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CAS No. : | 2170-06-1 | MDL No. : | MFCD00054860 |
Formula : | C11H14Si | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UZIXCCMXZQWTPB-UHFFFAOYSA-N |
M.W : | 174.31 | Pubchem ID : | 137464 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.27 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 56.67 |
TPSA : | 0.0 Ų |
GI absorption : | Low |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.44 cm/s |
Log Po/w (iLOGP) : | 2.9 |
Log Po/w (XLOGP3) : | 4.12 |
Log Po/w (WLOGP) : | 3.0 |
Log Po/w (MLOGP) : | 3.76 |
Log Po/w (SILICOS-IT) : | 1.87 |
Consensus Log Po/w : | 3.13 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.89 |
Solubility : | 0.0226 mg/ml ; 0.00013 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.83 |
Solubility : | 0.026 mg/ml ; 0.000149 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.74 |
Solubility : | 0.0316 mg/ml ; 0.000181 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.57 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
80% | In dichloromethane for 48h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With dichloromethane In toluene at 80℃; | |
55% | With dichloromethane In toluene at 80℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | Stage #1: 1-Phenyl-2-(trimethylsilyl)acetylene With Schwartz's reagent In tetrahydrofuran at 20℃; for 0.5h; Stage #2: methylsulphinyl chloride In tetrahydrofuran at 40℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With zinc(II) chloride In 1,4-dioxane at 100℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With bis(1,5-cyclooctadiene)nickel (0) In toluene at 100℃; for 35h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With triethylamine; lithium chloride;palladium diacetate; In N,N-dimethyl-formamide; at 100℃; for 3h; | <strong>[123158-75-8]2-Amino-5-chloro-3-nitro-phenyliodide</strong> (1.5 g, 4.90 mmol) prepared in <n="51"/>Preparation 19 and l-phenyl-2-trimethylsilylacetylene (4.3 g, 24.50 mmol) were dissolved in DMF (50 rnL). Palladium acetate (0.11 g, 0.5 mmol), lithium chloride (0.21 g, 4.90 mmol) and triethylamine (2.48 g, 24.50 mmol) were added thereto, and the mixture was stirred under heating for 3 h to 100C . After completion of the reaction, water was added to the reaction mixture, which was then extracted with ethyl acetate, washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the title compound (1.05 g, Yield 87%). 1H-NMR (400HMz, CDCl3); delta 9.78(br s, IH), 8.15(s, IH), 7.78(s, IH),7.38~7.48(m, 5H), 0.26(s, 9H) |
87% | With triethylamine; lithium chloride;palladium diacetate; In N,N-dimethyl-formamide; at 100℃; for 3h; | Preparation 41: 5-Chloro-3-phenyl-7-nitro-1H-indoleStep A: 5-Chloro-7-nitro-3-phenyl-2-trimethylsilyl-1H-indole; <strong>[123158-75-8]2-Amino-5-chloro-3-nitro-phenyliodide</strong> (1.5 g, 4.90 mmol) prepared in Preparation 19 and 1-phenyl-2-trimethylsilylacetylene (4.3 g, 24.50 mmol) were dissolved in DMF (50 mL). Palladium acetate (0.11 g, 0.5 mmol), lithium chloride (0.21 g, 4.90 mmol) and triethylamine (2.48 g, 24.50 mmol) were added thereto, and the mixture was stirred under heating for 3 h to 100 C. After completion of the reaction, water was added to the reaction mixture, which was then extracted with ethyl acetate, washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the title compound (1.05 g, Yield 87%).1H-NMR (400 MHz, CDCl3); delta 9.78(br s, 1H), 8.15(s, 1H), 7.78(s, 1H), 7.387.48(m, 5H), 0.26(s, 9H) |
87% | With triethylamine; lithium chloride;palladium diacetate; In N,N-dimethyl-formamide; at 100℃; for 3h; | (Step 2)<strong>[123158-75-8]2-Amino-5-chloro-3-nitro-phenyliodide</strong> (1.5 g, 4.90 mmol) obtained in Step 1 and 1-phenyl-2-trimethylsilylacetylene (4.3 g, 24.50 mmol) were dissolved in DMF (50 mL), and thereto palladium acetate (0.11 g, 0.5 mmol), lithium chloride (0.21 g, 4.90 mmol) and triethylamine (2.48 g, 24.50 mmol) were added. The mixture was heated under stirring for 3 hours at 100 C. At the end of reaction, added water and extracted with ethylacetate. The extract was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and filtered. The solvent was removed under reduced pressure and the residue was separated by column chromatography to give 5-chloro-7-nitro-3-phenyl-2-trimethylsilyl-1H-indole (1.05 g, Yield 87%).1H-NMR (400 MHz, CDCl3); delta 9.78 (br s, 1H), 8.15 (s, 1H), 7.78 (s, 1H), 7.387.48 (m, 5H), 0.26 (s, 9H) |
87% | With palladium diacetate; triethylamine; lithium chloride; In N,N-dimethyl-formamide; at 100℃; for 3h; | <strong>[123158-75-8]2-Amino-5-chloro-3-nitro-phenyliodide</strong> (1.5 g, 4.90 mmol) prepared in Preparation 19 and 1-phenyl-2-trimethylsilylacetylene (4.3 g, 24.50 mmol) were dissolved in DMF (50 mL). Palladium acetate (0.11 g, 0.5 mmol), lithium chloride (0.21 g, 4.90 mmol) and triethylamine (2.48 g, 24.50 mmol) were added thereto, and the mixture was stirred under heating for 3 h to 100 C. After completion of the reaction, water was added to the reaction mixture, which was then extracted with ethyl acetate, washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the title compound (1.05 g, Yield 87%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With Potassium benzoate; triphenylphosphine; copper(l) chloride In 1,3-dimethyl-2-imidazolidinone at 120℃; for 12h; Inert atmosphere; | |
69% | With tetrakis(triphenylphosphine) palladium(0); copper(l) chloride In N,N-dimethyl-formamide at 80℃; for 3h; | |
69% | With tetrakis(triphenylphosphine) palladium(0); copper(l) chloride In N,N-dimethyl-formamide at 80℃; for 3h; Inert atmosphere; | 4.3. General procedure for synthesis of unsymmetrically disubstituted ethynes with aryl iodides. Formation of (4-methoxyphenyl)(phenyl)ethyne (3a)29a General procedure: To a solution of CuCl (50 mg, 0.5 mmol, 50 mol %), tetrakis(triphenylphosphine)palladium (58 mg, 0.05 mmol, 5 mol %), and 4-iodoanisole (2a) (234 mg, 1 mmol) in DMF (5 mL) in a 20 mL of Schlenk tube was added trimethyl(phenylethynyl)silane (1a) (0.39 mL, 2 mmol). The reaction mixture was stirred for 3 h at 80 °C, quenched with 1.0 M HCl, and extracted with diethyl ether (20 mL×3). The combined ethereal layer was washed with brine and dried over MgSO4. Filtration and evaporation afforded a dark yellow oil. Column chromatography (silica gel, hexane/diethyl ether=9:1, Rf=0.14) gave the title compound (197 mg, 0.84 mmol, 84% yield) as white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With tetrakis(triphenylphosphine) palladium(0); copper(l) chloride; In N,N-dimethyl-formamide; at 80℃; for 3h;Inert atmosphere; | General procedure: To a solution of CuCl (50 mg, 0.5 mmol, 50 mol %), tetrakis(triphenylphosphine)palladium (58 mg, 0.05 mmol, 5 mol %), and 4-iodoanisole (2a) (234 mg, 1 mmol) in DMF (5 mL) in a 20 mL of Schlenk tube was added trimethyl(phenylethynyl)silane (1a) (0.39 mL, 2 mmol). The reaction mixture was stirred for 3 h at 80 C, quenched with 1.0 M HCl, and extracted with diethyl ether (20 mL×3). The combined ethereal layer was washed with brine and dried over MgSO4. Filtration and evaporation afforded a dark yellow oil. Column chromatography (silica gel, hexane/diethyl ether=9:1, Rf=0.14) gave the title compound (197 mg, 0.84 mmol, 84% yield) as white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With Potassium benzoate; triphenylphosphine; copper(l) chloride In 1,3-dimethyl-2-imidazolidinone at 120℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; benzyltri(n-butyl)ammonium chloride; sodium hydroxide; tri tert-butylphosphoniumtetrafluoroborate In water; toluene at 40℃; for 22h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With silver nitrate; In tetrahydrofuran; water; at 20℃; for 26h;Inert atmosphere; | General procedure: To a suspension of AgNO3 (0.187 g, 1 mmol) and p-tosylchloride 3a (95 mg, 0.5 mmol) in THF (10 mL) under nitrogen atmosphere, was added trimethylsilyl phenylacetylene 1a (1 mmol, 0.174 g, 196 muL). The resulting mixture was stirred at 20 C for 24 h. The reaction progress was monitored by analytical TLC. Following filtration, the filtrate was concentrated under reduced pressure to afford a crude residue. Purification of the crude residue by column chromatography using 25% (v/v) ethyl acetate-petroleum ether as the eluant afforded a colorless solid 5a, a mixture of Z-5a and E-5a(68 mg, 53% yield, 2:1 molar ratio of Z-5a to E-5a). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With 1,3-dimethyl-2-imidazolidinone; 4,4?,5,5?-Tetrahydro-2,2?-bioxazole; copper(l) chloride; In water; acetic acid; at 60℃; for 18h; | General procedure: 4.2. Typical procedure hydrosulfonylation of alkynes (Table 2 ): To a mixture of CuCl (1.5 mg, 0.015 mmol), 2,2'-bis(2-oxazoline) (2.1 mg, 0.015 mmol), and PhSO2Na (54.2 mg, 0.33 mmol), in DMI (0.1 mL), H2O (0.1 mL), and AcOH (0.1 mL) were added phenylacetylene (30.6 mg, 0.3 mmol), and the mixture was stirred at 60 C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with H2O and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (40% diethyl ether/hexane) gave (E)-1-phenylsulfonyl-2-phenylethene (61.8 mg, 85%):1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 79 %Spectr. 2: 7 %Spectr. | With [{Ir(H)((rac)-BINAP)}2(μ-Cl)3]Cl; hydrogen In 1,4-dioxane at 80℃; for 16h; | General procedure for the Ir-catalyzed semi-hydrogenation of alkynes General procedure: Iridium dinuclear complex (2.4 mol, 1.0 mol%) and alkyne (0.24 mmol) were added to a glasstube in the reactor and the tube was charged with argon gas. Dry 1,4-dioxane (1.5 mL) was addedinto a glass tube in the reactor, and replaced argon gas with H2 gas. The reaction mixture wasstirred for periodic time under optimal conditions. After removal of solvent, the mixture andphenanthrene were dissolved into CDCl3. Yield was determined by 1H NMR analysis usingphenanthrene as an internal standard and reference to literatures. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Oxone; potassium chloride / acetonitrile; water / 0.5 h / 20 °C 2: triethylamine / acetonitrile; water / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With cobalt acetylacetonate In acetonitrile at 80℃; for 12h; Sealed tube; regioselective reaction; | Typical Procedure for a Cobalt-Catalyzed [3+2] Regioselective Annulation of Ortho-Formyl and Acetyl Phenylboronic Acids with Alkynes: General procedure: A 25 mL sealed tube equipped with a magnetic stirring bar was charged with Co(acac)2 (0.05 mmol, 10 mol%), DPPE (0.05 mmol, 10 mol%), ortho-formylphenylboronic acid 1a (0.75 mmol, 1.5 equiv), an alkyne 2d (0.50 mmol, 1.0 equiv), and MeCN (2 mL). The reaction mixture was stirred at 80 °C for 12 h. The mixture was then filtered through silica gel pad. The filtrate was concentrated, and the residue was purified by column chromatography on silica gel to yield the desired product 3d as a yellow solid in 72% yield (121.6 mg, 0.359 mmol) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]gold bis(trifluoromethanesulfonyl)imidate In chloroform-d1 for 18h; Inert atmosphere; Sealed tube; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With silver hexafluoroantimonate; carbonyl(pentamethylcyclopentadienyl)cobalt diiodide In 1,2-dichloro-ethane at 120℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With boron trifluoride diethyl etherate; In dichloromethane; for 16h;Inert atmosphere; Reflux; | General procedure: To a mixture of 5-nitrosalicylaldehyde (30.0 mmol), trimethylsilylethynylbenzene (60.0 mmol) and trimethyl orthoformate (30.0 mmol) in dry CH2Cl2 (80 mL) under nitrogen, boron trifluoride etherate (20 mol%) was added. After being stirred at reflux for 16 h, the reaction mixture was quenched with 5% aq. NaHCO3. The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organic layer were washed with brine, dried over MgSO4, and filtered. The filtrate was concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel (hexane / EtOAc = 20 : 1) to afford product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With 1,4-bis((4S,5S)-1,3-bis(3,5-di-tert-butylbenzyl)-4,5-diphenylimidazolidin-2-ylidene)piperazine-1,4-diium dichloride; cesium fluoride In diethyl ether at 0℃; for 72h; stereoselective reaction; |
Tags: 2170-06-1 synthesis path| 2170-06-1 SDS| 2170-06-1 COA| 2170-06-1 purity| 2170-06-1 application| 2170-06-1 NMR| 2170-06-1 COA| 2170-06-1 structure
[ 38170-80-8 ]
1,3-Bis((trimethylsilyl)ethynyl)benzene
Similarity: 1.00
[ 275386-60-2 ]
(4-((Trimethylsilyl)ethynyl)phenyl)methanol
Similarity: 0.81
[ 16116-78-2 ]
((4-Bromophenyl)ethynyl)trimethylsilane
Similarity: 0.81
[ 130995-12-9 ]
((4-Fluorophenyl)ethynyl)trimethylsilane
Similarity: 0.81
[ 75867-39-9 ]
4-((Trimethylsilyl)ethynyl)aniline
Similarity: 0.81
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H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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