78137-76-5|4-Bromo-3-nitrophenol| Ambeed

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Quality Control of [ 78137-76-5 ] Purity: 97% SDS Specification

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Product Details of [ 78137-76-5 ]

CAS No. :	78137-76-5
Formula :	C₆H₄BrNO₃
M.W :	218.01
SMILES Code :	BrC1=C(C=C(C=C1)O)[N+](=O)[O-]
MDL No. :	MFCD11040194
InChI Key :	MTNZLOXGKDQNKA-UHFFFAOYSA-N
Pubchem ID :	15817867

Safety of [ 78137-76-5 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H315-H317-H318-H410
Precautionary Statements:	P261-P264-P270-P272-P273-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310-P333+P313-P391-P501
Class:	9
UN#:	3077
Packing Group:	Ⅲ

Computational Chemistry of [ 78137-76-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	44.99
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	66.05 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.08
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	1.54
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.06
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.	1.05
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	-0.1
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.13

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.5
Solubility	0.69 mg/ml ; 0.00317 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.	-2.54
Solubility	0.634 mg/ml ; 0.00291 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-2.06
Solubility	1.89 mg/ml ; 0.00867 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	No
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	No
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.	-6.54 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	0.0
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)	1.94

Application In Synthesis of [ 78137-76-5 ]

* 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 [ 78137-76-5 ]

[ 78137-76-5 ] Synthesis Path-Downstream 1~35

1
[ 554-84-7 ]
[ 78137-76-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With 1,2-ethanediylbis(triphenylphosphonium) ditribromide; In methanol; dichloromethane; at 20℃; for 0.0833333h;	General procedure: To a mixture of anilines or phenols (0.7 mmol) the brominatingagent (1) (0.72 g, 0.7 mmol) in dichloromethane(30 ml)-methanol (15 ml) was added. The reactionmixture was stirred at room temperature until decolorizationof the orange solution took place. The progress of thereaction was monitored by TLC (eluent: n-hexane/ethylacetate, 7:3). After completion of the reaction, the solventwas evaporated and diethyl ether (10 ml) was added to theresidue. The supernatant was decanted and the insolubleresidue was washed by ether (3 × 10 ml). The combinedether extracts were dried on magnesium sulfate and also evaporated under vacuum to afford monobromo anilines ormonobromo phenols which was purified by flash columnchromatography over silica gel (n-hexane/ethyl acetate,7:3).
	With hydrogenchloride; carbon dioxide; bromine;	a) A gaseous mixture of carbon dioxide and bromine was introduced into 10.5 g of molten m-nitrophenol heated in 120-140° C. until the calculated increase in weight had been reached. Pure carbon dioxide was introduced to remove residues of bromine from the reaction mixture. The product mixture was recrystallized twice for 10percent aqueous hydrochloric acid. This gave 8 g of 4-bromo-3-nitrophenol.

References: [1]Tetrahedron Letters,2009,vol. 50,p. 1007 - 1009.
[2]Synthetic Communications,2010,vol. 40,p. 647 - 653.
[3]Journal of the Iranian Chemical Society,2016,vol. 13,p. 2019 - 2028.
[4]Journal of the Chemical Society,1930,p. 928,933.
[5]Patent: US6143208,2000,A .

2
[ 610-81-1 ]
[ 78137-76-5 ]

Yield	Reaction Conditions	Operation in experiment
13.1 g		(1) diazotization reaction: take 12g3_ amino-4-nitrophenol,Dissolved in 64 g of hydrobromic acid at a concentration of 40 wtpercentLiquid, cooled to 0-10 ° C.36 g of a 20percent by weight aqueous solution of sodium nitrite was added dropwise at this temperature. Thermal insulation reaction 1h.The resulting yellow liquid was an aqueous solution of 3-nitrophenol-4-diazonium salt, which was used directly in the next reaction.(2) Bromination reaction:Take 1.2g cuprous bromide, dissolved in 27g concentration of 40wtpercent hydrobromic acid solution.After the temperature was raised to 40-45 ° C, the reaction solution obtained in step (1) was added dropwise. After the addition was completed, the reaction 1h Thermal insulation. Cool to 20-25 ° C, precipitated solid. The product is filtered off and the solid washed with a little water and dried.13.1 g of 3-nitro-4-bromophenol were obtained.Content of 95percent.

References: [1]Journal of the Chemical Society,1930,p. 928,933.
[2]Chemische Berichte,1909,vol. 42,p. 2192.
[3]Patent: CN102060717,2017,B .Location in patent: Paragraph 0007; 0016-0018.

3
[ 78137-76-5 ]
[ 78-95-5 ]
[ 78137-77-6 ]

References: [1]Tetrahedron Letters,1981,vol. 22,p. 95 - 96.

4
[ 78137-76-5 ]
[4-(tert-butyl-dimethyl-silanyloxy)-2-nitro-phenyl]-(2'-nitrophenyl)-amine [ No CAS ]

References: [1]Organic Letters,2005,vol. 7,p. 1549 - 1552.

5
[ 78137-76-5 ]
[ 1026914-86-2 ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 7189 - 7192.

6
[ 78137-76-5 ]
[ 53820-33-0 ]

References: [1]Tetrahedron Letters,1981,vol. 22,p. 95 - 96.

7
[ 78137-76-5 ]
[ 78137-78-7 ]

References: [1]Tetrahedron Letters,1981,vol. 22,p. 95 - 96.

8
[ 78137-76-5 ]
[ 78137-79-8 ]

References: [1]Tetrahedron Letters,1981,vol. 22,p. 95 - 96.

9
[ 78137-76-5 ]
[ 78137-80-1 ]

References: [1]Tetrahedron Letters,1981,vol. 22,p. 95 - 96.

10
[ 78137-76-5 ]
[ 78137-81-2 ]

References: [1]Tetrahedron Letters,1981,vol. 22,p. 95 - 96.

11
[ 78137-76-5 ]
[ 78137-82-3 ]

References: [1]Tetrahedron Letters,1981,vol. 22,p. 95 - 96.

12
[ 2243-69-8 ]
[ 78137-76-5 ]

References: [1]Journal of the Chemical Society,1930,p. 928,933.

13
[ 99-09-2 ]
[ 78137-76-5 ]

References: [1]Journal of the Chemical Society,1930,p. 928,933.

14
[ 78137-76-5 ]
[ 4514-29-8 ]

References: [1]Helvetica chimica acta,1965,vol. 48,p. 1590 - 1597.

15
[ 78137-76-5 ]
[ 108-24-7 ]
acetic acid 4-bromo-3-nitrophenyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In pyridine; at 20℃;	Synthesized from 4-bromo-3-nitroanisole according to an analogous synthetic method to Example 364 described below, to a solution of <strong>[78137-76-5]4-bromo-3-nitrophenol</strong> (2.0 g) was added pyridine (20 ml) and acetic anhydride (20 ml), and the solution was stirred overnight at room temperature. The reaction mixture was poured into ice water, extracted with ethyl acetate, then sequentially washed with 1N hydrochloric acid, water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. Obtained by purifying the residue by silica gel column chromatography (hexane-ethyl acetate system), acetic acid 4-bromo-3-nitrophenyl ester (1.8 g) and 4-acetoxystyrene (1.2 ml) were used according to an analogous synthetic method to Example 107 to provide the title compound (302 mg).1H-NMR (400MHz, CDCl3); delta (ppm): 2.29 (s, 3H), 2.31 (s, 3H), 6.46 (d, 1H), 6.53 (dd, 1H), 6.91 (d, 1H), 7.03 (d, 1H), 7.08 (d, 2H), 7.36 (d, 1H), 7.49 (d, 2H).

References: [1]Patent: EP1577288,2005,A1 .Location in patent: Page/Page column 181.

16
[ 78137-76-5 ]
[ 3282-30-2 ]
[ 344780-50-3 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine;	A. Preparation of 2-bromo-5-pivaloyloxynitrobenzene 2-Bromo-5-hydroxynitro benzene (2.8 g) was added to pyridine (50 mL) and the resulting mixture was cooled with ice. Pivaloyl chloride (5.2 mL) was added dropwise and the mixture was slowly brought back to room temperature with stirring over 3 hours. The reaction was completed, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (1:1 hexane/ethyl acetate) to yield the title compound (4.4 g). Rf=0.72 (1:1 hexane/ethyl acetate); 1H-NMR (DMSO-d6): 7.99 (1H, d, J=2.8), 7.97 (1H, d, J=8.8), 7.46 (1H, dd, J=8.8, 2.8), 1.32 (9H, s); Mass (m/e): 303 (MH+).

References: [1]Patent: US2003/40538,2003,A1 .

17
[ 78137-76-5 ]
[ 3163-27-7 ]
2-Bromo-5-(1-naphthalenylmethoxy)-nitrobenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate; In N-methyl-acetamide;	A. 2-Bromo-5-(1-naphthalenylmethoxy)-nitrobenzene To a solution of 4.0 g (18.3 mmol) of <strong>[78137-76-5]4-bromo-3-nitrophenol</strong> in 25 mL of dimethylformamide, 4.87 g (22.0 mmol) of 1-bromomethyl naphthalene and 3.04 g (22.0 mmol) of potassium carbonate were added and the mixture was stirred at room temperature overnight. The mixture was poured into 250 mL of ice/water and the precipitate was filtered and dried to afford compound A as a tan solid (6.1 g, 92percent). Melting point: 124°-126° C.

References: [1]Patent: US5420123,1995,A .

18
[ 78137-76-5 ]
[ 1313530-04-9 ]

References: [1]Tetrahedron Letters,2011,vol. 52,p. 3376 - 3378.

19
[ 78137-76-5 ]
[ 1313530-07-2 ]

References: [1]Tetrahedron Letters,2011,vol. 52,p. 3376 - 3378.

20
[ 78137-76-5 ]
(3S)-3-amino-1-hydroxy-7-[(1S)-2-methoxy-1-methylethoxy]-3,4-dihydroquinolin-2(1H)-one hydrochloride [ No CAS ]