[ CAS No. 782504-35-2 ] {[proInfo.proName]}

Name: 782504-35-2|4-(tert-Butyl)-N-(4-isopropylphenyl)aniline|97%
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SKU: A575454
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Quality Control of [ 782504-35-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 782504-35-2 ]

SDS Specification

Alternatived Products of [ 782504-35-2 ]

Product Details of [ 782504-35-2 ]

CAS No. :	782504-35-2	MDL No. :	MFCD28130382
Formula :	C₁₉H₂₅N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QSQSJBUBCKHJFG-UHFFFAOYSA-N
M.W :	267.41	Pubchem ID :	23106812
Synonyms :

Calculated chemistry of [ 782504-35-2 ]

Physicochemical Properties

Num. heavy atoms :	20
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.37
Num. rotatable bonds :	4
Num. H-bond acceptors :	0.0
Num. H-bond donors :	1.0
Molar Refractivity :	89.84
TPSA :	12.03 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-3.49 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.68
Log Po/w (XLOGP3) :	6.26
Log Po/w (WLOGP) :	5.85
Log Po/w (MLOGP) :	5.1
Log Po/w (SILICOS-IT) :	5.08
Consensus Log Po/w :	5.19

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-5.62
Solubility :	0.000639 mg/ml ; 0.00000239 mol/l
Class :	Moderately soluble
Log S (Ali) :	-6.3
Solubility :	0.000134 mg/ml ; 0.000000501 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-7.0
Solubility :	0.0000267 mg/ml ; 0.0000001 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.05

Safety of [ 782504-35-2 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 782504-35-2 ]

* 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 [ 782504-35-2 ]

[ 782504-35-2 ] Synthesis Path-Downstream 1~10

1
[ 782504-35-2 ]
[ 782504-33-0 ]
2,6-dicyclohexyl-N,N'-bis(4-isopropylphenyl)-N,N'-bis(4-t-butylphenyl)anthracene-9,10-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium t-butanolate In toluene at 100℃;	6 SYNTHESIS EXAMPLE 6: Synthesis of Compound (11); Under an argon flow, 5.0 g (10 mmol) of 2.6-dicyclohexyl anthracene, 6.7 g (25 mmol) of 4-t-butylphenyl -4-isopropylphenyl amine, 0.03 g (1.5 mol%) of palladium acetate, 0.06 g (3 mol%) of tri-t-butyl phosphine, 2.4 g (25 mmol) of t-butoxy sodium and 100 mL of dried toluene were charged into a 300 mL three-necked flask equipped with a condenser tube, and then stirred under heating at 100°C over night. After completion of the reaction, the precipitated crystals were separated from the reaction solution by filtration, and then washed with 50 mL of toluene and 100 mL of methanol, thereby obtaining 8.3 g of a light-yellow powder. The thus obtained powder was subjected to NMR spectrum analysis (Fig. 6) and FD-MS. As a result, the reaction product was identified as the compound (11) (yield: 95%). Meanwhile, the NMR spectrum was measured under the same conditions as described in SYNTHESIS EXAMPLE 1.

Reference： [1]Current Patent Assignee: IDEMITSU KOSAN CO LTD - EP1612202, 2006, A1 Location in patent: Page/Page column 17

2
[ 782504-35-2 ]
[ 914281-87-1 ]
C₆₄H₇₀N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium t-butanolate In toluene at 100℃;

Reference： [1]Current Patent Assignee: IDEMITSU KOSAN CO LTD - WO2006/117974, 2006, A1 Location in patent: Page/Page column 39-40; 3/3

3
[ 782504-35-2 ]
[ 106-37-6 ]
[ 1044870-00-9 ]

Yield	Reaction Conditions	Operation in experiment
70.4%	With sodium t-butanolate In toluene for 12h; Heating / reflux;	2-1 Preparation Example 2-1: Preparation of 4-bromo-N- (4-t- butylphenyl ) -N- ( 4-isopropylphenyl ) benzenamine ; As represented below in Reaction Scheme 5, 9.23g of 4-t- butyl-N- (4-isopropylphenyl) benzenamine (0.0345mol) prepared in Preparation Example 1-1 and 8.1g of dibromobenzene (0.0345mol) were dissolved in 25OmL of toluene, and 0.43g of Pd2(dba)3(0.471mmol) was added thereto under a nitrogen atmosphere. Then, 3.3g of NaOBu* (0.0345mol) and 0.19g of (t-bu)3P(0.94mmol) were added to the reaction solvent, and the reaction mixture was refluxed and stirred for 12 hours. The reaction mixture was checked for the completion of the reaction by means of TLC, and if the reaction was completed, the reaction product was cooled down to room temperature. The reacted solution was poured onto a thin Celite pad to perform short chromatography, and then was washed with MC several times. The washed solution was chromatographed using n-hexane to thereby obtain a white solid compound (1Og, 70.4%). [Reaction Scheme 5]

Reference： [1]Current Patent Assignee: DOOSAN CORP. - WO2009/91095, 2009, A1 Location in patent: Page/Page column 14-15

4
[ 5433-01-2 ]
[ 5369-19-7 ]
[ 782504-35-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In toluene; for 12h;Heating / reflux;	Preparation Example 1-1: Preparation of 4-t-butyl-N- (4- isopropylphenyl ) benzenamine; As represented below in Reaction Scheme 1, 25g of 3-t- butylaniline (0.125mol) and 37.3g of 3-bromoisopropylbenzene(0.25mol) were dissolved in 25OmL of toluene, and 3.43g ofPd2(dba)3 (0.0037mol) was added thereto under a nitrogen atmosphere. Then, 14.4g of NaOBufc (0.15mol) and 1.157g of (t- Bu)3P (0.0075mol) were added to the reaction solvent, and the reaction mixture was refluxed and stirred for 12 hours. The reaction mixture was checked for the completion of the reaction by means of TLC, and if the reaction was completed, the reaction product was cooled down to room temperature. The reacted solution was poured onto a thin silica pad to perform short chromatography, and then was washed with methylene chloride (MC) . The washed solution was subjected to distillation under reduced pressure to thereby remove the solvent, and was chromatographed using n-hexane to thereby obtain a desired white solid product (29.4g, 88percent). [Reaction Scheme 1]

Reference： [1]Patent: WO2009/91095,2009,A1 .Location in patent: Page/Page column 11-12

5
[ 782504-35-2 ]
6,13-dibromo-1,1,4,4,8,8,11,11-octamethyl-1,2,3,4,8,9,10,11-octahydropentacene [ No CAS ]
C₆₈H₈₄N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58.5%	With sodium t-butanolate In toluene for 12h; Heating / reflux;	1 Example 1: Preparation of Compound Dl According to the Invention; As represented below in Reaction Scheme 4, 8.7g of 6,13- dibromo-1, 1, 4, 4, 8, 8, 11, 11-octamethyl-l, 2, 3,4,8,9, 10, 11- octahydropentacene (0.0157mol) prepared in Preparation Example 1-3 and 9.23g of 4-t-butyl-N- (4-isopropylphenyl) benzenamine (0.0345mol) prepared in Preparation Example 1-1 were dissolved in 25OmL of toluene, and then 0.43g of Pd2(dba)3 (0.471mmol) was added thereto under a nitrogen atmosphere. 3.3g of NaOBut (0.0345mol) and 0.19g of (t-bu)3P (0.94mmol) were added to the reaction solvent, and then the reaction mixture was refluxed and stirred for 12 hours. The reaction mixture was checked for the completion of the reaction by means of TLC, and if the reaction was completed, the reaction product was cooled down to room temperature. The reacted solution was poured onto a thin silica pad to perform short chromatography, and then was washed with MC several times. All solids existing on the silica pad were put into a flask, 50OmL of tetrahydrofurane (THF) was added thereto, and then the resultant solution was heated and stirred. After the solution was stirred for about 1 hour, it was subjected to hot filtration. The filtered solution was subjected to distillation under reduced pressure to thereby obtain a solid, and then the obtained solid was washed with n- hexane and was filtered to finally obtain an orange-colored solid (8.5g, 58.5%) .1H NMR: 1.20 (d 4H), 1.33 (s 9H), 1.55 (s 12H), 5.98(s 4H), 6.38(d 4H), 7.01 (m 4H), 7.6 (s 4H). In a state where Compound Dl was dissolved in THF, the UV absorbance thereof was measured. As a result of the UV absorbance measurement, a maximum absorption wavelength of 474nm and a maximum emission wavelength of 536nm were confirmed (FIG. 1), and a HOMO energy level of 5.3IeV and a LUMO energy level of 2.95eV were also confirmed. [Reaction Scheme 4]

Reference： [1]Current Patent Assignee: DOOSAN CORP. - WO2009/91095, 2009, A1 Location in patent: Page/Page column 13-14

6
[ 782504-35-2 ]
[ 1174040-30-2 ]
[ 1174040-32-4 ]

Yield	Reaction Conditions	Operation in experiment
58.5%	With sodium t-butanolate In toluene for 12h; Heating / reflux;	2 Example 2 : Preparation of Compound D2 According to the Invention; 8g of 4-(13-bromo-l, 1,4,4, , 8, 8, 11, 11-octamethyl- 1,2,3,4,8,9, 10, ll-octahydropentacene-6-yl) -N- (4-t-bytylphenyl) - N- (4-isopropylphenyl) benzylamine (0.0097mol) prepared in Preparation Example 2-3 and 2.59g of 4-t-butyl-N- (4- isopropylphenyl)benzenamine (0.0097mol) prepared in Preparation Example 1-1 were dissolved in 250ml, of toluene. And then O.lβg of Pd2(dba)3 (0.24mmol) was added thereto under a nitrogen atmosphere. 1.8g of NaOBu*1 (0.0103mol) and 0.19g of (t-bu)3P (0.48mmol) were added to the reaction solvent, and then the reaction mixture was refluxed and stirred for 12 hours. The reaction mixture was checked for the completion of the reaction by means of TLC, and if the reaction was completed, the reaction product was cooled down to room temperature. The reacted solution was poured onto a thin silica pad to perform short chromatography, and then was washed with MC several times. All solids existing on the silica pad were put into a flask, 50OmL of tetrahydrofurane (THF) was added thereto, and then the resultant solution was heated and stirred. After the solution was stirred for about 1 hour, it was subjected to hot filtration. The filtered solution was subjected to distillation under reduced pressure to thereby obtain a solid, and then the obtained solid was washed with n-hexane and was filtered to finally obtain a dark orange-colored solid (8.5g, 58.5%).1H NMR: 1.20 (d 4H), 1.33 (s 9H), 1.55 (s 12H), 5.98(s 4H), 6.38(d 4H), β.52(d 2H), 7.01 (m 4H), 7.4β(d 2H), 7.6 (s 4H) .In a state where Compound D2 was dissolved in THF, the UV absorbance thereof was measured. As a result of the UV absorbance measurement, a maximum absorption wavelength of 424nm and a maximum emission wavelength of 527nm were confirmed (FIG. 2), and a HOMO energy level of 5.32eV and a LUMO energy level of 2.66eV were also confirmed.[Reaction Scheme 8]

Reference： [1]Current Patent Assignee: DOOSAN CORP. - WO2009/91095, 2009, A1 Location in patent: Page/Page column 17-18

7
[ 782504-35-2 ]
[ 1268515-14-5 ]
[ 1268515-15-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium t-butanolate In toluene at 110℃; for 18h; Inert atmosphere;	4.b Catalyst amount of tris(dibenzylidene-acetone)-dipalladium(0) (Pd2(dba)3 (0.17 g, 0.19 mmole) and ligand 1.1'-Bis(diphenylphosphino)-ferrocene (dppf) (0.21 g, 0.38 mmole) were dissolved in toluene (50 mL) and purged with N2. The mixture (dark brown) was stirred at RT for 10 min. Then dibromo Intermediate C (5.04 g, 7.5 mmole), 4-tert-butyl-phenyl-4'-isopropyl-phenyl amine (5.03 g, 20 mmole) and sodium tertbutyoxide (2.17 g, 20 mmole) dissolved in toluene (60 mL) and were added into the above catalyst mixture solution under N2. The mixture was bubbled with N2 for 15 min. (light brown solids), then heated at 115° C. (oil bath) for 18 h (dark brown solution). TLC checked no SM. The reaction mixture was poured into MeOH. The precipitate was filtered to give crude brown solid compound 8. It is highly blueish green fluorescence. The crude product was purified by running Florisil (registered trademark of U.S. Silica Company) column, eluting with hex/CHCl3 1.5:1, 1:1 as eluents to give off-white solid. 6.6 g, yield: 85%, white solid. C76H70H2: EI, MS m/z (%): 11042 (100, M+).

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - US2012/319571, 2012, A1 Location in patent: Page/Page column 28-29

8
[ 3972-65-4 ]
[ 99-88-7 ]
[ 782504-35-2 ]

Yield	Reaction Conditions	Operation in experiment
72%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene for 4h; Reflux;	5.1 At 250 mL reaction 4-aminocumen 10.0 g (0.074 mol),4-bromo-t-butylbenzene 17. 3 g (0.081 mol),1.4 g (0.001 mol) of Pd (dba) 3, 0.9 g (0.001 mol) of BINAP,14.2 g (0.148 mol) of sodium t-butoxide was dissolved in 100 mL of toluene and refluxed for 4 hours.TLC was confirmed whether the reaction was completed, and the filter was hot filtered when the reaction was completed.The organic layer was dried and separated by column chromatography, The separated solution was recrystallized from dichloromethane and hexane to give 14.2 g (72%).

Reference： [1]Current Patent Assignee: HODOGAYA CHEMICAL CO LTD - KR101996650, 2019, B1 Location in patent: Paragraph 0199-0205

9
[ 782504-35-2 ]
[ 1044870-01-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 4 h / Reflux 2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 2.2: 8 h / -78 - 20 °C / Inert atmosphere 2.3: 1 h / Inert atmosphere

Reference： [1]Current Patent Assignee: HODOGAYA CHEMICAL CO LTD - KR101996650, 2019, B1

10
[ 782504-35-2 ]
[ 589-87-7 ]
[ 1044870-00-9 ]

Yield	Reaction Conditions	Operation in experiment
71%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene for 4h; Reflux;	5.2 At 250 mL reactionIntermediate 5-a 14.0 g (0.052 mol),16.3 g (0.058 mol) of 1,4-bromoiodobenzene,1.0 g (0.001 mol) of Pd (dba) 3, 0.7 g (0.001 mol) of BINAP,10.1 g (0.105 mol) of sodium t-butoxide was dissolved in 140 mL of toluene and refluxed for 4 hours.TLC was confirmed whether the reaction was completed, and the filter was hot filtered when the reaction was completed. The organic layer was dried, separated by column chromatography, and the separated solution was recrystallized from dichloromethane and hexane to obtain 15.6 g (71%).

Reference： [1]Current Patent Assignee: HODOGAYA CHEMICAL CO LTD - KR101996650, 2019, B1 Location in patent: Paragraph 0199; 0206-0211

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H200	Unstable explosive
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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. 782504-35-2 ] {[proInfo.proName]}

Quality Control of [ 782504-35-2 ]

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[ 782504-35-2 ] Synthesis Path-Downstream 1~10

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