[ CAS No. 136-17-4 ]

Name: 136-17-4|N1-Phenylbenzene-1,2,4-triamine|98%
Brand: Ambeed
SKU: A770441
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Quality Control of [ 136-17-4 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 136-17-4 ]

CAS No. :	136-17-4	MDL No. :	MFCD00025285
Formula :	C₁₂H₁₃N₃	Boiling Point :	389.1°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	199.25 g/mol	Pubchem ID :	-
Synonyms :

Calculated chemistry of of [ 136-17-4 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	0.0
Num. H-bond donors :	3.0
Molar Refractivity :	64.79
TPSA :	64.07 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.02 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.58
Log Po/w (XLOGP3) :	2.1
Log Po/w (WLOGP) :	2.61
Log Po/w (MLOGP) :	2.07
Log Po/w (SILICOS-IT) :	1.27
Consensus Log Po/w :	1.92

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.86
Solubility :	0.276 mg/ml ; 0.00139 mol/l
Class :	Soluble
Log S (Ali) :	-3.08
Solubility :	0.167 mg/ml ; 0.00084 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.25
Solubility :	0.0111 mg/ml ; 0.0000558 mol/l
Class :	Moderately soluble

Medicinal Chemistry

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

Safety of [ 136-17-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312+P362+P364-P304+P340+P312-P501	UN#:	N/A
Hazard Statements:	H302+H312+H332	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 136-17-4 ]

* 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 [ 136-17-4 ]

[ 136-17-4 ] Synthesis Path-Downstream 1~31

1
[ 136-17-4 ]
[ 2876-23-5 ]

Yield	Reaction Conditions	Operation in experiment
	With lead dioxide
1.11 g	With magnesium sulfate In nitrobenzene for 24h; Reflux;	4.2.1 General procedure for the synthesis of intermediates A and B Compound A was immediately refluxed for 24 h in nitrobenzene (100 mL) containing MgSO4 in a flask. After nitrobenzene removal in vacuo, and the residue was quenched with water, extracted with dichloromethane and dried over anhydrous Na2SO4. The solvent was removed under vacuum and the residue was purified by silica gel column chromatography, using petroleum ether/ethyl acetate, 3:1-1:1. The product phenazin-2-amine (B) was obtained as a red solid (1.11 g, 30%): mp 285-286 °C (lit. mp 280 °C) [25] . IR (KBr, cm-1): 3309, 3194, 2918, 1640, 1597, 1514, 1476, 1453, 1335, 1232, 1132, 827, 755. 1H NMR (DMSO-d6, 500 MHz) δ: 8.06-8.04 (d, J = 8.5 Hz, 1H, Ar-H), 7.99-7.97 (d, J = 8.5 Hz, 1H, Ar-H), 7.91-7.89 (d, J = 9.2 Hz, 1H, Ar-H), 7.78-7.75 (t, J = 7.5 Hz, 1H, Ar-H), 7.67-7.64 (t, J = 7.5 Hz, 1H, Ar-H), 7.46-7.44 (d, J = 9.2 Hz, 1H, Ar-H), 6.91 (s, 1H, Ar-H), 6.47 (s, 2H, NH2). 13C NMR (DMSO-d6, 125 MHz) δ: 151.0 (Ar-C), 145.8 (Ar-C), 143.2 (Ar-C), 139.7 (Ar-C), 139.3 (Ar-C), 130.1 (Ar-C), 130.0 (Ar-C), 129.2 (Ar-C), 128.0 (Ar-C), 127.0 (Ar-C), 126.7 (Ar-C), 101.2 (Ar-C). HRMS (ESI): m/z [M + H]+ calcd for C12H9N3: 196.08747, found: 196.08707.
	With magnesium sulfate; nitrobenzene

Reference： [1]Besthorn bei O.Fischer [Chemische Berichte, 1896, vol. 29, p. 1875]
[2]Gao, Xiaochun; Lu, Yuanyuan; Fang, Lei; Fang, Xubin; Xing, Yingying; Gou, Shaohua; Xi, Tao [European Journal of Medicinal Chemistry, 2013, vol. 69, p. 1 - 9]
[3]Zhong, Yucheng; Liu, Jing; Cheng, Xiangyu; Zhang, Hao; Zhang, Chunhua; Xia, Zhuolu; Wu, Zhongxi; Zhang, Lu; Zheng, Yuting; Gao, Zhanyu; Jiang, Zhidong; Wang, Zhixiang; Huang, Dechun; Lu, Yuanyuan; Jiang, Feng [Bioorganic Chemistry, 2021, vol. 109]

2
[ 136-17-4 ]
[ 53897-95-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; formic acid

Reference： [1]Phillips [Journal of the Chemical Society, 1929, p. 2828]

3
[ 136-17-4 ]
benzoic acid-(5-amino-2-anilino-anilide) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Benzoylierung das Hydrochlorid;
	bei Benzoylierung;

Reference： [1]Battegay; Vechot [Bulletin de la Societe Chimique de France, 1925, vol. <4> 37, p. 1277]
[2]Battegay; Vechot [Bulletin de la Societe Chimique de France, 1925, vol. <4> 37, p. 1277]

4
[ 961-68-2 ]
[ 136-17-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	With hydrazine In tetrahydrofuran; ethanol at 20℃; for 0.333333h;	To a solution of 2, 4-DINITROPHENYLAMINE (1.5 g, 5.8 MMOL) in ethanol-THF (150: 50 mL) were added hydrazine hydrate (2 mL, 65 MMOL) and Raney Nickel (2.0 g). The reaction mixture was stirred at rt for 20 min, filtered through Celite. Evaporation of the solvent gave a black residue, which was purified by flash chromatography (methanol-DCM gradient elution). A black crystalline solid (1.0 g, 87%) was obtained. Mp 128-129°C ; TLC single spot at Rf 0.46 (8% METHANOL/DCM) ; 1H NMR (270 MHz, DMSO) : 5 7.25 (2H, t, J = 7.5 Hz, ArH), 6.73 (1H, s, NH), 6.61 (1H, d, J = 8. 3 Hz, ArH), 6.49-6. 55 (3H, m, ArH), 5.99 (1H, d, J = 2.5 Hz, ArH), 5.83 (1H, dd, J = 8. 2,2. 5 Hz, ArH), 4.66 (2H, s, NH2), 4.44 (2H, s, NH2) ; APCI-MS 198 (M-H+).
	With hydrogenchloride; iron
	With hydrogenchloride; tin

	With ethanol; iron; acetic acid
	With ammonium chloride; iron
	With hydrogen In ethyl acetate
	With 5%-palladium/activated carbon; hydrogen In ethyl acetate for 24h;	4.2.1 General procedure for the synthesis of intermediates A and B N-(2,4-Dinitrophenyl)benzeneamine (5.0g, 19.3mmol) was dissolved in ethyl acetate (300mL), then catalytically reduced in a Parr apparatus for 24h using a 5% Pd/C catalyst under hydrogen atmosphere. After reduction, the reaction mixture was filtered into ethyl acetate. The solvent was removed in vacuo, giving the desired N1-phenylbenzene-1,2,4-triamine A (3.76g, 18.9mmol, 98%), which was used without further purification. Compound A was immediately refluxed for 24h in nitrobenzene (100mL) containing MgSO4 in a flask. After nitrobenzene removal in vacuo, and the residue was quenched with water, extracted with dichloromethane and dried over anhydrous Na2SO4. The solvent was removed under vacuum and the residue was purified by silica gel column chromatography, using petroleum ether/ethyl acetate, 3:1-1:1. The product phenazin-2-amine (B) was obtained as a red solid (1.11g, 30%): mp 285-286°C (lit. mp 280°C) [25].
	With hydrogen In ethyl acetate at 20℃;	1.2 [0118] Step 2:To a solution of crude starting material from step 1 in EtOAc was added a scoop of 10% Pd/C (~50 mg). The vial was sealed, flushed with Argon, and then placed under H2 balloon. The mixture was stirred at room temperature overnight. The reaction mixture was filtered through a pad of Celite and eluted with EtOAc. The solvent was removed in vacuo and crude material was carried forward without purification.
	With palladium on activated charcoal; hydrogen

Reference： [1]Current Patent Assignee: IPSEN SA - WO2004/37251, 2004, A1 Location in patent: Page/Page column 122; 123
[2]Nietzki; Almenraeder [Chemische Berichte, 1895, vol. 28, p. 2971]
[3]Kehrmann; Messinger [Chemische Berichte, 1892, vol. 25, p. 1627]
[4]Gibson; Johnson; Vining [Recueil des Travaux Chimiques des Pays-Bas, 1930, vol. 49, p. 1006,1022]
[5]Current Patent Assignee: GOODYEAR TIRE & RUBBER CO - US1948330, 1931, A
[6]Carpenter, Andrew J.; Al-Barazanji, Kamal A.; Barvian, Kevin K.; Bishop, Michael J.; Britt, Christy S.; Cooper, Joel P.; Goetz, Aaron S.; Grizzle, Mary K.; Hertzog, Donald L.; Ignar, Diane M.; Morgan, Ronda O.; Peckham, Gregory E.; Speake, Jason D.; Swain, Will R. [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 19, p. 4994 - 5000]
[7]Gao, Xiaochun; Lu, Yuanyuan; Fang, Lei; Fang, Xubin; Xing, Yingying; Gou, Shaohua; Xi, Tao [European Journal of Medicinal Chemistry, 2013, vol. 69, p. 1 - 9]
[8]Current Patent Assignee: KINETA INC. - WO2007/103111, 2007, A2 Location in patent: Page/Page column 40
[9]Zhong, Yucheng; Liu, Jing; Cheng, Xiangyu; Zhang, Hao; Zhang, Chunhua; Xia, Zhuolu; Wu, Zhongxi; Zhang, Lu; Zheng, Yuting; Gao, Zhanyu; Jiang, Zhidong; Wang, Zhixiang; Huang, Dechun; Lu, Yuanyuan; Jiang, Feng [Bioorganic Chemistry, 2021, vol. 109]

5
N-(2,4-dinitro-phenyl)-N-phenyl-hydroxylamine [ No CAS ]
[ 136-17-4 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; acetic acid; zinc

Reference： [1]Wieland; Gambarjan [Chemische Berichte, 1906, vol. 39, p. 3041]

6
[ 136-17-4 ]
[ 108-24-7 ]
[ 3018-68-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride

Reference： [1]Phillips [Journal of the Chemical Society, 1929, p. 2828]

7
[ 136-17-4 ]
[ 108-24-7 ]
[ 156118-85-3 ]

Reference： [1]Nietzki; Almenraeder [Chemische Berichte, 1895, vol. 28, p. 2971]

8
[ 136-17-4 ]
[ 134-81-6 ]
6-amino-1,2,3-triphenyl-1,2-dihydro-quinoxalin-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol Versetzen mit Eisenchlorid-Loesung und Behandeln des Eisenchlorid-Doppelsalzes mit Ammoniak;

Reference： [1]Kehrmann; Messinger [Chemische Berichte, 1892, vol. 25, p. 1627]

9
[ 136-17-4 ]
[ 82-86-0 ]
10-amino-7-phenyl-acenaphtho[1,2-b]quinoxalinium; hydroxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid isoliert als Chlorid;

Reference： [1]Ullmann; Cassirer [Chemische Berichte, 1910, vol. 43, p. 441]

Yield	Reaction Conditions	Operation in experiment
	Rk. m. KBrO3, chemischer Oszillator;

11
[ 136-17-4 ]
[ 2876-23-5 ]

Reference： [1]Besthorn bei O.Fischer [Chemische Berichte, 1896, vol. 29, p. 1875]

12
[ 7647-01-0 ]
[ 961-68-2 ]
[ 136-17-4 ]

Reference： [1]Nietzki; Almenraeder [Chemische Berichte, 1895, vol. 28, p. 2971]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; bromate In water chemical oscillation with and without a catalyst;

15
N-(2,4-dinitro-phenyl)-N-phenyl-hydroxylamine [ No CAS ]
[ 64-19-7 ]
[ 136-17-4 ]

Reference： [1]Wieland; Gambarjan [Chemische Berichte, 1906, vol. 39, p. 3041]

16
[ 851875-39-3 ]
[ 136-17-4 ]
[ 851875-41-7 ]

Yield	Reaction Conditions	Operation in experiment
76%	With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃;

Reference： [1]Xie, Jian; Seto, Christopher T. [Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 8, p. 2981 - 2991]

17
[ 136-17-4 ]
[ 75-36-5 ]
[ 156118-85-3 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In N,N-dimethyl-formamide

Reference： [1]Carpenter, Andrew J.; Al-Barazanji, Kamal A.; Barvian, Kevin K.; Bishop, Michael J.; Britt, Christy S.; Cooper, Joel P.; Goetz, Aaron S.; Grizzle, Mary K.; Hertzog, Donald L.; Ignar, Diane M.; Morgan, Ronda O.; Peckham, Gregory E.; Speake, Jason D.; Swain, Will R. [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 19, p. 4994 - 5000]

18
[ 136-17-4 ]
6-(4-chloro-phenyl)-3-(2-methyl-1-phenyl-1H-benzoimidazol-5-yl)-3H-thieno[3,2-d]pyrimidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: Et₃N / dimethylformamide 2: aq. HCl / 100 °C 3: phenol / 110 - 130 °C

19
[ 136-17-4 ]
[ 3018-68-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Et₃N / dimethylformamide 2: aq. HCl / 100 °C

20
[ 584-48-5 ]
[ 136-17-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: alcohol 2: methanol; zinc; glacial acetic acid

Reference： [1]Wieland; Gambarjan [Chemische Berichte, 1906, vol. 39, p. 3041]

21
[ 100-65-2 ]
[ 136-17-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: alcohol 2: methanol; zinc; glacial acetic acid

Reference： [1]Wieland; Gambarjan [Chemische Berichte, 1906, vol. 39, p. 3041]

22
[ 136-17-4 ]
[ 108-24-7 ]
[ 299927-16-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: 2,4-diaminodiphenylamine; acetic anhydride With acetic acid at 80℃; for 6h; Stage #2: With sodium hydrogencarbonate In water at 20℃;	N'-PHENYL-BENZENE-1, 2,4-triamine (800 mg, 4 MMOL) was dissolved in acetic acid (10 mL), acetic anhydride (1.0 mL) was added to the solution. The mixture was stirred at 80°C for 6h, cooled to rt and neutralized with 5% sodium carbonate, then extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulphate and concentrated to give a residue, which was crystallized from ethanol. A brown crystalline solid (0.85 g, 80%) was obtained. Mp 231-232°C ; TLC single spot at Rf 0.39 (10% methanol/DCM) ;'H NMR (270 MHz, DMSO): 8 9.92 (1H, s, NH), 7.97 (1H, d, J = 1.6 Hz, ArH), 7.51-7. 67 (5H, m, ArH), 7.31 (1H, dd, J = 8.3, 1.9 Hz, ArH), 7.04 (1H, d, J = 8.3 Hz, ArH),, 2. 41 (3H, s, CH3), 2.05 (3H, s, CH3) ; APCI-MS 264 (M-H+).

Reference： [1]Current Patent Assignee: IPSEN SA - WO2004/37251, 2004, A1 Location in patent: Page/Page column 123

Yield	Reaction Conditions	Operation in experiment
		Among these anilinoamines, the following compounds are most preferred: 4-Methoxy-2-methylaniline; 4-Anilino-m-phenylenediamine; 4-Cyclohexylaniline; m-Anilinophenol; 2-Aminoacetophenone; ...

24
[ 64-18-6 ]
[ 136-17-4 ]
[ 53897-95-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogenchloride at 110℃;
	Stage #1: formic acid; 4-anilino-m-phenylenediamine With hydrogenchloride In water monomer at 100℃; for 1.5h; Stage #2: With sodium hydroxide In water monomer at 20℃;	1.3 [0119] Step 3:The crude material from step 2 was suspended in 4N HCI (2ml) and formic acid (0.5 ml). The mixture was heated to 1000C for 1.5 hours. The reaction was cooled to room temperature and 5 N NaOH was added to adjust pH to ~13. The mixture was extracted with DCM (3x 5ml). The combined organic layers were dried over MgSO-j, filtered, and solvent evaporated in vacuo to give the crude product that was carried forward without purification.

Reference： [1]Garcia-Manero, G.; Hu, Yumin; Huang, Kezhi; Huang, Peng; Li, Yiqing; Liu, Qiao; Lu, Wenhua; Luo, Bingling; Tian, Tian; Wen, Shijun; Yin, Feng; Zhang, Shengyi [Journal of Medicinal Chemistry, 2022, vol. 65, # 4, p. 3597 - 3605]
[2]Current Patent Assignee: KINETA INC. - WO2007/103111, 2007, A2 Location in patent: Page/Page column 40

25
[ 504-15-4 ]
[ 327-92-4 ]
[ 136-17-4 ]
[ 1246084-39-8 ]