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[ CAS No. 1951-38-8 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 1951-38-8
Chemical Structure| 1951-38-8
Chemical Structure| 1951-38-8
Structure of 1951-38-8 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 1951-38-8 ]

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Product Details of [ 1951-38-8 ]

CAS No. :1951-38-8 MDL No. :MFCD00134097
Formula : C9H8O5 Boiling Point : -
Linear Structure Formula :- InChI Key :ZRWAPLTWCQQSAN-UHFFFAOYSA-N
M.W : 196.16 Pubchem ID :4558811
Synonyms :

Calculated chemistry of [ 1951-38-8 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.11
Num. rotatable bonds : 3
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 46.85
TPSA : 83.83 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.82 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.66
Log Po/w (XLOGP3) : 0.95
Log Po/w (WLOGP) : 1.09
Log Po/w (MLOGP) : 0.95
Log Po/w (SILICOS-IT) : 0.65
Consensus Log Po/w : 0.86

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.77
Solubility : 3.3 mg/ml ; 0.0168 mol/l
Class : Very soluble
Log S (Ali) : -2.3
Solubility : 0.989 mg/ml ; 0.00504 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.28
Solubility : 10.4 mg/ml ; 0.0528 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.41

Safety of [ 1951-38-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1951-38-8 ]

* 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 [ 1951-38-8 ]

[ 1951-38-8 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 1004-66-6 ]
  • [ 1951-38-8 ]
YieldReaction ConditionsOperation in experiment
94% For example to a 500 mL round bottom flask charged with 170 mL of water and compound of formula 54, wherein R3, R4 and R5 are hydrogen, i.e., 2-methoxy-1,3-dimethylbenzene, (5 g, 36.7 mmol) was added KMnO4 (12.2 g, 77.2 mmol). The solution was heated to a gentle reflux using an oil bath until the purple color had disappeared (2 hour). Another batch of KMnO4 (12.2 g, 77.2 mmol) was added and the heating was continued until the purple color was destroyed (2-2.5 hour). The reaction mixture was cooled slightly and the precipitated oxides of manganese were filtered through Celite. After washing the precipitates with warm water (2×50 mL), the filtrate was concentrated under reduced pressure to about its original volume. This concentrated filtrate was acidified to pH 2.5 and the resulting fine white precipitate was filtered and dried overnight under reduced pressure on a high vacuum pump, yielding 2-methoxy isophthalic acid 55 as a white powder (6.8 g, 94% yield).1H-NMR (300 MHz, DMSO-d6) delta: 7.97 (d, 2H), 6.9 (t, 1H), 2.5 (s, 3H).
  • 2
  • [ 67639-61-6 ]
  • [ 1951-38-8 ]
  • 3
  • [ 26507-91-5 ]
  • [ 1951-38-8 ]
YieldReaction ConditionsOperation in experiment
85% To a mixture of 2-methoxy-3-methylbenzoic acid (75 gram, 0.45 mol) and water (4 L) in a 5 liter flask equipped with a mechanic stirrer and a heating mantle, sodium hydroxide (20 g, 0.5 mol) was added, and the mixture turned to be a clear solution. The solution was heated to 75 0C, and potassium permanganate (158 g, 1 mol) was added in several batches during 6 hrs. The resulting brown slurry was stirred overnight; in the meantime, the temperature of the reaction mixture was kept in the range of 80 - 85 0C.[0195] The oxidation process was monitored by proton NMR (in D2O-NaOD). If the characteristic peak of 3-methyl at 2.06 ppm in NMR was still recognizable, several grams more of potassium permanganate may be added to ensure the completion of the oxidation reaction. The slurry was then filtered to remove the large amount Of MnO2 and the filtrate was acidified with cone. HCl. It is noted that the precipitation of the crystalline product is slow. Pure product was obtained as snow- white crystals and was collected by filtration yield 75 grams, 85%. 1H NMR (500 MHz, DMSO-J6, 25 0C) delta: 3.79 (s, 3H, CH3), 7.24 (t, J = 7.5, IH, ArH), 7.79 (d, J = 7.5, 2H, ArH).
  • 4
  • [ 1951-38-8 ]
  • [ 606-19-9 ]
YieldReaction ConditionsOperation in experiment
95% In hydrogen iodide; Reference Example 119 2-Hydroxyisophthalic Acid A solution of <strong>[1951-38-8]2-methoxyisophthalic acid</strong> (1.0 g) in 55% hydriodic acid (10 ml) was heated at 80 C. for 1 hour. The reaction mixture was poured into iced water and the precipitate was collected by filtration to give the desired compound (0.9 g, yield 95%) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) delta ppm: 6.93 (1H, t, J=8.0), 7.96 (2H, d, J=8.0).
89% With hydrogen bromide; acetic acid; In water; for 48h;Reflux; 2-Methoxyisophthalic acid 5 (25 g, 0.127 mol) was dissolved in a 1 : 1 mixture of 48% HBr and glacial acetic acid (700 mL) in a 1 L round bottom flask. The mixture was heated at reflux for 48 hr, whereupon the 2-hydroxyisophthalic acid deposited after cooling as slight pink crystals. These were collected by filtration and dried in vacuo to provide 2-hydroxyisophthalic acid (20.5 g, 89%). 1H NMR (500 MHz, DMSO-d6, 25 C) delta: 6.942 (t, J = 7.5, 1H, ArH), 7.950 (d, J = 7.5, 1H, ArH), 10.51 (s, br, 1H, phenol H). 13C NMR (500 MHz, DMSO-d6, 25 C) delta: 117.19, 118.21, 135.66, 161.25, 169.24.
With hydrogen bromide; sodium iodide; In water; at 100℃; for 2h; Synthesis of dimethyl-2-hydroxyisophthalic acid: 200 mg of <strong>[1951-38-8]2-methoxyisophthalic acid</strong> was placed in a screw cap vial with 1.1 equivalents of sodium iodide and 10 mL of hydrogen bromide solution (48%). The vial was sealed and heated to 100 C. in a water bath for 2 hours. The white precipitate was isolated by centrifugation and washed with dilute aqueous hydrochloric acid solution. The methyl diester was synthesized by reaction with methanol (100 mL) and concentrated sulfuric acid (10 mL) refluxing for 3 hours. The methanol was then removed by rotary evaporation and the mixture was partitioned between water and ethyl acetate. The organic layer was isolated, dried with sodium sulfate and concentrated to a white solid, which was purified by silica gel chromatography eluting with a hexane/ethyl acetate gradient. Acetal 3 (FIG. 1) was synthesized by alkylation of chloromethyl menthol (0.5 equivalent from Aldrich) in dimethylformamide using sodium hydride (1 equivalent) as a base. The diester acetal was converted to diacid acetal by 5 eq potassium hydroxide in methanol. After 3 hours, the ortho carboxy phenolate acetal 3 was purified by reverse phase HPLC using a C18 column using methanol and water containing 0.1 wt % ammonium carbonate as eluents.
  • 5
  • [ 606-19-9 ]
  • [ 77-78-1 ]
  • [ 1951-38-8 ]
  • 6
  • [ 109-79-5 ]
  • [ 1951-38-8 ]
  • 2-Methoxy-benzene-1,3-dicarbothioic acid di-S-butyl ester [ No CAS ]
  • 7
  • [ 124-38-9 ]
  • [ 38474-03-2 ]
  • [ 2206-43-1 ]
  • [ 1951-38-8 ]
  • 8
  • [ 1951-38-8 ]
  • [ 2390-40-1 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride;N,N-dimethyl-formamide; In 1,4-dioxane;Heating / reflux; To a solution of 2-methyoxyisophthalic acid E-2 (75 g, 0.41 mol) in dry dioxane, thionyl chloride (119 g, 1 mol) and a drop of DMF were added with stirring. The mixture was refluxed overnight under N2, then all the volatiles were removed by reduced pressure distillation, the residue was dried under vacuum (0.1 mm Hg) for at least 8 h. This moisture sensitive compound is pure enough for the next reaction step.
With thionyl chloride; N,N-dimethyl-formamide; In 1,4-dioxane; for 16h;Reflux; Inert atmosphere; To a stirred suspension of<strong>[1951-38-8]2-methoxyisophthalic acid</strong> (a) (5.00 g, 25.5 mmol) in 50ml of 1,4-dioxane was carefully added thionyl chloride (6.5 ml, 89.3 mmol) and 50 111 ofanhydrous dimethylformamide. The reaction was heated, and refluxed for 16 hours under aninert atmosphere. Once cooled, the reaction was concentrated by rotary evaporation whichhad been flushed with argon, and immediately dried under high vacuum for 16 hours. The crude acid chloride (b) was dissolved in 62 ml of anhydrous dichloromethane and cooled to -78 C. A solution ofthiazolidine-2-thione (6.70 g, 56.1 mmol) and triethylamine (7.0 ml,50.2 mmol) dissolved in 85 ml of anhydrous dichloromethane was added dropwise at thattemperature, and the reaction was stirred at room temperature for 16 hours under an inertatmosphere. The bright yellow reaction mixture was washed with brine, 10% hydrochloric acid (aq.), and twice with 10% sodium hydroxide (aq.). The combined organics were driedover sodium sulfate and concentrated in vacuo. The crude material was purified via flashchromatography (silica gel, 120g, 15-70% ethyl acetate/hexane) to provide (2-methoxy-1,3-phenylene)bis((2-thioxothiazolidin-3-yl)methanone) (c) (6.56 g, 77% yield) as a yellowpowder. 1HNMR (499 MHz, Chloroform-d) 8 7.43 (d, J= 7.6 Hz, 2H), 7.13 (t, J= 7.7 Hz,1H), 4.59 (t, J = 7.3 Hz, 4H), 3.90 (s, 3H), 3.41 (t, J = 7.3 Hz, 4H); MS: mass calculated forC1sH14N203S4: 397.99; found: positive: 399.7 (M+Ht, 421.6 (M+Nat.
  • 10
  • [ 1951-38-8 ]
  • C9H8(2)H4O3 [ No CAS ]
  • 11
  • [ 1951-38-8 ]
  • [ 109-89-7 ]
  • [ 98360-99-7 ]
  • 12
  • [ 7647-01-0 ]
  • [ 1951-38-8 ]
  • [ 606-19-9 ]
  • 13
  • [ 1951-38-8 ]
  • potash [ No CAS ]
  • [ 606-19-9 ]
  • 15
  • [ 141778-90-7 ]
  • aqueous KOH-solution [ No CAS ]
  • potassium permanganate [ No CAS ]
  • [ 1951-38-8 ]
  • 16
  • [ 774236-28-1 ]
  • [ 1951-38-8 ]
  • N,N'-bis[2,4-dimethoxy-5-[2-methoxy-3-[2,4-dimethoxy-5-(2-methoxybenzoylamino)benzoylamino]]phenyl]-2-methoxyisophthalamide [ No CAS ]
  • 17
  • [ 1951-38-8 ]
  • [ 1129-15-3 ]
  • [ 774236-27-0 ]
  • 18
  • [ 1951-38-8 ]
  • [ 74-88-4 ]
  • [ 288099-33-2 ]
  • 19
  • 4,6-dibutoxy-benzene-1,3-diamine [ No CAS ]
  • [ 1951-38-8 ]
  • <i>N</i>,<i>N</i>'-bis-(5-amino-2,4-dibutoxy-phenyl)-2-methoxy-isophthalamide [ No CAS ]
  • 20
  • [ 935510-49-9 ]
  • [ 1951-38-8 ]
  • [ 935510-50-2 ]
  • 21
  • [ 939374-76-2 ]
  • [ 1951-38-8 ]
  • C69H88N8O27 [ No CAS ]
  • 22
  • [ 134469-06-0 ]
  • [ 1951-38-8 ]
  • (2-methoxy-1,3-phenylene)bis[(2-thioxothiazolidin-3-yl)methanone] [ No CAS ]
YieldReaction ConditionsOperation in experiment
29% With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 5h;Inert atmosphere; (2-Methoxy-l,3-phenylene)bis((2-thioxothiazolidin-3-yl)methanone) (29): The synthesis of this compound was adapted from a literature procedure (Cohen, S. M. et al. Inorg. Chem. 1999, 38, 4522). To a solution of <strong>[1951-38-8]2-methoxyisophthalic acid</strong> (2.7 g, 13.8 mmol) (28) in 120 mL of CH2CI2 was added thiazolidine-2-thione (3.3 g, 28 mmol), a catalytic amount of N,N- dimethylaminopyridine (DMAP), and N,N -dicyclohexylcarbodiimide (DCC, 5.7 g, 28 mmol) at room temperature. The mixture was stirred for 5 h under nitrogen. The solution was then filtered and the solvent was removed from the filtrate under vacuum. The compound was purified via flash silica column chromatography using CH2C12 as eluant to give the product as a bright yellow solid (1.6 g, 3.9 mmol). Yield = 29%. 1H NMR (400 MHz, CDC13, 25 C): delta = 3.42 (t, J=8.0 Hz, 4H), 3.90 (s, 3H), 4.60 (t, J=8.0 Hz, 4H), 7.14 (t, J=8.0 Hz, 1H; ArH), 7.43 (d, J=4.0 Hz, 2H; ArH). ESI-MS(+) m/z 398.67 [M+H]+.
  • 23
  • [ 1951-38-8 ]
  • C31H35N3O9 [ No CAS ]
  • 24
  • [ 1951-38-8 ]
  • [ 1020092-51-6 ]
  • 25
  • [ 1951-38-8 ]
  • [ 916922-80-0 ]
  • 26
  • [ 1951-38-8 ]
  • [ 916922-79-7 ]
  • 28
  • [ 1951-38-8 ]
  • <i>N</i>,<i>N</i>'-bis-[5-(5-acetylamino-2-methoxy-benzoylamino)-2,4-dibutoxy-phenyl]-2-methoxy-isophthalamide [ No CAS ]
  • 29
  • [ 576-26-1 ]
  • [ 1951-38-8 ]
  • 30
  • [ 1951-38-8 ]
  • [ 900150-09-6 ]
  • 31
  • [ 1951-38-8 ]
  • [ 900150-13-2 ]
  • 32
  • [ 1951-38-8 ]
  • [ 900150-11-0 ]
  • 33
  • [ 1951-38-8 ]
  • [ 512780-13-1 ]
  • 34
  • [ 1951-38-8 ]
  • [ 865357-79-5 ]
  • 35
  • [ 1951-38-8 ]
  • 2-hydroxy-N,N'-bis-[2-(2,2,2-triphenyl-acetylamino)-ethyl]-isophthalamide [ No CAS ]
  • 36
  • [ 1951-38-8 ]
  • [ 774236-28-1 ]
  • 37
  • [ 1951-38-8 ]
  • N,N'-bis[2,4-dimethoxy-5-(2-methoxybenzoylamino)phenyl]-2-methoxyisophthalamide [ No CAS ]
  • 38
  • [ 1951-38-8 ]
  • N,N'-(4,6-dimethoxy-m-phenylene)bis[2-methoxy-3-[2,4-dimethoxy-5-(2-methoxybenzoylamino)phenyl]aminocarbonyl]benzamide [ No CAS ]
  • 39
  • [ 1951-38-8 ]
  • N1,N3-bis(5-(5-ethynyl-2-(n-octyloxy)benzamido)-2,4-dimethoxyphenyl)-2-methoxyisophthalamide [ No CAS ]
  • 40
  • [ 1951-38-8 ]
  • N,N'-di-((2-methoxybenzoyl)amino)-2-methoxy-iso-phthalamide [ No CAS ]
  • 41
  • [ 1951-38-8 ]
  • [ 16281-43-9 ]
  • 42
  • [ 1951-38-8 ]
  • [ 216967-80-5 ]
  • 43
  • [ 1951-38-8 ]
  • [ 216967-83-8 ]
  • 44
  • [ 1951-38-8 ]
  • <i>N</i>1,<i>N</i>1,<i>N</i>3,<i>N</i>3-tetraethyl-4-(2-hydroxy-propyl)-2-methoxy-isophthalamide [ No CAS ]
  • 45
  • [ 1951-38-8 ]
  • [ 216967-81-6 ]
  • 46
  • [ 1951-38-8 ]
  • N-[(3RS)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-isochromen-7-yl]-carbonyl}-L-phenylalanine [ No CAS ]
  • 47
  • [ 1951-38-8 ]
  • ochratoxin B amide [ No CAS ]
  • 48
  • [ 1951-38-8 ]
  • 2,6-bis(bromomethyl-d2)anisole [ No CAS ]
  • 49
  • [ 1951-38-8 ]
  • C32H38(2)H8N6O4 [ No CAS ]
  • 50
  • [ 1951-38-8 ]
  • [ 140362-01-2 ]
  • 51
  • [ 1951-38-8 ]
  • [ 103867-89-6 ]
  • 52
  • [ 1951-38-8 ]
  • 2-methoxy-1,3-diacetylbenzene [ No CAS ]
  • 53
  • [ 1951-38-8 ]
  • [ 127154-55-6 ]
  • 54
  • [ 1951-38-8 ]
  • [ 875257-33-3 ]
  • 55
  • [ 1951-38-8 ]
  • [ 127154-53-4 ]
  • 56
  • [ 1951-38-8 ]
  • [ 127154-54-5 ]
  • 58
  • [ 83-40-9 ]
  • [ 1951-38-8 ]
  • 59
  • [ 1951-38-8 ]
  • [ 420-37-1 ]
  • [ 36727-13-6 ]
YieldReaction ConditionsOperation in experiment
330 mg (90%) With N-ethyl-N,N-diisopropylamine; In dichloromethane; Example 4 Dimethyl 2-methoxyisophthalate 2-Methoxyisophthalic acid (320 mg, 1.63 mmol) was suspended in CH2 Cl2 (6 ml) and N,N-diisopropylethylamine (0.68 ml, 3.9 mmol, 2.4 equiv.) was added. After 5 minutes, trimethyloxonium tetrafluoroborate (615 mg, 2.6 equiv.) was added, and the reaction mixture was stirred for 1 hour at room temperature. After evaporation of the solvent, column chromatography with 3:7 EtOAc:petroleum ether gave the product as a white solid. Yield: 330 mg (90%). 1 H NMR (CDCl3) delta: 7.93 (d, 2 H, aryl), 7.21 (t, 1 H, aryl), 3.94 (s, 9 H, OCH3 and CO2 CH3).
  • 60
  • [ 1031691-47-0 ]
  • [ 1951-38-8 ]
  • [ 1031691-48-1 ]
  • 61
  • copper(II) nitrate trihydrate [ No CAS ]
  • [ 1951-38-8 ]
  • [ 68-12-2 ]
  • [Cu2(2-methoxy-1,3-benzenedicarboxylate)2(DMF)2].infin. [ No CAS ]
  • 62
  • [ 67-56-1 ]
  • [ 1951-38-8 ]
  • [ 36727-13-6 ]
YieldReaction ConditionsOperation in experiment
82% With thionyl chloride; at 0 - 20℃; for 16h;Inert atmosphere; Under an atmosphere of Ar, SOCl2 (0.4 mL, 5.5 mmol) was added dropwise at 0 C to 2-methoxyiso-phthalic acid 3 (500 mg, 2.5 mmol) in anhydrous methanol (4 mL). The reaction mixture was then allowed to reach room temperature. After stirring overnight, the reaction mixture was evaporated under reduced pressure. The crude residue was then dissolved in AcOEt. This organic layer was successively washed with a saturated aqueous solution of NaHCO3 and water. After drying with MgSO4, the solvent was evaporated under reduced pressure to afford 4 (468 mg, 82%), which was used in the next step without further purification. Mp and 1H NMR were in agreement with the literature values.
  • 63
  • [ 1198616-71-5 ]
  • [ 1951-38-8 ]
  • [ 1198616-66-8 ]
  • 64
  • [ 1096836-13-3 ]
  • [ 1951-38-8 ]
  • [ 1318209-01-6 ]
YieldReaction ConditionsOperation in experiment
52% General procedure: The aryl carboxylic acid monomer (6 mmol, comp. 4-6), Mukaiyama reagent (6 mmol) and Et3N (12 mmol) were dissolved in an anhydrous dichloromethane (100 mL). The solution was refluxed for 15 min. under N2. Then a solution of the corresponding arylamine (5 mmol, comp. 7-9) in an anhydrous dichloromethane (20 mL) was added to the reaction mixture and resulting solution was refluxed for 2 days. The solvent was evaporated under vacuum and the residue was subjected to the column of silica gel using the mixture of hexanes/ dichloromethane (2:3) as an eluent to give amide coupling products in moderate to good yields. Note: for the synthesis of 18, 2.5 eq. of corresponding aryl amine over <strong>[1951-38-8]2-methoxyisophthalic acid</strong> was used.
  • 65
  • [ 31949-21-0 ]
  • [ 1951-38-8 ]
  • [ 1315312-63-0 ]
  • 66
  • [ 1951-38-8 ]
  • [ 1315312-64-1 ]
  • 67
  • [ 1951-38-8 ]
  • 2,6-bis(4-(2-hydroxyphenyl)imidazol-2-yl)phenol sesquihydroiodide [ No CAS ]
  • 68
  • [ 1951-38-8 ]
  • [ 1233346-14-9 ]
  • 69
  • [ 1951-38-8 ]
  • [ 1233346-21-8 ]
  • 70
  • [ 1951-38-8 ]
  • [ 1233346-16-1 ]
  • 71
  • [ 1951-38-8 ]
  • (2-methoxy-1,3-phenylene)bis[(2-thioxothiazolidin-3-yl)methanone] [ No CAS ]
  • 73
  • [ 1951-38-8 ]
  • [ 1350895-00-9 ]
  • 74
  • [ 1951-38-8 ]
  • [ 1350895-01-0 ]
  • 75
  • [ 1951-38-8 ]
  • [ 1350895-02-1 ]
  • 76
  • [ 1951-38-8 ]
  • [ 1350895-03-2 ]
  • 77
  • [ 1951-38-8 ]
  • [ 1350895-04-3 ]
  • 78
  • [ 1951-38-8 ]
  • [ 1364917-04-3 ]
  • 79
  • [ 1951-38-8 ]
  • N1,N1'-(((2-(2-iodoacetamido)ethyl)azanediyl)bis(ethane-2,1-diyl))bis(2-hydroxy-N3-methylisophthalamide) [ No CAS ]
  • 80
  • [ 1951-38-8 ]
  • [ 1364917-03-2 ]
  • 81
  • [ 1951-38-8 ]
  • [ 1392440-39-9 ]
  • 82
  • [ 1951-38-8 ]
  • [ 1392440-41-3 ]
  • 83
  • [ 1951-38-8 ]
  • [ 1392440-42-4 ]
  • 85
  • [ 1951-38-8 ]
  • [ 1417905-51-1 ]
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