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Chemical Structure| 1823-59-2 Chemical Structure| 1823-59-2

Structure of 4,4-Oxydiphthalic anhydride
CAS No.: 1823-59-2

Chemical Structure| 1823-59-2

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Product Details of [ 1823-59-2 ]

CAS No. :1823-59-2
Formula : C16H6O7
M.W : 310.22
SMILES Code : O=C1OC(C2=C1C=CC(OC3=CC4=C(C(OC4=O)=O)C=C3)=C2)=O
MDL No. :MFCD00039144
InChI Key :QQGYZOYWNCKGEK-UHFFFAOYSA-N
Pubchem ID :74574

Safety of [ 1823-59-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Computational Chemistry of [ 1823-59-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 23
Num. arom. heavy atoms 12
Fraction Csp3 0.0
Num. rotatable bonds 2
Num. H-bond acceptors 7.0
Num. H-bond donors 0.0
Molar Refractivity 72.45
TPSA ?

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

95.97 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.39
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

2.19
Log Po/w (WLOGP)?

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

2.1
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.

1.96
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

2.78
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.08

Water Solubility

Log S (ESOL):?

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

-3.4
Solubility 0.124 mg/ml ; 0.000401 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.

-3.84
Solubility 0.0449 mg/ml ; 0.000145 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

-4.78
Solubility 0.00517 mg/ml ; 0.0000167 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

No
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.

-6.64 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)

2.34

Application In Synthesis of [ 1823-59-2 ]

* 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 [ 1823-59-2 ]

[ 1823-59-2 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 1823-59-2 ]
  • [ 101-80-4 ]
  • [ 33976-43-1 ]
  • poly(amic acid), terminated by 4-(aminophenyl)trimethoxysilane; monomer(s): 4,4\-oxydiphthalic anhydride; 4,4\-oxydianiline; 4-(aminophenyl)trimethoxysilane [ No CAS ]
  • 2
  • [ 1823-59-2 ]
  • [ 118-45-6 ]
  • [ 89-20-3 ]
  • [ 7717-76-2 ]
YieldReaction ConditionsOperation in experiment
With phosphoric acid; water; In 1,2-dichloro-benzene; at 80℃;vacuum;Product distribution / selectivity; The purpose of this Example was to show that without decantation, a relatively higher level of impurities levels were present in the 4,4'-oxydiphthalic anhydride that was produced, as compared to Examples 4 and 5 where decantation is practiced. 2645 parts of a WC of material consisting of 68.7 wt% 4,4'-oxydiphthalic anhydride, 13.3 wt% of potassium chloride, 18 wt% of ortho-dichlorobenzene based on total weight of the WC, and some minor impurities such as hexaethylguanidinium chloride (1146 ppm) and chlorophthalic anhydride (1591ppm), was mixed with 528 parts of phosphoric acid (85 wt%) and 11877 parts of water and heated under vacuum until boiling, about 80 C. Under these conditions, 4,4'-oxydiphthalic anhydride and <n="41"/>chlorophthalic anhydride react with the water to form 4,4'-oxydiphthalic tetraacid (ODTA) and chlorophthalic acid (ClDA). The oDCB was removed from the mixture as an azeotrope with water. The weight of the reactor was maintained constant by adding the corresponding amount of water back to the reactor. The process took approximately 25 hours. Subsequently, the mixture was cooled to 14 C and centrifuged. The WC was washed with 10 parts of water per part of 4,4'- oxydiphthalic tetraacid. 1492 parts of the final WC was obtained and it contained 85% of 4,4'-oxydiphthalic tetraacid and less than 30 ppm of hexaethylguanidinium chloride, 464 ppm of chlorophthalic acid and 64 ppm of potassium, with the balance (-15 wt%) being water.[0082] The example illustrates a method of purifying 4,4'-oxydiphthalic anhydride by aqueous hydrolysis and centrifugation.
  • 3
  • [ 1823-59-2 ]
  • [ 2657-87-6 ]
  • [ 119389-05-8 ]
  • poly(4-phenyl-ethynyl-phthalic anhydride)-co-(3,4'-oxydianiline) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In 1-methyl-pyrrolidin-2-one; at 100 - 350℃; for 1h; Example 5; Synthesis of imide oligomer by Using 4-phenyl ethynyl phthalic anhydride Obtained in Example 3 and Comparative Examples 1 to 3 as Terminal End Groups; In accordance with the method as described in Non-Patent Document No. 2, a solution of an amide-acid oligomer having an average molecular weight of about 9,000 was prepared from the 4-phenyl ethynyl phthalic anhydrides obtained in Example 3 and Comparative Examples 1 to 3, and 3,4'-oxydianiline and an N-methylpyrrolidone solution of 4,4'-oxydiphthalic anhydride. The thus-prepared amide-acid oligomer was centrifuged, applied, dried and subjected to thermal treatments for one hour at 100° C., 225° C. and 350° C. in this order, to thereby obtain films of cross-linked imide oligomer. On the other hand, toluene was added to an N-methylpyrrolidone solution of the amide-acid oligomer and, the mixture was subjected to the steps of azeotropic dehydration, cooling, filtration, rinsing with water and methanol in this order, and drying, to thereby isolate an imide oligomer. Tg and kinetic properties at 23° C. of each film prepared in accordance with the above-described method corresponding to 4-phenyl ethynyl phthalic anhydrides obtained in Example 3 and Comparative Examples 1 to 3 were measured in accordance with a method as specified in ASTM D882 and, also a temperature at which 5percent by mass of the imide oligomer was reduced was measured by using a thermobalance. These results are shown in Table 1. TABLE 1 Production method for 4-phenyl Film of cross-linked Temper- ethynyl imide oligomer (23° C.) ature of phthalic Tensile Elastic Elongation 5percent mass anhydride Tg strength modulus at break reduction Example 3 252° C. 122.2 MPa 3.0 GPa 55percent 518° C. Comparative 250° C. 120.1 Mpa 2.6 GPa 31percent 514° C. Example 1 Comparative 252° C. 118.8 MPa 2.8 GPa 36percent 511° C. Example 2 Comparative 251° C. 119.7 MPa 2.7 GPa 36percent 514° C. Example 3
  • 4
  • [ 1823-59-2 ]
  • [ 10526-07-5 ]
  • [ 119389-05-8 ]
  • poly(4,4'-oxydiphthalic acid dianhydride-co-1,3-bis(3-aminophenoxy)benzene-co-4-phenylethynylphthalic anhydride) [ No CAS ]
  • [ 2387-23-7 ]
 

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