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Chemical Structure| 93-97-0 Chemical Structure| 93-97-0

Structure of Benzoic anhydride
CAS No.: 93-97-0

Chemical Structure| 93-97-0

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Product Details of [ 93-97-0 ]

CAS No. :93-97-0
Formula : C14H10O3
M.W : 226.23
SMILES Code : O=C(OC(C1=CC=CC=C1)=O)C2=CC=CC=C2
MDL No. :MFCD00003073
InChI Key :CHIHQLCVLOXUJW-UHFFFAOYSA-N
Pubchem ID :7167

Safety of [ 93-97-0 ]

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

Computational Chemistry of [ 93-97-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 17
Num. arom. heavy atoms 12
Fraction Csp3 0.0
Num. rotatable bonds 4
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 62.63
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

43.37 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.05
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

2.26
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.68
Log Po/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.

3.54
Log Po/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 Po/w?

Consensus Log Po/w: Average of all five predictions

2.67

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.92
Solubility 0.269 mg/ml ; 0.00119 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.

-2.81
Solubility 0.353 mg/ml ; 0.00156 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

-4.56
Solubility 0.00625 mg/ml ; 0.0000276 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

No
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.

-6.08 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<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)

1.53

Application In Synthesis of [ 93-97-0 ]

* 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 [ 93-97-0 ]

[ 93-97-0 ] Synthesis Path-Downstream   1~25

  • 1
  • [ 109-06-8 ]
  • [ 14257-84-2 ]
  • [ 93-97-0 ]
  • [ 573-34-2 ]
  • [ 885-75-6 ]
  • 2
  • [ 484-29-7 ]
  • [ 93-97-0 ]
  • 9-benzoyl-9<i>H</i>-furo[2,3-<i>b</i>]quinolin-4-one [ No CAS ]
  • 3
  • [ 1776-37-0 ]
  • [ 93-97-0 ]
  • 1-benzoyl-5-methyl-1<i>H</i>-indazole [ No CAS ]
  • 4
  • [ 99-14-9 ]
  • [ 93-97-0 ]
  • [ 100953-23-9 ]
YieldReaction ConditionsOperation in experiment
78% With pyridine; In m-xylene; at 140℃; General procedure: Into a one-necked 25 mL flask, tricarballylic acid (518 mg, 2.95 mmol, 1.0 equiv) and the appropriate anhydride (8.83 mmol, 3 equiv) were suspended in m-xylene (5 mL, 0.6 M). Pyridine was added (47 muL, 0.59 mmol, 0.2 equiv) in one portion, then the mixture was heated to 140 C and stirred until the completion of the reaction was indicated by GC-MS (5-21 h). After cooling to r.t., CH2Cl2 (100 mL) was added and the mixture was passed through a short pad of Celite to remove insoluble side-products. The solution was washed with saturated Na2CO3 solution (2 10 mL) then with brine (10 mL). The organic phase was dried over Na2SO4, filtered, and evaporated to dryness. Purification by flash chromatography (hexanes/EtOAc) afforded the pure Fittig lactone.
  • 5
  • [ 1818-27-5 ]
  • [ 93-97-0 ]
  • [ 38183-04-9 ]
  • 6
  • [ 1818-27-5 ]
  • [ 93-97-0 ]
  • [ 38183-04-9 ]
  • 3-benzoyl-6,7-dihydroxy-2-phenyl-chromen-4-one [ No CAS ]
  • 7
  • [ 65982-77-6 ]
  • [ 93-97-0 ]
  • [ 548-83-4 ]
  • 8
  • [ 84-16-2 ]
  • [ 93-97-0 ]
  • [ 6033-44-9 ]
  • 9
  • [ 10212-25-6 ]
  • [ 93-97-0 ]
  • [ 38823-20-0 ]
  • 10
  • [ 694-31-5 ]
  • [ 98-88-4 ]
  • [ 132417-20-0 ]
  • [ 93-97-0 ]
  • 11
  • [ 5117-87-3 ]
  • [ 93-97-0 ]
  • [ 98061-61-1 ]
  • 12
  • [ 93-97-0 ]
  • 2.3.4-trioxy-acetophenone [ No CAS ]
  • [ 38183-03-8 ]
  • 13
  • [ 93-97-0 ]
  • [ 169048-83-3 ]
  • (S)-3-benzoyl-5-chloromethyl-oxazolidin-2-one [ No CAS ]
  • 14
  • [ 340-05-6 ]
  • [ 93-97-0 ]
  • [ 10531-50-7 ]
  • [ 340-06-7 ]
  • [ 17659-27-7 ]
  • (R)-2,2,2-trifluoro-1-(phenyl)ethyl benzoate [ No CAS ]
  • 15
  • [ 33893-89-9 ]
  • [ 93-97-0 ]
  • [ 25433-30-1 ]
  • 16
  • [ 16687-60-8 ]
  • [ 93-97-0 ]
  • [ 1090-82-0 ]
  • 17
  • [ 39959-67-6 ]
  • [ 93-97-0 ]
  • [ 1198107-19-5 ]
  • [ 1198107-13-9 ]
  • 18
  • [ 15980-22-0 ]
  • [ 93-97-0 ]
  • N-(4-hydroxy-3,5-dimethylphenyl)benzamide [ No CAS ]
  • 19
  • [ 39959-67-6 ]
  • [ 93-97-0 ]
  • [ 1198107-13-9 ]
  • 20
  • [ 93-97-0 ]
  • [ 1575-37-7 ]
  • [ 1741-50-0 ]
  • 21
  • [ 93-97-0 ]
  • [ 4760-34-3 ]
  • [ 2622-63-1 ]
YieldReaction ConditionsOperation in experiment
99% In 1-methyl-pyrrolidin-2-one; water; at 445℃; under 187519.0 Torr; for 0.00277778h;Supercritical conditions; Under the same conditions as in Example 1-5 except that N-methyl-1,2-phenylenediamine (manufactured by Sigma-Aldrich) and benzoic acid hydride (manufactured by Tokyo Chemical Industry Co., Ltd.) were used at a pressure of 25 MPa, (13) was carried out in supercritical water. As a result, the reaction time was 10 seconds, and the yield was 99percent
  • 22
  • [ 93-97-0 ]
  • [ 815-57-6 ]
  • [ 68285-27-8 ]
  • (R,Z)-4-((1-(3-fluorophenyl)ethyl)amino)-3-methylpent-3-en-2-one [ No CAS ]
  • (S,Z)-4-((1-(3-fluorophenyl)ethyl)amino)-3-methylpent-3-en-2-one [ No CAS ]
  • C15H14FNO [ No CAS ]
  • C15H14FNO [ No CAS ]
  • 23
  • [ 57053-02-8 ]
  • [ 93-97-0 ]
  • dimethyl 2-benzamidoisophthalate [ No CAS ]
  • 24
  • [ 93-97-0 ]
  • [ 112811-71-9 ]
  • C28H20BF2NO8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
93.2% Add 19g of diboron trioxide to a 1L three-neck bottle,181g benzoic acidAnd 439g benzoic anhydride,Mechanical stirring,Heating reaction (200±5C) reaction for 5h,After the reaction is over,Cool down to 5090C,Add 150 g of ethyl 1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylate,After continuing to heat the reaction (200±5C) for 4 hours,Thin layer chromatography was monitored until the reaction was completed (developer: ethyl acetate:methanol=20:1, UV 254 nm; the disappearance of the starting material indicates complete reaction).After the reaction was completed, the reaction solution was cooled to room temperature (10 to 30 C.), and the cooled material solution was placed in a refrigerator. Crystallization was continued for 12 hours (0 to 5 C.), and suction filtration was performed to obtain a brown-yellow solid, which was used as a filter cake. Anhydrous ethanol (0 ± 5 C) was beaten and washed three times, and suction filtration was continued until dry. The filter cake was laid flat on a watch glass and placed in a drying oven at 50 ± 5 C for 5 hours.Received, obtained 237g light yellow solid, yield 93.2%, namely 1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinoline The carboxylic acid-O3,O4-dibenzoic acid boron (compound III) was used in the next step without purification.
  • 25
  • [ 1663-39-4 ]
  • [ 100-39-0 ]
  • [ 93-97-0 ]
  • [ 103962-05-6 ]
  • tert-butyl (E)-3-(2-benzoyl-6-benzyl-4-(trifluoromethoxy)phenyl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With trifuran-2-yl-phosphane; norbornene; caesium carbonate; palladium dichloride; In 1,4-dioxane; at 90℃; for 12h;Sealed tube; General procedure: Unless otherwise noted, in a glovebox, a 5.0 mL vial equipped with a Teflon coated stir bar was charged with PdCl2 (1.7 mg, 0.03mmol), P(2-furyl)3 (16.4 mg, 0.06 mmol), Cs2CO3 (391.0 mg,1.20 mmol), 1 (0.30 mmol), 2 (0.45 mmol), 3 (0.45 mmol), 4 (0.36 mmol) and NBE (56.5 mg, 0.6mmol) followed by sequential addition of 1,4-dioxane (3.0 mL). Next, the vial was sealed with a Teflon screw cap and removed from glovebox, and then, the mixture was allowed warm to 90 C refluxed for an additional 12 h. After completion of the reaction, the mixture was filtered through a thin pad of celite. The filter cake was washed with ethyl acetate (3 × 2.0 mL), then the combined filtrate was concentrated in vacuo to provide a crude reaction mixture that was purified by silica gel column chromatography to affored the desired product 5.
References: [1]Chem,2020.
 

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