124840-61-5|2-(5-Bromo-2-nitrophenyl)acetic acid| Ambeed

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Quality Control of [ 124840-61-5 ] Purity: 95% SDS Specification

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Product Details of [ 124840-61-5 ]

CAS No. :	124840-61-5
Formula :	C₈H₆BrNO₄
M.W :	260.04
SMILES Code :	O=C(O)CC1=CC(Br)=CC=C1[N+]([O-])=O
MDL No. :	MFCD01096363
InChI Key :	ZKKCLKYKTRUIKW-UHFFFAOYSA-N
Pubchem ID :	555991

Safety of [ 124840-61-5 ]

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

Computational Chemistry of [ 124840-61-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	6
Fraction Csp3	0.12
Num. rotatable bonds	3
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	54.51
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	83.12 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.29
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	1.9
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.98
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.	1.31
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	0.11
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.32

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.77
Solubility	0.443 mg/ml ; 0.0017 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.	-3.27
Solubility	0.14 mg/ml ; 0.000539 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	-2.41
Solubility	1.01 mg/ml ; 0.00387 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	No
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.	-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.	0.56

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<0.0
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)	2.12

Application In Synthesis of [ 124840-61-5 ]

* 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 [ 124840-61-5 ]

[ 124840-61-5 ] Synthesis Path-Downstream 1~35

1
[ 125914-22-9 ]
[ 124840-61-5 ]

Yield	Reaction Conditions	Operation in experiment
64%	With hydrogenchloride; acetic acid; for 4.0h;Reflux;	General procedure: 1 equivalent of nitrile was dissolved in a mixture of AcOH/HCl (1:5) andrefluxed for 4 h. The product was extracted with ethyl acetate, dried over Na2SO4and evaporated.

References: [1]Archiv der Pharmazie,1989,vol. 322,p. 483 - 487.
[2]Tetrahedron Letters,2015,vol. 56,p. 89 - 94.

2
4-(5-bromo-2-nitro-phenyl)-3-oxo-butyric acid [ No CAS ]
[ 124840-61-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 421 - 426.

3
[ 124840-61-5 ]
[ 20870-78-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 421 - 426.

4
[ 52414-98-9 ]
[ 124840-61-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 421 - 426.

5
[ 124840-61-5 ]
[ 276884-13-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 421 - 426.

6
[ 124840-61-5 ]
5-Bromo-3-[1-(2,3-dimethoxy-phenyl)-meth-(Z)-ylidene]-1,3-dihydro-indol-2-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 421 - 426.

7
[ 124840-61-5 ]
[ 856435-10-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 421 - 426.

8
[ 124840-61-5 ]
5-Bromo-3-[1-(7-methyl-1H-indol-3-yl)-meth-(Z)-ylidene]-1,3-dihydro-indol-2-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 421 - 426.

9
[ 124840-61-5 ]
(3Z)-5-(4-hydroxy-3-methoxyphenyl)-3-(1H-pyrrol-2-ylmethylene)-1,3-dihydro-2H-indol-2-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 421 - 426.

10
[ 124840-61-5 ]
3-[1-(2,3-Dimethoxy-phenyl)-meth-(Z)-ylidene]-5-(4-hydroxy-3-methoxy-phenyl)-1,3-dihydro-indol-2-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 421 - 426.

11
[ 124840-61-5 ]
5-(4-Hydroxy-3-methoxy-phenyl)-3-[1-(1H-indol-3-yl)-meth-(Z)-ylidene]-1,3-dihydro-indol-2-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 421 - 426.

12
[ 124840-61-5 ]
5-(4-Hydroxy-3-methoxy-phenyl)-3-[1-(7-methyl-1H-indol-3-yl)-meth-(Z)-ylidene]-1,3-dihydro-indol-2-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 421 - 426.

13
[ 31938-07-5 ]
[ 124840-61-5 ]

References: [1]Archiv der Pharmazie,1989,vol. 322,p. 483 - 487.

14
[ 124840-61-5 ]
methyl 5-(2-amino-5-bromobenzyl)oxazole-4-carboxylate [ No CAS ]

References: [1]Tetrahedron Letters,2015,vol. 56,p. 89 - 94.

15
[ 124840-61-5 ]
(5-bromo-1H-indol-2-yl)methanamine hydrochloride [ No CAS ]

References: [1]Tetrahedron Letters,2015,vol. 56,p. 89 - 94.

16
[ 39687-95-1 ]
[ 124840-61-5 ]
methyl 5-(5-bromo-2-nitrobenzyl)oxazole-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%		General procedure: 1 equivalent of o-methoxy-/nitrophenylaceticacid and 1.2 equivalents of CDI were dissolved in 10 ml THF. The mixture wasstirred for 3 h at rt. To this mixture 1.1 equivalents of alpha-isocyano acetate and 1 equiv of NaHMDS (1 mmol) were added. It wasstirred over night at rt. The solvent was evaporated and the crude product wasdiluted in 50 ml ethyl acetetate. The solution was washed with water andconcentrated under reduced pressure. The crude product was purified by flashchromatography.

References: [1]Tetrahedron Letters,2015,vol. 56,p. 89 - 94.

17
[ 586-78-7 ]
[ 124840-61-5 ]

References: [1]Tetrahedron Letters,2015,vol. 56,p. 89 - 94.

18
1,3-diethyl 2-nitro-5-bromophenylpropanedioate [ No CAS ]
[ 124840-61-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	With hydrogenchloride; In water; acetic acid; at 110℃;	To 250 ml three-necked bottle adding 60 ml 6N hydrochloric acid, 60 ml AcOH and 2 - nitro -3 - bromophenylacetic malonic acid diethyl ester (18.0g, 50mmol), a thermometer and a condenser is installed, is put into the 110 C stirring the reaction overnight. After the reaction is finished taking-out device cooling to room temperature, take out the solder, uses a vacuum pump to the Rotavapor turns on lathe does solvent, to obtain 12.5g white 2 - nitro -3 - bromophenylacetic acid
98%	With hydrogenchloride; acetic acid; In water;Heating;	To a solutuion of 60 ml 6 N HCl and 60 ml AcOH, dissove 17.9 g 2 (50 mmol) and stir at 110 oC overnight. Romve all sovent and obtain 12.5 g 5-Bromo-2-Nitrophenylacetic acid (3), mp. 174.4-175.9 oC, yield 98%. Intermediate 3 proceed to next step without further purification. To a solution of 100 ml dehydrated EtOH and 0.5 ml conc. H2SO4, add 12.9 g 3 (50 mmol).

References: [1]Patent: CN106316923,2017,A .Location in patent: Paragraph 0062; 0063.
[2]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 944 - 954.

19
[ 124840-61-5 ]
ethyl 2-(2-nitro-5-(p-tolylamino)phenyl)acetate [ No CAS ]

References: [1]Patent: CN106316923,2017,A .
[2]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 944 - 954.

20
[ 124840-61-5 ]
(E)-3-n-butenyl-5-(4-methylanilino)indole-2(1H)-one [ No CAS ]

References: [1]Patent: CN106316923,2017,A .
[2]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 944 - 954.

21
[ 124840-61-5 ]
C₁₅H₁₄N₂O [ No CAS ]

References: [1]Patent: CN106316923,2017,A .
[2]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 944 - 954.

22
[ 64-17-5 ]
[ 124840-61-5 ]
[ 870274-21-8 ]

Yield	Reaction Conditions	Operation in experiment
99.2%	With sulfuric acid;Reflux;	Taking 250 ml of three-necked bottle, adding 100 ml anhydrous ethanol, 0.5 ml of concentrated sulfuric acid and 2 - nitro -3 - bromophenylacetic acid (12.9g, 50mmol), the assembly of the thermometer and a condenser, is put into the oil bath to reflux overnight. Stopping the reaction, to container and gradually cooling to room temperature, then put into the -5 C refrigerator overnight, separate out a large amount of white floc, machines for filtering, to obtain the 12.5g white solid 2 - nitro -3 - bromo ethyl acetate, yield 99.2%.

References: [1]Patent: CN106316923,2017,A .Location in patent: Paragraph 0064; 0065.

23
[ 321-23-3 ]
[ 124840-61-5 ]

References: [1]Patent: CN106316923,2017,A .
[2]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 944 - 954.

24
[ 124840-61-5 ]
(E)-3-(3,4-methylenedioxyphenyl)methylidene-5-(4-fluoroanilino)indole-2(1H)-one [ No CAS ]