[ CAS No. 117-78-2 ] {[proInfo.proName]}

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2D 3D

Structure of 117-78-2 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 117-78-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 117-78-2 ]

SDS Specification

Alternatived Products of [ 117-78-2 ]

Product Details of [ 117-78-2 ]

CAS No. :	117-78-2	MDL No. :	MFCD00001231
Formula :	C₁₅H₈O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ASDLSKCKYGVMAI-UHFFFAOYSA-N
M.W :	252.22	Pubchem ID :	67030
Synonyms :		Chemical Name :	9,10-Dioxo-9,10-dihydroanthracene-2-carboxylic acid

Calculated chemistry of [ 117-78-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	19
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	66.71
TPSA :	71.44 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.34 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.4
Log Po/w (XLOGP3) :	3.52
Log Po/w (WLOGP) :	2.16
Log Po/w (MLOGP) :	1.39
Log Po/w (SILICOS-IT) :	2.93
Consensus Log Po/w :	2.28

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-4.02
Solubility :	0.0239 mg/ml ; 0.0000949 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.7
Solubility :	0.00498 mg/ml ; 0.0000198 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.62
Solubility :	0.00602 mg/ml ; 0.0000239 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	1.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.34

Safety of [ 117-78-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 117-78-2 ]

* 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 [ 117-78-2 ]

[ 117-78-2 ] Synthesis Path-Downstream 1~15

1
[ 67-56-1 ]
[ 117-78-2 ]
[ 32114-48-0 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1932,vol. 7,p. 114,117, 118

2
[ 75-93-4 ]
[ 117-78-2 ]
[ 32114-48-0 ]

Reference： [1]Patent: DE609401,1932,
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 21,p. 1031

3
[ 64-17-5 ]
[ 117-78-2 ]
[ 32114-49-1 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1932,vol. 7,p. 114,117, 118

4
[ 37649-98-2 ]
[ 117-78-2 ]

Reference： [1]Patent: DE243788,
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 10,p. 598

5
[ 76213-20-2 ]
[ 117-78-2 ]

Reference： [1]Helvetica Chimica Acta,1931,vol. 14,p. 369,375

6
[ 613-12-7 ]
[ 117-78-2 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1915,vol. <2> 92,p. 51
[2]Chemische Berichte,1874,vol. 7,p. 1184

7
[ 84-54-8 ]
[ 117-78-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	With chromium(VI) oxide; acetic acid; at 85℃; for 16h;	2-Methylanthraquinone (1) (1 g, 4.5 mmol) and acetic acid (50 mL) were added to a double-necked flask fittedwith a condenser. A mechanical stirrer and a thermocouple were also placed into the flask. The reactionmixture was warmed gently with stirring to dissolve 2-methylanthraquinone. Then anhydrous CrO3 (5.4 g,54 mmol) was added slowly with vigorous stirring. The solution mixture was heated to 85 C and kept atthat temperature overnight (16 h) with stirring. Then the completed reaction mixture was cooled at roomtemperature and diluted with 150 mL of distilled water. The resulting precipitate was filtered and washedwith water until the blue color of chromium salts disappeared. The obtained solid was recrystallized in aceticacid to yield anthraquinone-2-carboxylic acid (2) as white crystalline solid. Yield: 85percent. 1 H NMR (400 MHz,DMSO-d6) 13.73 (s, 1H), 8.64 (d, J = 1.7 Hz, 1H), 8.38 (dd, J = 8.0, 1.6 Hz, 1H), 8.28 (dd, J = 8.0, 1.9Hz, 1H), 8.21 (dd, J = 5.1, 2.2 Hz, 2H), 8.01?7.90 (m, 2H). 13 C NMR (100 MHz, d6 -DMSO) 181.9, 181.8,165.9, 135.6, 135.5, 134.7, 134.7, 134.4, 133.1, 133.0 (2C), 127.3, 127.2, 126.8 (2C).
42.9%	With chromium(VI) oxide; acetic acid; at 80 - 120℃; for 1h;	To a 500 mL reaction flask was added 2-methyl-9,10-anthraquinone (8.9 g, 40 mmol) And glacial acetic acid (180 mL, 20 mL / g), stirred at 80 ° C, Silica oxide (40 g, 0.4 mol) was slowly added in portions, After the temperature is stable, the temperature is raised to 120 ° C. After cooling, the mixture was washed with water to obtain 4.32 g of a pale yellow cotton solid in a yield of 42.9percent.
	With ammonium hydroxide; sodium dichromate; In sulfuric acid; water;	Reference Preparation 6 -Anthraquinone-2-carboxylic acid. 2-Methylanthraquinone (3 g.) was dissolved in sulphuric acid (15 ml) and the solution cooled and diluted with water (15 ml) The mixture was then cooled and stirred vigorously during the portionwise addition of powdered sodium dichromate (9 g.) and finally heated on the steam-bath for 3 hours, cooled and treated with water (100 ml.). The precipitated solid was filtered, washed well with water and treated with hot dilute aqueous ammonia (60 ml. water and 2 ml. of 0.880 ammonia). The solution was filtered hot and acidified with hydrochloric acid; the pale yellow precipitate was filtered, washed with water and dried to give anthraquinone-2-carboxylic acid, m.p. 291°-292° unchanged by recrystallisation from dimethylformamide.

With ammonium hydroxide; sodium dichromate; In sulfuric acid; water;

REFERENCE PREPARATION 6 Anthraquinone-2-carboxylic acid 2-Methylanthraquinone (3 g.) was dissolved in sulphuric acid (15 ml) and the solution cooled and diluted with water (15 ml). The mixture was then cooled and stirred vigorously during the portionwise addition of powered sodium dichromate (9 g.) and finally heated on the steam-bath for 3 hours, cooled and treated with water (100 ml.). The precipitated solid was filtered washed well with water and treated with hot dilute aqueous ammonia (60 ml. water and 2 ml. of 0.880 ammonia). The solution was filtered hot and acidified with hydrochloric acid; the pale yellow precipitate was filtered, washed with water and dried to give anthraquinone-2-carboxylic acid, m.p. 291°-292° unchanged by recrystallisation from dimethylformamide.

Reference： [1]Turkish Journal of Chemistry,2018,vol. 42,p. 1136 - 1145
[2]Patent: CN104788333,2017,B .Location in patent: Paragraph 0184-0186
[3]Zhurnal Obshchei Khimii,1941,vol. 11,p. 16,21, 22
    Chem.Abstr.,1941,p. 5487
[4]Chemische Berichte,1883,vol. 16,p. 2610
[5]Chemische Berichte,1878,vol. 11,p. 88
[6]Chemische Berichte,1884,vol. 17,p. 890
[7]Doklady Akademii Nauk SSSR,1938,vol. 20,p. 555,556, 559
[8]Patent: DE250742,
    Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 11,p. 594
[9]Chemische Berichte,1925,vol. 58,p. 320
    Chemisches Zentralblatt,1924,vol. 95,p. 1713
[10]Journal of the American Chemical Society,1929,vol. 51,p. 859
[11]Patent: US2794813,1953,
[12]Journal of Medicinal Chemistry,1982,vol. 25,p. 369 - 373
[13]Tetrahedron Letters,1996,vol. 37,p. 4541 - 4544
[14]Patent: US3987088,1976,A
[15]Structural Chemistry,2010,vol. 21,p. 1079 - 1083
[16]Chemical Biology and Drug Design,2018,vol. 91,p. 893 - 901
[17]Patent: US3939276,1976,A
[18]Patent: DE383030,
    Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 14,p. 442
[19]Patent: DE174984,

8
[ 84-54-8 ]
[ 117-78-2 ]
[ 96416-33-0 ]

Reference： [1]Chemische Berichte,1925,vol. 58,p. 320
Chemisches Zentralblatt,1924,vol. 95,p. 1713
[2]Patent: DE383030,
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 14,p. 442

9
[ 1758-68-5 ]
[ 117-78-2 ]
2-(9,10-dioxo-9,10-dihydro-[2]anthryl)-3H-anthra[1,2-d]imidazole-6,11-dione [ No CAS ]

Reference： [1]Justus Liebigs Annalen der Chemie,1915,vol. 407,p. 186

10
[ 117-78-2 ]
[ 605-22-1 ]
2-(9,10-dioxo-9,10-dihydro-[2]anthryl)-1H-anthra[2,3-d]imidazole-5,10-dione [ No CAS ]

Reference： [1]Justus Liebigs Annalen der Chemie,1915,vol. 407,p. 186

11
[ 117-78-2 ]
[ 613-08-1 ]

Yield	Reaction Conditions	Operation in experiment
72%	With copper(ll) sulfate pentahydrate; ammonia; water; zinc; at 70 - 85℃; for 7.5h;	Anthraquinone-2-carboxylic acid (2) (0.5 g, 2 mmol), zinc dust (2.6 g, 40 mmol), CuSO4 .5H2 O (0.1 g, 0.4mmol), and aqueous ammonia (35 mL, 26percent) were added to a 100-mL flask. The reaction mixture was stirredwith a magnetic stirrer under reflux at 70 C for 5.5 h. Then the reaction temperature was increased to 85 Cand kept for 2 h at this temperature. The completed hot reaction mixture was filtered to remove insolubleresidues and the filtrate was cooled. After that, the filtrate was acidified with dilute HCl (1:1) until pH wasbetween 4 and 5. The precipitated yellow solid was filtered and dried in a freeze dryer. Then the yellow solid wasrecrystallized in acetic acid. The reaction was completed with 72percent yield. 1 H NMR (400 MHz, DMSO-d6) 8.76 (s, 2H), 8.62 (s, 1H), 8.30?7.92 (m, 4H), 7.66-7.50 (m, 2H). 13 C NMR (100 MHz, DMSO-d6) 167.4,132.5, 132.1, 131.6, 131.5, 130.0, 128.5, 128.5, 128.3, 128.1, 127.5, 127.5, 126.7, 126.0, 124.1.

Reference： [1]Turkish Journal of Chemistry,2018,vol. 42,p. 1136 - 1145
[2]Bulletin of the Chemical Society of Japan,1994,vol. 67,p. 891 - 894
[3]Chemische Berichte,1883,vol. 16,p. 2610
[4]Tetrahedron,1971,vol. 27,p. 935 - 944
[5]Tetrahedron Letters,1995,vol. 36,p. 8427 - 8430
[6]Tetrahedron Letters,1996,vol. 37,p. 4541 - 4544

12
[ 117-78-2 ]
[ 19591-45-8 ]

Reference： [1]Patent: DE84505,
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 4,p. 300

13
[ 117-78-2 ]
[ 61157-85-5 ]

Reference： [1]Patent: US1991191,1933,
[2]Patent: US1991191,1933,

14
[ 117-78-2 ]
[ 6470-87-7 ]

Yield	Reaction Conditions	Operation in experiment
	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; for 2h;Inert atmosphere;	This example and the following Examples 2 and 3 describe compounds and methods of the invention for making an ASM-amide-linked sol-gel matrix material and corresponding WE of the invention. Anthraquinone-2-carboxylic acid (0.500 g, 1.98 mmol) was suspended in dichloromethane (20 mL) in a vial, and then the vial was purged with nitrogen. 0.2 mL of dimethylformamide (DMF) was added dropwise, followed by addition of oxalyl chloride (0.18 mL, 2.2 mmol). The solution was stirred for 2 h. Then, diethylaminomethylpolystyrene (1.97 g, 6.3 mmol of amine) was added followed by 3-aminopropyltrimethoxysilane (APTOS) (0.37 mL, 2.1 mmol). Stirring was continued for 16 h at ambient temperature. The resultant liquid was filtered to remove the diethylaminomethylpolystyrene solid. Additional dichloromethane was used to rinse the retained solid to recover entrained product. The dichloromethane was removed in a rotary evaporator to obtain an amber oily liquid. Anhydrous alcohol was used to reconstitute the oily liquid to obtain 20 mL of the amide-linked AQ silane solution.
	With thionyl chloride; N,N-dimethyl-formamide; In dichloromethane;Reflux;	9,10-<strong>[117-78-2]anthraquinone-2-carboxylic acid</strong> (1.86 g, 7.4 mmol) was added to a 100 mL reaction flask,Thionyl chloride (1.05 g, 8.9 mmol), dichloromethane (30 mL), catalytic amount of DMF, reflux reaction overnight, to be completely clear solution to be -9,10-anthraquinone-2-formyl chloride in dichloromethane solution, Directly for the next step

Reference： [1]European Journal of Medicinal Chemistry,2007,vol. 42,p. 752 - 771
[2]Journal of Organic Chemistry,1992,vol. 57,p. 6143 - 6150
[3]Chemistry - A European Journal,2002,vol. 8,p. 5630 - 5643
[4]Journal of the American Chemical Society,1994,vol. 116,p. 9847 - 9859
[5]Journal of the Indian Chemical Society,1932,vol. 9,p. 375
[6]Bulletin of the Chemical Society of Japan,1932,vol. 7,p. 114,117, 118
[7]Chemische Berichte,1884,vol. 17,p. 890
[8]Helvetica Chimica Acta,1926,vol. 9,p. 802
[9]Liebigs Annalen der Chemie,1981,p. 792 - 810
[10]Journal of Medicinal Chemistry,1982,vol. 25,p. 369 - 373
[11]Journal of the American Chemical Society,1989,vol. 111,p. 5542 - 5551
[12]Helvetica Chimica Acta,1980,vol. 63,p. 413 - 419
[13]Journal of Organic Chemistry,1996,vol. 61,p. 1297 - 1301
[14]Journal of Physical Chemistry A,2000,vol. 104,p. 8315 - 8322
[15]Bulletin of the Chemical Society of Japan,2000,vol. 73,p. 2051 - 2058
[16]Organic letters,2000,vol. 2,p. 3413 - 3416
[17]Journal of Organic Chemistry,2000,vol. 65,p. 5355 - 5359
[18]Chemical Communications,2009,p. 5281 - 5283
[19]European Journal of Inorganic Chemistry,2014,vol. 2014,p. 1984 - 2001
[20]Patent: US9417204,2016,B2 .Location in patent: Page/Page column 24; 25
[21]Patent: CN104788333,2017,B .Location in patent: Paragraph 0189-0191
[22]Chemical Biology and Drug Design,2018,vol. 91,p. 893 - 901
[23]Chemical Communications,2018,vol. 54,p. 3038 - 3041
[24]Angewandte Chemie - International Edition,2018,vol. 57,p. 16871 - 16876
Angew. Chem.,2018,vol. 130,p. 17113 - 17118,6

15
[ 613-08-1 ]
[ 117-78-2 ]

Reference： [1]Chemische Berichte,1880,vol. 13,p. 47
[2]Journal of the Chemical Society. Perkin transactions I,1997,p. 127 - 133
[3]Journal of the Chemical Society. Perkin transactions I,1997,p. 127 - 133
[4]Journal of the Chemical Society. Perkin transactions I,1997,p. 127 - 133
[5]Journal of the Chemical Society. Perkin transactions I,1997,p. 127 - 133
[6]Journal of Nanoscience and Nanotechnology,2015,vol. 15,p. 1171 - 1179

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Technical Information

? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Friedel-Crafts Reaction ? Heat of Combustion ? Hydrogenolysis of Benzyl Ether ? Preparation of Alkylbenzene ? Reactions of Benzene and Substituted Benzenes ? Vilsmeier-Haack Reaction

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H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
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. 117-78-2 ] {[proInfo.proName]}

Quality Control of [ 117-78-2 ]

Related Doc. of [ 117-78-2 ]

Product Details of [ 117-78-2 ]

Calculated chemistry of [ 117-78-2 ] Expand+

Physicochemical Properties

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Lipophilicity

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[ 117-78-2 ] Synthesis Path-Downstream 1~15

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