853234-57-8|2,8-Dibromoindeno[1,2-b]fluorene-6,12-dione| Ambeed

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Quality Control of [ 853234-57-8 ] Purity: 98% SDS Specification

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Product Details of [ 853234-57-8 ]

CAS No. :	853234-57-8
Formula :	C₂₀H₈Br₂O₂
M.W :	440.08
SMILES Code :	O=C1C2=C(C3=CC(C4=O)=C(C5=C4C=C(Br)C=C5)C=C31)C=CC(Br)=C2
MDL No. :	MFCD22571712
InChI Key :	PFFSYBJLQOJRQU-UHFFFAOYSA-N
Pubchem ID :	12173629

Safety of [ 853234-57-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501

Computational Chemistry of [ 853234-57-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	24
Num. arom. heavy atoms	20
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	106.78
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	34.14 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	3.13
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	5.58
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	5.42
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.	4.07
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	6.89
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	5.02

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-6.7
Solubility	0.0000877 mg/ml ; 0.000000199 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-6.06
Solubility	0.000385 mg/ml ; 0.000000874 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly 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	-9.65
Solubility	0.0000000974 mg/ml ; 0.0000000002 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly 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.	-5.02 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	0.0 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<2.0
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)	2.28

Application In Synthesis of [ 853234-57-8 ]

* 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 [ 853234-57-8 ]

[ 853234-57-8 ] Synthesis Path-Downstream 1~35

1
[ 853234-56-7 ]
[ 853234-57-8 ]

References: [1]Organic Letters,2005,vol. 7,p. 4229 - 4232.

2
[ 853234-57-8 ]
2-C₆H₅CH₂MgBr [ No CAS ]
6,12-bis-(2-benzyl-phenyl)-2,8-dibromo-6,12-dihydro-indeno[1,2-<i>b</i>]fluorene-6,12-diol [ No CAS ]

References: [1]Organic Letters,2005,vol. 7,p. 4229 - 4232.

3
[ 853234-55-6 ]
[ 853234-57-8 ]

References: [1]Organic Letters,2005,vol. 7,p. 4229 - 4232.

4
[ 853234-57-8 ]
[ 853234-58-9 ]

References: [1]Organic Letters,2005,vol. 7,p. 4229 - 4232.

5
[ 589-87-7 ]
<CF3Cu> [ No CAS ]
[ 853234-57-8 ]

References: [1]Organic Letters,2005,vol. 7,p. 4229 - 4232.

6
[ 303006-89-5 ]
[ 853234-57-8 ]

References: [1]Organic Letters,2005,vol. 7,p. 4229 - 4232.

7
[ 853234-57-8 ]
[ 208053-19-4 ]
[ 1040516-19-5 ]

Yield	Reaction Conditions	Operation in experiment
35%	bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 120℃;	2-Tributylstannyl-3-dodecylthiophene (24) (0.320 g, 0.591 mmol), 2,8- dibromo-indeno[l,2-b]fluorene-6,12-dione 18 (0.120 g, 0.273 mmol), and Pd(PPh3)2Cl2 (30.0 mg, 0.043 mmol) in anhydrous DMF (12.0 mL) were heated at 125C under nitrogen overnight. The reaction mixture was cooled to room <n="68"/>temperature and concentrated to dryness. The crude product was purified by column chromatography on silica gel (CHCl3/hexanes (7:3)) to provide 2,8-di-(3- dodecylthien-2-yl)-indeno[l,2-b]fluorene-6,12-dione (19) as a purple solid (70.0 mg, 35% yield). 1H NMR (CDCl3): δ 0.88-1.66 (m, 46H), 2.70 (t, 4H), 7.02 (d, 2H, J = 4.5 Hz), 7.29 (d, 2H, J - 4.5 Hz), 7.59 (d, 2H, J = 7.5 Hz), 7.61(d, 2H, J = 7.5 Hz), 7.74 (s, 2H), 7.81 (s, 2H) ppm; 13C NMR (CDCl3): δ 14.4, 22.96, 29.0, 29.6, 29.7,29.8, 29.9, 30.0, 31.2, 32.2, 116.3, 121.0, 124.7, 125.5, 130.1, 134.6, 136.1, 136.4, 136.8, 139.8, 140.0, 142.3, 145.9, 192.8 ppm; m.p: 152-153C; MS(MALDI-TOF) m/z (M+): 783.0; and Elemental Analysis: C, 79.50; H, 7.89

References: [1]Journal of the American Chemical Society,2008,vol. 130,p. 8580 - 8581.
[2]Patent: WO2009/17798,2009,A1 .Location in patent: Page/Page column 66-67.
[3]Journal of the American Chemical Society,2009,vol. 131,p. 5586 - 5608.

8
[ 1040516-00-4 ]
[ 853234-57-8 ]

Yield	Reaction Conditions	Operation in experiment
92%	With sulfuric acid; In water; at 120℃; for 10h;Acidic aqueous solution;	4,4"-Dibromo-2,2"-methoxycarbonyl-[l,l ';4',l"]terphenyl 17 (0.50 g, 0.99 mmol) was added to H2SO4 (80%, 50.0 mL, prepared from 10.0 mL Of H2O and 40.0 mL of concentrated (99.99%) H2SO4) and the mixture was heated with stirring at 120C for 10 hours. The reaction mixture was poured into ice and the resulting mixture was filtered. The solid was washed with sodium hydrogen carbonate solution and water to provide 2,8-dibromo-indeno[l,2-b]fluorene-6,12-dione (18) (0.40 g, 92%). The crude product was used for the next step without any further purification, m.p: > 300C; MS(MALDI-TOF) m/z (M+): 440.7; and Elemental Analysis: C, 54.12; H, 1.72

References: [1]Patent: WO2009/17798,2009,A1 .Location in patent: Page/Page column 66.
[2]RSC Advances,2015,vol. 6,p. 212 - 226.
[3]Journal of Materials Chemistry C,2017,vol. 5,p. 2368 - 2379.
[4]Journal of the American Chemical Society,2008,vol. 130,p. 8580 - 8581.
[5]Journal of the American Chemical Society,2009,vol. 131,p. 5586 - 5608.

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 13 Preparation of 2,8-dibromo-indeno[1,2-b]fluorene-6,12-dione (18) 4,4"-Dibromo-2,2"-methoxycarbonyl-[1,1';4',1"]terphenyl 17 (0.50 g, 0.99 mmol) was added to H2SO4 (80%, 50.0 mL, prepared from 10.0 mL of H2O and 40.0 mL of concentrated (99.99%) H2SO4) and the mixture was heated with stirring at 120 C. for 10 hours. The reaction mixture was poured into ice and the resulting mixture was filtered. The solid was washed with sodium hydrogen carbonate solution and water to provide 2,8-dibromo-indeno[1,2-b]fluorene-6,12-dione (18) (0.40 g, 92%). The crude product was used for the next step without any further purification. m.p: >300 C.; MS(MALDI-TOF) m/z (M+): 440.7; and Elemental Analysis: C, 54.12; H, 1.72.

10
[ 853234-57-8 ]
[ 1110785-57-3 ]
[ 1110785-51-7 ]

Yield	Reaction Conditions	Operation in experiment
25.0%	bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 125℃;	5-Trimethylstannyl-4,4'-didodecyl-2,2'-bithiophene (29, 0.457 g, 0.686 mmol), compound 18 (0.140 g, 0.312 mmol), and Pd(PPh3)2Cl2 (45.0 mg, 0.064 mmol) in anhydrous DMF (25.0 mL) were heated at 125C overnight under nitrogen. The reaction mixture was cooled to room temperature and concentrated to dryness. The crude product was purified by column chromatography on silica gel (CHCl3/hexanes (4:6)) to give 2,8-di-(4'-dodecylthien-2'-yl-4-dodecylthien-2-yl)- indeno[l,2-b]fluorene-6,12-dione (30) as a green solid (100.0 mg, 25% yield). 1H NMR (CDCl3): δ 0.88-1.66 (m, 92H), 2.60 (t, 4H), 2.67(t, 4H), 6.83 (s, 2H), 7.03 (s, 2H), 7.05 (d, 2H), 7.61(q, 4H), 7.77 (s, 2H), 7.83 (s, 2H) ppm; m.p: <n="73"/>96-97C; MS(MALDI-TOF) m/z (M+): 1284.0; and Elemental Analysis: C, 78.20; H, 8.60.

References: [1]Patent: WO2009/17798,2009,A1 .Location in patent: Page/Page column 71-72.
[2]Journal of the American Chemical Society,2009,vol. 131,p. 5586 - 5608.

11
[ 853234-57-8 ]
[ 128796-39-4 ]
[ 1104876-70-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium fluoride;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In toluene; for 8h;Inert atmosphere; Reflux;	2.2 g of 3,9-dibromo-indenofluorenedione prepared according to a synthesis method described in a document (Organic Letters, vol. 7, issue 19, page 4229) was mixed with 2.1 g of 4-(trifluoromethyl)phenylboronic acid, 0.14 g of tris(dibenzylideneacetone)dipalladium (0), 0.091 g of tris-t-butylphosphine, 1.9 g of potassium fluoride and 40 ml of toluene under argon stream. The mixture was stirred with reflux for 8 hours. After cooling, the reaction liquid was filtered and a reddish purple solid was washed with water and methanol. As a result of mass spectroscopy of the resulting solid, a peak was observed at M/Z=570.

References: [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 11103 - 11106.
[2]Patent: US2010/19659,2010,A1 .Location in patent: Page/Page column 29.

12
[ 853234-57-8 ]
[ 73852-19-4 ]
[ 1104877-02-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In toluene; for 12h;Inert atmosphere; Reflux;	2.4 g of 3,9-dibromo-indenofluorenedione was mixed with 3.4 g of 3,5-bis(trifluoromethyl)phenylboronic acid, 0.23 g of tetraxis(triphenylenephosphine)palladium (0), 20 ml of 2M sodium carbonate and 130 ml of toluene under argon stream. The mixture was stirred with reflux for 12 hours. After cooling, the reaction liquid was filtered, washed with water and methanol, whereby 3.5 g of a reddish purple solid as an intermediate A was obtained.As a result of mass spectroscopy of the resulting solid, a peak was observed at M/Z=706.

References: [1]Patent: US2010/19659,2010,A1 .Location in patent: Page/Page column 30; 31.

13
[ 853234-57-8 ]
4-fluoro-3-(trifluoromethyl)phenylboronic acid [ No CAS ]
[ 1104877-23-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In toluene; for 12h;Inert atmosphere; Reflux;	3.0 g of 3,9-dibromo-indenofluorenedione was mixed with 3.3 g of 4-fluoro-3-(trifluoromethyl)phenylboronic acid, 0.29 g of tetraxis(triphenylenephosphine)palladium (0), 25 ml of 2M sodium carbonate and 160 ml of toluene under argon stream. The mixture was stirred with reflux for 12 hours. After cooling, the reaction liquid was filtered, washed with water and methanol, whereby 3.7 g of a reddish purple solid as an intermediate D was obtained. As a result of mass spectroscopy of the resulting solid, a peak was observed at M/Z=606.

References: [1]Patent: US2010/19659,2010,A1 .Location in patent: Page/Page column 31; 32.

14
[ 853234-57-8 ]
[ 1352800-80-6 ]