21563-29-1|4-Bromobenzo[de]isochromene-1,3-dione| Ambeed

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Quality Control of [ 21563-29-1 ] Purity: 96% SDS Specification

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Product Details of [ 21563-29-1 ]

CAS No. :	21563-29-1
Formula :	C₁₂H₅BrO₃
M.W :	277.07
SMILES Code :	O=C(C1=CC=CC2=CC=C(Br)C3=C12)OC3=O
MDL No. :	MFCD01013787
InChI Key :	TZUREPOYENXNME-UHFFFAOYSA-N
Pubchem ID :	3663371

Safety of [ 21563-29-1 ]

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

Computational Chemistry of [ 21563-29-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	16
Num. arom. heavy atoms	10
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	61.39
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	43.37 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.72
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	3.23
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.91
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.	3.32
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	3.52
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.94

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.06
Solubility	0.0244 mg/ml ; 0.0000881 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.81
Solubility	0.0425 mg/ml ; 0.000154 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	-4.99
Solubility	0.00282 mg/ml ; 0.0000102 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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.	-5.7 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<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)	2.29

Application In Synthesis of [ 21563-29-1 ]

* 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 [ 21563-29-1 ]

[ 21563-29-1 ] Synthesis Path-Downstream 1~29

1
[ 21563-29-1 ]
[ 59-88-1 ]
2-anilino-4-bromo-benz[<i>de</i>]isoquinoline-1,3-dione [ No CAS ]

References: [1]Bulletin International de l'Academie Polonaise des Sciences et des Lettres, Classe des Sciences Mathematiques et Naturelles, Serie A: Sciences Mathematiques,1928,p. 427.
Chemisches Zentralblatt,1929,vol. 100,p. 650.

2
[ 21563-29-1 ]
4-bromo-benz[<i>de</i>]isoquinoline-1,3-dione [ No CAS ]

3
[ 5209-31-4 ]
[ 21563-29-1 ]

References: [1]Chemija,1959,p. 322.
Chem.Abstr.,1960,p. 444.
[2]Journal of Organic Chemistry USSR (English Translation),1968,vol. 4,p. 1233 - 1236.
Zhurnal Organicheskoi Khimii,1968,vol. 4,p. 1282 - 1286.

4
[ 21563-29-1 ]
[ 109-73-9 ]
[ 75853-01-9 ]

References: [1]Journal of the Chemical Society. Perkin transactions II,1990,p. 837 - 842.

5
[ 75839-71-3 ]
[ 21563-29-1 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1980,vol. 16,p. 1102 - 1104.
Zhurnal Organicheskoi Khimii,1980,vol. 16,p. 1275 - 1277.

6
[ 20371-51-1 ]
[ 21563-29-1 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1968,vol. 4,p. 1233 - 1236.
Zhurnal Organicheskoi Khimii,1968,vol. 4,p. 1282 - 1286.

9
[ 39981-72-1 ]
[ 21563-29-1 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1980,vol. 16,p. 1102 - 1104.
Zhurnal Organicheskoi Khimii,1980,vol. 16,p. 1275 - 1277.

10
[ 75839-69-9 ]
[ 21563-29-1 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1980,vol. 16,p. 1102 - 1104.
Zhurnal Organicheskoi Khimii,1980,vol. 16,p. 1275 - 1277.

11
[ 109-01-3 ]
[ 21563-29-1 ]
[ 207594-39-6 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In pyridine;	EXAMPLE L 4-(4-Methylpiperazinyl)-1,8-naphthalic anhydride 4-Methylpiperazine (0.6 g, 6.6 mmol) and DBU (1 mL) were added to <strong>[21563-29-1]4-bromo-1,8-naphthalic anhydride</strong> (1.5 g, 5.4 mmol) in pyridine (10 mL). The solution was refluxed for 8 hours, concentrated in vacuo, and the residue was triturated with water. The separated solid was filtered and dried to give 0.8 g of the title compound.

References: [1]Patent: US6177423,2001,B1 .

12
[ 21563-29-1 ]
[ 39684-28-1 ]
[ 207596-47-2 ]

Yield	Reaction Conditions	Operation in experiment
	In pyridine; water;	EXAMPLE K2 6-Bromo-2-tert-butyloxy-benzo[de]isoquinoline-1,3-dione O-tert-Butylhydroxylamine hydrochloride (3.0 g, 23.9 mmol) was added to <strong>[21563-29-1]4-bromo-1,8-naphthalic anhydride</strong> (5.0 g, 18.0 mmol) in pyridine (30.0 mL). the mixture was refluxed for 4 hours, concentrated, and the residue suspended in water. The solid was filtered and dried to give 5.9 g of the title compound.

References: [1]Patent: US6177423,2001,B1 .

13
[ 21563-29-1 ]
[ 31166-84-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydroxylamine hydrochloride; In pyridine;	EXAMPLE 4 6-Bromo-2-hydroxy-benzo[de]isoquinoline-1,3-dione 4-Bromo-1,8-naphthalic anhydride (1.6 g, 5.8 mmol) and hydroxylamine hydrochloride (0.8 g, 11.5 mmol) were reacted in pyridine (30 mL) following the procedure of Example 1 to give 1.4 g of the title compound, mp 248-251° C.; 1H NMR (DMSO-d6): delta 10.9 (1H, s), 8.6 (2H, dd merge to t), 8.4 (1H, dd, J=7.2, 1.2), 8.2 (1H, dd, J=7.1, 1.2), 8.0 (1H, dd, J=7.2, 7.1).

References: [1]Patent: US6177423,2001,B1 .

14
[ 21563-29-1 ]
[ 2687-43-6 ]
[ 207594-40-9 ]

Yield	Reaction Conditions	Operation in experiment
	In pyridine;	EXAMPLE M 2-Benzyloxy-6-bromo-benzo[de]isoquinoline-1,3-dione O-Benzyl hydroxylamine hydrochloride (2.0 g, 12.5 mmol) and <strong>[21563-29-1]4-bromo-1,8-naphthalic anhydride</strong> (2.9 g, 10.5 mmol) were reacted in pyridine (50 mL) following the procedure of Example D to give 3.5 g of the title compound.

References: [1]Patent: US6177423,2001,B1 .

15
[ 21563-29-1 ]
[ 106-49-0 ]
[ 86202-08-6 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; In water;	Step A: Preparation of 6-bromo-2-p-tolyl-benzo[de]isoquinoline-1,3-dione. A mixture of 4-Bromo 1,8 naphthalic anhydride (10 g), p-toluidine (4.08 g) and acetic acid (75 ml) was refluxed with stirring for 10 hours. Water (200 ml) was added at room temperature, the separated solid was filtered, washed with acetic acid followed by water and dried at 100 C. for 8 hours to yield 11.5 g of the product.

References: [1]Patent: US2007/117887,2007,A1 .

16
[ 21563-29-1 ]
[ 84216-52-4 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; aniline;	Step A: Preparation of 6-bromo-2-phenyl-benzo[de]isoquinoline-1,3-dione. A mixture of <strong>[21563-29-1]4-bromo-1,8-naphthalic anhydride</strong> (10 g), aniline (3.54 g) and acetic acid (75 ml) was refluxed with stirring for 10 hrs. The reaction mixture was then cooled to room temperature, whereupon solid separated out. The solid was filtered, washed with water (50 ml) followed by acetic acid (50 ml) and dried at 100° C. for 8 hours (Yield=10.8 gm).

References: [1]Patent: US2007/117887,2007,A1 .

17
[ 21563-29-1 ]
[ 52821-19-9 ]

Yield	Reaction Conditions	Operation in experiment
73%	With sulfuric acid; nitric acid; at 0 - 4℃; for 2.0h;	Step 1: Synthesis of 3-nitro-<strong>[21563-29-1]4-bromo-1,8-naphthalic anhydride</strong> 4-Bromo-1,8-naphthalic anhydride (50.0 g, 180 mmol) was dissolved in sulfuric acid (150 mL). The reaction vessel was cooled in an ice bath, and a mixed solution of fuming nitric acid (26.0 ml, 612 mmol) and sulfuric acid (34.0 ml, 684 mmol) was added dropwise while the internal temperature was kept below 4°C. Then, the reaction solution was stirred for 2 hours while keeping the internal temperature below 4°C. Ice water (500 mL) was slowly added to the reaction solution, and stirred at room temperature for 30 minutes. Water (500 mL) was added, and the resulting precipitate was filtered. The precipitate was suspended in acetonitrile (300 mL). The suspension was stirred at room temperature for 4 hours, and filtered. After washing with acetonitrile, the resulting precipitate was again suspended in acetonitrile (200 mL). The same treatment was repeated, and the precipitate was dried under reduced pressure to give the title compound as pale yellow solid (42.5 g, 73percent). 1H-NMR (300 MHz, in DMSO-d6) chemical shifts delta: 8.19 (1H, dd, J = 8.8, 7.2 Hz), 8.74 (1H, d, J = 8.8 Hz), 8.83 (1H, d, J = 7.2 Hz), 8.92 (1H, s).

References: [1]Patent: EP2036895,2009,A1 .Location in patent: Page/Page column 91.

18
[ 21563-29-1 ]
[ 95-54-5 ]
[ 26559-67-1 ]

Yield	Reaction Conditions	Operation in experiment
10.6 g (84%)	With zinc diacetate; In quinoline;	Example I.k3-Bromobenzo[de]benzo[4,5]imidazo[2,1-a]isoquinolin-7-oneA mixture of 10.0 g (36 mmol) of <strong>[21563-29-1]4-bromo-1,8-naphthalic anhydride</strong>, 4.68 g (43.3 mmol) of 1,2-phenylenediamine, 6.62 g of zinc acetate (36 mmol) and 100 ml of quinoline was heated at reflux at 145° C. while stirring for 5 hours.The product was then stirred into 500 ml of 1 molar hydrochloric acid.The precipitate was filtered off with suction, washed with hot water and recrystallized in toluene.This gave 10.6 g (84percent) of the title compound as a yellow substance. Rf (2:1 cyclohexane:ethyl acetate)=0.29.

References: [1]Patent: US2012/234380,2012,A1 .

19
[ 111-26-2 ]
[ 21563-29-1 ]
[ 101721-89-5 ]

Yield	Reaction Conditions	Operation in experiment
74%	In chloroform; toluene; for 1.0h;	Step 1: Synthesis of 6-Bromo-2-hexyl-1H-benzo[de]isoquinoline-1,3 (2H)-dione A mixture of <strong>[21563-29-1]4-bromo-1,8-naphthalic anhydride</strong> (21.40 g, 77.2 mmol), n-hexylamine (13.1 mL, 100 mmol), toluene (200 mL), and chloroform (200 mL) was heated to boil for 1 hour. Precipitate formed making stirring difficult. The mixture was acidified with acetic acid, and heating was continued at 90° C. with distillation of chloroform. After all precipitate dissolved, the reaction mixture was poured onto crushed ice (300 g) and acidified with concentrated HCl to pH 1. After the ice melted, the solid was filtered off and dried. The crude product was purified by column chromatography (silica gel, hexane/ethyl acetate 2:1) to give 6-bromo-2-hexyl-1H-benzo[de]isoquinoline-1,3(2H)-dione (20.66 g, 74percent).

References: [1]Patent: US2013/74927,2013,A1 .Location in patent: Paragraph 0174.

20
[ 111-26-2 ]
[ 21563-29-1 ]
[ 1428418-31-8 ]

References: [1]Patent: US2013/74927,2013,A1 .

21
[ 21563-29-1 ]
[ 154487-83-9 ]
C₁₃₆H₁₂₀Br₈N₁₄O₁₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	In ethanol; at 70℃; for 4.0h;Reflux;	_Poly(propylenamine) (0.78 ml, 1.0 mmol) from second generation and <strong>[21563-29-1]4-bromo-1,8-naphthalic anhydride</strong> (2.21 g, 8.0 mmol) were dissolved in ethanol (30 ml) for 2 h at 70 °C. The solution was refluxed and the reaction was monitored using thin layer chromatography (TLC). After 2 h the resulting precipitate was filtered and dried in vacuum. Yield: 2.10 g (74percent). FTIR (cm-1): 748, 776, 849, 1231, 1341, 1568, 1586, 1652, 1698, 2801, 2948, 3065. 1H NMR (CDCl3, 600 MHz, ppm): 8.36 (d, J=8.8 Hz, 16H, Ar-H), 8.08 (d, J=8.0 Hz, 16H, Ar-H), 7.65 (t, J=7.8Hz, 8H, Ar-H), 4.10 (t, J=6.8 Hz, 16H, (OC)2NCH2), 2.74-2.35 (m, 36H, CH2N?), 2.08-1,34 (m, 24H, ?NCH2CH2CH2N?+4H, ?NCH2CH2CH2CH2N?). 13C NMR (CDCl3, 150.9 MHz, ppm): 164.6, 163.1, 150.3, 133.9, 131.4, 129.8, 128.2 124.1, 122.8, 119.1, 108.8, 104.6, 52.8, 42.1, 37.70, 36.2, 24.3. 20.1.

References: [1]Tetrahedron,2015,vol. 71,p. 1080 - 1087.

22
[ 21563-29-1 ]
[ 536-74-3 ]
[ 170804-03-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 20 - 55℃; for 2.5h;Inert atmosphere;	First step: Synthesis of 4-phenylethynyl-1,8-naphthalic anhydride) (0071) (0072) Into a 1 L three-neck flask equipped with stirrer, nitrogen gas inlet tube, and thermometer, 5.0 g (18 mmol) of <strong>[21563-29-1]4-bromo-1,8-naphthalic anhydride</strong> (Compound 7) as a reactant, 2.3 g (23 mmol) of ethynylbenzene, 0.24 g (0.9 mmol) of triphenylphosphine, 0.63 g (0.9 mmol) of bis(trirphenylphosphine)paradium (II) dichloride, 0.17 g (0.9 mmol) of copper iodide (I), and 18 ml of triethylamine as a reaction reagent, and 180 mL of dehydrated dimethylformamide as a reaction solvent were charged and stirred at a room temperature for 30 minutes under nitrogen gas inflow. The temperature was increased to 55° C. and the reacted for 2 hours at the temperature. After the end of the reaction, triethylamine and dimethylformamide were distilled out at a reduced pressure. By reprecipitation and drying thereof under reduced pressure, 5.1 g (yield: 95percent) of 4-phenylethynyl-1,8-naphthalic anhydride in pale yellow powder form were obtained. (0073) It was identified by analysis of 1H NMR and mass spectrometry below that the product obtained was Compound 8. In addition, corresponding hydrogen atoms are represented in italics below. (0074) 1H-NMR (400 MHz, DMSO-d6): 7.535-7.508 (3H, m, C6H5?), 7.818-7.794 (2H, in, C6H5?), 8.038 (1H, t, J=7.8 Hz, C10H5?), 8.126 (1H, dd, J=7.6, 1.2 Hz, C10H5?), 8.498 (1H, dd, J=7.6, 1.2 Hz, C10H5?), 8.598 (1H, dd, J=7.6, 1.2 Hz, C10H5?), 8.862 (1H, dd, J=8.4, 7.2 Hz, C10H5?) ppm. [ 0072]

References: [1]Patent: US2015/299132,2015,A1 .Location in patent: Paragraph 0071-0074.

23
[ 21563-29-1 ]
N-hydroxy-4-phenylethynyl-1,8-naphthalimide [ No CAS ]

References: [1]Patent: US2015/299132,2015,A1 .

24
[ 21563-29-1 ]
N-trifluoromethanesulfonyloxy-4-phenylethynyl-1,8-naphthalimide [ No CAS ]

References: [1]Patent: US2015/299132,2015,A1 .

25
[ 21563-29-1 ]
[ 36780-18-4 ]