[ CAS No. 76275-14-4 ] {[proInfo.proName]}

Name: 76275-14-4|9,10-Dibutoxyanthracene|95%
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SKU: A234523
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2D 3D

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Quality Control of [ 76275-14-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 76275-14-4 ]

SDS Specification

Alternatived Products of [ 76275-14-4 ]

Product Details of [ 76275-14-4 ]

CAS No. :	76275-14-4	MDL No. :	MFCD22495163
Formula :	C₂₂H₂₆O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KSMGAOMUPSQGTB-UHFFFAOYSA-N
M.W :	322.44	Pubchem ID :	21987539
Synonyms :

Calculated chemistry of [ 76275-14-4 ]

Physicochemical Properties

Num. heavy atoms :	24
Num. arom. heavy atoms :	14
Fraction Csp3 :	0.36
Num. rotatable bonds :	8
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	103.28
TPSA :	18.46 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-3.39 cm/s

Lipophilicity

Log Po/w (iLOGP) :	4.31
Log Po/w (XLOGP3) :	6.87
Log Po/w (WLOGP) :	6.35
Log Po/w (MLOGP) :	4.68
Log Po/w (SILICOS-IT) :	6.35
Consensus Log Po/w :	5.71

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	1.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-6.07
Solubility :	0.000274 mg/ml ; 0.000000849 mol/l
Class :	Poorly soluble
Log S (Ali) :	-7.07
Solubility :	0.0000276 mg/ml ; 0.0000000855 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-8.41
Solubility :	0.00000125 mg/ml ; 0.0000000039 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.29

Safety of [ 76275-14-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 76275-14-4 ]

* 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 [ 76275-14-4 ]

[ 76275-14-4 ] Synthesis Path-Downstream 1~9

1
[ 109-65-9 ]
[ 84-65-1 ]
9,10-dibutoxyanthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With tetrabutylammomium bromide; iron; sodium hydroxide; zinc In water; toluene at 50 - 65℃; for 2h;	1-2; 4 Preparation of 9,10-dibutoxyanthracene: Add 41.6g anthraquinone, 25.0g zinc powder, 5.0g iron powder, 10.0g tetrabutylammonium bromide into 85.0g water, adjust the temperature to 50°C, mix well, and then add 60.0g 45% sodium hydroxide aqueous solution dropwise After that, adjust the temperature to 60°C, and then add 120.0g of bromobutane dropwise, and adjust the temperature to 65°C. When reacting for 60 minutes, the content of anthraquinone is less than 0.5%. Add toluene and stir for 1 hour, separate the liquids, filter, and remove the A large amount of solid precipitated out after part of toluene. After adding methanol, the temperature was lowered to 5°C to crystallize for 5 hours, filtered, the filter cake was washed with acetone/methanol mixture, and dried to obtain 61.8g of 9,10-dibutoxanthracene as a bright yellow-green solid. The purity was 99.1%, and the yield was 96.0%
85%	In butanone	7 The same operation was carried out by the method disclosed in Example 3 except that instead of using methyl ethyl ketone as an organic solvent, butyl bromide was increased to 57 g, whereby the yield of 9,10-dibutoxyanthracene was 85 mol%.
82%	In 4-methyl-2-pentanone	8 The same operation was carried out by the method disclosed in Example 3 except that methyl isobutyl ketone was used instead of methyl ethyl ketone, whereby the yield of 9,10-dibutoxyanthracene was 82 mol%.

50%	In isopropyl alcohol	4 The same operation was carried out by the method disclosed in Example 3 except that isopropyl alcohol was used instead of methyl ethyl ketone, whereby the yield of 9,10-dibutoxyanthracene was 50 mol%.
43%	In o-xylene	5 The same operation was carried out by the method disclosed in Example 3 except that o-xylene was used instead of methyl ethyl ketone, whereby the yield of 9,10-dibutoxyanthracene was 43 mol%.
14%		3 The same operation was carried out by the method disclosed in Example 3 except that no tetrabutylammonium bromide was added, whereby the yield of 9,10-dibutoxyanthracene was 14 mol%.

Reference： [1]Current Patent Assignee: DALIAN TRICO CHEMICAL - CN112939758, 2021, A Location in patent: Paragraph 0018-0025; 0029-0031
[2]Current Patent Assignee: HIROYUKI HONDA ET EL; KAWASAKI KASEI CHEMICALS LTD. - EP1574493, 2005, A1 Location in patent: Page/Page column 9
[3]Current Patent Assignee: HIROYUKI HONDA ET EL; KAWASAKI KASEI CHEMICALS LTD. - EP1574493, 2005, A1 Location in patent: Page/Page column 9
[4]Current Patent Assignee: HIROYUKI HONDA ET EL; KAWASAKI KASEI CHEMICALS LTD. - EP1574493, 2005, A1 Location in patent: Page/Page column 9
[5]Current Patent Assignee: HIROYUKI HONDA ET EL; KAWASAKI KASEI CHEMICALS LTD. - EP1574493, 2005, A1 Location in patent: Page/Page column 9
[6]Current Patent Assignee: HIROYUKI HONDA ET EL; KAWASAKI KASEI CHEMICALS LTD. - EP1574493, 2005, A1 Location in patent: Page/Page column 9

2
[ 109-65-9 ]
[ CAS Unavailable ]
[ 76275-14-4 ]
[ 96403-34-8 ]
[ 84-65-1 ]

Yield	Reaction Conditions	Operation in experiment
9%	In DMF (N,N-dimethyl-formamide); water at 65 - 70℃; for 2h;	2 Firstly, by the method disclosed in Example 1, an aqueous solution of the sodium salt of 9,10-anthracenediol was prepared. Then, into the autoclave used in the method disclosed in Example 1, this aqueous solution of the sodium salt of 9,10-anthracenediol was charged, and the internal temperature was raised to and maintained at 65°C with stirring. A solution having 108 g of butyl bromide dissolved in 300 g of dimethylformamide, was added over a period of one hour. After completion of the addition of butyl bromide, the internal temperature was further raised to and maintained at 70°C for one hour. Then, the internal temperature was lowered to 30°C to have crystals precipitated, followed by filtration and drying in the same manner as in Example 1 to obtain a product. However, the product was a mixture of 9,10-dibutoxyanthracene, 9,10-anthracenedione and 9-hydro-9-oxo-10-butylanthracene having the structure assumed by NMR. The purity of 9,10-dibutoxyanthracene in the product was calculated, whereby the yield was 9 mol%.

Reference： [1]Current Patent Assignee: KAWASAKI KASEI CHEMICALS LTD.; HIROYUKI HONDA ET EL - EP1574493, 2005, A1 Location in patent: Page/Page column 8

3
[ 109-65-9 ]
[ CAS Unavailable ]
[ 76275-14-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	In DMF (N,N-dimethyl-formamide); water at 65 - 70℃; for 2h;	2 Firstly, by the method disclosed in Example 1, an aqueous solution of the sodium salt of 9,10-anthracenediol was prepared. Then, into the autoclave used in the method disclosed in Example 1, a solution having 108 g of butyl bromide (1-bromobutane, the same applies hereinafter) dissolved in 300 g of dimethylformamide, was charged, and the internal temperature was raised to and maintained at 65°C. To this autoclave, the aqueous solution of the sodium salt of 9,10-anthracenediol prepared by the method disclosed in Example 1, was added over a period of one hour with stirring. After adding the aqueous solution of the sodium salt of 9,10-anthracenediol, the internal temperature was further raised to and maintained at 70°C for one hour with stirring. Then, the internal temperature was lowered to 30°C to have crystals of the product precipitated. The crystals were collected by filtration, washed with methanol and dried to obtain a product. the product had a melting point of 107°C, and was confirmed to be 9,10-dibutoxyanthracene by the NMR spectrum. The amount of the product was 59 g, and the yield was 70 mol%.
70%	In water; butanone for 3h;	4 As an addition method reverse to the method disclosed in Example 3, the same operation was carried out except that a solution having 40 g of butyl bromide dissolved in 70 g of methyl ethyl ketone, was added over a period of three hours to the aqueous solution of the sodium salt of 9,10-anthracenediol having tetrabutylammonium bromide added, whereby the yield of 9,10-dibutoxyanthracene was 70 mol%.
	In water; butanone at 65 - 70℃; for 4h;	3 Into an autoclave having a capacity of 300 ml and equipped with a stirrer, a thermometer, a heating jacket and a charge inlet, a solution having 40 g of butyl bromide and 1.9 g of tetrabutylammonium bromide dissolved in 70 g of methyl ethyl ketone, was charged, and the internal temperature was raised to and maintained at 65°C. To this autoclave, 100 g of the aqueous solution of the sodium salt of 9,10-anthracenediol prepared by the above-mentioned method, was added over a period of 3 hours with stirring. After completion of the addition of the aqueous solution of the sodium salt of 9,10-anthracenediol, the internal temperature was further raised to and maintained at 70°C for one hour. Then, the internal temperature was lowered to 30°C, and 50 ml of methanol was added to the autoclave to have crystals of the product precipitated. The crystals were collected by filtration, washed with 100 ml of methanol and dried to obtain a product. The amount of the product was 33 g, the yield of 9,10-dibutoxyanthracene was 90 mol%.

Reference： [1]Current Patent Assignee: KAWASAKI KASEI CHEMICALS LTD.; HIROYUKI HONDA ET EL - EP1574493, 2005, A1 Location in patent: Page/Page column 8
[2]Current Patent Assignee: KAWASAKI KASEI CHEMICALS LTD.; HIROYUKI HONDA ET EL - EP1574493, 2005, A1 Location in patent: Page/Page column 9
[3]Current Patent Assignee: KAWASAKI KASEI CHEMICALS LTD.; HIROYUKI HONDA ET EL - EP1574493, 2005, A1 Location in patent: Page/Page column 8

4
[ 76275-14-4 ]
[ 2370850-70-5 ]

Yield	Reaction Conditions	Operation in experiment
58%	With air In ethyl acetate for 2h; Irradiation;	1 (Raw Material Synthesis Example 1) Synthesis of 9,10-dibutoxyanthracene-9,10-endoperoxide (DBAEPO, 9,10-dibutoxy-9,10-dihydro-9,10-epidioxyanthracene) In a 50 ml Erlenmeyer flask, 226 mg (0.701 mmol) of 9,10-dibutoxyanthracene was dissolved in 7.5 ml of ethyl acetate (manufactured by Wako Pure Chemical Industries, Ltd., for spectroscopic analysis) under air. A 385 nm, 122 mW / cm2 LED lamp (LED385 / L-STND manufactured by Optcode Co., Ltd.) was irradiated for 2 hours, dried under reduced pressure, and then thin layer chromatography (silica gel, ethyl acetate: hexane = 1: 20, Rf value). Isolated in 0.31) to obtain 144 mg (0.406 mmol) of 9,10-dibutoxyanthracene-9,10-endoperoxide in a clear and colorless liquid. The yield based on the raw material 9,10-dibutoxyanthracene was 58.0 mol%.

Reference： [1]Current Patent Assignee: YOKOHAMA NATIONAL UNIVERSITY; KAWASAKI KASEI CHEMICALS LTD. - JP2021/17417, 2021, A Location in patent: Paragraph 0149-0150

5
[ 109-69-3 ]
[ 84-65-1 ]
9,10-dibutoxyanthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With tetrabutylammomium bromide; iron; sodium hydroxide; zinc In water; toluene at 50 - 65℃; for 2h;	3 Preparation of 9,10-dibutoxyanthraquinone: Add 41.6g anthraquinone, 28.0g zinc powder, 2.0g nickel powder, 1.0g tetrabutylammonium bromide toAdjust the temperature to 50°C in 85.0g of water, mix well, add 90.0g of 30% sodium hydroxide aqueous solution, and adjust the temperature to 65°C, then add 170.0g of bromobutane, and adjust the temperature to 75°C., When the reaction time is 60min, the content of anthraquinone is less than 0.5%, add toluene and stirAfter 1h, separate liquids, filter, remove most of the toluene, a large amount of solids precipitate out, add methanol and then cool to 5 to crystallize for 5h, filter, wash the filter cake with acetone/methanol mixture, and dry to obtain 61.2g of bright yellow-green solid 9 , 10-Dibutoxyanthraquinone, the purity is 99.5%, and the yield is 95.0%.

Reference： [1]Current Patent Assignee: DALIAN TRICO CHEMICAL - CN112939758, 2021, A Location in patent: Paragraph 0026-0028

6
[ 109-65-9 ]
[ 89398-66-3 ]
[ 76275-14-4 ]

Yield	Reaction Conditions	Operation in experiment
93.34%	In methanol at 40 - 45℃;	1.2; 2.2; 3.2; 4.2 (2) drip 75g of bromo-n-butane, the time for dripping is 1h,After the completion of the dropwise addition, the reaction was carried out for 2 to 3 hours, and the reaction was allowed to stand for 15 minutes after the completion of the reaction. Add methanol 40g,After stirring for 0.5 hour, suction filtration, the solid material was dried by blasting at 40-45° C. for 2-3 hours to obtain 28.9 g of finished product, yield: 93.34%, purity 99.28%.

Reference： [1]Current Patent Assignee: HUNAN WUJIANG HIGH TECH MAT - CN114195630, 2022, A Location in patent: Paragraph 0030-0031; 0033-0038; 0040-0044; 0046-0050; 0052

7
[ 76275-14-4 ]
[ 1118-02-1 ]
[ 2942242-05-7 ]

Yield	Reaction Conditions	Operation in experiment
	With aluminum (III) chloride In tetrahydrofuran at 90℃;	2 Example 2 Inject 20g of anthracene-9,10-diol, 10g of potassium carbonate, 60g of bromobutane and 70g of water into a closed three-necked flask with condensation, raise the temperature to 90°C, react for 16h, extract, wash and dry Compound 1 was obtained.20 g of compound 1 was dissolved in 130 g of tetrahydrofuran, 50 g of trimethylsilyl isocyanate and 1.5 g of aluminum chloride were added to the reaction solution, and the reaction was carried out at 90°C for 2.5 h, and compound 2 was obtained after separation and purification.Add 20 g of compound 2 and 100 g of ethyl acetate into an anhydrous and oxygen-free glass bottle, slowly add 40 g of lithium aluminum tetrahydride into the reaction bottle at room temperature, stir for 3 hours, quench with water, separate and purify to obtain anthracenyl organic amine.

Reference： [1]Current Patent Assignee: WANHUA CHEMICAL GROUP CO LTD - CN116217419, 2023, A Location in patent: Paragraph 0051-0052

8
[ 109-65-9 ]
[ 4981-66-2 ]
[ 76275-14-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In water at 90℃;	2 Example 2 Inject 20g of anthracene-9,10-diol, 10g of potassium carbonate, 60g of bromobutane and 70g of water into a closed three-necked flask with condensation, raise the temperature to 90°C, react for 16h, extract, wash and dry Compound 1 was obtained.20 g of compound 1 was dissolved in 130 g of tetrahydrofuran, 50 g of trimethylsilyl isocyanate and 1.5 g of aluminum chloride were added to the reaction solution, and the reaction was carried out at 90°C for 2.5 h, and compound 2 was obtained after separation and purification.Add 20 g of compound 2 and 100 g of ethyl acetate into an anhydrous and oxygen-free glass bottle, slowly add 40 g of lithium aluminum tetrahydride into the reaction bottle at room temperature, stir for 3 hours, quench with water, separate and purify to obtain anthracenyl organic amine.

Reference： [1]Current Patent Assignee: WANHUA CHEMICAL GROUP CO LTD - CN116217419, 2023, A Location in patent: Paragraph 0051-0052

9
[ 76275-14-4 ]
[ 2942242-06-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: aluminum (III) chloride / tetrahydrofuran / 2.5 h / 90 °C 2: lithium aluminium tetrahydride / ethyl acetate / 3 h / 20 °C

Reference： [1]Current Patent Assignee: WANHUA CHEMICAL GROUP CO LTD - CN116217419, 2023, A

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Ghs Precautionary Statements

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Physical hazards
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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
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H221	Flammable gas
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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. 76275-14-4 ] {[proInfo.proName]}

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[ 76275-14-4 ] Synthesis Path-Downstream 1~9

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Aryls

Ethers

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[ 76275-14-4 ]