58259-34-0|N-Butyl-4-nitroaniline| Ambeed

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Quality Control of [ 58259-34-0 ] Purity: 97% SDS Specification

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Product Details of [ 58259-34-0 ]

CAS No. :	58259-34-0
Formula :	C₁₀H₁₄N₂O₂
M.W :	194.23
SMILES Code :	O=[N+](C1=CC=C(C=C1)NCCCC)[O-]
MDL No. :	MFCD00024635
InChI Key :	KCTYPOBEIDJYGF-UHFFFAOYSA-N
Pubchem ID :	3801140

Safety of [ 58259-34-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H319
Precautionary Statements:	P305+P351+P338

Computational Chemistry of [ 58259-34-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	6
Fraction Csp3	0.4
Num. rotatable bonds	5
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	58.99
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	57.85 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.15
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.41
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.62
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.38
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	0.37
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.18

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.18
Solubility	0.128 mg/ml ; 0.000661 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-4.3
Solubility	0.00963 mg/ml ; 0.0000496 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.44
Solubility	0.0713 mg/ml ; 0.000367 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	Yes
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.06 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	2.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.69

Application In Synthesis of [ 58259-34-0 ]

* 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 [ 58259-34-0 ]

[ 58259-34-0 ] Synthesis Path-Downstream 1~35

1
[ 124-04-9 ]
[ 58259-34-0 ]
N,N'-dibutyl-N,N'-bis-(4-nitro-phenyl)-adipamide [ No CAS ]

References: [1]Patent: US2311754,1940,A .

2
[ 109-73-9 ]
[ 350-46-9 ]
[ 58259-34-0 ]

References: [1]Journal of Materials Chemistry,1999,vol. 9,p. 1699 - 1705.
[2]Journal of Organic Chemistry,2019,vol. 84,p. 181 - 190.
[3]Bulletin de la Societe Chimique de France,1956,p. 311,315.
[4]New Journal of Chemistry,2012,vol. 36,p. 1519 - 1526.
[5]ChemPlusChem,2019,vol. 84,p. 465 - 473.

3
[ 58259-34-0 ]
[ 123-72-8 ]
[ 100-01-6 ]

References: [1]Journal of the Chemical Society. Perkin transactions II,1985,p. 1963 - 1968.

4
[ 14150-94-8 ]
[ 109-73-9 ]
[ 67-64-1 ]
[ 58259-34-0 ]

References: [1]Bulletin of the Chemical Society of Japan,1982,vol. 55,p. 2174 - 2180.

5
[ 54191-12-7 ]
[ 58259-34-0 ]

Yield	Reaction Conditions	Operation in experiment
72%	With borane-THF; In tetrahydrofuran; at 20℃; for 2h;	To a solution of 56 (2.95 g, 14.2 mmol) in tetrahydrofuran (10 mL) was added borane-tetrahydrofuran complex (1 M in tetrahydrofuran, 18.0 mL) at ambient temperature. After stirring for2 h at this temperature, the reaction mixture was quenched with addition of methanol and water. Themixture was concentrated in vacuo and diluted with ethyl acetate. The organic layer was washed withwater and brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified withsilica gel column chromatography (n-hexane/ethyl acetate = 5:1) to afford the title compound (1.98 g,10.2 mmol, 72%) as a yellow solid.

References: [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 2781 - 2787.
[2]Journal of the Chemical Society. Perkin transactions II,1985,p. 1963 - 1968.

6
[ 56269-49-9 ]
[ 58259-34-0 ]
[ 100-15-2 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 828 - 832.
[2]Journal of the Chemical Society. Perkin transactions I,1980,p. 828 - 832.

7
[ 123-72-8 ]
[ 100-01-6 ]
[ 58259-34-0 ]

References: [1]Synthesis,1993,p. 121 - 125.

8
[ 21724-51-6 ]
[ 98-95-3 ]
[ 58259-34-0 ]

References: [1]Journal of Organic Chemistry,1988,vol. 53,p. 3978 - 3982.

9
[ 100-00-5 ]
[ 109-73-9 ]
[ 33513-42-7 ]
[ 58259-34-0 ]
[ 100-23-2 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1986,vol. 22,p. 403 - 404.
Zhurnal Organicheskoi Khimii,1986,vol. 22,p. 455 - 456.

10
[ 100-00-5 ]
[ 109-73-9 ]
[ 58259-34-0 ]

References: [1]Bulletin of the Chemical Society of Japan,1991,vol. 64,p. 42 - 49.
[2]Journal of Organic Chemistry,2019,vol. 84,p. 181 - 190.

11
[ 636-98-6 ]
[ 109-73-9 ]
[ 58259-34-0 ]

Yield	Reaction Conditions	Operation in experiment
6%Spectr.	With copper(I) oxide; In acetonitrile; for 6h;Reflux;	General procedure: In a 10 mL flask were placed aryl halide (0.5 mmol), diamine (1.0; 2.0 or 3.7 mmol), copper catalyst (0.5; 1.0 or 10 mol %), and acetonitrile (2-3 mL). The reaction was then kept under stirring and reflux. After the reaction was complete (TLC), the resulting mixture was diluted with brine (2-3 mL) and extracted with ethyl acetate (4 Χ 7 mL). Then the organic phase was dried over anhydrous sodium sulfate, filtered under Celite, and the solvent was eliminated by vacuum. The crude product was then analyzed by 1H NMR. When necessary, the mixture was purified by column chromatography on silica gel or by thin layer chromatography plates with UV 254 nm to afford the desired product.

References: [1]Tetrahedron,2008,vol. 64,p. 11230 - 11236.
[2]ChemCatChem,2016,vol. 8,p. 1319 - 1328.
[3]Synlett,2011,p. 1859 - 1862.
[4]Journal of Organic Chemistry,2011,vol. 76,p. 800 - 810.
[5]Organic Letters,2003,vol. 5,p. 4987 - 4990.
[6]Journal of Organic Chemistry,2020,vol. 85,p. 11080 - 11093.
[7]Journal of Organic Chemistry,2019,vol. 84,p. 181 - 190.
[8]Journal of Organic Chemistry,2017,vol. 82,p. 5416 - 5423.
[9]Bulletin of the Chemical Society of Japan,1991,vol. 64,p. 42 - 49.
[10]Tetrahedron Letters,2013,vol. 54,p. 2332 - 2335.

12
[ 14368-49-1 ]
[ 109-73-9 ]
[ 59453-65-5 ]
[ 59453-64-4 ]
[ 52010-79-4 ]
[ 58259-34-0 ]
[ 59453-63-3 ]
[ 100-00-5 ]

References: [1]Arzneimittel-Forschung/Drug Research,1980,vol. 30,p. 581 - 584.

13
[ 100-17-4 ]
[ 109-73-9 ]
[ 58259-34-0 ]

References: [1]Tetrahedron Letters,1984,vol. 25,p. 4147 - 4150.

14
[ 68906-00-3 ]
[ 109-73-9 ]
[ 67-64-1 ]
[ 58259-34-0 ]

References: [1]Russian Chemical Bulletin,1994,vol. 43,p. 1041 - 1043.
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1994,p. 1102 - 1104.

16
[ 100-01-6 ]
HgS, CO₂ [ No CAS ]
[ 58259-34-0 ]

References: [1]Journal of the Chemical Society. Perkin transactions II,1985,p. 1963 - 1968.

17
[ 58259-34-0 ]
N,N'-bis-(4-amino-phenyl)-N,N'-dibutyl-adipamide [ No CAS ]

References: [1]Patent: US2311754,1940,A .

18
[ 15676-66-1 ]
p-nitrobenzenediazonium o-benzenedisulfonimide [ No CAS ]
[ 4482-01-3 ]
[ 58259-34-0 ]

References: [1]European Journal of Organic Chemistry,2008,p. 862 - 868.

19
[ 98-95-3 ]
[ 109-73-9 ]
[ 58259-34-0 ]
[ 42896-66-2 ]

References: [1]European Journal of Organic Chemistry,2009,p. 564 - 574.

20
[ 109-65-9 ]
[ 100-01-6 ]
[ 58259-34-0 ]

References: [1]Catalysis Letters,2011,vol. 141,p. 178 - 182.
[2]European Journal of Organic Chemistry,2016,vol. 2016,p. 3824 - 3835.

21
[ 1516-60-5 ]
[ 60669-69-4 ]
[ 58259-34-0 ]

References: [1]Journal of Organic Chemistry,2011,vol. 76,p. 7017 - 7026.

22
[ 109-69-3 ]
[ 100-01-6 ]
[ 58259-34-0 ]

References: [1]European Journal of Organic Chemistry,2012,p. 3105 - 3111.

23
[ 830-03-5 ]
[ 109-73-9 ]
[ 58259-34-0 ]

References: [1]New Journal of Chemistry,2012,vol. 36,p. 1519 - 1526.

24
[ 109-73-9 ]
[ 586-78-7 ]
[ 58259-34-0 ]

Yield	Reaction Conditions	Operation in experiment
80%	With copper(l) iodide; C12H13N3O; potassium carbonate; In diethylene glycol; at 10℃; for 12h;Sealed tube;	The 201 mg (1mmol) 4 - nitro-bromophenylacetic, 110 mg (1.5mmol) n-butylamine, 4.8 mg (0.025mmol) CuI, 10.8 mg (0.05mmol) ligand L2, 552mg (4mmol) K2CO3, 2 ml DEG, adding 10 ml reaction tube, sealing, 10 C reaction under the condition 12h. After the stop of the reaction, water, extracted with ethyl acetate, washing, saturated salt water washing, after drying with anhydrous sodium sulfate, filtered, the filtrate is distilled under reduced pressure, purification by silica gel chromatography separation column column, shall be N - n-butylamine -4 - nitroaniline 155 mg, yield 80%.
51%	With copper(l) iodide; tetrabutylammomium bromide; potassium hydroxide; In water; at 90℃; for 16h;Green chemistry;	General procedure: A 10 mL of vial was charged with CuI (10 mg, 0.05 mmol), PSP (0.25 mmol, size less than 90 μM), TBAB (40 mg, 0.25 mmol), base (1.0 mmol), aryl halides (0.5 mmol), arylamine (2.0 mmol), H2O (1.0 mL), and a magnetic stir bar. The vessel was sealed with a septum and placed into an oil bath, which was preheated to 70 C (90 C for alkyl amine, 120 C for imidazole). The reaction mixture was stirred for another 16 h (8 h for imidazole). After allowing the mixture to cool to room temperature, the reaction mixture was filtrated, the precipitates were washed with water and ethyl acetate thoroughly. The filtrate was extracted with ethyl acetate (3×25 mL). The combined organic phases was washed with water and brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatograph on silica gel to afford the desired products.
15%	With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; In tetrahydrofuran; at 80℃; for 12h;Inert atmosphere;	To the mixture of butylamine (0.524 mmol) and t-BuONa (0.75 mmol) in anhydrous THF (3 mL) was added 4-bromo-1-nitrobenzene (0.49 mmol), Pd(dba)2 (0.02 mmol) and BINAP (0.02 mmol) in 2 mL THF under Ar. The mixture was degassed via freeze-thaw and finally, the reaction was carried out at 80 oC. After 12 h, the solution was cooled down to ambient temperature and the solvent was removed in vacuo. The residue was purified via flash chromatography to yield the product (yield 15%): IR (neat) 3317, 3085, 1586, 1537 cm-1; 1H NMR (400 MHz, CDCl3): δ 8.1-7.8 (m, 2H), 7.6-7.4 (m, 2H), 3.0-2.8 (m, 2H), 2.1-0.9 (m, 7H); HRMS m/z: found 193.71, calculated 194.105.

References: [1]Patent: CN106883132,2017,A .Location in patent: Paragraph 0075-0077.
[2]Journal of Organic Chemistry,2019,vol. 84,p. 181 - 190.
[3]Journal of Organic Chemistry,2017,vol. 82,p. 5416 - 5423.
[4]Tetrahedron,2013,vol. 69,p. 8974 - 8977.
[5]Tetrahedron Letters,2013,vol. 54,p. 6665 - 6668.

25
[ 58259-34-0 ]
[ 104-15-4 ]
N-butyl-4-nitroanilinium p-toluenesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; at 20℃; for 2h;	The mixture of N-butyl-2-nitroaniline (32 mg) and p-toluenesulfonic acid (33 mg) in 3 mL of toluene was stirred at ambient temperature for 2 h. The solvent was evaporated in vacuo to yield catalyst 2.

References: [1]Tetrahedron Letters,2013,vol. 54,p. 6665 - 6668.

26
[ 58259-34-0 ]
[ 7154-66-7 ]
C₁₇H₁₇BrN₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; triethylamine; In dichloromethane; at 20℃;	To a solution of 57 (339 mg, 1.75 mmol), N,N-dimethyl-4-aminopyridine (10.0 mg) andtriethylamine (0.5 mL) in dichloromethane (5 mL) was added 2-bromobenzoyl chloride (439 mg, 2.00mmol). After stirring overnight at ambient temperature, the reaction mixture was concentrated invacuo and the residue was diluted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified with silica gelcolumn chromatography (n-hexane/ethyl acetate = 4:1) to afford a colorless oil. To a solution of thisamide in N,N-dimethylacetamide (5 mL) were added palladium (II) acetate (39.7 mg 0.177 mmol),tricyclohexylphosphine tetrafluoroborate (97.6 mg, 0.265 mmol) and cesium carbonate (1.15 g, 3.53mmol). After stirring for 5 h at 130 C under argon, the reaction mixture was diluted with ethylacetate. The organic solution was filtered with celite and rinsed with ethyl acetate. The combinedorganic layer was washed with water and brine, dried over sodium sulfate and concentrated in vacuo.The residue was purified with silica gel column chromatography (n-hexane/ethyl acetate = 4:1) toafford the title compound (357 mg, 1.20 mmol, 68%) as a colorless solid.