[ CAS No. 51207-85-3 ] {[proInfo.proName]}

Name: 51207-85-3|4-Amino-N,N-diethylbenzamide|98%
Brand: Ambeed
SKU: A825223
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3d Animation Molecule Structure of 51207-85-3

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Quality Control of [ 51207-85-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 51207-85-3 ]

SDS Specification

Alternatived Products of [ 51207-85-3 ]

Product Details of [ 51207-85-3 ]

CAS No. :	51207-85-3	MDL No. :	MFCD00461426
Formula :	C₁₁H₁₆N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RNVOPVJRSRXPSX-UHFFFAOYSA-N
M.W :	192.26	Pubchem ID :	458760
Synonyms :

Calculated chemistry of [ 51207-85-3 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.36
Num. rotatable bonds :	4
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	58.36
TPSA :	46.33 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.02 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.96
Log Po/w (XLOGP3) :	0.64
Log Po/w (WLOGP) :	1.76
Log Po/w (MLOGP) :	1.83
Log Po/w (SILICOS-IT) :	1.27
Consensus Log Po/w :	1.49

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.49
Solubility :	6.25 mg/ml ; 0.0325 mol/l
Class :	Very soluble
Log S (Ali) :	-1.19
Solubility :	12.5 mg/ml ; 0.0648 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.91
Solubility :	0.237 mg/ml ; 0.00123 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 51207-85-3 ]

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 [ 51207-85-3 ]

* 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 [ 51207-85-3 ]

[ 51207-85-3 ] Synthesis Path-Downstream 1~4

1
[ 5323-47-7 ]
[ 51207-85-3 ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium tetrahydridoborate In tetrahydrofuran; lithium hydroxide monohydrate at 20℃; for 3h; Green chemistry;
87%	With sodium tetrahydridoborate In ethanol; lithium hydroxide monohydrate at 20℃; for 4h; Green chemistry;	4.5 General procedure for the reduction of nitro aromatic using starch-crt(at)Au General procedure: To a flask containing nitroarene (0.5 mmol), starch-crt(at)Au (0.1 mol%, 25 mg) and NaBH4 (2.5 mmol, 45 mg), 2 mL of H2O:EtOH (1:1) was added. Reaction mixture was stirred at room temperature for the appropriate reaction times (see Tables 2 and 3). Progress of the reactions were monitored by GC, TLC and or 1H NMR. After completion of the reaction, the crude product was extracted with ethyl acetate (3 × 5 mL). The solvent was evaporated and the residue was purified using column or plate chromatography.
85%	With palladium 10% on activated carbon; hydrogen In methanol; dichloromethane at 20℃;

83%	With palladium 10% on activated carbon; ammsnium formate In methanol for 1h; Cooling with ice;	E Preparation E4-(N ,N -diethylcarboxamido )aniline [0059] Ammonium formate (20.0 g, 317 mmol) was added to a vigorously stirred mixture ofN,N-diethyl4-nitrobenzamide (20.0 g, 90 mmol) and 1.0 g of 10% palladium/charcoal in400 mL of methanol cooled on ice. The reaction warms with vigorous gas evolution. After 1 h,TLC ( 60/40 hexane/EtOAc) indicated complete conversion of the starting material. The mixture was filtered through a pad of Celite and evaporated to a crystalline solid. This wassuspended in water and collected by vacuum filtration. The product was recrystallized fromwater and dried to provide 14.14 g (83%) of white crystals. 1H-NMR (400 MHz, CDCb): 87.22 (2H, m), 6.65 (2H, m), 3.81 (2H, br s), 3.42 (4H, br s), 1.17 (6H, t, J = 6.8 Hz).
80%	With hydrazine hydrate monohydrate In ethanol for 4h; Heating;
78.2%	With iron⁽⁰⁾; ammonia hydrochloride In methanol; lithium hydroxide monohydrate at 70℃;
75%	With hydrogen; C₄₅H₅₆BN₅OPRh⁽²⁺⁾*2F₆Sb^(1-) In toluene at 60℃; for 15h; Glovebox; chemoselective reaction;
	With hydrogenchloride; glacial acetic acid; stannous chloride
	With ammsnium formate In methanol at 20℃; for 2h;	28.2 A mixture of N,N-diethyl 4- nitrobenzamide (4.44 g) and 10% palladium on carbon (0.2 g) in 100 mL of methanol was treated with ammonium formate (4.0 g) for 2 h at ambient temperature. The mixture was filtered through diatomaceous earth and concentrated. The residue was redissolved in DCM, washed successively with 0.5 M Na2C03, water, and brine, then dried over MgS04, filtered, and evaporated to provide a crystalline material. Recrystallization from ethyl acetate/hexane provided the product aniline.
	With palladium 10% on activated carbon; ammsnium formate In methanol at 20℃; for 2h;	12.2 (2) 4-(N,N-diethylcarboxamido)aniline: A mixture of N,N-diethyl 4- nitrobenzamide (4.44 g) and 10% palladium on carbon (0.2 g) in 100 mL of methanol was treated with ammonium formate (4.0 g) for 2 h at ambient temperature. The mixture was filtered through Celite and concentrated. The residue was redissolved in DCM, washed successively with 0.5 M Na2C03, water, and brine, then dried over MgS04, filtered, and evaporated to provide a crystalline material. Recrystallization from ethyl acetate/hexane provided the product aniline. [0086] Also prepared according to the same procedure was 4-(morpholinocarbonyl)aniline by replacing diethylamine with morpholine.
	With palladium 10% on activated carbon; ammsnium formate In methanol at 20℃; for 2h;	12.2 2) 4-(N,N-diethylcarboxamido)aniline (2) 4-(N,N-diethylcarboxamido)aniline: A mixture of N,N-diethyl 4-nitrobenzamide (4.44 g) and 10% palladium on carbon (0.2 g) in 100 mL of methanol was treated with ammonium formate (4.0 g) for 2 h at ambient temperature. The mixture was filtered through Celite and concentrated. The residue was redissolved in DCM, washed successively with 0.5 M Na2C03, water, and brine, then dried over MgS04, filtered, and evaporated to provide a crystalline material. Recrystallization from ethyl acetate/hexane provided the product aniline.
	With palladium 10% on activated carbon; hydrogen In methanol; dichloromethane for 12.5h;
	With palladium 10% on activated carbon; ammsnium formate In methanol at 20℃; for 2h;	12 Preparation of 4-(N,N-Diethylcarboxamido)Aniline (2) 4-(N,N-diethylcarboxamido)aniline A mixture of N,N-diethyl 4-nitrobenzamide (4.44 g) and 10% palladium on carbon (0.2 g) in 100 mL of methanol was treated with ammonium formate (4.0 g) for 2 h at ambient temperature. The mixture was filtered through Celite and concentrated. The residue was redissolved in DCM, washed successively with 0.5 M Na2CO3, water, and brine, then dried over MgSO4, filtered, and evaporated to provide a crystalline material. Recrystallization from ethyl acetate/hexane provided the product aniline.
90 %Chromat.	With sodium tetrahydridoborate In ethanol; lithium hydroxide monohydrate at 20℃; for 1.5h;

Reference： [1]Gholinejad, Mohammad; Oftadeh, Erfan; Shojafar, Mohammad; Sansano, José M.; Lipshutz, Bruce H. [ChemSusChem, 2019, vol. 12, # 18, p. 4240 - 4248]
[2]Gholinejad, Mohammad; Dasvarz, Neda; Shojafar, Mohammad; Sansano, José M. [Inorganica Chimica Acta, 2019, vol. 495]
[3]Chiba, Mayumi; Ichikawa, Yuki; Kamiya, Mako; Komatsu, Toru; Ueno, Tasuku; Hanaoka, Kenjiro; Nagano, Tetsuo; Lange, Norbert; Urano, Yasuteru [Angewandte Chemie - International Edition, 2017, vol. 56, # 35, p. 10418 - 10422][Angew. Chem., 2017, vol. 129, # 35, p. 10554 - 10558]
[4]Current Patent Assignee: PROLYNX - WO2015/51307, 2015, A1 Location in patent: Paragraph 0059
[5]Srivastava, Neera; Gupta, Anurag Ateet; Gupta, Anil K. Sen [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, p. 787 - 789]
[6]Li, Xinyu; Shi, Binyu; Teng, Yu; Cheng, Yu; Yang, Huizhu; Li, Jiurong; Wang, Lianjian; He, Siying; You, Qidong; Xiang, Hua [MedChemComm, 2019, vol. 10, # 2, p. 294 - 299]
[7]Chugh, Vishal; Chatterjee, Basujit; Chang, Wei-Chieh; Cramer, Hanna H.; Hindemith, Carsten; Randel, Helena; Weyhermüller, Thomas; Farès, Christophe; Werlé, Christophe [Angewandte Chemie - International Edition, 2022, vol. 61, # 36][Angew. Chem., 2022, vol. 134, # 36]
[8]Wenker [Journal of the American Chemical Society, 1938, vol. 60, p. 1081]
[9]Current Patent Assignee: PROLYNX - WO2011/140393, 2011, A1 Location in patent: Page/Page column 44
[10]Current Patent Assignee: PROLYNX - WO2013/36857, 2013, A1 Location in patent: Paragraph 0085
[11]Current Patent Assignee: PROLYNX - WO2013/36847, 2013, A1 Location in patent: Paragraph 0114
[12]Piao, Wen; Hanaoka, Kenjiro; Fujisawa, Tomotsumi; Takeuchi, Satoshi; Komatsu, Toru; Ueno, Tasuku; Terai, Takuya; Tahara, Tahei; Nagano, Tetsuo; Urano, Yasuteru [Journal of the American Chemical Society, 2017, vol. 139, # 39, p. 13713 - 13719]
[13]Current Patent Assignee: PROLYNX - US2017/312368, 2017, A1 Location in patent: Paragraph 01
[14]Khosravi, Faezeh; Gholinejad, Mohammad; Sansano, José M.; Luque, Rafael [Applied Organometallic Chemistry, 2022, vol. 36, # 7]

2
[ 50-00-0 ]
[ 536-17-4 ]
[ 51207-85-3 ]
[ 104183-56-4 ]

Yield	Reaction Conditions	Operation in experiment
81%	In ethanol; water Heating;

Reference： [1]Husain, M. I.; Shukla, Sarveshwar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 761 - 764]

3
[ 5892-99-9 ]
[ 51207-85-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; lithium hexamethyldisilazane; CyJohnPhos In 1,4-dioxane at 80℃; for 15h;
94%	With dicyclohexyl(2',4',6'-triisopropyl-5-methoxy-3,4,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; C₅₀H₇₀NO₄PPdS; C₅₀H₇₀NO₄PPdS; dicyclohexyl(2',4',6'-triisopropyl-4-methoxy-3,5,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 20℃; for 36h; Inert atmosphere;

Reference： [1]Huang; Buchwald [Organic letters, 2001, vol. 3, # 21, p. 3417 - 3419]
[2]Cheung, Chi Wai; Surry, David S.; Buchwald, Stephen L. [Organic Letters, 2013, vol. 15, # 14, p. 3734 - 3737]

4
[ 1336-21-6 ]
Ti(Oi-Pr)4 [ No CAS ]
[ 775-16-6 ]
[ 51207-85-3 ]
[ 209902-32-9 ]

Yield	Reaction Conditions	Operation in experiment
44%	With sodium tetrahydroborate; In ethanol; n-heptane; ethyl acetate;	(i) Preparation of 4-[N-(1-benzyl-pyrrolidin-3-yl)-amino]-N,N-diethyl benzamide (compound 19) STR30 Ti(Oi-Pr)4 (3.1 ml, 10.4 mmol) was added to a mixture of 4-amino-(N,N-diethyl) benzamide (0.50 g, 2.51 mmol) and 1-benzyl-3-pyrrolidone (0.85 mL, 5.30 mmol) at room temperature. The mixture was sonicated at 40 C. for 3 h, and stirred at room temperature for 16 h. The mixture was cooled in an ice-bath and EtOH (30 mL) and NaBH4 (0.30 g, 8.00 mmol) were added. After stirring for 16 h at room temperature, 2M NH4 OH (20 mL) was added. The mixture was stirred at room temperature for 30 min, diluted with CH2 Cl2 (20 mL) and filtered through a pad of Celite. The layers in the filtrate were separated, the aqueous layer extracted with CH2 Cl2 (320 mL). The combined organic phases were washed with 10% HCl (220 mL). The pH in the combined aqueous extracts was adjusted to 10 with 2N NaOH, and extracted with CH2 Cl2 (3*20 mL). The combined organic extracts were dried over Na2 SO4, filtered, concentrated and the residue purified by chromatography (gradient, 9:1:0.5 to 9:0:1 EtOAc/heptane/Et3 N) to give the title compound 19 (0.40 g, 44%) as a pale yellow viscous oil. IR (neat): 3322, 1609, 1527, 1455 cm-1. 1 H NMR (CDCl3): 7.40-7.10 (7H, m), 6.60-6.40 (2H, m), 4.20 (1H, m), 3.95 (1H, m), 3.55 (2H, s), 3.35 (4H, bs), 2.70 (2H, m), 2.50-2.35 (2H, m), 2.25 (1H, m), 1.60 (1H, m), 1.15 (6H, bt). 13 C NMR (CDCl3): 171.4, 148.2, 138.4, 128.5, 128.2, 128.1, 126.7, 126.1, 113.8, 112.1, 60.5, 59.9, 52.5, 51.9, 41 (b), 32.2, 13.3.

Reference： [1]Patent: US6153626,2000,A

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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 51207-85-3 ] {[proInfo.proName]}

Quality Control of [ 51207-85-3 ]

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Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 51207-85-3 ]

Application In Synthesis of [ 51207-85-3 ]

[ 51207-85-3 ] Synthesis Path-Downstream 1~4

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry