylammonium bromide ,  Palladium ;  60 min, 100 °C

Reference

Application of a new phosphorus-free palladium heterogeneous nanocatalyst supported on modified MWCNT the highly selective and efficient cleavage of propargyl, allyl, and benzyl phenol ethers under mild conditions

Sharghi, Hashem; et al, Molecular Diversity, 2015, 19(3), 481-500

Production Method 5

475-38-7

81-64-1

Reaction Conditions

1.1 Catalysts: Benzoic acid ,  L-Proline Solvents: Toluene ;  5 h, 50 °C

Reference

Organocatalyzed benzannulation for the construction of diverse anthraquinones and tetracenediones

Somai Magar, Krishna Bahadur; et al, Chemical Communications (Cambridge, 2015, 51(41), 8592-8595

Production Method 6

28736-42-7

81-64-1

Reaction Conditions

1.1 Reagents: 2-Butyn-1-ol ,  Potassium tert-butoxide Solvents: Dimethyl sulfoxide

Reference

Rapid, one-pot conversion of aryl fluorides into phenols with 2-butyn-1-ol and potassium t-butoxide in DMSO

Levin, Jeremy I.; et al, Synthetic Communications, 2002, 32(9), 1401-1406

Production Method 7

88-95-9

150-78-7

81-64-1

Reaction Conditions

1.1 Catalysts: Aluminum chloride Solvents: Nitrobenzene

Reference

A new methodological approach to anthraquinone and anthracyclidone synthesis

Sartori, Giovanni; et al, Gazzetta Chimica Italiana, 1990, 120(1), 13-19

Production Method 8

88-95-9

81-64-1

Reaction Conditions

1.1 Catalysts: Aluminum chloride Solvents: Nitrobenzene

Reference

A new methodological approach to anthraquinone and anthracyclidone synthesis

Sartori, Giovanni; et al, Gazzetta Chimica Italiana, 1990, 120(1), 13-19

Production Method 9

88-95-9

81-64-1

Reaction Conditions

1.1 Reagents: Aluminum chloride Solvents: Nitrobenzene

Reference

Synthesis and Activity of Substituted Anthraquinones against a Human Filarial Parasite, Brugia malayi

Dhananjeyan, Mugunthu R.; et al, Journal of Medicinal Chemistry, 2005, 48(8), 2822-2830

Production Method 10

51287-54-8

81-64-1

Reaction Conditions

1.1 Reagents: Lithium tert-butoxide Solvents: Tetrahydrofuran ;  25 min, -60 °C
1.2 Solvents: Tetrahydrofuran ;  1 h, -60 °C; 2 - 6 h, rt
1.3 Reagents: Ammonium chloride Solvents: Water

Reference

Direct Access to 1,4-Dihydroxyanthraquinones: The Hauser Annulation Reexamined with p-Quinones

Mal, Dipakranjan; et al, Journal of Organic Chemistry, 2007, 72(13), 4981-4984

Production Method 11

106909-80-2

81-64-1

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Platinum dioxide Solvents: Acetic acid

Reference

Some experiments with aminodihydroxyanthraquinones

Morris, Gareth A.; et al, Tetrahedron, 1986, 42(12), 3303-9

Production Method 12

111422-40-3

81-64-1

Reaction Conditions

1.1 Reagents: Aluminum chloride Solvents: Nitrobenzene

Reference

Metal template ortho-acylation of phenols. A new general approach to anthracyclinones

Sartori, Giovanni; et al, Tetrahedron Letters, 1987, 28(14), 1533-6

Production Method 13

81-64-1

Reaction Conditions

1.1 Reagents: Sulfuric acid ,  Boric acid (H3BO3) Solvents: Water ;  rt → 205 °C
1.2 Reagents: Sulfuric acid Solvents: Water ;  5 h, 205 °C
1.3 Reagents: Water ;  cooled; 30 min, 85 °C

Reference

Synthesis of 1,4-dihydroxyanthraquinone

Li, Kun-lan; et al, Dalian Gongye Daxue Xuebao, 2009, 28(4), 305-308

Production Method 14

81-64-1

Reaction Conditions

1.1 Reagents: Aluminum chloride ,  Sulfuric acid Solvents: Water ;  10 min, 95 - 110 °C

Reference

Facile, efficient and one-pot synthesis of anthraquinone derivatives catalyzed by AlCl3/H2SO4 under heterogeneous and mild conditions

Hossei, Naeimi; et al, Cuihua Xuebao, 2008, 29(1), 86-90

Production Method 15

41099-45-0

81-64-1

Reaction Conditions

1.1 Reagents: Sulfuric acid

Reference

Reaction of α-hydroxyanthraquinones with thionyl chloride. Preparation of 1,10-anthraquinone derivatives

Gorelik, M. V.; et al, Zhurnal Organicheskoi Khimii, 1979, 15(1), 157-66

Production Method 16

6119-74-0

81-64-1

Reaction Conditions

1.1 Reagents: Boron tribromide Solvents: Dichloromethane
1.2 Reagents: Sodium carbonate Solvents: Water

Reference

The synthesis of ventilone A

Piggott, Matthew J.; et al, Australian Journal of Chemistry, 2000, 53(9), 749-754

Production Method 17

1709-63-3

81-64-1

Reaction Conditions

1.1 Reagents: Trifluoroacetic acid ,  Triethylsilane

Reference

Ionic and organometallic-catalyzed organosilane reductions

Larson, Gerald L.; et al, Organic Reactions (Hoboken, 2008, 71, 1-737

Production Method 18

1045-75-6

81-64-1

Reaction Conditions

1.1 Reagents: Cesium carbonate Catalysts: Tetrabutylammonium bromide ,  Palladium ;  60 min, 100 °C

Reference

Application of a new phosphorus-free palladium heterogeneous nanocatalyst supported on modified MWCNT the highly selective and efficient cleavage of propargyl, allyl, and benzyl phenol ethers under mild conditions

Sharghi, Hashem; et al, Molecular Diversity, 2015, 19(3), 481-500

Production Method 19

88-99-3

81-64-1

Reaction Conditions

1.1 Reagents: Sulfuric acid ,  Boric acid (H3BO3)

Reference

Synthesis of Quinizarin and Its Derivatives under Conditions of Microwave Activation

El'tsov, A. V.; et al, Russian Journal of General Chemistry (Translation of Zhurnal Obshchei Khimii), 2002, 72(2), 255-258

Production Method 20

17648-03-2

81-64-1

Reaction Conditions

1.1 Reagents: Benzoyl peroxide ,  Triethylamine Solvents: Tetrahydrofuran

Reference

Highly selective oxidation of hydroquinones to quinones with dibenzoyl peroxide

McKay, Peter G.; et al, Australian Journal of Chemistry, 1989, 42(12), 2295-7

Production Method 21

17648-03-2

81-64-1

Reaction Conditions

1.1 Reagents: Nitric acid

Reference

Reaction of hydroquinones with supported oxidizing reagents in solvent-free conditions

Gomez-Lara, J.; et al, Synthetic Communications, 2000, 30(15), 2713-2720

Production Method 22

88-95-9

150-78-7

81-64-1

Reaction Conditions

1.1 Reagents: Aluminum chloride Solvents: Nitrobenzene
2.1 Reagents: Aluminum chloride Solvents: Nitrobenzene

Reference

Metal template ortho-acylation of phenols. A new general approach to anthracyclinones

Sartori, Giovanni; et al, Tetrahedron Letters, 1987, 28(14), 1533-6

Production Method 23

29525-00-6

81-64-1

Reaction Conditions

1.1 Reagents: Iron Solvents: Acetic acid
1.2 Reagents: Sodium hydroxide Solvents: Water
1.3 Reagents: Oxygen
1.4 Reagents: Hydrochloric acid Solvents: Water

Reference

The reductive dehalogenation of halo-substituted naphthazarins and quinizarins as a simple route to parent compounds

Anufriev, Victor Ph.; et al, Synthetic Communications, 1998, 28(12), 2149-2157

Production Method 24

27613-27-0

81-64-1

Reaction Conditions

1.1 Reagents: Lithium tert-butoxide Solvents: Tetrahydrofuran ;  25 min, -60 °C
1.2 Solvents: Tetrahydrofuran ;  1 h, -60 °C; 2 - 6 h, rt
1.3 Reagents: Ammonium chloride Solvents: Water

Reference

Direct Access to 1,4-Dihydroxyanthraquinones: The Hauser Annulation Reexamined with p-Quinones

Mal, Dipakranjan; et al, Journal of Organic Chemistry, 2007, 72(13), 4981-4984

Production Method 25

65131-08-0

81-64-1

Reaction Conditions

1.1 Reagents: Lithium tert-butoxide Solvents: Tetrahydrofuran ;  25 min, -60 °C
1.2 Solvents: Tetrahydrofuran ;  1 h, -60 °C; 2 - 6 h, rt
1.3 Reagents: Ammonium chloride Solvents: Water

Reference

Direct Access to 1,4-Dihydroxyanthraquinones: The Hauser Annulation Reexamined with p-Quinones

Mal, Dipakranjan; et al, Journal of Organic Chemistry, 2007, 72(13), 4981-4984

Quinizarin Raw materials

• 9-chloro-10-hydroxyanthracene-1,4-dione
• 1,4-dimethoxyanthracene-9,10-dione
• 1,3-dihydro-3-oxo-1-Isobenzofurancarbonitrile
• 1,4-bis(prop-2-en-1-yloxy)anthracene-9,10-dione
• 9,10-Anthracenedione, 2,3-dichloro-1,4-dihydroxy-
• 9,10-Dihydroxy-2,3-dihydroanthracene-1,4-dione
• 1,4,9,10-tetrahydroanthracene-1,4,9,10-tetrone
• Naphthazarin
• 1(3H)-Isobenzofuranone, 3-(phenylsulfonyl)-
• 1(3H)-Isobenzofuranone, 3-(phenylthio)-
• o-Phthaloyl dichloride
• 1,4-Dimethoxybenzene
• Phthalic acid
• 9,10-Anthracenedione, 1,4-bis(2-propyn-1-yloxy)-
• 1,4-Difluoroanthraquinone

Quinizarin Preparation Products

• Quinizarin (81-64-1)

• 1. Exchangeability of amino acid residues with similar physicochemical properties in coiled-coil interactions?
  Guiying Zhang,Maosheng Cheng,Yanni Li,Keliang Liu,Lifeng Cai Chem. Commun., 2013,49, 11086-11088
• 2. Fc microparticles can modulate the physical extent and magnitude of complement activity?
  David White,Sean R. Stowell Biomater. Sci., 2017,5, 463-474
• 3. Establishment and implications of a characterization method for magnetic nanoparticle using cell tracking velocimetry and magnetic susceptibility modified solutions
  Huading Zhang,Lee R. Moore,Maciej Zborowski,P. Stephen Williams,Shlomo Margel,Jeffrey J. Chalmers Analyst, 2005,130, 514-527
• 4. Excess electrons in lithium–ethylamine solutions—density, electrical conductivity and EPR studies
  Phys. Chem. Chem. Phys., 1999,1, 3561-3565
• 5. Fe(ii)-Assisted one-pot synthesis of ultra-small core–shell Au–Pt nanoparticles as superior catalysts towards the HER and ORR?
  Yi Cao,Yujiao Xiahou,Lixiang Xing,Xiang Zhang,Hong Li,ChenShou Wu,Haibing Xia Nanoscale, 2020,12, 20456-20466

• Solvents and Organic Chemicals Organic Compounds Benzenoids Anthracenes Anthraquinones
• Anthraquinones
• Solvents and Organic Chemicals Organic Compounds Heterocyclic Compounds
• Solvents and Organic Chemicals Organic Compounds Aldehyde/Ketone

• 2549-78-2(1-Hydroxy-3-methylanthraquinone)
• 29482-75-5(Xylospyrin)
• 34425-60-0(1,8-Dihydroxy-2-methyl-anthrachinon)
• 1401-16-7(Rhodomycin)
• 2961-04-8(9,10-Anthracenedione,1,4,5-trihydroxy-)
• 67533-82-8(cyclo-Trijuglon)
• 29482-55-1(Xylospyrin)
• 25060-18-8(9,10-Anthracenedione,1,4-dihydroxy-2,3-dimethyl-)
• 2589-39-1(9,10-Anthracenedione,1,4-dihydroxy-2-methyl-)
• 27742-92-3(5,6,11,12,17,18-Trinaphthylenehexone, 2,8,15-triacetyl-1,7,16-trihydroxy-3,9,14-trimethyl-)