20357-21-5|2-Bromo-6-nitrobenzaldehyde| Ambeed

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Quality Control of [ 20357-21-5 ] Purity: 98% SDS Specification

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Product Details of [ 20357-21-5 ]

CAS No. :	20357-21-5
Formula :	C₇H₄BrNO₃
M.W :	230.02
SMILES Code :	O=CC1=C([N+]([O-])=O)C=CC=C1Br
MDL No. :	MFCD09040530
InChI Key :	WRIAMYXQKSDDRP-UHFFFAOYSA-N
Pubchem ID :	15063174

Safety of [ 20357-21-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 20357-21-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	48.35
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	62.89 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.06
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	0.87
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.17
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.	1.02
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	0.51
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.	-2.05
Solubility	2.04 mg/ml ; 0.00887 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.	-1.77
Solubility	3.86 mg/ml ; 0.0168 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-2.59
Solubility	0.597 mg/ml ; 0.00259 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	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.	-7.09 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	3.0 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)	1.89

Application In Synthesis of [ 20357-21-5 ]

* 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 [ 20357-21-5 ]

[ 20357-21-5 ] Synthesis Path-Downstream 1~35

1
<i>N</i>-(2-bromo-6-nitro-benzyl)-aniline [ No CAS ]
[ 20357-21-5 ]

References: [1]Bulletin de la Societe Chimique de France,1917,vol. <4> 21,p. 111.

2
[ 109513-33-9 ]
[ 20357-21-5 ]

References: [1]Journal of the Chemical Society,1957,p. 3807.

3
[ 20357-21-5 ]
[ 135484-74-1 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1991,p. 1565 - 1569.
[2]Journal of the American Chemical Society,2003,vol. 125,p. 2084 - 2093.

4
[ 109513-33-9 ]
[ 20357-21-5 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1996,p. 1699 - 1704.
[2]Journal of the Chemical Society. Perkin transactions I,1991,p. 1565 - 1569.

5
[ 20357-21-5 ]
[ 107-21-1 ]
[ 135484-72-9 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1991,p. 1565 - 1569.

6
[ 51223-59-7 ]
[ 20357-21-5 ]
N-(2-[1-(2-Bromo-6-nitro-phenyl)-meth-(E)-ylidene]-amino}-4-chloro-phenyl)-acetamide [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1996,p. 1699 - 1704.

7
[ 20357-21-5 ]
[ 87049-66-9 ]
N-(2-[1-(2-Bromo-6-nitro-phenyl)-meth-(E)-ylidene]-amino}-5-chloro-phenyl)-acetamide [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1996,p. 1699 - 1704.

8
[ 20357-21-5 ]
[ 95-54-5 ]
N-(2-Bromo-6-nitrobenzylidene)-o-phenylenediamine [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1996,p. 1699 - 1704.

10
[ 109513-33-9 ]
[ 20357-21-5 ]

References: [1]Journal of the American Chemical Society,2003,vol. 125,p. 2084 - 2093.

11
[ 20357-21-5 ]
[ 90965-06-3 ]
[ 916978-57-9 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate; In methanol; at 20℃; for 2h;	Example 36; This example describes the synthesis of Acetylene 12: To a stirred solution of 10 (5.48 g, 23.6 mmol), K2CO3 (6.52 g, 47.2 mmol), and MeOH (236 mL) was added diazophosphonate reagent 11 (5.44 g, 28.3 mmol) at r.t. After 2 h, the solution was diluted with EtOAc (100 mL) and washed with sat. aq. NaHCO3 (100 mL), H2O (100 mL) and sat. aq. NaCl (100 mL). The dried extract (MgSO4) was concentrated in vacuo and purified by chromatography over silica gel, eluting with 50percent CH2Cl2 / Hexanes to give 12 (4.53 g, 20.0 mmol, 85percent) as a pale yellow solid. MP 110-110.50C; IR (neat) 2115, 1526, 1352 cm'1; 1H NMR (400 MHz, CDCl3) delta 7.94 (m, 2H), 7.39 (t, J= 8.2 Hz, IH), 3.86 (s, IH); 13C NMR (100 MHz, CDCl3) delta 152.3, 136.8, 129.6, 128.7, 123.2, 119.0, 90.7, 76.7; HRMS (CI+) calcd. for C8H5NO2Br (M+H) 225.9493, found 225.9504.

References: [1]Angewandte Chemie - International Edition,2006,vol. 45,p. 6737 - 6741.
[2]Journal of the American Chemical Society,2007,vol. 129,p. 9109 - 9116.
[3]Patent: WO2008/156656,2008,A2 .Location in patent: Page/Page column 58; 66; 121.

12
[ 55289-35-5 ]
[ 20357-21-5 ]

References: [1]Angewandte Chemie - International Edition,2006,vol. 45,p. 6737 - 6741.
[2]Journal of the American Chemical Society,2007,vol. 129,p. 9109 - 9116.
[3]Journal of the American Chemical Society,2003,vol. 125,p. 2084 - 2093.
[4]Journal of the Chemical Society. Perkin transactions I,1991,p. 1565 - 1569.
[5]Bulletin de la Societe Chimique de France,1917,vol. <4> 21,p. 111.

13
[ 101975-16-0 ]
[ 20357-21-5 ]
[ 957212-63-4 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In 2-methyl THF; at 30℃; for 0.666667h;	A 2L 4-neck flask equipped with an overhead stirrer, thermocouple, addition funnel, nitrogen purge, and condenser was charged with anhydrous 2-methyl THF (330 mL). To the flask was then added <strong>[20357-21-5]2-bromo-6-nitrobenzaldehyde</strong> (110.0 g, 478.2 mmol) and cesium carbonate (311.6 g, 956.4 mmol) and the resulting mixture stirred under nitrogen. To the reaction mixture was then added 3-(1,1,2,2-tetrafluoroethoxyl)acetophenone (112.9 g, 478.2 mmol) slowly via an addition funnel over 40 minutes. The reaction mixture was maintained at a temperature below 45° C. and preferably below 30° C. The resultant suspension was stirred until the reaction was complete. To the reaction mixture was then added water (220 mL) at room temperature, which dissolved the cesium carbonate. The resulting mixture was allowed to cool to room temperature while agitating, then transferred to a separatory funnel. The aqueous layer was removed and the organic layer which contains the title compound (QQ'3) was used in the next step without further purification or isolation.Note: An aliquot of the reaction mixture was purified by evaporating the solvent on a rotary evaporator to yield a dark solid, which was dissolved in CDCl3, filtered to remove any undissolved solid and concentrated again on a rotary evaporator to yield the title compound as a dark solid.1H NMR (300 MHz, CDCl3) d 7.93-7.82(m, 5 H), 7.55 (t, J=8.0 Hz, 1 H), 7.46 (dd, J=1.2, 8.3 Hz, 1 H), 7.41 (t, J=8.1 Hz, 1 H), 7.05 (d, J=16.1 Hz, 1 H), 5.95 (tt, J=2.8, 53.0 Hz, 1 H); MH+ (API-ES) calculated for C17H11BrF4NO4 448, measured: 448.

References: [1]Patent: US2007/265304,2007,A1 .Location in patent: Page/Page column 101-102.

14
[ 105205-47-8 ]
[ 20357-21-5 ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 9109 - 9116.

15
[ 20357-21-5 ]
[ 916978-58-0 ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 9109 - 9116.
[2]Angewandte Chemie - International Edition,2006,vol. 45,p. 6737 - 6741.
[3]Patent: WO2008/156656,2008,A2 .

16
[ 20357-21-5 ]
[ 916978-59-1 ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 9109 - 9116.
[2]Angewandte Chemie - International Edition,2006,vol. 45,p. 6737 - 6741.
[3]Patent: WO2008/156656,2008,A2 .

17
[ 20357-21-5 ]
6'-bromo-2-(diphenyl-phosphinoyl)-6-methoxy-2'-nitro-biphenyl [ No CAS ]