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Chemical Structure| 119389-05-8

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Product Details of [ 119389-05-8 ]

CAS No. :119389-05-8
Formula : C16H8O3
M.W : 248.23
SMILES Code : O=C1OC(C2=C1C=CC(C#CC3=CC=CC=C3)=C2)=O
MDL No. :MFCD10574892
InChI Key :UPGRRPUXXWPEMV-UHFFFAOYSA-N
Pubchem ID :11053989

Safety of [ 119389-05-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P305+P351+P338

Computational Chemistry of [ 119389-05-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 19
Num. arom. heavy atoms 12
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 68.61
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.

2.55
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

3.62
Log Po/w (WLOGP)?

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

2.48
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.

3.57
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

3.8
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.2

Water Solubility

Log S (ESOL):?

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

-4.13
Solubility 0.0185 mg/ml ; 0.0000746 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.

-4.22
Solubility 0.015 mg/ml ; 0.0000605 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

-5.07
Solubility 0.0021 mg/ml ; 0.00000847 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

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

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.

-5.24 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

3.0 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)

2.63

Application In Synthesis of [ 119389-05-8 ]

* 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 [ 119389-05-8 ]

[ 119389-05-8 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 2657-87-6 ]
  • [ 2420-87-3 ]
  • [ 10526-07-5 ]
  • [ 119389-05-8 ]
  • polymer; monomer(s); 3,3',4,4'-biphenyltetracarboxylic dianhydride; 3,4'-oxydianiline; 1,3-bis(3-aminophenoxy)benzene; 4-phenylethynylphthalic anhydride [ No CAS ]
  • 2
  • [ 86-90-8 ]
  • [ 536-74-3 ]
  • [ 119389-05-8 ]
YieldReaction ConditionsOperation in experiment
70.6 - 82.3% Product distribution / selectivity; Comparative Example 1; Compound No. 10: Synthesis of: 4-phenyl ethynyl phthalic anhydride 10 by Using the Method as Described in the Above-Described Patent Document No. 3 (JP-A No. 2003-73372); In accordance with the method as described in Patent Document No. 3, 4-phenyl ethynyl phthalic anhydride was synthesized from 4-bromophthalic anhydride and phenyl acetylene. The resultant 4-phenyl ethynyl phthalic anhydride was yellowish brown crystalline powder. The yield thereof was 79.1percent. Physical properties were as follows (measurement conditions were the same as those in Example 3): Melting point: 149.1 to 149.8° C.; Turbidity: 8.1 ppm; Visible light absorption: 0.058 (400 nm), 0.015 (450 nm); and GC purity: 97.5percent.; Comparative Example 2; Synthesis of 4-phenyl ethynyl phthalic anhydride by Using the Method as Described in the Above-Described Patent Document No. 2; In accordance with the method as described in Example 1 of Patent Document No. 2 (JP-A No. 11-180970), 4-phenyl ethynyl phthalic anhydride was synthesized from 4-bromophthalic anhydride and phenyl acetylene. The resultant 4-phenyl ethynyl phthalic anhydride was pale yellow crystalline powder. Physical properties were as follows (measurement conditions were the same as those in Example 3). The yield of the product was 82.3percent: Melting point: 151.1 to 151.8° C.; Turbidity: 10.5 ppm; Visible light absorption: 0.050 (400 nm), 0.022 (450 nm); and GC purity: 98.7percent;. Comparative Example 3; Synthesis of 4-phenyl ethynyl phthalic anhydride by Using the Method as Described in Non-Patent Document No. 2; In accordance with the method as described in Non-Patent Document No. 2 (Polymer, vol. 35, pp. 4858, 1994), 4-phenyl ethynyl phthalic anhydride was synthesized from 4-bromophthalic anhydride and phenyl acetylene. The resultant 4-phenyl ethynyl phthalic anhydride was pale yellow crystalline powder. Physical properties were as follows (measurement conditions were the same as those in Example 3). The yield of the product was 70.6percent: Melting point: 150.5 to 151.1° C.; Turbidity: 12.1 ppm; Visible light absorption: 0.049 (400 nm), 0.023 (450 nm); and GC purity: 98.8percent.
  • 3
  • [ 865354-04-7 ]
  • [ 119389-05-8 ]
YieldReaction ConditionsOperation in experiment
94% 4-phenyl ethynyl dimethyl phthalate (33.6 g) was suspended in a mixed medium comprising water and methanol and a 25percent by mass aqueous solution of sodium hydroxide (40 g) was dropwise added thereto with stirring. The resultant reaction mixture was stirred at 60° C. for 3 hours and, then, after confirming the completion of the reaction, cooled to the inside temperature of 30° C. Thereafter, 1 g of active carbon was added thereto, and, then, stirred for 30 minutes maintaining the same temperature. The resultant mixture was filtered to remove the active carbon, and rinsed with water. The filtrate and a rinsing solution were combined and, then, toluene and ethyl acetate were added to the resultant mixture. Concentrated hydrochloric acid (28 g) was dropwise added to the resultant 2-layered reaction mixture. The mixture was stirred for 30 minutes at room temperature and was allowed to stand, so that an organic layer containing 4-phenyl ethynyl phthalic acid was separated. After partially concentrating the organic layer, acetic anhydride (17 g) was added thereto, and the reaction mixture was refluxed with heating for 4 hours. After the reaction was completed, the resultant reaction mixture was cooled, so that 4-phenyl ethynyl phthalic anhydride was precipitated as a crystal. The crystal was filtered, rinsed and dried, to thereby obtain 26.6 g of 4-phenyl ethynyl phthalic anhydride as a pale yellow crystal. The yield was 94percent on the basis of 4-phenyl ethynyl dimethyl phthalate. Physical properties of the substance thus obtained were as follows: Melting point: 152.1 to 152.3° C.; IR vmax (KBr): 3070 (w), 2200 (m), 1775 (w), 1770 (s), 1755 (vs), 1620 (s), 1495 (m), 1340 (m), 1240 (vs), 940 (m), 900 (vs) cm-1;
  • 4
  • 4-phenylethynylphthalic acid [ No CAS ]
  • [ 119389-05-8 ]
YieldReaction ConditionsOperation in experiment
With acetic anhydride; In toluene; for 4h;Heating / reflux;Product distribution / selectivity; An entire amount of the thus-obtained crystal was suspended in toluene and, acetic anhydride (17 g) was added thereto. The resultant reaction mixture was refluxed with heating for 4 hours. After the reaction was completed, the resultant reaction mixture was cooled, so that 4-phenyl ethynyl phthalic anhydride was precipitated as a crystal. The crystal was filtered, rinsed and dried, to thereby obtain 26.3 g of 4-phenyl ethynyl phthalic anhydride as a pale yellow crystal. The yield was 93percent on the basis of 4-phenyl ethynyl dimethyl phthalate. Physical properties of the substance thus obtained were as follows: Melting point: 152.1 to 152.2° C.; IR: coincided with those in Example 3; Turbidity: 0.1 ppm (conditions were set to be same as those in Example 3); Visible light absorption: 0.015 (400 nm), 0.003 (450 nm) (conditions were the same as those in Example 3); and GC purity: 99.9percent or more (measurement conditions were the same as those in Example 3).
  • 5
  • [ 919-30-2 ]
  • [ 119389-05-8 ]
  • 3-(4-phenylethynyl phthalimide)-propyl triethoxy silane [ No CAS ]
YieldReaction ConditionsOperation in experiment
98.9% at 20 - 220℃; for 11h;Inert atmosphere; Under the protection of nitrogen,3-Aminopropyltrimethoxysilane (purity 99percent) (0.02 mol, 3.58 g) was added to a three-necked flask.Then 4-phenylacetylene phthalic anhydride (0.02 mol, 4.96 g) was added.The reaction was stirred at room temperature for 6 h.The stirring rate is controlled at 500r/min.Then, the temperature of the reaction solution was adjusted to 220 ° C at a heating rate of 40 ° C / min.Continue to react for 5h,Finally stop stirring,Squeeze after cooling the sample,That is, the sample was 8.09 g, and the yield was 98.9percent.
464.1 g (85%) With pyridine; In toluene; EXAMPLE 2 Synthesis of gamma-[N-(4-phenylethynylphthalimido)]propyltriethoxysilane (APEIS-2) To a flame dried 3 necked 3 L round bottom flask equipped with nitrogen inlet, mechanical stirrer, and Dean-Stark trap was charged 1250 mL of toluene. gamma-Aminopropyltriethoxysilane (266.3 g, 1.2029 mol) was then added via a syringe under the toluene surface. Prior to use <strong>[119389-05-8]4-phenylethynylphthalic anhydride</strong> was recrystallized from toluene. 4-Phenylethynylphthalic anhydride (298.6 g, 1.2029 mol) was added to the stirred solution and washed in with an additional 250 mL of toluene. Approximately 4 mL of pyridine was subsequently added to the stirred solution. The stirred solution was heated at a mild reflux for 48 hrs under a nitrogen atmosphere. The solution was subsequently cooled to room temperature and the toluene removed under vacuum to afford 464.1 g (85percent) of a viscous brown gum. No melting point was observed as determined by differential scanning calorimetry at a heating rate of 10° C./min. By a Fisher Johns melting point apparatus a broad melt was observed from 65° C. to 115° C. Infrared (KBr, cm-1): 2212 (phenylethynyl); 1770, 1715 (imide); 1089 (Si-O-C). M+452 (molecular weight, 452 g/mol.)
  • 6
  • [ 119389-05-8 ]
  • 3-(4-phenylethynyl phthalimide)-propyl triethoxy silane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 1 4-phenylethynyl-N [3-triethoxysilylpropyl] phthalimide was synthesised as follows. <strong>[119389-05-8]4-phenylethynyl phthalic anhydride</strong> (PEPA) was added to a round bottom flask containing sufficient tetrahydrafuran (THF) to dissolve the PEPA. An equimolar amount of 3-aminopropytriethoxy silane (3-APS) was added to the mixture at room temperature. The mixture was then heated over a steam bath until the THF mixture began to boil (T=65° C.). The heating continued for approximately 5 minutes. The solution was then removed from the steam bath and allowed to cool. The solvent was removed using a rotovaporator at 40° C. The resulting product is a thick, viscous, yellow (amber) liquid.
  • 7
  • [ 54060-30-9 ]
  • [ 119389-05-8 ]
  • N-(3-ethynylphenyl)-4'-phenylethynylphthalisoimide [ No CAS ]
  • [ 2387-23-7 ]
  • 8
  • [ 54060-30-9 ]
  • [ 119389-05-8 ]
  • N-(3-ethynylphenyl)-4'-phenylethynylphthalimide [ No CAS ]
  • 9
  • [ 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
  • 10
  • [ 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 ]
  • 11
  • C55H50N2O13Si9 [ No CAS ]
  • [ 119389-05-8 ]
  • C87H62N2O17Si9 [ No CAS ]
  • 12
  • 3,5,7,9,11,13,15-hepta(isobutyl)pentacyclo[9.5.1.13,9.15,15.17,13]octasiloxan-1-ol [ No CAS ]
  • [ 119389-05-8 ]
  • [ 1250263-72-9 ]
  • 13
  • [ 1417051-73-0 ]
  • [ 119389-05-8 ]
  • phenyl<SUB>7</SUB> POSS mono-phenylethynyl phthalic imide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl acetamide; toluene; for 6h;Inert atmosphere; Dean-Stark; 2. Synthesis of Phenyl7 POSS Mono-phenylethynyl Phthalic Imide In a 50 mL round bottom flask, a solution of PEPA (0.246 g, 1 mmol) in 35 mL toluene is added to a stirring solution of POSS phenylamine (1.05 g, 1 mmol) in 5 mL dimethylacetamide (DMAC). This is attached to a reverse Dean Stark apparatus, which is dried in an oven, evacuated, and backfilled with GN2 prior to use. The entire set up is equipped with a condenser and a thermometer. The stirring reaction mixture is heated in an oil bath at 1500° C. for 6 hr and allowed to cool to room temperature. White precipates obtained at the bottom of the reaction flask are filtered, washed with anhydrous diethyl ether, and air dried under nitrogen for 6 hr. These are further dried under vacuum at 1200° C. for 24 hr. 29Si NMR (CDCl3) -78.07 ppm, -78.16 ppm, -78.67 ppm (ratio=3:4:1).
  • 14
  • bis(para-aniline, methyl)silyloxy-octaphenylsilsesquioxane [ No CAS ]
  • [ 119389-05-8 ]
  • C94H70N2O18Si10 [ No CAS ]
  • 15
  • [ 591-50-4 ]
  • [ 73819-76-8 ]
  • [ 119389-05-8 ]
  • 16
  • [ 108-86-1 ]
  • [ 73819-76-8 ]
  • [ 119389-05-8 ]
  • 17
  • [ 73819-76-8 ]
  • [ 108-90-7 ]
  • [ 119389-05-8 ]
  • 18
  • [ 107-21-1 ]
  • [ 119389-05-8 ]
  • [ 1398110-00-3 ]
  • 19
  • [ 2420-87-3 ]
  • [ 101-80-4 ]
  • [ 119389-05-8 ]
  • C128H82N8O28 [ No CAS ]
  • 20
  • [ 2657-87-6 ]
  • [ 2420-87-3 ]
  • [ 119389-05-8 ]
  • C128H82N8O28 [ No CAS ]
  • 21
  • [ 1107-00-2 ]
  • [ 106-50-3 ]
  • [ 119389-05-8 ]
  • C139H61F24N9O20 [ No CAS ]
  • 22
  • [ 23738-81-0 ]
  • [ 119389-05-8 ]
  • C24H23B10NO2 [ No CAS ]
  • 23
  • [ 119389-05-8 ]
  • 2,3-bis(methoxymethyl)-6-(phenylethynyl)naphthalene [ No CAS ]
  • 24
  • [ 119389-05-8 ]
  • C16H14O2 [ No CAS ]
  • 25
  • [ 119389-05-8 ]
  • C16H12Cl2 [ No CAS ]
  • 26
  • [ 5434-21-9 ]
  • [ 119389-05-8 ]
  • C24H13NO6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In 1-methyl-pyrrolidin-2-one; at 75 - 180℃;Inert atmosphere; In a nitrogen protection device,Magnetic stirring,And equipped with a spherical condenser trap 250mL three-necked flask,Add 10 g of 5-aminophthalic acid and 80 mL of NMP.Under nitrogen protection,Stirred for 30min to obtain a homogeneous solution,Then, 13 g of 4-phenylacetylene phthalic anhydride was added,The solution was heated to 75 ° C,Hold 2h; then add 20g of toluene,The reaction was gradually warmed to 180 ° C,The generated water is taken out by the water trap; after 6-8 hours of reaction,Cooled to 120 ° C,The mixed solution was poured into excess deionized water,Suction filtration, washing and drying.That is, 4- (4-phenylacetophenyleneiminide) -1,2-dibenzoic acid was obtained.
  • 27
  • [ 10312-55-7 ]
  • [ 119389-05-8 ]
  • C24H13NO6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In 1-methyl-pyrrolidin-2-one; at 75 - 180℃;Inert atmosphere; In a nitrogen protection device,Magnetic stirring,And equipped with a spherical condenser trap 250mL three-necked flask,Add 10 g of 5-aminoterephthalic acid and 80 mL of NMP.Under nitrogen protection,Stirred for 30min to obtain a homogeneous solution,Then, 13 g of 4-phenylacetylene phthalic anhydride was added,The solution was heated to 75 ° C for 2h;Then 20g of toluene was added,The reaction was gradually warmed to 180 ° C,The generated water is taken out by the water trap;After 6-8h reaction,Cooled to 120 ° C,The mixed solution was poured into excess deionized water,Suction filtration, washing and drying.That is, 2- (4-phenylethynylideneimide) -1,4-dibenzoic acid was obtained.
  • 28
  • [ 99-27-4 ]
  • [ 119389-05-8 ]
  • C26H17NO6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In 1-methyl-pyrrolidin-2-one; toluene; at 75 - 180℃;Inert atmosphere; In a nitrogen protection device,Magnetic stirring,And equipped with a spherical condenser trap 250mL three-necked flask,Add 10 g of dimethyl 5-aminoisophthalate and 80 mL of NMP.Under nitrogen protection,Stirred for 30min to obtain a homogeneous solution,Then, 11.9 g of 4-phenylacetylene phthalic anhydride was added,The solution was heated to 75 ° C,Keep 2h;Then 20g of toluene was added,The reaction was gradually warmed to 180 ° C,The generated water is taken out by the water trap;After 6-8h reaction,Cooled to 120 ° C,The mixed solution was poured into excess deionized water,A yellow-green solid was obtained,Suction filtration,Washed and dried.Thus, dimethyl 5- (4-phenylethynylidene) -1,3-dibenzoate was obtained.
  • 29
  • 5-amino-1-(4'-aminophenyl)-1,3,3-trimethylindane [ No CAS ]
  • [ 1204-28-0 ]
  • [ 119389-05-8 ]
  • C77H62N4O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.3 g of 6-amino-1- (4-aminophenyl) -1,3,3-trimethylindane (PIDA, diamine monomer)Was dissolved in 4 volumes of NMP by stirring,Adding 5percent triethylamine (the mass ratio of adding triethylamine is 1: 1) as acid-binding agent to obtain a light yellow transparent solution,Placed under N2 atmosphere;The corresponding amount of trimellitic anhydride acid chloride (TMAC) was dissolved in NMP,Stir into the reaction flask,The reaction was carried out at room temperature (about 20 ° C) for 2h.Then4-phenylacetylene phthalic anhydride(PEPA) added to the reaction system,Continue to react 20h.In the above reaction, the molar ratio of PIDA, TMAC and PEPA is 1: 2: 2,A light yellow transparent polyamic acid having a constant viscosity of repeating units n = 1 was obtained. Marked as PAI-1.
  • 30
  • [ 78589-34-1 ]
  • [ 2421-28-5 ]
  • [ 119389-05-8 ]
  • C77H58B20N4O9 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Under a nitrogen atmosphere, a round bottom flask was charged with the prepared single carboranediamine monomer 1,2-bis (4-aminophenyl) -1,2-o-carborane(5.0000 g, 15.314 mmol) and 30ml DMF,Stir until the diamine monomer is completely dissolved and slowly add BTDA (2.4672 g, 7.657 mmol) and add 17.5 ml DMF to dilute the solution.After 4 h at room temperature, 4-PEPA (3.8014 g, 15.314 mmol) was added and the reaction continued for 12 h to obtain a 20percent solids polyamic acid solution.Additional acetic anhydride (9.43 g, 92.4 mmol) and triethylamine (1.56 g, 15.4 mmol) were added and the reaction was continued for 12 h at room temperature for chemical imidization.After the reaction was completed, the solution was poured into a large amount of deionized water, the precipitate was filtered, and the filter cake was washed with water until the filtrate became neutral.The solid was dried in a vacuum oven at 120°C for 12 h to give a yellow prepolymer, named "oligomer PI-CBA" (structure shown in Figure 8).
  • 31
  • [ 92-87-5 ]
  • [ 2421-28-5 ]
  • [ 119389-05-8 ]
  • C73H38N4O9 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Under a nitrogen atmosphere, biphenyldiamine (5.0000 g, 27.14 mmol) and 50 ml DMF were added to a round bottom flaskStir until the diamine monomer is completely dissolved, slowly add BTDA (4.3723 g, 13.57 mmol), and add 18.0 ml DMF to dilute the solution.After 4 h at room temperature, 4-PEPA (6.7367 g, 27.14 mmol) was added.The reaction was continued for 12 hours to obtain a polyamic acid solution having a solid content of 20percent.Additional acetic anhydride (16.88 g, 165.36 mmol) and triethylamine (2.79 g, 27.56 mmol) were addedThe reaction was continued at room temperature for 12 hours for chemical imidization.After the reaction was completed, the solution was poured into a large amount of deionized water, the precipitate was filtered, and the filter cake was washed with water until the filtrate became neutral.The solid was dried in a vacuum oven at 120[deg.] C. for 12 h to give a yellow prepolymer, which was named "oligomer PI-BPA" (structure shown in FIG. 8).
  • 32
  • [ 89-32-7 ]
  • C22H36B20N2 [ No CAS ]
  • [ 119389-05-8 ]
  • C86H82B40N4O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Under a nitrogen atmosphere,The carborane-containing diamine monomer prepared in Example 1 was added to a round bottom flask.(5.0000g, 9.178mmol) and 20ml DMF,Stir until the diamine monomer is completely dissolved and slowly add PMDA (1.0009 g, 4.589 mmol) and add 11.7 ml DMF to dilute the solution.After 4 h at room temperature, 4-PEPA (2.2782 g, 9.178 mmol) was added.The reaction was continued for 12 hours to obtain a polyamic acid solution having a solid content of 20percent.Additional acetic anhydride (4.68 g, 45.9 mmol) and triethylamine (0.93 g, 9.19 mmol) were added to continue the chemical imidization at room temperature for 12 h.After the reaction is complete, pour the solution into a large volume of deionized water and filter the precipitate.The filter cake was washed with water until the filtrate became neutral. The solid was dried in a vacuum oven at 120°C for 12 h to give a yellow prepolymer, designated "oligomer PI-1-c".
  • 33
  • C22H36B20N2 [ No CAS ]
  • [ 119389-05-8 ]
  • C54H48B20N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Under a nitrogen atmosphere, a carborane-containing diamine monomer prepared in Example 1 (5.0000 g, 9.178 mmol) and 38 ml of DMF were added to a round bottom flask.Stir until the diamine monomer is completely dissolved, slowly add 4-PEPA (4.5566 g, 18.356 mmol), and rinse the bottle wall with 2.3 ml DMF,Reaction 12h to obtain a 20percent solids polyamic acid solution.Additional acetic anhydride (4.68 g, 45.9 mmol) and triethylamine (0.93 g, 9.19 mmol) were added to continue the chemical imidization at room temperature for 12 h.After the reaction was completed, the solution was poured into a large amount of deionized water, the precipitate was filtered, and the filter cake was washed with water until the filtrate became neutral.The solid was dried in a vacuum oven at 120°C for 12 h to give a yellow prepolymer, designated "oligomer PI-0".
  • 34
  • [ 23843-88-1 ]
  • [ 119389-05-8 ]
  • C60H31N3O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
To 1.00 g (4.65 mmol) of 2,4,4'-triaminodiphenyl ether, 18.78 g of dehydrated THF was added and stirred to completely dissolve.To this solution was added 4-phenylethynyl-1,2-dicarboxylic anhydride (product name: 4-PEPA, manufactured by Changzhou City Sunshine Co., Ltd.)(13.94 mmol), and the mixture was reacted at room temperature for 1 hour to obtain an amic acid solution D.An amic acid solution D was obtained in the same manner as in Example 4 except that NMP was used as a solvent. 10 g of a mixed solution of acetic anhydride: pyridine = 3: 7 (weight ratio) was added to the amic acid solution D, and stirred at room temperature for 1 hour to obtain an imide solution H.The imide solution H was gradually added dropwise to a mixed solvent of an excess amount of diethyl ether: cyclohexane = 1: 10 (weight ratio), and the precipitated crystals were separated by filtration to obtain crude crystals. The crude crystals were recrystallized from cyclohexanone, filtered and vacuum dried to obtain an imide compound represented by the formula (15). The structure was confirmed by 1 H-NMR and 13 C-NMR.
  • 35
  • [ 119389-05-8 ]
  • C16H10O3 [ No CAS ]
 

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