[ CAS No. 84-60-6 ] {[proInfo.proName]}

Name: 84-60-6|2,6-Dihydroxyanthracene-9,10-dione|97%
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Quality Control of [ 84-60-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 84-60-6 ]

SDS Specification

Alternatived Products of [ 84-60-6 ]

Product Details of [ 84-60-6 ]

CAS No. :	84-60-6	MDL No. :	MFCD00001228
Formula :	C₁₄H₈O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	APAJFZPFBHMFQR-UHFFFAOYSA-N
M.W :	240.21	Pubchem ID :	6776
Synonyms :	2,6-Dihydroxyanthraquinone;Anthraflavin	Chemical Name :	2,6-Dihydroxyanthracene-9,10-dione

Calculated chemistry of [ 84-60-6 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	63.8
TPSA :	74.6 Å²

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 :	Yes
Log Kp (skin permeation) :	-5.44 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.25
Log Po/w (XLOGP3) :	3.28
Log Po/w (WLOGP) :	1.87
Log Po/w (MLOGP) :	0.67
Log Po/w (SILICOS-IT) :	2.55
Consensus Log Po/w :	1.92

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.89
Solubility :	0.031 mg/ml ; 0.000129 mol/l
Class :	Soluble
Log S (Ali) :	-4.52
Solubility :	0.00723 mg/ml ; 0.0000301 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.1
Solubility :	0.0191 mg/ml ; 0.0000794 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	1.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.18

Safety of [ 84-60-6 ]

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

Application In Synthesis of [ 84-60-6 ]

* 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.

Upstream synthesis route of [ 84-60-6 ]
Downstream synthetic route of [ 84-60-6 ]

[ 84-60-6 ] Synthesis Path-Upstream 1~12

1
[ 99-06-9 ]
[ 84-60-6 ]
[ 569-08-4 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1894, vol. 280, p. 17
[2] Justus Liebigs Annalen der Chemie, 1873, vol. 170, p. 101
[3] Bulletin de la Societe Chimique de France, 1878, vol. <2>29, p. 401,434[4] Chemische Berichte, 1876, vol. 9, p. 946
[5] Chemische Berichte, 1877, vol. 10, p. 1225[6] Chemische Berichte, 1878, vol. 11, p. 969,1176

2
[ 860597-60-0 ]
[ 84-60-6 ]

Reference： [1] Journal of the Indian Chemical Society, 1936, vol. 13, p. 228,233

3
[ 120-12-7 ]
[ 83-72-7 ]
[ 72-48-0 ]
[ 84-60-6 ]
[ 108-95-2 ]

Reference： [1] Chemosphere, 2000, vol. 40, # 12, p. 1435 - 1441

4
[ 63712-32-3 ]
[ 84-60-6 ]

Reference： [1] Journal of the Indian Chemical Society, 1936, vol. 13, p. 228,233

5
[ 860561-54-2 ]
[ 84-60-6 ]

Reference： [1] Journal of the Indian Chemical Society, 1936, vol. 13, p. 228,233

6
[ 100-66-3 ]
[ 84-60-6 ]

Reference： [1] Journal of the Indian Chemical Society, 1936, vol. 13, p. 228,233

7
[ 84-50-4 ]
[ 84-60-6 ]
[ 85918-30-5 ]

Reference： [1] Chemische Berichte, 1876, vol. 9, p. 681

8
[ 84-50-4 ]
[ 84-60-6 ]
[ 82-29-1 ]

Reference： [1] Ullmanns Enzyklopaedie der technischen Chemie, Bd.I<Berlin u. Wien 1914>, S.200,202,

9
[ 99-06-9 ]
[ 84-60-6 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1913, vol. 398, p. 171

10
[ 99-06-9 ]
[ 117-12-4 ]
[ 84-60-6 ]
[ 569-08-4 ]

Reference： [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 21, p. 1033
[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 21, p. 1033

11
[ 7647-01-0 ]
[ 84-60-6 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1894, vol. 280, p. 17

12
[ 7647-01-0 ]
[ 7664-93-9 ]
[ 84-60-6 ]
[ 99-06-9 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1894, vol. 280, p. 17

[ 84-60-6 ] Synthesis Path-Downstream 1~9

1
[ 84-60-6 ]
[ 36319-03-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: K₂CO₃ / acetone 2: 60 percent / Zn; glacial acetic acid / 24 h / Heating
	Multi-step reaction with 3 steps 1: amalgamated aluminium; ammonia 2: pyridine 3: sulfuric acid
	Multi-step reaction with 3 steps 1: amalgamated aluminium; ammonia 2: pyridine

	Multi-step reaction with 2 steps 1: amalgamated aluminium; ammonia
	Multi-step reaction with 3 steps 1: potassium carbonate / acetone / 5 h / 100 °C / Inert atmosphere 2: ammonium hydroxide; zinc / ethanol; water / 2 h / Reflux 3: lithium aluminium tetrahydride / diethyl ether / 1.5 h / 0 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 8 h / Reflux 2: sodium tetrahydroborate / isopropyl alcohol / Inert atmosphere; Reflux
	Multi-step reaction with 2 steps 1: sodium tetrahydroborate; sodium carbonate / 29 h / 20 °C / Inert atmosphere; Large scale 2: potassium carbonate / acetone / 16 h / 20 - 75 °C / Inert atmosphere

Reference： [1]Lu, Lingang; Chen, Qiyin; Zhu, Xiaozhang; Chen, Chuanfeng [Synthesis, 2003, # 16, p. 2464 - 2466]
[2]Hall; Perkin [Journal of the Chemical Society, 1923, vol. 123, p. 2036]
[3]Hall; Perkin [Journal of the Chemical Society, 1923, vol. 123, p. 2036]
[4]Hall; Perkin [Journal of the Chemical Society, 1923, vol. 123, p. 2036]
[5]Keller, Friedrich; Ruechardt, Christoph [Journal fur Praktische Chemie - Chemiker-Zeitung, 1998, vol. 340, # 7, p. 642 - 648]
[6]Geiseler, Oliver; Müller, Monika; Podlech, Joachim [Tetrahedron, 2013, vol. 69, # 18, p. 3683 - 3689]
[7]Current Patent Assignee: DUPONT DE NEMOURS INC - WO2020/18617, 2020, A1

2
[ 18908-66-2 ]
[ 84-60-6 ]
[ 332083-42-8 ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium carbonate In DMF (N,N-dimethyl-formamide) at 90℃;	1.1 Synthesis of 2,6-di(2-ethylhexyloxy)anthraquinone Into a 500 ml flask, 10 g (42 mmole) of 2,6-dihydroxyanthraquinone, 16.5 g (86 mmole) of 2-ethylhexyl bromide, 12 g (87 mmole) of anhydrous potassium carbonate and 200 ml of dimethylformamide (DMF) were placed, and the resultant mixture was heated at 90°C under stirring for one night. After the reaction was completed, DMF was removed by distillation, and 50 ml of water was added. The reaction solution was treated by extraction with diethyl ether, washed with a saturated aqueous solution of sodium chloride and dried with magnesium sulfate. After the concentration under a reduced pressure, the obtained crude product was recrystallized from methanol, and 12.5 g of the quinone compound of the object compound was obtained (the yield: 65%; a yellow powder).
62%	Stage #1: anthraflavic acid With potassium carbonate In ISOPROPYLAMIDE at 80℃; for 1h; Stage #2: 3-bromomethylheptane In ISOPROPYLAMIDE at 80℃; for 8.5h;	A.2 Preparation of 2,6-bis[2-ethylhexyloxy]anthraquinone 85 g of 2,6-dihydroxy-anthraquinone are added to a 2 liter round-bottom flask equipped with mechanical stirrer, thermometer and reflux condenser and containing 1000 ml of N,N'-dimethylacetamide. The mixture is heated to 80° C. until the 2,6-dihydroxy-anthraquinone is dissolved. 122 g of K2CO3 are added and the mixture is stirred for one hour. Then, 205.4 g of 2-ethylhexyl bromide are added dropwise within 30 minutes. Subsequently, the reaction is left at 80° C. for 8 hours. The reaction is then filtered and the solvent is evaporated by means of a rotary evaporator. The residue is taken up in toluene, washed three times with water, treated successively with active carbon, tonsil earth and filtered. After removing the solvent by evaporation, the desired product is obtained as a yellow solid which is purified by recrystallization from 400 ml of isopropanol.Melting point: 70.9-74.7° C. (Yield: 62%)
30%	With potassium carbonate In N,N-dimethyl-formamide for 60h; Reflux;

Reference： [1]Current Patent Assignee: IDEMITSU KOSAN CO LTD - EP1440959, 2004, A1 Location in patent: Page 19
[2]Current Patent Assignee: BASF SE - US2011/15295, 2011, A1 Location in patent: Page/Page column 16
[3]Location in patent: experimental part Bhowmik, Pradip K.; Nedeltchev, Alexi K.; Han, Haesook [Molecular Crystals and Liquid Crystals, 2009, vol. 501, p. 125 - 137]

3
[ 40258-78-4 ]
[ 84-60-6 ]
[ 1110718-21-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In ISOPROPYLAMIDE; at 80 - 100℃; for 9h;	50 g of 2,6-dihydroxyanthraquinone are dissolved in 300ml of dimethylacetamide and while stirring, 71 g of potassium carbonate are added to the mixture. The reaction is heated at 800C for 1 hour, then 87g of bromoisopropylacetate are added drop wise to the reaction mixture. The reaction mixture is then heated and maintained at 1000C for 8 hours and after that concentrated under reduced pressure. The residue is dissolved in dichloromethane and washed several times with water. The organic phase is then concentrated under vacuum. 64.5 g of 2,6-bis(methyl ester propionoxy) 9,10-dianthraquinone are obtained as yellow solid with a melting point of 169-176°C. The proposed structure is confirmed by NMR analysis.

Reference： [1]Patent: WO2009/16083,2009,A1 .Location in patent: Page/Page column 59

4
[ 84-60-6 ]
[ 112-89-0 ]
[ 912278-40-1 ]

Yield	Reaction Conditions	Operation in experiment
71%	With potassium carbonate In N,N-dimethyl acetamide; water; toluene	A.3 Preparation of 2,6-bis[octadecyloxy]anthraquinone EXAMPLE (A-3) Preparation of 2,6-bis[octadecyloxy]anthraquinone In a 500 ml round-bottom flask equipped with mechanical stirrer, thermometer, dropping funnel and condenser 10 g of 2,6-dihydroxy-anthraquinone and 16.2 g of K2CO3 are suspended in 100 ml of N,N'-dimethylacetamide and heated to 120° C. After one hour, 39.1 g of 1-bromo-octadecane are added dropwise. After completion of the addition, the mixture is heated for further 5 hours. After cooling to room temperature, the reaction mixture is allowed to stand overnight, during which a yellow precipitate is formed. TLC (Thin Layer Chromatography) analysis shows the presence of the starting material 2,6-dihydroxy anthraquinone, so another 5 g of K2CO3 are added and the reaction is re-heated for further two hours. Repeating TLC analysis confirms the complete conversion of 2,6-dihydroxy-anthraquinone. After cooling to room temperature, the mixture is filtered and a brown solid is obtained. The crude product is redissolved in toluene at 70° C. and washed three times with 100 ml of water. After evaporation of the organic solvent, the desired product is obtained as a yellow powder which is recrystallized from toluene. Melting point: 112-122° C. (Yield: 71%)
71%	Stage #1: anthraflavic acid With potassium carbonate In ISOPROPYLAMIDE at 120℃; for 1h; Stage #2: 1-Bromooctadecane In ISOPROPYLAMIDE at 120℃;	A.3 Preparation of 2,6-bis[octadecyloxy]anthraquinone In a 500 ml round-bottom flask equipped with mechanical stirrer, thermometer, dropping funnel and condenser 10 g of 2,6-dihydroxy-anthraquinone and 16.2 g of K2CO3 are suspended in 100 ml of N,N'-dimethylacetamide and heated to 120° C. After one hour, 39.1 g of 1-bromo-octadecane are added dropwise. After completion of the addition, the mixture is heated for further 5 hours. After cooling to room temperature, the reaction mixture is allowed to stand overnight, during which a yellow precipitate is formed. TLC (Thin Layer Chromatography) analysis shows the presence of the starting material 2,6-dihydroxy anthraquinone, so another 5 g of K2CO3 are added and the reaction is re-heated for further two hours. Repeating TLC analysis confirms the complete conversion of 2,6-dihydroxy-anthraquinone. After cooling to room temperature, the mixture is filtered and a brown solid is obtained. The crude product is redissolved in toluene at 70° C. and washed three times with 100 ml of water. After evaporation of the organic solvent, the desired product is obtained as a yellow powder which is recrystallized from toluene.Melting point: 112-122° C. (Yield: 71%)

Reference： [1]Current Patent Assignee: BASF SE - US2009/76206, 2009, A1
[2]Current Patent Assignee: BASF SE - US2011/15295, 2011, A1 Location in patent: Page/Page column 16

5
[ 84-60-6 ]
[ 2312-15-4 ]
[ 1079900-78-9 ]

Yield	Reaction Conditions	Operation in experiment
79%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 40h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Isoda, Kyosuke; Yasuda, Takuma; Kato, Takashi [Journal of Materials Chemistry, 2008, vol. 18, # 38, p. 4522 - 4528]

6
[ 84-60-6 ]
[ 117241-31-3 ]
[ 1079900-68-7 ]

Reference： [1]Journal of Materials Chemistry,2008,vol. 18,p. 4522 - 4528

7
[ 84-60-6 ]
[ 594838-61-6 ]

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 6193 - 6201
[2]Chemical Communications,2015,vol. 51,p. 11777 - 11779
[3]Journal of the American Chemical Society,2017,vol. 139,p. 17261 - 17264
[4]Patent: CN110627602,2019,A

8
[ 3575-31-3 ]
[ 84-60-6 ]
C₄₄H₄₈O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%		Specific steps:1 g (4.2 mmol) of the reaction monomer 2,6-dihydroxyanthraquinone was dissolved in an anhydrous dichloromethane solvent, To this was added 1.8 g (8.7 mmol) of dicyclohexylcarbodiimide (DCC) and 0.05 g (0.42 mmol) of 4-dimethylaminopyridine (DMAP).Stirring at room temperature for 10min,Then, 2.05 g (8.7 mmol) of <strong>[3575-31-3]n-<strong>[3575-31-3]octylbenzoic acid</strong></strong> was added thereto,Reaction 24hAfter the reaction,Steamed to the solvent methylene chloride,The product was then purified by column chromatography on silica gel (200-300 mesh)Dichloromethane as developing solvent, and finally dried to give the title product as a white solid (yield:83%).The target product obtained in this example was examined by a polarizing microscope. As a result, as shown in Fig. 1,It can be seen from Fig. 1 that the target product has a liquid crystal property and a typical texture of the smectic phase at 120 C.

Reference： [1]Patent: CN106366689,2017,A .Location in patent: Paragraph 0026; 0027; 0028; 0029

9
[ 358-23-6 ]
[ 84-60-6 ]
[ 594838-61-6 ]

Yield	Reaction Conditions	Operation in experiment
5.132 mg	With triethylamine; In dichloromethane; at -40 - 20℃; for 14.0h;Inert atmosphere;	To a 250 mL two neck round bottom flask charged with magnetic bar, crude product 1 (3.35 g,15.95 mmol) was added, then protected under argon, dry dichloromethane (50 mL) and triethylamine (50 mL). After cooling to -40 C, triflicanhydride (13.39 mL, 79.62 mmol) was slowly added dropwise via syringe. The mixture was stirred for 2 h and then warmed up to room temperature for another 12 h. Dichloromethane (100 mL) was added and the mixture was washed with water (20 mL×3) and brine (20 mL×3). The organic layer was separated, dried over Na2SO4 and evaporated under reduced pressure, and the crude product was purified by column chromatography (silica, petroleum/dichloromethane) to afford white solid (5.132 mg, 68%yield). 1H NMR (400 MHz, CDCl3): delta (ppm) 8.36 (s, 2H,ArH), 8.01 (d, 2H, ArH), 7.86 (d, 2H, ArH), 7.39 (dd, 2H,ArH). MS (EI): m/z 474 (M+).

Reference： [1]Science China Chemistry,2019,vol. 62,p. 251 - 255

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P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
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

[ CAS No. 84-60-6 ] {[proInfo.proName]}

Quality Control of [ 84-60-6 ]

Related Doc. of [ 84-60-6 ]

Product Details of [ 84-60-6 ]

Calculated chemistry of [ 84-60-6 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 84-60-6 ]

Application In Synthesis of [ 84-60-6 ]

[ 84-60-6 ] Synthesis Path-Upstream 1~12

[ 84-60-6 ] Synthesis Path-Downstream 1~9

Related Functional Groups of [ 84-60-6 ]

Aryls

Ketones

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 84-60-6 ]