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CAS No. : | 31661-59-3 | MDL No. : | MFCD06200769 |
Formula : | C16H12N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FMZHYPYMCCZVCA-UHFFFAOYSA-N |
M.W : | 232.28 | Pubchem ID : | 15143342 |
Synonyms : |
|
Num. heavy atoms : | 18 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 75.45 |
TPSA : | 52.04 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.61 cm/s |
Log Po/w (iLOGP) : | 2.56 |
Log Po/w (XLOGP3) : | 2.97 |
Log Po/w (WLOGP) : | 2.43 |
Log Po/w (MLOGP) : | 3.3 |
Log Po/w (SILICOS-IT) : | 2.85 |
Consensus Log Po/w : | 2.82 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.64 |
Solubility : | 0.0527 mg/ml ; 0.000227 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.73 |
Solubility : | 0.0437 mg/ml ; 0.000188 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.37 |
Solubility : | 0.00993 mg/ml ; 0.0000428 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.45 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With pyrrolidine; 1-(4-nitrophenyl)-3-N,N-dimethylamino-2-propen-1-one; copper(ll) bromide; In dichloromethane; at 25℃; for 12h; | General procedure: To a 10 mL round bottom flask were employed terminal alkynes 0.6 mmol (for homo-coupling) or two different terminal alkynes 0.3 mmol each (for cross coupling),0.06 mmol CuBr2, 0.06 mmol L2 and 0.6 mmol pyrrolidine. Then dichloromethane (1 mL) was added and the resulting mixture was stirred at room temperature (25 C) for 12 h (TLC). The solvent was removed at reduced pressure and water (8 mL) was added, and the resulting mixture was extracted with ethyl acetate (8 mL 3). The organic phases were combined and dried with anhydrous Na2SO4. After removing solvent at reduced pressure, the residue was subjected to column chromatography or preparative TLC with petroleum ether as eluent to provide pure product. |
85% | With sodium acetate; silver sulfate; In dimethyl sulfoxide; at 90℃; for 9h; | General procedure: A mixture of alkyne 1 (0.2 mmol), nano-Pd (0.1 mol% Pd), Ag2SO4(30 mol%), NaOAc (1 equiv), and DMSO (1 mL) was stirred at 90 oC until complete consumption of starting material as judged by TLC. After the mixture was filtered and evaporated, the residue was purified by flash column chromatography to afford the product 2 (petroleum ether or petroleum ether/ethyl acetate). |
85% | With oxygen; caesium carbonate; In ethanol; at 80℃; for 8h; | General procedure: Glaser homo-coupling reaction was evaluated in a 25 mL round bottomed flask under constant magnetic stirring. Typically, a mixture of phenylacetylene (1 mmol), catalyst, base and solvent (2 mL) were added into round the bottomed flask. Subsequently O2 was introduced into the reaction system instead of air. The mixture solution was stirred at 80 C for 8 h. After the reaction was finished, the reaction solution was cooled down to room temperature naturally. The solid catalyst was centrifuged recovered and organic phase was extracted with ethyl acetate to get crude products. All crude products were purified by column chromatography to calculate the yields and identified by 1H NMR and 13C NMR spectra. |
84% | With [2,2]bipyridinyl; oxygen; copper(l) chloride; In N,N-dimethyl-formamide; at 50℃; for 3h; | General procedure: Phenylacetylene (102 mg, 1.0 mmol), 2,2'-Dipyridyl (15.6 mg, 10 mol%), CuCl (4.9 mg, 5 mol%) were added under ambient temperature to 1 mL of DMF in air. The reaction mixture was vigorously stirred under room temperature for 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction 2 mL H2O was added, the mixture was extracted with petroleum ether, concentrated under vacuum, purified by column chromatography over silica gel (petroleum ether) to afford 2a (109 mg, 99 % yield) as a white solid. |
84% | With copper(II) carboxymethylcellulose; In dimethyl sulfoxide; at 110℃; for 4h; | 0.3004 g (1 mmol) of copper(II) carboxymethylcelluloseAnd m-aminophenylacetylene0.5863 g (5 mmol),Add 10mL of dimethyl sulfoxide, stirring at 110 , TLC monitoring of the reaction process,After 4h, TLC monitoring, raw material point disappear,The reaction was stopped, filtered, the residue washed with ethyl acetate, the residue was filtered off to a brown color.The filtrate was extracted three times with deionized water,Vacuum distillation concentrated to give the crude product,The product was isolated by column chromatography0.4911g,Yield 84%, purity 97%. |
52% | With potassium tert-butylate; 1-n-butyl-3-methylimidazolim bromide; copper(II) trifluoroacetate hydrate name...; at 20℃; for 24h;Green chemistry; | General procedure: t-BuOK (0.2 mmol) was added to a mixture of Cu(CF3COO)2·H2O (0.1mmol), [BMIm][Br] (0.6 mmol), and THF (4 mL). The mixture wasreacted at 50 C for 3h. Then, the solvent was evaporated under reducedpressure, and phenylacetylene (0.5 mmol) was added. The mixture wasstirred under air at room temperature for 24 h.Gram-reaction was carried on under the similar conditions except 1.02g (10 mmol) 1b was used as substrate and with a longer reaction time(72h). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.6%; 7.3% | With sodium hydroxide; In water; toluene; at 90℃; for 1h;Product distribution / selectivity; | 3-ethynyl aniline was synthesized without using ascorbic acid in Example 1, and was taken out from distillation under reduced pressure (yield: 20.5 g, percent yield: 87.6%).When the distillation residue was analyzed by HPLC, 1,4-bis(3-aminophenyl)-1,3-butadiyne that is an oxidation by-product was detected. The amount thereof detected was 1.7 g (which amount corresponds to 7.3% in terms of yield). |
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