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[ CAS No. 91136-43-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 91136-43-5
Chemical Structure| 91136-43-5
Chemical Structure| 91136-43-5
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Quality Control of [ 91136-43-5 ]

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Product Details of [ 91136-43-5 ]

CAS No. :91136-43-5 MDL No. :MFCD17012437
Formula : C11H8O2 Boiling Point : -
Linear Structure Formula :- InChI Key :PLCQXZXTFCITAJ-UHFFFAOYSA-N
M.W : 172.18 Pubchem ID :13225222
Synonyms :

Calculated chemistry of [ 91136-43-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 51.36
TPSA : 37.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.08 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.43
Log Po/w (XLOGP3) : 1.79
Log Po/w (WLOGP) : 2.36
Log Po/w (MLOGP) : 1.82
Log Po/w (SILICOS-IT) : 2.64
Consensus Log Po/w : 2.01

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.54
Solubility : 0.498 mg/ml ; 0.00289 mol/l
Class : Soluble
Log S (Ali) : -2.19
Solubility : 1.11 mg/ml ; 0.00643 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.44
Solubility : 0.0622 mg/ml ; 0.000361 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 91136-43-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 91136-43-5 ]

* 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 [ 91136-43-5 ]

[ 91136-43-5 ] Synthesis Path-Downstream   1~42

  • 1
  • [ 2591-86-8 ]
  • [ 5498-31-7 ]
  • [ 91136-43-5 ]
  • 2
  • [ 3923-52-2 ]
  • [ 91136-43-5 ]
  • [ 227471-73-0 ]
  • 3
  • [ 91136-43-5 ]
  • [ 74-88-4 ]
  • [ 856204-26-7 ]
YieldReaction ConditionsOperation in experiment
45% Sodium hydride (115 mg, 2.64 mmol) was suspended in N,N-dimethylformamide (20 mL), and known <strong>[91136-43-5]3-hydroxy-1-naphthaldehyde</strong> [Tetrahedron, 1999, Vol. 55, p.5821-5830] (250 mg, 1.45 mmol) was added at 0C. After stirring for 30 minutes, iodomethane (230 muL, 3.69 mmoL) was added, and the mixture was stirred at room temperature for one hour. A saturated ammonium chloride aqueous solution (20 mL) was added to the reaction solution, followed by extraction with diethyl ether (50 mL). The organic layer was washed with brine and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate = 10/1) to give the target compound (122 mg, yield: 45%) as a light yellow solid. 1H-NMR (CDCl3, 500MHz):delta ppm: 4.86 (3H, s), 7.38 (1H, m), 7.55-7.51 (2H, m), 7.64 (1H, m), 7.79 (1H, m), 9.90 (1H, m), 10.35 (1H, s).
  • 4
  • [ 91136-43-5 ]
  • [ 79-44-7 ]
  • [ 925441-62-9 ]
YieldReaction ConditionsOperation in experiment
89% With pyridine; at 20℃; for 17h; Known <strong>[91136-43-5]3-hydroxy-1-naphthaldehyde</strong> [Tetrahedron, 1999, Vol. 55, p.5821-5830] (300 mg, 1.74 mmol) was dissolved in pyridine (3 mL). Dimethylcarbamoyl chloride (750 muL, 8.15 mmol) was added, and the mixture was stirred at room temperature for 17 hours. A saturated ammonium chloride aqueous solution (10 mL) was added to the reaction solution, followed by extraction with diethyl ether (40 mL). The organic layer was washed with brine and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate = 4/1) to give the target compound (378 mg, yield: 89%) as a light yellow oil. 1H-NMR (CDCl3,400MHz):delta ppm: 3.06 (3H, s), 3.17 (3H, s), 7.55 (1H, m), 7.62(1H, m), 7.85-7.80 (3H, m), 9.15 (1H, d, J=8.6Hz), 10.34 (1H, s). MS (EI) m/z: 243 (M+).
  • 5
  • [ 91136-43-5 ]
  • 6-(2,2-dicyanoethen-1-yl)-3,3-diphenyl-<3H>-naphtho<2,1-b>pyran [ No CAS ]
  • 6
  • [ 91136-43-5 ]
  • 6-(2-carboethoxy-2-cyanoethen-1-yl)-3,3-diphenyl-<3H>-naphtho<2,1-b>pyran [ No CAS ]
  • 7
  • [ 108-24-7 ]
  • [ 91136-43-5 ]
  • [ 925441-48-1 ]
YieldReaction ConditionsOperation in experiment
With pyridine; for 4h; Known <strong>[91136-43-5]3-hydroxy-1-naphthaldehyde</strong> [Tetrahedron, 1999, Vol. 55, p.5821-5830] (233 mg, 1.35 mmol) was dissolved in pyridine (10 mL) and acetic anhydride (5 mL), and the mixture was stirred for four hours. The solvent was evaporated under reduced pressure, and the resulting residue was directly used for the next reaction.
  • 8
  • [ 37595-74-7 ]
  • [ 91136-43-5 ]
  • 4-formyl-2-naphthyl trifluoromethanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
~ 100% Sodium hydride (1.38 g, 31.6 mmol) was suspended in tetrahydrofuran (100 mL), and known <strong>[91136-43-5]3-hydroxy-1-naphthaldehyde</strong> [Tetrahedron, 1999, Vol. 55, p.5821-5830] (3.50 g, 20.3 mmol) was added at 0C. After stirring for 30 minutes, N-phenyl-bis(trifluoromethanesulfonimide) (7.30 g, 20.4 mmoL) was added, and the mixture was stirred at 0C for 1.5 hours. A saturated ammonium chloride aqueous solution (100 mL) was added to the reaction solution, followed by extraction with diethyl ether (200 mL). The organic layer was washed with brine and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (elution solvent: hexane/diethyl ether = 5/1) to give the target compound (6.50 g, yield: ~100%) as a light yellow solid. 1H-NMR (CDCl3, 400MHz):delta ppm: 7.69 (1H, m), 7.77 (1H, m), 7.87 (1H, brd, J=2.7Hz), 7.95 (1H, brd, J=8.2Hz), 8.00 (1H, brd, J=2.7Hz), 9.17 (1H, d, J=8.6Hz), 10.42 (1H, s).
  • 9
  • [ 75-03-6 ]
  • [ 91136-43-5 ]
  • [ 1360448-73-2 ]
  • 10
  • [ 91136-43-5 ]
  • [ 925439-97-0 ]
  • 11
  • [ 91136-43-5 ]
  • C32H27NO9 [ No CAS ]
  • 12
  • [ 91136-43-5 ]
  • [ 925440-02-4 ]
  • 13
  • [ 91136-43-5 ]
  • [ 925440-03-5 ]
  • 14
  • [ 91136-43-5 ]
  • C33H31NO9 [ No CAS ]
  • 15
  • [ 91136-43-5 ]
  • C32H29NO9 [ No CAS ]
  • 17
  • [ 91136-43-5 ]
  • [ 1360448-84-5 ]
  • 18
  • [ 91136-43-5 ]
  • [ 1360448-85-6 ]
  • 22
  • [ 91136-43-5 ]
  • [ 925440-07-9 ]
  • 23
  • [ 91136-43-5 ]
  • [ 925441-49-2 ]
  • 24
  • [ 91136-43-5 ]
  • [ 925439-90-3 ]
  • 25
  • [ 91136-43-5 ]
  • [ 925439-89-0 ]
  • 26
  • [ 91136-43-5 ]
  • C30H27NO8 [ No CAS ]
  • 27
  • [ 91136-43-5 ]
  • [ 925439-96-9 ]
  • 29
  • [ 91136-43-5 ]
  • [ 603113-12-8 ]
  • [ 1402354-23-7 ]
  • 30
  • [ 5498-31-7 ]
  • [ 68-12-2 ]
  • [ 91136-43-5 ]
  • 31
  • [ 134-32-7 ]
  • [ 84-11-7 ]
  • [ 91136-43-5 ]
  • 1-(1-(naphthalen-1-yl)-1H-phenanthro[9,10-d]imidazol-2-yl)naphthalen-3-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With ammonium acetate; titanium(IV) oxide; at 120℃; General procedure: A mixture of hydroxyl naphthaldehyde (1mmol), phenanthrene-9,10-dione (1mmol), naphthylamine (1mmol), ammonium acetate (1mmol) and TiO2 (1mol%) was stirred at 120C with continuous stirring with a bar magnet. The progress of the reaction was monitored by TLC (Scheme S4). After completion of the reaction, 10ml ethyl acetate was added to the reaction mixture and shaken well to dissolve the organic components and the mass filtered to separate out TiO2 and the residue was washed with ethyl acetate. The solid TiO2 residue was further washed with hot acetone and then dried up. The product was purified by column chromatography using benzene:ethyl acetate (9:1) as the eluent. The newly synthesised phenanthrimidazoles have been characterized by 1H and 13C NMR and mass (MS) spectra.
  • 32
  • [ 91136-43-5 ]
  • [ 925441-50-5 ]
  • 33
  • [ 91136-43-5 ]
  • [ 925441-68-5 ]
  • 34
  • [ 91136-43-5 ]
  • [ 925441-56-1 ]
  • 35
  • [ 91136-43-5 ]
  • [ 925441-67-4 ]
  • 36
  • [ 141-97-9 ]
  • [ 57-13-6 ]
  • [ 91136-43-5 ]
  • C18H18N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With copper doped mesoporous silica MCM-41 supported dual acidic ionic liquid-HSO4; In ethanol; at 80℃; for 1h; General procedure: In a typical process, 0.05 mol aromatic aldehyde, 0.05 mol ethylacetoacetate, 0.05 mol urea, 10 mL EtOH, and 0.5 g (0.5)IL-HSO4MCM-41Cu(15) were mixed and stirred at 80 C for the desiredtime. After the completion of the reaction,monitored by LC-MS, the solutionwascooled down to roomtemperature and centrifugalized to obtainthe catalyst. The catalyst was washed with ethanol for reuse. Thefiltrate was concentrated under reduced pressure to give the correspondingpure product. Fresh substrates were then recharged to the recoveredcatalyst and then recycled under identical reaction conditions.The productswere identified by 1H NMR, LC-MS and Elemental analysis,and the characterization data and spectras are provided in thesupporting information.
  • 37
  • 4,4-difluoro-8-(4-amino-3-hydroxy-phenyl)-1,3,5,7- tetramethyl-4-bora-3a,4a-diaza-s-indacene [ No CAS ]
  • [ 91136-43-5 ]
  • C30H26BF2N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With acetic acid; In ethanol; for 5h;Inert atmosphere; Reflux; To the mixture of AP-BODIPY (72 mg, 0.2 mmol) and <strong>[91136-43-5]3-hydroxy-1-naphthaldehyde</strong> (40 mg, 0.24 mmol) dissolved in EtOH (20 ml), twodrops of glacial acetic acid were added under N2 atmosphere. The resulting reaction mixture was refluxed for 5 h and then cooled to roomtemperature. The red precipitate was filtrated and washed by EtOH.Recrystallization from CHCl3 and MeOH yielded pure sample of NAPBODIPYas red powder, 57 mg, 56%. 1H NMR (DMSO, 400 MHz): delta15.75 (d, 1H, J=8 Hz), 10.74 (s, 1H), 9.61 (d, 1H, J=12 Hz), 8.46 (d,1H, J=8 Hz), 8.18 (s, 1H, J=8 Hz), 7.84 (d, 1H, J=8 Hz), 7.70 (d,1H, J=8 Hz), 7.51 (t, 1H, J=12 Hz), 7.30 (t, 1H, J=12 Hz), 6.97 (d,1H, J=12 Hz), 6.92 (s, 1H), 6.82 (d, 1H, J=8 Hz), 6.21 (s, 2H), 2.46(s, 6H), 1.54 (s, 6H); 13C NMR (100 MHz, DMSO) delta178.2, 155.4, 140.0,149.6, 143.2, 141.8, 138.8, 134.3, 132.3, 131.1, 130.0, 129.5, 128.7,126.5, 125.4, 123.8, 121.9, 120.5, 119.8, 118.9, 115.6, 108.2, 14.7,14.6; MS (MALDI-TOF): one isotopic cluster peaking at m/z 509.13(Calcd. For M+ 509.21); Anal. Calcd for C30H26BF2N3O2: C, 70.74; H,5.15; N, 8.25. Found: C, 70.56; H, 5.31; N, 8.35.
Reference: [1]Dyes and Pigments,
  • 38
  • 4,4-difluoro-8-(4-amino-3-hydroxy-phenyl)-1,3,5,7- tetramethyl-4-bora-3a,4a-diaza-s-indacene [ No CAS ]
  • [ 91136-43-5 ]
  • C30H24BBiF2N3O2(1+) [ No CAS ]
Reference: [1]Dyes and Pigments,
  • 39
  • [ 91136-43-5 ]
  • (3-(pyrimidin-2-ylmethoxy)naphthalen-1-yl)methanol [ No CAS ]
  • 40
  • [ 91136-43-5 ]
  • 2-(((4-(chloromethyl)naphthalen-2-yl)oxy)methyl)pyrimidine [ No CAS ]
  • 41
  • [ 936643-80-0 ]
  • [ 91136-43-5 ]
  • 3-(pyrimidin-2-ylmethoxy)-1-naphthaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
250 mg With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; To a stirred a solution of 3 -hydroxy- l-naphthaldehyde (250 mg, 1.45 mmol) in DMF ( 6.0 mL) was added cesium carbonate (1.5 g, 4.36 mmol) followed by 2- (chloromethyl)pyrimidine hydrogen chloride (238 mg, 1.45 mmol). The reaction mixture was stirred at room temperature. After reaction completion, quenched with water and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and evaporated under reduced pressure to give the crude compound which purified using combi flash with 30% Ethyl acetate in Hexane as an eluent to get pure compound. 250 mg, LCMS: 265 (M+l)+.
  • 42
  • [ 109-04-6 ]
  • [ 91136-43-5 ]
  • C16H11NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
100 mg With 2-Picolinic acid; potassium phosphate; copper(l) iodide; In dimethyl sulfoxide; at 120℃; for 16h; To a stirred solution of 3 -hydroxy- l-naphthaldehyde (250 mg, 1.45 mmol) in DMSO, were added potassium phosphate (630 mg, 2.90 mmol), 2-bromopyridine (455 mg, 2.90 mmol) Copper iodide (26.6 mg, 0.14 mmol) and picolinic acid (17.2 mg, 0.14 mmol). Then the reaction mixture stirred at l20C for 16 h. After reaction completion, cooled to rt, quenched with water and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and evaporated under reduced pressure to give the crude compound which purified using combi flash with 25% Ethyl acetate in Hexane as an eluent to get pure compound 100 mg, LCMS: 250.1 (M+l)+.
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Technical Information

• 1,4-Addition of an Amine to a Conjugated Enone • 1,4-Addition of an Amine to a Conjugated Enone • 1,4-Additions of Organometallic Reagents • Acetal Formation • Acidity of Phenols • Add Hydrogen Cyanide to Aldehydes and Ketones to Produce Alcohols • Alcohol Syntheses from Aldehydes, Ketones and Organometallics • Aldehydes and Ketones Form Hemiacetals Reversibly • Aldehydes May Made by Terminal Alkynes Though Hydroboration-oxidation • Aldol Addition • Aldol Condensation • Alkenes React with Ozone to Produce Carbonyl Compounds • Alkylation of Aldehydes or Ketones • Amides Can Be Converted into Aldehydes • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Bucherer-Bergs Reaction • Chan-Lam Coupling Reaction • Clemmensen Reduction • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Complex Metal Hydride Reductions • Conjugate Additions of p-Benzoquinones • Conjugated Enone Takes Part in 1,4-Additions • Conversion of Amino with Nitro • Convert Aldonic Acid into the Lower Aldose by Oxidative Decarboxylation • Convert Esters into Aldehydes Using a Milder Reducing Agent • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Cyanohydrins can be Convert to Carbonyl Compounds under Basic Conditions • Decomposition of Arenediazonium Salts to Give Phenols • Deoxygenation of the Carbonyl Group • Deprotonation of a Carbonyl Compound at the α -Carbon • Deprotonation of Methylbenzene • Diazo Coupling • DIBAL Attack Nitriles to Give Ketones • Directing Electron-Donating Effects of Alkyl • Dithioacetal Formation • Electrophilic Chloromethylation of Polystyrene • Electrophilic Substitution of the Phenol Aromatic Ring • Enamine Formation • Enamines Can Be Used to Prepare Alkylated Aldehydes • Enol-Keto Equilibration • Etherification Reaction of Phenolic Hydroxyl Group • Exclusive 1,4-Addition of a Lithium Organocuprate • Fischer Indole Synthesis • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • Grignard Reaction • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Benzene • Halogenation of Phenols • Hantzsch Dihydropyridine Synthesis • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hemiaminal Formation from Amines and Aldehydes or Ketones • Henry Nitroaldol Reaction • HIO4 Oxidatively Degrades Vicinal Diols to Give Carbonyl Derivatives • Horner-Wadsworth-Emmons Reaction • Hydration of the Carbonyl Group • Hydride Reductions • Hydride Reductions of Aldehydes and Ketones to Alcohols • Hydride Reductions of Aldehydes and Ketones to Alcohols • Hydroboration of a Terminal Alkyne • Hydrogenation by Palladium on Carbon Gives the Saturated Carbonyl Compound • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Hydrolysis of Imines to Aldehydes and Ketones • Imine Formation from Amines and Aldehydes or Ketones • Julia-Kocienski Olefination • Knoevenagel Condensation • Kolbe-Schmitt Reaction • Leuckart-Wallach Reaction • Lithium Organocuprate may Add to the α ,β -Unsaturated Carbonyl Function in 1,4-Fashion • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nitration of Benzene • Nozaki-Hiyama-Kishi Reaction • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Alcohols to Carbonyl Compounds • Oxidation of Aldehydes Furnishes Carboxylic Acids • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Oxidation of Phenols • Passerini Reaction • Paternò-Büchi Reaction • Pechmann Coumarin Synthesis • Periodic Acid Degradation of Sugars • Petasis Reaction • Phenylhydrazone and Phenylosazone Formation • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Pyrroles, Furans, and Thiophenes are Prepared from γ-Dicarbonyl Compounds • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reduction of an Ester to an Aldehyde • Reductive Amination • Reductive Removal of a Diazonium Group • Reformatsky Reaction • Reimer-Tiemann Reaction • Reverse Sulfonation——Hydrolysis • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Selective Eduction of Acyl Chlorides to Produce Aldehydes • Stetter Reaction • Stobbe Condensation • Strecker Synthesis • Sulfonation of Benzene • Synthesis of 2-Amino Nitriles • Tebbe Olefination • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Cycloaddition of Dienes to Alkenes Gives Cyclohexenes • The Nitro Group Conver to the Amino Function • The Wittig Reaction • Thiazolium Salt Catalysis in Aldehyde Coupling • Thiazolium Salts Catalyze Aldehyde Coupling • Thiazolium Salts Catalyze Aldehyde Coupling • Ugi Reaction • Use 1,3-dithiane to Prepare of α-Hydroxyketones • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction
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; ;