Abstract: The transition away from fossil-fuel-based electricity production is critical for cutting the emissions of climate change causing carbon dioxide emissions. Renewable energy sources, including solar and wind energy, are now cost-competitive with fossil fuels. This has generated serious interest in energy storage technologies to help manage the intermittency of these energy sources. Redox flow batteries provide a promising technology for providing grid-scale energy storage. Chapter 1 describes the current state of renewable energy and energy storage in electricity generation. The design and current state of redox flow batteries are discussed. Chapter 2 details the synthesis and characterization of a new anthraquinone, 2,6- D2PEAQ. A novel method of installing branched side chains to improve the aqueous solubility of anthraquinones is presented. Cell studies demonstrating a daily capacity fade of

Purchased from AmBeed: 605-32-3 ; 84-60-6

Product Details of 2-Hydroxyanthraquinone

CAS No. :	605-32-3
Formula :	C₁₄H₈O₃
M.W :	224.21
SMILES Code :	O=C(C1=C2C=CC=C1)C3=CC=C(O)C=C3C2=O
Synonyms :	2-hydroxy-9,10-Anthraquinone; NSC 2595; β-Hydroxyanthraquinone
MDL No. :	MFCD00027374
InChI Key :	GCDBEYOJCZLKMC-UHFFFAOYSA-N
Pubchem ID :	11796

Safety of 2-Hydroxyanthraquinone

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H315-H318-H335-H411
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P362+P364-P403+P233-P501
Class:	9
UN#:	3077
Packing Group:	Ⅲ

Application In Synthesis of 2-Hydroxyanthraquinone

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 605-32-3 ]

[ 605-32-3 ] Synthesis Path-Downstream 1~54

1
[ 67-56-1 ]
[ 605-32-3 ]
[ 3274-20-2 ]

References: [1]Journal of Biochemistry,1956,vol. 443,p. 21,23.

2
[ 107-10-8 ]
[ 605-32-3 ]
2-hydroxy-anthraquinone; propylamine salt [ No CAS ]

References: [1]Chemische Berichte,1941,vol. 74,p. 1129,1150, 1167.

3
[ 56-23-5 ]
2-hydroxy-2,4a-dihydro-anthraquinone [ No CAS ]
[ 605-32-3 ]
[ 434-85-5 ]

References: [1]Zhurnal Obshchei Khimii,1940,vol. 10,p. 869,877,878.
Chemisches Zentralblatt,1940,vol. 111,p. 3179.

4
[ 85-44-9 ]
[ 108-95-2 ]
[ 605-32-3 ]
[ 129-43-1 ]

References: [1]Chemische Berichte,1874,vol. 7,p. 972.

5
[ 118-29-6 ]
[ 605-32-3 ]
N-(2-hydroxy-9,10-dioxo-9,10-dihydro-[1]anthrylmethyl)-phthalimide [ No CAS ]
[ 858011-51-5 ]

References: [1]Helvetica Chimica Acta,1928,vol. 11,p. 1120.
Helvetica Chimica Acta,1930,vol. 13,p. 126.
[2]Patent: DE507049, .
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 16,p. 1235.

6
[ 64-17-5 ]
[ 605-32-3 ]
[ 61219-62-3 ]

References: [1]Journal of the Chemical Society,1922,vol. 121,p. 298.

7
[ 909878-64-4 ]
[ 605-32-3 ]
4-hydroxy-7-oxo-7H-benz[de]anthracene-3-carboxylic acid [ No CAS ]

References: [1]Journal of the Chemical Society,1922,vol. 121,p. 916.

8
[ 69-65-8 ]
[ 605-32-3 ]
4-hydroxy-7-oxo-7H-benz[de]anthracene-3-carboxylic acid [ No CAS ]

References: [1]Journal of the Chemical Society,1922,vol. 121,p. 916.

9
[ 57-48-7 ]
[ 605-32-3 ]
4-hydroxy-7-oxo-7H-benz[de]anthracene-3-carboxylic acid [ No CAS ]

References: [1]Journal of the Chemical Society,1922,vol. 121,p. 916.

10
[ 50-99-7 ]
[ 605-32-3 ]
4-hydroxy-7-oxo-7H-benz[de]anthracene-3-carboxylic acid [ No CAS ]

References: [1]Journal of the Chemical Society,1922,vol. 121,p. 916.

11
[ 67-66-3 ]
[ 605-32-3 ]
[ 860732-92-9 ]

References: [1]Journal of the Indian Chemical Society,1932,vol. 9,p. 173,177.

12
[ 34891-76-4 ]
[ 605-32-3 ]
[ 860746-46-9 ]

References: [1]Helvetica Chimica Acta,1928,vol. 11,p. 1120.
Helvetica Chimica Acta,1930,vol. 13,p. 126.
[2]Patent: DE507049, .
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 16,p. 1235.

13
[ 623-11-0 ]
2-hydroxy-2,4a-dihydro-anthraquinone [ No CAS ]
[ 605-32-3 ]
[ 72-48-0 ]

References: [1]Zhurnal Obshchei Khimii,1940,vol. 10,p. 869,877,878.
Chemisches Zentralblatt,1940,vol. 111,p. 3179.

14
[ 605-32-3 ]
[ 82-44-0 ]
1,2'-oxy-di-anthraquinone [ No CAS ]

References: [1]Patent: DE216268, .

15
[ 605-32-3 ]
[ 131-09-9 ]
[ 187729-11-9 ]

References: [1]Journal of the Chemical Society,1923,vol. 123,p. 3038.

16
[ 605-32-3 ]
[ 861075-99-2 ]
[ 72668-05-4 ]

References: [1]Patent: DE484665, .
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 16,p. 1244.
[2]Patent: DE484665, .
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 16,p. 1244.

17
[ 605-32-3 ]
[ 5449-65-0 ]

References: [1]Journal of the Chemical Society,1922,vol. 121,p. 299.
[2]Justus Liebigs Annalen der Chemie,1882,vol. 212,p. 28.
[3]Journal of the Chemical Society,1922,vol. 121,p. 299.
[4]Chemische Berichte,1969,vol. 102,p. 1053 - 1070.

18
[ 605-32-3 ]
[ 613-14-9 ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium tetrahydroborate; sodium carbonate; In isopropyl alcohol; for 0.333333h;Heating;	NaBH4 (3.8 g, 100 mmol) was dissolved in 1M Na2CO3 (150 mL) in a large beaker (2 L), isopropanol (25 mL) was added and the resulting solution was heated to boiling point. Then solution of hydroxyanthraquinone 6 (2.5 g, 10 mmol) in 1M Na2CO3 (50 mL) was added portionwise with vigorous stirring and breaking the foam with a glass rod. The reaction mixture was heated at boiling point for 20 min, cooled to rt and acidified with 3M HCl. The product was filtered and washed thoroughly with water and finally dried in evacuated dessicator over KOH for 2 days to afford the product (2 g, 93%) in the form of yellow solid. The product was pure enough for the next step, no purification was needed.

References: [1]Tetrahedron,2017,vol. 73,p. 5892 - 5899.
[2]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 735 - 739.
[3]Justus Liebigs Annalen der Chemie,1882,vol. 212,p. 26.
[4]Journal of the Chemical Society,1922,vol. 121,p. 298.
[5]Journal of the Chemical Society,1922,vol. 121,p. 298.
[6]Journal of Organic Chemistry,2003,vol. 68,p. 216 - 226.
[7]Angewandte Chemie - International Edition,2012,vol. 51,p. 3837 - 3841.
[8]Journal of Organic Chemistry,2014,vol. 79,p. 4390 - 4397.
[9]Journal of Materials Chemistry C,2015,vol. 3,p. 10695 - 10698.
[10]Journal of Organic Chemistry,2018,vol. 83,p. 8036 - 8053.

19
[ 605-32-3 ]
[ 81-64-1 ]

References: [1]Patent: DE86630, .
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 4,p. 301.

20
[ 605-32-3 ]
[ 72-48-0 ]

References: [1]Chemische Berichte,1874,vol. 7,p. 972.
[2]Doklady Akademii Nauk SSSR,1949,vol. 67,p. 1033.
Chem.Abstr.,1950,p. 1948.

21
[ 605-32-3 ]
[ 72668-05-4 ]

Yield	Reaction Conditions	Operation in experiment
68%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 4h;	<strong>[605-32-3]2-hydroxy anthraquinone</strong> (10 g, 44.63 mmol) with dimethylformamide (100 mL)Dissolved in NBS (8.34 g, 46.85 mmol)Was dissolved in dimethylformamide (100 ml), and then laminated at room temperature.Stir for 4 hours. After completion of the reaction, the solid produced during the reaction is filtered, washed with distilled water, and dried to obtain compound B-1. (9.62 g, 68%).

References: [1]Patent: KR2019/140741,2019,A .Location in patent: Paragraph 0147-0150.
[2]Patent: DE484665, .
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 16,p. 1244.

22
[ 605-32-3 ]
[ 568-98-9 ]

References: [1]Doklady Akademii Nauk SSSR,1949,vol. 67,p. 1033.
Chem.Abstr.,1950,p. 1948.

23
[ 605-32-3 ]
[ 767225-44-5 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1878,vol. <2>18,p. 179.
[2]Chemisches Zentralblatt,1905,vol. 76,p. 1515.

24
[ 605-32-3 ]
[ 118184-87-5 ]

References: [1]Journal of the Chemical Society,1929,p. 190.

25
[ 605-32-3 ]
[ 861075-99-2 ]

References: [1]Journal of the Chemical Society,1922,vol. 121,p. 1388.
[2]Journal of the Chemical Society,1929,p. 190.
[3]Patent: DE175663, .

26
[ 605-32-3 ]
[ 116557-48-3 ]

References: [1]Justus Liebigs Annalen der Chemie,1929,vol. 472,p. 104.

27
[ 605-32-3 ]
[ 6471-81-4 ]

References: [1]Chemische Berichte,1906,vol. 39,p. 114.

28
[ 605-32-3 ]
[ 873387-30-5 ]

References: [1]Journal of the Chemical Society,1929,p. 190.
[2]Zhurnal Obshchei Khimii,1952,vol. 22,p. 1594,1597; engl. Ausg. S. 1635, 1637.

29
[ 605-32-3 ]
[ 56600-62-5 ]

References: [1]Dissertation <Freiburg 1911>, S.10.,.

30
[ 605-32-3 ]
[ 182566-24-1 ]

References: [1]Journal of the Chemical Society,1922,vol. 121,p. 295.

31
[ 605-32-3 ]
[ 6407-61-0 ]

References: [1]Chemische Berichte,1881,vol. 14,p. 464.

32
[ 605-32-3 ]
[ 855266-71-6 ]

References: [1]Journal of the Chemical Society,1922,vol. 121,p. 291.

33
[ 605-32-3 ]
[ 141625-26-5 ]

References: [1]Journal of the Chemical Society,1922,vol. 121,p. 916.

34
[ 605-32-3 ]
[ 141600-18-2 ]

References: [1]Journal of the Chemical Society,1922,vol. 121,p. 916.

35
[ 605-32-3 ]
2-hydroxy-anthraquinone; barium compound [ No CAS ]

References: [1]Justus Liebigs Annalen der Chemie,1876,vol. 183,p. 160,163.

36
[ 605-32-3 ]
2-hydroxy-anthraquinon; ammonium salt [ No CAS ]

References: [1]Chemische Berichte,1941,vol. 74,p. 1129,1150, 1167.
[2]Journal fur praktische Chemie (Leipzig 1954),1930,vol. <2>126,p. 97,125.

37
[ 72-48-0 ]
[ 605-32-3 ]

References: [1]Chemische Berichte,1875,vol. 8,p. 975.

38
[ 131-09-9 ]
[ 605-32-3 ]

References: [1]Industrial and Engineering Chemistry,1929,vol. 21,p. 372.
Chemisches Zentralblatt,1929,vol. 100,p. 40.

39
[ 572-83-8 ]
[ 605-32-3 ]
[ 72-48-0 ]

References: [1]Justus Liebigs Annalen der Chemie,1871,vol. 160,p. 126.

40
[ 605-27-6 ]
[ 917-58-8 ]
[ 605-32-3 ]
[ 3274-20-2 ]

References: [1]Chemische Berichte,1904,vol. 37,p. 63.

41
[ 605-27-6 ]
[ 605-32-3 ]
[ 3274-20-2 ]

References: [1]Chemische Berichte,1904,vol. 37,p. 63.

42
[ 84-48-0 ]
[ 605-32-3 ]

References: [1]Chemische Berichte,1879,vol. 12,p. 1567.
[2]Patent: DE106505, .
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 5,p. 276.

43
[ 84-48-0 ]
[ 605-32-3 ]
[ 72-48-0 ]

References: [1]Justus Liebigs Annalen der Chemie,1871,vol. 160,p. 126.

44
[ 16433-87-7 ]
[ 605-32-3 ]

References: [1]Justus Liebigs Annalen der Chemie,1882,vol. 212,p. 63.

45
[ 568-98-9 ]
[ 605-32-3 ]

References: [1]Justus Liebigs Annalen der Chemie,1876,vol. 183,p. 211.

46
[ 5452-86-8 ]
[ 605-32-3 ]

References: [1]Journal of the American Chemical Society,1932,vol. 54,p. 1446,1451.

47
[ 374705-59-6 ]
[ 605-32-3 ]

References: [1]Helvetica Chimica Acta,1928,vol. 11,p. 1120.
Helvetica Chimica Acta,1930,vol. 13,p. 126.
[2]Helvetica Chimica Acta,1928,vol. 11,p. 1120.
Helvetica Chimica Acta,1930,vol. 13,p. 126.

48
[ 634602-13-4 ]
[ 605-32-3 ]
[ 129-43-1 ]

References: [1]Patent: DE148110, .

49
[ 131-08-8 ]
[ 605-32-3 ]

References: [1]Chemische Berichte,1881,vol. 14,p. 464.

50
[ 605-32-3 ]
[ 108-24-7 ]
[ 1629-57-8 ]

References: [1]Chemische Berichte,1872,vol. 5,p. 868.
[2]Chemische Berichte,1921,vol. 54,p. 3029.
Justus Liebigs Annalen der Chemie,1926,vol. 446,p. 98,108,109.

51
[ 84-65-1 ]
[ 605-32-3 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1896,vol. <2>54,p. 88,90.
Frdl.,vol. 4,p. 278,279.
[2]Patent: DE249368, .
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 11,p. 586.

52
[ 605-32-3 ]
[ 75-03-6 ]
[ 22924-21-6 ]

References: [1]Chemische Berichte,1882,vol. 15,p. 1796.

53
[ 99-06-9 ]
[ 65-85-0 ]
[ 605-32-3 ]
[ 129-43-1 ]

References: [1]Justus Liebigs Annalen der Chemie,1887,vol. 240,p. 262.
[2]Justus Liebigs Annalen der Chemie,1887,vol. 240,p. 262.

54
[ 605-32-3 ]
[ 109-89-7 ]
2-hydroxy-anthraquinone; diethylamine salt [ No CAS ]

References: [1]Chemische Berichte,1941,vol. 74,p. 1129,1150, 1167.

Historical Records

Technical Information

• Acidity of Phenols • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Chan-Lam Coupling Reaction • Clemmensen Reduction • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Electrophilic Substitution of the Phenol Aromatic Ring • Etherification Reaction of Phenolic Hydroxyl Group • Fischer Indole Synthesis • Friedel-Crafts Reaction • Grignard Reaction • Halogenation of Phenols • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Oxidation of Phenols • Passerini Reaction • Paternò-Büchi Reaction • Pechmann Coumarin Synthesis • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reformatsky Reaction • Reimer-Tiemann Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

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Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 605-32-3

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CAS No.: 605-32-3

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Product Details of 2-Hydroxyanthraquinone

Safety of 2-Hydroxyanthraquinone

Application In Synthesis of 2-Hydroxyanthraquinone

[ 605-32-3 ] Synthesis Path-Downstream 1~54

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