16611-67-9|(2,5-Dichlorophenyl)(phenyl)methanone| Ambeed

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Quality Control of [ 16611-67-9 ] Purity: 98% SDS Specification

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Product Details of [ 16611-67-9 ]

CAS No. :	16611-67-9
Formula :	C₁₃H₈Cl₂O
M.W :	251.11
SMILES Code :	ClC1=CC(C(=O)C2=CC=CC=C2)=C(Cl)C=C1
MDL No. :	MFCD00079746
Boiling Point :	No data available
InChI Key :	FAVKIHMGRWRACA-UHFFFAOYSA-N
Pubchem ID :	458188

Safety of [ 16611-67-9 ]

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

Computational Chemistry of [ 16611-67-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	16
Num. arom. heavy atoms	12
Fraction Csp3	0.0
Num. rotatable bonds	2
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	66.34
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	17.07 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.43
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	4.38
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	4.22
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.	4.05
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	4.65
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.95

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.58
Solubility	0.00662 mg/ml ; 0.0000263 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.	-4.45
Solubility	0.00881 mg/ml ; 0.0000351 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	-6.1
Solubility	0.000199 mg/ml ; 0.000000794 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	Yes
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.	-4.72 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<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)	1.81

Application In Synthesis of [ 16611-67-9 ]

* 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 [ 16611-67-9 ]

[ 16611-67-9 ] Synthesis Path-Downstream 1~37

1
[ 16611-67-9 ]
[ 124-41-4 ]
(2,5-dichlorophenyl)(phenyl)methanol [ No CAS ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1931,vol. 50,p. 753,779.

2
[ 16611-67-9 ]
(2,5-dichlorophenyl)(phenyl)methanol [ No CAS ]

References: [1]Chinese Journal of Chemistry,2021,vol. 39,p. 3297 - 3302.
[2]Recueil des Travaux Chimiques des Pays-Bas,1931,vol. 50,p. 753,779.

3
[ 16611-67-9 ]
2,5-dichloro-benzophenone oxime [ No CAS ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1931,vol. 50,p. 753,779.

4
[ 106-46-7 ]
[ 98-88-4 ]
[ 16611-67-9 ]

Yield	Reaction Conditions	Operation in experiment
97%	With sodium hydroxide;aluminium trichloride; In water; toluene;	Example 1 2,5-Dichlorobenzophenone To a 22 L, three-necked flask fitted with a thermometer, mechanical stirrer and a Vigreux column connected to an aqueous NaOH scrubbing tower, was added 1,4-dichlorobenzene (3 Kg, 26.4 mol) and benzoyl chloride (2.6 Kg, 18.55 mol). The mixture was heated to 80 C. to give a homogeneous solution. Aluminum chloride (5.5 Kg, 41.25 mol) was added over 12 min. with stirring. (The molar ratio of reactants was 2.2:1.4:1.0 (AlCl3: Dichlorobenzene:Benzoyl Chloride)). The resulting mixture was heated to 140 C. over 60 min followed by heating to 175 C. over 30 min. Heating was stopped at 175 C. The mixture was allowed to cool to 80 C. over two hours and poured into a well stirred mixture of ice and water (ca. 25 L water and 15 Kg of ice) over 30 min. The organic solid was collected by filtration and dissolved in 7 L of toluene. The solution was washed with aqueous sodium bicarbonate and dried. Toluene was removed by distillation. Pure 2,5-dichlorobenzophenone was isolated in 80% yield after recrystallization from hexane and toluene. Gas chromatography indicated an absolute yield of 97%.
64%	aluminium trichloride;	Example 11 A mixture of 5.4 g of 1,4-dichlorobenzene, 4.2 g of aluminum chloride and 0.5 ml of benzoyl chloride was stirred at 170 C. Additional benzoyl chloride, up to a total of 4 g, was slowly added to the mixture over 2.5 hours, and the resulting mixture was stirred for another hour at 170 C. The molar ratio of reactants was 1.1/1.3/ (AClCl3:Dichlorobenzene:Benzoyl Chloride). After work-up of the crude mixture as in Examples 7 through 10, 2,5-dichlorobenzophenone was obtained in 64% yield, as determined by gas chromatography using 3-chlorobenzophenone as the internal standard.

References: [1]Patent: US5210313,1993,A .
[2]Patent: US5210313,1993,A .
[3]Recueil des Travaux Chimiques des Pays-Bas,1931,vol. 50,p. 753,779.

5
[ 106-46-7 ]
[ 36967-85-8 ]
[ 16611-67-9 ]

References: [1]Chemische Berichte,1983,vol. 116,p. 1195 - 1208.

6
[ 16611-67-9 ]
[ 23974-72-3 ]
[ 88048-89-9 ]

References: [1]Phosphorus and Sulfur and the Related Elements,1983,vol. 16,p. 97 - 110.

7
[ 16611-67-9 ]
[ 1937-19-5 ]
[ 146470-09-9 ]

References: [1]Pharmazie,1992,vol. 47,p. 758 - 764.

8
[ 16611-67-9 ]
[ 109-81-9 ]
[ 2898-12-6 ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 9189 - 9190.

9
[ 56-23-5 ]
[ 16611-67-9 ]
KOH [ No CAS ]
[ 106-46-7 ]
[ 65-85-0 ]

References: [1]Chemische Berichte,1939,vol. 72,p. 861,868.

10
[ 16611-67-9 ]
KMnO₄ [ No CAS ]
aqueous NaOH [ No CAS ]
[ 50-79-3 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1931,vol. 50,p. 753,779.

11
[ 5995-76-6 ]
[ 16611-67-9 ]

References: [1]Organic Preparations and Procedures International,2004,vol. 36,p. 192 - 194.
[2]Organic Preparations and Procedures International,2004,vol. 36,p. 600 - 604.

12
[ 85-19-8 ]
[ 16611-67-9 ]

References: [1]Journal of Chemical Crystallography,2004,vol. 34,p. 637 - 640.
[2]Organic Preparations and Procedures International,2004,vol. 36,p. 600 - 604.
[3]Organic Preparations and Procedures International,2004,vol. 36,p. 600 - 604.

13
[ 5721-63-1 ]
[ 16611-67-9 ]
[ 2524-64-3 ]

References: [1]Organic Preparations and Procedures International,2004,vol. 36,p. 600 - 604.

14
[ 16611-67-9 ]
poly(2,5-benzophenone), M_n 5.56E4 g/mol, [η] 1.15 dl/g; monomer(s): 2,5-dichlorobenzophenone [ No CAS ]

References: [1]Macromolecules,2004,vol. 37,p. 4748 - 4754.

15
[ 2905-61-5 ]
[ 71-43-2 ]
[ 16611-67-9 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: 2-Chloro-4-nitrobenzoic acid (201 mg, 1.0 mmol) and cyanuric chloride (368 mg, 2 mmol) in 2 mL CH2Cl2 were treated with pyridine (79 mg, 1.0 mmol) and irradiated in the microwave for 15 min at 50 C. Then, the resulting mixture was treated with FeCl3 (324 mg, 2.0 mmol) and irradiated in the microwave for 5 min at 30 C. Finally, 3 mL of toluene was added to the solution and irradiated in the microwave for 15 min at 70 C. Then the reaction mixture was filtered from Celite. The filtrate was washed with sodium thiosulphate followed by brine solution. The separated organic layer was dried on Na2SO4 and concentrated under reduced pressure to give pure product 6a (269.5 mg, 93% yield). Mp 110-112 C (lit. 1 111.2 C). 1H NMR (500 MHz, CDCl3): δ 2.39 (s, 3H), 7.26 (d, J = 7.45 Hz, 2H), 7.54 (d, J = 7.45 Hz, 1H), 7.61 (d, J = 6.85 Hz, 2H), 8.26 (dd, J = 6.85, 2.7 Hz, 1H), 8.30 (d, J = 7.4 Hz, 1H); 13C NMR (500 Hz, CDCl3): δ 21.4 (CH3), 122.0 (CH), 125.1 (CH), 129.6 (CH), 129.7 (CH), 130.15 (CH), 132.2 (C), 144.6 (C), 146.2 (C), 148.9 (C), 193.5 (CO); IR (cm-1): 638.3, 740.8, 801.5, 836.3, 863.0, 1000.7, 1025.9, 1052.5, 1005.1, 1133.9, 1158.3, 1180.7, 1272.5, 1294.3, 1315.8, 1349.1, 1403.2, 1449.5, 1461.2, 1528.8, 1573.3, 1595.7, 1607.9, 1673.9, 3087.5; GC/MS: 275 [M+]; HRMS: calcd for C14H10ClNO3: 275.0349. Found: 275.0467.

References: [1]Macromolecules,2004,vol. 37,p. 4748 - 4754.
[2]Tetrahedron Letters,2011,vol. 52,p. 2594 - 2596.

16
[ 78650-61-0 ]
[ 16611-67-9 ]
bis{4-(4-isopropylbenzoyl)phenyl}-terminated poly(benzophenone-2,5-diyl), product of nickel⁽⁰⁾-catalyzed polymerization; monomer(s): 4-chloro-4-isopropylbenzophenone; 2,5-dichlorobenzophenone [ No CAS ]