[ CAS No. 100727-07-9 ]

Name: 100727-07-9|4-(Phenylamino)benzaldehyde|95%
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Product Details of [ 100727-07-9 ]

CAS No. :	100727-07-9	MDL No. :	MFCD03950803
Formula :	C₁₃H₁₁NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XXWHZIJHYNPASE-UHFFFAOYSA-N
M.W :	197.23	Pubchem ID :	2396509
Synonyms :

Safety of [ 100727-07-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338-P304+P340-P405	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 100727-07-9 ]

* 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 [ 100727-07-9 ]

[ 100727-07-9 ] Synthesis Path-Downstream 1~28

1
[ 122-39-4 ]
[ 100727-07-9 ]

Yield	Reaction Conditions	Operation in experiment
	With formaldehyd; 4-hydroxyl-amino-toluene-sulfonic acid-⁽²⁾ man zersetzt das Reaktionsprodukt durch Kochen mit verd. Essigsaeure;

Reference： [1]Current Patent Assignee: Geigy & Co. - DE103578, 1800, C [Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 5, p. 101][Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 5, p. 101]

2
[ 67-66-3 ]
[ 122-39-4 ]
[ 100727-07-9 ]
[ 95888-33-8 ]

Yield	Reaction Conditions	Operation in experiment
1: 16% 2: 32%	for 30h; Irradiation;

Reference： [1]Chowdhury; Saha; Podder [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1990, vol. 29, # 5, p. 405 - 406]

3
[ 100727-07-9 ]
LY₂₆₄₈₂₆ triacetate [ No CAS ]
C₈₆H₉₉Cl₂N₁₁O₂₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium cyanoborohydride In methanol for 3h; Heating;

Reference： [1]Rodriguez, Michael J.; Snyder, Nancy J.; Zweifel, Mark J.; Wilkie, Stephen C.; Stack, Douglas R.; Cooper, Robin D. G.; Nicas, Thalia I.; Mullen, Deborah L.; Butler, Thomas F.; Thompson, Richard C. [Journal of Antibiotics, 1998, vol. 51, # 6, p. 560 - 569]

4
[ 75-52-5 ]
[ 100727-07-9 ]
[ 936343-43-0 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium acetate; acetic acid at 100℃; for 6h;	69.1.2 A mixture of 4-phenylamino-benzaldehyde (3 g, 15.2 mmol) described in Manufacturing Example 69-1-1, nitromethane (1.63 mL, 30.4 mmol), ammonium acetate (1.76 g, 22.8 mmol) and acetic acid (30 mL) was stirred for 6 hours at 100° C. This mixture was cooled to room temperature, concentrated under a reduced pressure, and diluted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (3.2 g). This compound was used in the following reaction without being purified.

Reference： [1]Current Patent Assignee: EISAI CO LTD - US2007/105904, 2007, A1 Location in patent: Page/Page column 123

5
[ 36602-01-4 ]
[ 100727-07-9 ]

Yield	Reaction Conditions	Operation in experiment
98%	Stage #1: 4-(phenylamino)benzonitrile With diisobutylaluminium hydride In toluene at -78 - 20℃; for 5h; Stage #2: With rochelle salt In water; ethyl acetate; toluene	69.1.1 To a toluene (20 mL) solution of 4-phenylamino-benzonitrile (3 g, 15.4 mmol) was added diisobutyl aluminum hydride (22.9 mL, 1.01 M toluene solution, 23.1 mmol) under nitrogen atmosphere at -78° C. This mixture was stirred for 5 hours at room temperature. The mixture was partitioned into ethyl acetate and 20% aqueous Rochelle salt solution. After removal of insoluble matter by filtering through a Celite pad, the filtrate was partitioned. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (3 g, 98%). This compound was used in the following reaction without further purification.

Reference： [1]Current Patent Assignee: EISAI CO LTD - US2007/105904, 2007, A1 Location in patent: Page/Page column 122-123

6
[ 104-88-1 ]
[ 62-53-3 ]
[ 100727-07-9 ]

Yield	Reaction Conditions	Operation in experiment
89%	With potassium carbonate In <i>tert</i>-butyl alcohol at 110℃; for 1h;
89%	With dichloro(3-chloropyridinyl)(1,3-(diisopropylphenyl)-4,5-bis(dimethylamino)imidazol-2-ylidene)palladium(II); caesium carbonate In 1,2-dimethoxyethane at 80℃; for 24h; Schlenk technique; Sealed tube; Inert atmosphere;
83 %Chromat.	With potassium phosphate In dimethyl sulfoxide at 120℃; for 24h;	2.3 N-arylation of Aniline General procedure: A mixture of aryl halide (1 mmol), aniline (1.2 mmol), Pd/AlO(OH) (0.31 mol%), potassium phosphate (1.5 mmol) andDMSO (3 mL) was stirred at 120 °C for the appropriatetime (Scheme 2). After completion of the reaction as indicatedby TLC or GC, the reaction mixture was centrifugedto recover the catalyst. The centrifugate was diluted with3 mL of ethyl acetate and treated with 3 mL of HCl (2 M)to separate the product. Then, the organic layers were driedover anhydrous sodium sulphate, filtered, concentrated, andthe resulting product was purified by column chromatographyusing hexane:ethyl acetate (80:20) mixture.

Reference： [1]Biscoe, Mark R.; Fors, Brett P.; Buchwald, Stephen L. [Journal of the American Chemical Society, 2008, vol. 130, # 21, p. 6686 - 6687]
[2]Zhang, Yin; César, Vincent; Lavigne, Guy [European Journal of Organic Chemistry, 2015, vol. 2015, # 9, p. 2042 - 2050]
[3]Ganesh Babu, Sundaram; Emayavaramban, Balakumar; Jerome, Peter; Karvembu, Ramasamy [Catalysis Letters, 2017, vol. 147, # 10, p. 2619 - 2629]

7
[ 100727-07-9 ]
4(Z)-6-(4-o-hydroxyphenyl-2,2-dimethyl-1,3-dioxan-cis-5-yl) hexenoic acid [ No CAS ]
[ 1056950-27-6 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene for 24h;	12 An amount of 100 mg (0.31 mmol) racemic acetonide was mixed with 1 ml. toluene and 10 mg p-toluenesulfonic acid. To the mixture was added 2 eq (0.62 mmol, 122 mg) of 4- phenylaminobenzaldehyde. The mixture was stirred for 24h and evaporated using a nitrogen flow. The crude reaction mixture was purified over a miniature silica gel column, using methanol(1 )/DCM(19). Pure fractions were identified by TLC, collected, evaporated and analyzed by HPLC and mass spectrometry.

Reference： [1]Current Patent Assignee: EVOLVA HOLDING AG - WO2008/89461, 2008, A1 Location in patent: Page/Page column 63-64

8
6-[4-(2-hydroxyphenyl)-2,2-dimethyl-[1,3]dioxan-5-yl]hex-4-enoic acid [ No CAS ]
[ 100727-07-9 ]
C₂₈H₂₉NO₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene for 24h;	11 An amount of 100 mg (0.31 mmol) racemic acetonide was mixed with 1 mL toluene and 10 mg p-toluenesulfonic acid. To the mixture was added 2 eq (0.62 mmol, 122 mg) of 4-phenylaminobenzaldehyde. The mixture was stirred for 24 h and evaporated using a nitrogen flow. The crude reaction mixture was purified over a miniature silica gel column, using methanol(1)/DCM(19). Pure fractions were identified by TLC, collected, evaporated and analyzed by HPLC and mass spectrometry.

Reference： [1]Current Patent Assignee: EVOLVA HOLDING AG - US2011/178112, 2011, A1 Location in patent: Page/Page column 18

9
[ 123-08-0 ]
[ 62-53-3 ]
[ 100727-07-9 ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: 4-hydroxy-benzaldehyde; aniline With caesium carbonate; chloroacetyl chloride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: In N,N-dimethyl-formamide at 150℃; Microwave irradiation;

Reference： [1]Location in patent: experimental part Tian, Xiao; Wu, Ren-Min; Liu, Gang; Li, Zhu-Bo; Wei, He-Lin; Yang, Hao; Shin, Dong-Soo; Wang, Li-Ying; Zuo, Hua [ARKIVOC, 2011, vol. 2011, # 10, p. 118 - 126]

10
4-(1,3-dioxolan-2-yl)-N-phenylaniline [ No CAS ]
[ 100727-07-9 ]

Yield	Reaction Conditions	Operation in experiment
97%	With trifluoroacetic acid In dichloromethane at 20 - 25℃; for 5h; Inert atmosphere;

Reference： [1]Dhayalan, Vasudevan; Sämann, Christoph; Knochel, Paul [Chemical Communications, 2015, vol. 51, # 15, p. 3239 - 3242]

11
[ 1122-91-4 ]
[ 62-53-3 ]
[ 100727-07-9 ]

Yield	Reaction Conditions	Operation in experiment
93%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 110℃; for 16h; Inert atmosphere;	4 Synthesis of Compound 4-2 To a suspension of compound 4-1 (1 g, 5.4 mmol) and compound 4-1-1 (0.5 g, 5.4 mmol) in toluene (30 mL) was added successively Pd2(dba)3 (123 mg, 0.135 mmol), Xantphos (78 mg, 0.135 mmol) and Cs2CO3 (cesium carbonate) (3.52 g, 10.8 mmol) under nitrogen atmosphere, and then the reaction solution was heated to 110° C. and stirred for 16 h. The reaction was monitored by TLC (PE/EA=5:1) until the completion of reaction. The reaction solution was diluted with EtOAc (20 mL), filtered, concentrated and stripped to give a residue which was purified by silica gel column chromatography (PE/EA=4:1) to afford compound 4-2 (1.067 g, Yield 93%). LCMS (ESI) m/z: 198 (M+1)
71%	With potassium hydroxide In water at 20℃; for 6h; Green chemistry;
69%	With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene for 16h; Reflux; Inert atmosphere;	4-(phenylamino)benzaldehyde. 4-(phenylamino)benzaldehyde. Aniline (130 mg, 1.40 mmol) and4-bromobenzaldehyde (291 mg, 1.68 mmol) was added into a solution of PhMe (l0mL) with Pd(OAc)2 (15.7 mg, 0.07mmol), BINAP(60.96 mg, 0.10 mmol), Cs2CO3 (910 mg, 2.8 mmol). Then the mixture was heated at reflux under N2. After 1 6hrs, the solvent was partitioned between H20 and EtOAc. The organic layer was concentrated and purified by column chromatography(Petroleum ether:EtOAc =5:1) to give 4-(phenylamino)benzaldehyde (236.6 mg, yield 69%).

63%	With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene for 12h; Inert atmosphere; Reflux;
96 %Chromat.	With potassium phosphate In dimethyl sulfoxide at 120℃; for 24h;	2.3 N-arylation of Aniline General procedure: A mixture of aryl halide (1 mmol), aniline (1.2 mmol), Pd/AlO(OH) (0.31 mol%), potassium phosphate (1.5 mmol) andDMSO (3 mL) was stirred at 120 °C for the appropriatetime (Scheme 2). After completion of the reaction as indicatedby TLC or GC, the reaction mixture was centrifugedto recover the catalyst. The centrifugate was diluted with3 mL of ethyl acetate and treated with 3 mL of HCl (2 M)to separate the product. Then, the organic layers were driedover anhydrous sodium sulphate, filtered, concentrated, andthe resulting product was purified by column chromatographyusing hexane:ethyl acetate (80:20) mixture.

Reference： [1]Current Patent Assignee: HUMANWELL HEALTHCARE (GROUP) CO., LTD.; HUBEI BIO PHARMACEUTICAL INDUSTRIAL TECHNOLOGICAL INSTITUTE; HUBEI BIO PHARMACEUTICAL INDUSTRIAL TECHNOLOGICAL; HUBEI BIO PHARMACEUTICAL INDUSTRIAL TECH INSTITUTE; HUBEI BIO PHARMACEUTICAL INDUSTRY TECHNOLOGY INSTITUTE INC - US2017/313683, 2017, A1 Location in patent: Paragraph 0266-0267
[2]Hajipour, Abdol R.; Check, Maryam; Khorsandi, Zahra [Applied Organometallic Chemistry, 2017, vol. 31, # 11]
[3]Current Patent Assignee: BROAD INSTITUTE; WUXI APPTEC CO., LTD. - WO2016/19588, 2016, A1 Location in patent: Page/Page column 86
[4]Zhang, Jian; Poongavanam, Vasanthanathan; Kang, Dongwei; Bertagnin, Chiara; Lu, Huamei; Kong, Xiujie; Ju, Han; Lu, Xueyi; Gao, Ping; Tian, Ye; Jia, Haiyong; Desta, Samuel; Ding, Xiao; Sun, Lin; Fang, Zengjun; Huang, Boshi; Liang, Xuewu; Jia, Ruifang; Ma, Xiuli; Xu, Wenfang; Murugan, Natarajan Arul; Loregian, Arianna; Huang, Bing; Zhan, Peng; Liu, Xinyong [Journal of Medicinal Chemistry, 2018, vol. 61, # 14, p. 6379 - 6397]
[5]Ganesh Babu, Sundaram; Emayavaramban, Balakumar; Jerome, Peter; Karvembu, Ramasamy [Catalysis Letters, 2017, vol. 147, # 10, p. 2619 - 2629]

Yield	Reaction Conditions	Operation in experiment
95%	With η⁵‐cyclopentadienyl‐η³‐1‐phenylallylpalladium; potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 80℃; for 12h; Inert atmosphere;	3 Example 3 General procedure: I n this Example, an aryl fluorosulfonate is reacted with aniline as shown in Equation 7: Equation 7 [0051] The present Example is performed in a nitrogen- filled glovebox. To each of 12 30 mL vials are added one of the aryl fluorosulfonates selected from Table 1 where R in Equation 7 represents one or more groups joined to the aryl ring as shown (2.50 mmol), Xantphos (0.017 g; 0.03 mmol); potassium carbonate (0.691 g; 5.00 mmol), and 1,4-dioxane (5 mL). To each stirring mixture is added aniline (274 uL) and CpPd (cinnamyl) (0.007 g in 100 uL 1,4-dioxane). Each reaction mixture is heated at 80 °C for 12 to 24 hours. The reaction mixture is cooled to room temperature and adsorbed onto silica gel. The product is purified by flash chromatography (ISCO, manufactured by Teledyne) and the volatiles are removed by vacuum to reveal the desired product having yields recorded in Table 1.

13
4-formylphenyl sulfurofluoridate [ No CAS ]
[ 62-53-3 ]
[ 100727-07-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With η⁵‐cyclopentadienyl‐η³‐1‐phenylallylpalladium; potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 80℃; for 12h;

Reference： [1]Hanley, Patrick S.; Clark, Thomas P.; Krasovskiy, Arkady L.; Ober, Matthias S.; O'Brien, John P.; Staton, Tina S. [ACS Catalysis, 2016, vol. 6, # 6, p. 3515 - 3519]

14
[ 954137-80-5 ]
[ 100727-07-9 ]
3-[4-({11,11-dimethylbenzo[a]fluoren-9-yl}-N-phenylamino)phenyl]-2-cyanoacrylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-t-butylphosphonium tetraphenylborate complex; sodium t-butanolate / toluene / 18 h / Inert atmosphere; Reflux 2: piperidine / ethanol / 3 h / Reflux

Reference： [1]Current Patent Assignee: SAGAMI CHEMICAL RESEARCH INSTITUTE; TOSOH CORPORATION - JP6077826, 2017, B2

15
[ 954137-80-5 ]
[ 100727-07-9 ]
4-({11,11-dimethylbenzo[a]fluoren-9-yl}-N-phenylamino)benzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23.4%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium t-butanolate; tri-t-butylphosphonium tetraphenylborate complex In toluene for 18h; Inert atmosphere; Reflux;	3 To a solution of 9-chloro-11,11-dimethylbenzo[a]fluorene (1.05 g, 3.78 mmol) in toluene (20 mL) under an argon atmosphere, 4-(phenylamino)benzaldehyde (745 mg, 3.78 mmol), tris(dibenzylideneacetone)dipalladium (174 mg, 0.19 mmol), tri(tert-butyl)phosphonium tetraphenylborate (198 mg, 0.38 mmol), sodium-tert-butoxide (1.09 g, 11.3 mmol) was added, and refluxed for 18 hours. After completion of the reaction, 1M hydrochloric acid (100 mL) and water (300 nL) were added to the reaction mixture and the mixture was extracted with ethyl acetate (300 mL). Further, the aqueous layer was extracted again with ethyl acetate (150 mL). Then, the combined organic layer was washed with water (400 mL), dried over anhydrous magnesium sulfate, the desiccant was filtered off and the solvent was distilled off under reduced pressure. The obtained residue was purified with an automatic setting medium pressure column chromatography system (manufactured by Yamazen) to obtain 4-({11,11-dimethylbenzo[a]fluoren-9-yl}-N-phenylamino)benzaldehyde (1.66 g,23.4%) was obtained.

Reference： [1]Current Patent Assignee: SAGAMI CHEMICAL RESEARCH INSTITUTE; TOSOH CORPORATION - JP6077826, 2017, B2 Location in patent: Paragraph 0061-0063

16
[ 459-57-4 ]
[ 62-53-3 ]
[ 100727-07-9 ]

Yield	Reaction Conditions	Operation in experiment
60 %Chromat.	With potassium phosphate In dimethyl sulfoxide at 120℃; for 24h;	2.3 N-arylation of Aniline General procedure: A mixture of aryl halide (1 mmol), aniline (1.2 mmol), Pd/AlO(OH) (0.31 mol%), potassium phosphate (1.5 mmol) andDMSO (3 mL) was stirred at 120 °C for the appropriatetime (Scheme 2). After completion of the reaction as indicatedby TLC or GC, the reaction mixture was centrifugedto recover the catalyst. The centrifugate was diluted with3 mL of ethyl acetate and treated with 3 mL of HCl (2 M)to separate the product. Then, the organic layers were driedover anhydrous sodium sulphate, filtered, concentrated, andthe resulting product was purified by column chromatographyusing hexane:ethyl acetate (80:20) mixture.

Reference： [1]Ganesh Babu, Sundaram; Emayavaramban, Balakumar; Jerome, Peter; Karvembu, Ramasamy [Catalysis Letters, 2017, vol. 147, # 10, p. 2619 - 2629]

17
[ 100727-07-9 ]
C₂₂H₂₁Cl₂N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: triethylamine; dmap / dichloromethane / 1 h / 40 °C 2.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 2 h / -78 °C

18
[ 100727-07-9 ]
C₂₂H₁₉Cl₂N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: triethylamine; dmap / dichloromethane / 1 h / 40 °C 2.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 2 h / -78 °C 3.1: manganese(IV) oxide / dichloromethane / 5 h / 40 °C

19
[ 100727-07-9 ]
C₂₂H₂₁ClN₄O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: triethylamine; dmap / dichloromethane / 1 h / 40 °C 2.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 2 h / -78 °C 3.1: manganese(IV) oxide / dichloromethane / 5 h / 40 °C 4.1: ammonium hydroxide / tetrahydrofuran / 1 h / 80 °C / Microwave irradiation

20
[ 100727-07-9 ]
C₃₂H₄₀N₆O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: triethylamine; dmap / dichloromethane / 1 h / 40 °C 2.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 2 h / -78 °C 3.1: manganese(IV) oxide / dichloromethane / 5 h / 40 °C 4.1: ammonium hydroxide / tetrahydrofuran / 1 h / 80 °C / Microwave irradiation 5.1: diisopropylamine / isopropyl alcohol / 2 h / 110 °C / Microwave irradiation

21
[ 100727-07-9 ]
C₂₂H₂₄N₆O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: triethylamine; dmap / dichloromethane / 1 h / 40 °C 2.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 2 h / -78 °C 3.1: manganese(IV) oxide / dichloromethane / 5 h / 40 °C 4.1: ammonium hydroxide / tetrahydrofuran / 1 h / 80 °C / Microwave irradiation 5.1: diisopropylamine / isopropyl alcohol / 2 h / 110 °C / Microwave irradiation 6.1: hydrogenchloride / dichloromethane; methanol / 0.5 h / 20 °C

22
[ 100727-07-9 ]
C₂₅H₂₆N₆O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: triethylamine; dmap / dichloromethane / 1 h / 40 °C 2.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 2 h / -78 °C 3.1: manganese(IV) oxide / dichloromethane / 5 h / 40 °C 4.1: ammonium hydroxide / tetrahydrofuran / 1 h / 80 °C / Microwave irradiation 5.1: diisopropylamine / isopropyl alcohol / 2 h / 110 °C / Microwave irradiation 6.1: hydrogenchloride / dichloromethane; methanol / 0.5 h / 20 °C 7.1: HATU; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 16 °C

23
[ 24424-99-5 ]
[ 100727-07-9 ]
C₁₈H₁₉NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With dmap; triethylamine In dichloromethane at 40℃; for 1h;	4 Synthesis of Compound 4-3 To a solution of compound 4-2 (1 g, 5.07 mmol) in DCM (20 mL) was added successively Boc2O (1.33 g, 6.08 mmol), TEA (1.03 g, 10.14 mmol) and DMAP (0.12 g, 1.01 mmol) and then the reaction solution was stirred at 40° C. for 1 h. The reaction was monitored by TLC (PE/EA=5:1) until the completion of reaction. The reaction solution was washed with saturated brine, dried over anhydrous Na2SO4, filtered and concentrated to give a residue which was purified by silica gel column chromatography (PE/EA=5:1) to afford compound 4-3 (1.5 g, Yield 66%). LCMS (ESI) m/z: 298 (M+1)

24
[ 51554-93-9 ]
[ 100727-07-9 ]
C₃₄H₃₇N [ No CAS ]

Reference： [1]Patent: US9822299,2017,B2

25
[ 51554-93-9 ]
[ 100727-07-9 ]
4-(4-n-octylphenylphenylamino)benzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In para-xylene; for 16h;Reflux;	a) Synthesis of 4-(4-n-octylphenylphenylamino)benzaldehyde (0231) 50.0 g (254 mmol) of 4-phenylaminobenzaldehyde, 75.1 g (279 mmol) of p-bromo-n-octylphenyl and 73.1 g (760 mmol) of NaOtBu are suspended in 1 l of p-xylene. 1.1 g (5 mmol) of Pd(OAc)2 and 3.8 ml of a 1M tri-tert-butylphosphine solution are added to this suspension. The reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, washed three times with 200 ml of water and subsequently evaporated to dryness. The residue is extracted with hot toluene, and employed in the subsequent reaction without further purification. The yield is 81.7 g (212 mmol, 83.6%)

Reference： [1]Patent: US9822299,2017,B2 .Location in patent: Page/Page column 41; 42

26
[ 100727-07-9 ]
[ 204255-11-8 ]
ethyl (3R,4R,5S)-4-acetamido-3-(pentan-3-yloxy)-5-((4-(phenylamino)benzy)amino)cyclohex-1-ene-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium cyanoborohydride In methanol; ethanol at 20℃; for 6h;

Reference： [1]Zhang, Jian; Poongavanam, Vasanthanathan; Kang, Dongwei; Bertagnin, Chiara; Lu, Huamei; Kong, Xiujie; Ju, Han; Lu, Xueyi; Gao, Ping; Tian, Ye; Jia, Haiyong; Desta, Samuel; Ding, Xiao; Sun, Lin; Fang, Zengjun; Huang, Boshi; Liang, Xuewu; Jia, Ruifang; Ma, Xiuli; Xu, Wenfang; Murugan, Natarajan Arul; Loregian, Arianna; Huang, Bing; Zhan, Peng; Liu, Xinyong [Journal of Medicinal Chemistry, 2018, vol. 61, # 14, p. 6379 - 6397]

27
[ 100727-07-9 ]
[ 204255-11-8 ]
(3R,4R,5S)-4-acetamido-3-(pentan-3-yloxy)-5-((4-(phenylamino)benzyl)amino)cyclohex-1-ene-1-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium cyanoborohydride / methanol; ethanol / 6 h / 20 °C 2: sodium hydroxide / methanol; water / 20 °C

28
[ 555-16-8 ]
[ 98-80-6 ]
[ 100727-07-9 ]

Yield	Reaction Conditions	Operation in experiment
94%	With tungsten hexacarbonyl; triphenylphosphine at 22℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube; Irradiation;
65%	Stage #1: 4-nitrobenzaldehdye In toluene for 0.0333333h; Stage #2: phenylboronic acid With triphenylphosphine In toluene at 100℃; for 24h; Inert atmosphere;
39 %Spectr.	With molybdenum trioxide; triphenylphosphine In toluene at 20℃; for 24h; Irradiation;

Reference： [1]Cai, Xingwei; Ding, Danli; Shen, Yang; Song, Heng; Wang, Yemei; Xu, Chen; Yang, Fu; Zhou, Hu [Journal of Organic Chemistry, 2022, vol. 87, # 8, p. 5303 - 5314]
[2]Yang, Fu; Dong, Xuexue; Shen, Yang; Liu, Mengting; Zhou, Hu; Wang, Xuyu; Li, Lulu; Yuan, Aihua; Song, Heng [ChemSusChem, 2021, vol. 14, # 16, p. 3413 - 3421]
[3]Dong, Xuexue; Yang, Yiying; Shen, Yang; Yuan, Aihua; Guo, Zengjing; Song, Heng; Yang, Fu [Green Chemistry, 2022, vol. 24, # 10, p. 4012 - 4025]

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
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. 100727-07-9 ]

Quality Control of [ 100727-07-9 ]

Related Doc. of [ 100727-07-9 ]

Product Details of [ 100727-07-9 ]

Safety of [ 100727-07-9 ]

Application In Synthesis of [ 100727-07-9 ]

[ 100727-07-9 ] Synthesis Path-Downstream 1~28

Related Functional Groups of [ 100727-07-9 ]

Aryls

Aldehydes

Amines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 100727-07-9 ]