54109-03-4|5-Chloroisobenzofuran-1(3H)-one| Ambeed

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Quality Control of [ 54109-03-4 ] Purity: 95% SDS Specification

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Product Details of [ 54109-03-4 ]

CAS No. :	54109-03-4
Formula :	C₈H₅ClO₂
M.W :	168.58
SMILES Code :	O=C1OCC2=C1C=CC(Cl)=C2
MDL No. :	MFCD09842447
Boiling Point :	No data available
InChI Key :	UBRQBEBBOSKYLQ-UHFFFAOYSA-N
Pubchem ID :	241737

Safety of [ 54109-03-4 ]

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

Computational Chemistry of [ 54109-03-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.12
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	40.78
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	26.3 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.76
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	1.43
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.86
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.	2.13
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	2.81
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.0

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.19
Solubility	1.09 mg/ml ; 0.00646 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.	-1.59
Solubility	4.36 mg/ml ; 0.0259 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	-3.19
Solubility	0.11 mg/ml ; 0.00065 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.	-6.31 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)	1.62

Application In Synthesis of [ 54109-03-4 ]

* 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 [ 54109-03-4 ]

[ 54109-03-4 ] Synthesis Path-Downstream 1~41

1
[ 54109-03-4 ]
[ 4673-39-6 ]

References: [1]Journal of the American Chemical Society,1946,vol. 68,p. 1314.
[2]Journal of Heterocyclic Chemistry,2006,vol. 43,p. 1195 - 1204.

2
[ 54109-03-4 ]
[ 110706-49-5 ]

Yield	Reaction Conditions	Operation in experiment
83%	With phenylsilane; potassium hydroxide; In tetrahydrofuran; for 4h;Schlenk technique; Inert atmosphere; Reflux;	General procedure: Isobenzofuran-1(3H)-one (0.4 mmol), KOH (0.4 mmol), PhSiH3 (1.2 mmol), dried THF (2 mL) were charged in a Schlenk tube(15 mL) under N2 atmosphere. The mixture was refluxed for 4 h. After cooling to rt, the reaction was quenched with EtOH(0.5-1 mL). Solvent was removed under reduced pressure and the crude residue was purified by column chromatography on silica gel with petroleum ether-ethyl acetate as the eluent to afford the desired product.

References: [1]Chinese Chemical Letters,2019,vol. 30,p. 725 - 728.
[2]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1954,vol. 238,p. 2246.

3
[ 54109-03-4 ]
[ 100448-59-7 ]

References: [1]Journal of the Chemical Society,1931,p. 867,869.

4
[ 54109-03-4 ]
4-chloro-2-hydroxymethyl-benzoic acid hydrazide [ No CAS ]

References: [1]Bulletin de la Societe Scientifique de Bretagne,1951,vol. 26,p. Sonderheft 5, S. 7, 96.
Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1952,vol. 235,p. 962.

5
[ 65399-05-5 ]
[ 54109-03-4 ]

References: [1]Journal of the Chemical Society,1931,p. 867,869.
[2]Journal of Heterocyclic Chemistry,2006,vol. 43,p. 1195 - 1204.
[3]European Journal of Medicinal Chemistry,2010,vol. 45,p. 1941 - 1946.

6
[ 54109-03-4 ]
[ 100-10-7 ]
[ 95834-48-3 ]

References: [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1985,vol. 34,p. 141 - 144.
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1985,p. 151 - 155.

7
[ 118-45-6 ]
[ 54109-03-4 ]

References: [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1985,vol. 34,p. 141 - 144.
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1985,p. 151 - 155.
[2]Australian Journal of Chemistry,1989,vol. 42,p. 787 - 795.

8
[ 118-45-6 ]
[ 54109-03-4 ]
[ 110706-49-5 ]

References: [1]Australian Journal of Chemistry,1989,vol. 42,p. 787 - 795.

9
[ 201230-82-2 ]
[ 873-63-2 ]
[ 54109-03-4 ]

References: [1]Journal of the American Chemical Society,1982,vol. 104,p. 1900 - 1907.

10
[ 7499-07-2 ]
[ 54109-03-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogensulfite; sodium chloride; In water; ethyl acetate; for 0.25h;	100mL and 150mL o-xylene was added dichloromethane 1000mL four-necked flask, 3g of zinc powder, placed on a magnetic stirrer, to 200r / min speed stirring 10min; At the end of the flask was introduced chlorine gas, aeration rate was washed with 10mL / min, aeration time was 10min, the reaction was allowed to stand after the aeration 1h, with a concentration of 10percent sodium hydroxide solution to colorless, into a distillation apparatus, was heated to 70 , dichloromethane was removed by distillation, to precipitate a white solid; white solid was placed in the above-described three-necked flask equipped with a thermometer, a condenser and a stirrer was charged with 50g and 10g of glacial acetic acid and potassium permanganate 3g solid sodium hydroxide, transferred to the water bath temperature was raised to 70 deg.] C shaking bed oscillating reaction 1h, placed in a rotary evaporator, heated to 80 , rotary evaporated to remove acetic acid to give white crystals; added 200mL ethyl acetate equipped with a stirrer and a thermometer four flask, 50g and 20g of sodium chloride sodium hydrogen sulfite and 800mL of distilled water, start agitator 500r / min stirring speed at the stirring process, the white crystals obtained above was added 5 min the flask, stirring was continued for 10min; after stirring was complete, 300mL layered ethyl acetate, poured into a separatory funnel and the organic layer was separated, was added 20mL of 10percent concentration sodium hydroxide solution to wash pale yellow, ethyl acetate was distilled off; the mixture of ethyl acetate was distilled off after added 20g of iodine chlorobenzene and 3g magnesium, and 50mL tetrahydrofuran, placed in an ultrasonic shaker, the ultrasonic oscillating reaction 10min, ultrasonic frequency of 25KHz, ultrasonic power 100W, ultrasound was added 50mL reaction was continued concentration of 95percent ethanol solution and immediately transferred to an ice bath pot was allowed to stand at 4 6h, until no precipitation, transferred to a Buchner funnel after filtration to give 1- (4-iodophenyl) -5-chloro-isobenzofuran .

References: [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 947 - 959.
[2]Patent: CN105801539,2016,A .Location in patent: Paragraph 0007.

11
[ 110706-49-5 ]
[ 54109-03-4 ]
[ 19641-29-3 ]

References: [1]Australian Journal of Chemistry,1989,vol. 42,p. 787 - 795.

12
[ 100448-59-7 ]
[ 54109-03-4 ]

References: [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 947 - 959.

13
[ 146516-83-8 ]
[ 54109-03-4 ]

References: [1]Monatshefte fur Chemie,1992,vol. 123,p. 1125 - 1134.

16
[ 60666-70-8 ]
Mo(CO)6 [ No CAS ]
[ 54109-03-4 ]