Home Cart Sign in  
Chemical Structure| 77123-59-2 Chemical Structure| 77123-59-2

Structure of 77123-59-2

Chemical Structure| 77123-59-2

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 77123-59-2 ]

CAS No. :77123-59-2
Formula : C13H16O2Si
M.W : 232.35
SMILES Code : O=C(OC)C1=CC=CC(C#C[Si](C)(C)C)=C1
MDL No. :MFCD18206269

Safety of [ 77123-59-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Application In Synthesis of [ 77123-59-2 ]

* 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 [ 77123-59-2 ]

[ 77123-59-2 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 618-89-3 ]
  • [ 1066-54-2 ]
  • [ 77123-59-2 ]
YieldReaction ConditionsOperation in experiment
95% Methyl 3-bromobenzoate (110 g, 0.51 mol), dry acetonitrile (500 mL), ethynyl(trimethyl)silane (60.0 g, 0.61 mol), diisopropylamine (62.0 g, 0.61 mol) and tetra(triphenylphosphine)palladium (23.6 g, 0.02 mol) were placed under an atmosphere of argon in a three-necked round-bottomed 1 liter flask, equipped with a magnetic stirrer and a thermometer. The mixture was stirred for 30 minutes and then cooled to 10 0C. Copper iodide (9.7 g, 0.06 mol) was added, and the obtained suspension was stirred for a further 2.5 hours at 20 0C and finally for 3 hours at 60 0C. Then the mixture was left to stand at room temperature overnight and filtered. The precipitate of hydrobromide was washed with ether, and the combined filtrate was washed with saturated aqueous solutions of NH4CI and NaCI, dried over Na2SO4 and evaporated. The crude product was purified by chromatography (hexane) on a silica gel column to give methyl 3-(2- (trimethylsilyl)ethynyl)benzoate in 95% (112.8 g) yield.A suspension of methyl 3-(2-(trimethylsilyl)ethynyl)benzoate (112.8 g, 0.48 mol), mercury(2+) diacetate (16.2 g, 0.005 mol) in THF (350 mL) and concentrated H2SO4 (40 mL) was stirred at 60 0C for 3 hours. Then the mixture was cooled, diluted with ether (500 mL), filtered to remove precipitated mercury salts and washed to obtained neutral medium. Then the solution was dried over Na2SO4 and evaporated. The residue was purified by chromatography (hexane/ethyl acetate 4:1) on a silica gel column to give methyl 3-acetylbenzoate in 75% (65.2 g) yield.(Dimethoxymethyl)dimethylamine (90 mL) was added to a suspension of methyl 3-acetylbenzoate (65.2 g, 0.27 mol) in toluene (90 mL). The mixture was refluxed for 9 hours, during which time forming <n="39"/>methanol was distilled off. The solution was then concentrated in vacuo, and the residue was purified from ether by crystallization to give methyl 3-(3-(dimethylamino)acryloyl)benzoate as yellow prismatic crystals in 80% (68.1 g) yield. ' . lmidoformamide acetate (20.3 g, 0.19 mol) was added to a suspension of methyl 3-(3- (dimethylamino)acryloyl)benzoate (30.3 g, 0.13 mol) in toluene (300 mL). The reaction mixture was refluxed for 20 hours, during which time toluene and dimethylamine acetate were distilled off* Then imidoformamide acetate (6.7 g) and toluene (175 mL) were added again, and after 8 hours the mixture was evaporated in vacuo. The residue was purified by chromatography (ethylacetate/hexane 3:1) on a silica gel column to afford methyl 3-(pyrimidin-4-yl)benzoate in 70% (19.5 g) yield.A suspension of methyl 3-(pyrimidin-4-yl)benzoate (19.5 g, 0.091 mol), sodium methylate (7.6 g, 0.14 mol) in ethanol (250 mL) was refluxed for 30 minutes. Then the reaction mixture was cooled, and the formed-precipitate was separated by filtration was dissolved in water. The obtained solution was acidified with concentrated HCI to pH about 2 that caused precipitation. The precipitate was separated by filtration, washed with water and dried to give the title compound as crystals in 94% (17.2 g) yield.
69% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 90℃; for 36h; Preparation 17Synthesis of methyl 3-(2-trimethylsilylethynyl)benzoate.In a round bottom flask place <strong>[618-89-3]methyl 3-bromobenzoate</strong> (1.88 g, 8.73 mmoles), triethylamine (10.00 mL, 71.74 mmoles), (trimethylsilyl)acetylene (1.48 mL, 10.49 mmoles), bis(triphenylphosphine)palladium(II) chloride (0.146 g, 0.205 mmoles), and copper(I) iodide (23 mg, 0.121 mmoles). The reaction mixture is heated at 90 for 18 hours. The reaction mixture is degassed and more (trimethylsilyl)acetylene (1.48 mL, 10.49 mmoles), <strong>[618-89-3]methyl 3-bromobenzoate</strong> (1.88 g, 8.73 mmoles) and copper(I) iodide (23 mg, 0.121 mmoles) is added and the mixture is heated at 90 for 18 hours. Quench the reaction with 75 mL IN hydrochloric acid and extract three times with ethyl acetate. Wash one time with brine and dry over sodium sulfate, filter and concentrate under reduced pressure. The residue is purified by normal phase chromatography using ethyl acetate/hexane to give the title compound (1.4 g, 69%). LCMS (m/z): 233.0 (M+l).
  • 2
  • [ 77123-59-2 ]
  • [ 10601-99-7 ]
YieldReaction ConditionsOperation in experiment
99% With sodium hydroxide; In methanol; water; at 20℃; for 7h;Cooling with ice; Obtained in Step 2 3-[(trimethylsilyl)ethynyl]benzoic acid methyl ester(105) (2.42 g) was dissolved in methanol (30 mL), under ice cooling 2N aqueous sodium hydroxide solution (10.4 mL) was added, 7 hours and stirred at room temperature. The reaction mixture was acidified (pH 3 ~ 4) with 2N hydrochloric acid, and concentrated under reduced pressure. The residue Water (100 mL) was added, followed by extraction with ethyl acetate (100mL). The organic layer was washed with saturated brine (100 mL), dried over anhydrous sodium sulfate, and filtered. Thefiltrate was concentrated under reduced pressure to give 3-ethynylbenzoic acid (106) and (1.50 g, 99% yield) as a white solid.
0.26 g With lithium hydroxide; In tetrahydrofuran; water; at 50℃; Preparation 18Synthesis of 3-ethynylbenzoic acid.Place methyl 3-(2-trimethylsilylethynyl)benzoate (0.399 g, 1.55 mmoles) and tetrahydrofuran (3.68 mL) in a round bottom flask. Add lithium hydroxide (0.162 g, 3.86 mmoles) and water (3.68 mL) and heat at 50C. Quench the reaction with 1.3 mL 5N hydrochloric acid and extract three times with ethyl acetate. Wash one time with brine and dry over sodium sulfate, filter and concentrate under reduced pressure to give the title compound (0.26g, >100%).]H NMR (400 MHz, DMSO-d6) ppm: 4.39 (s, 3H), 7.50 (m, 2H), 7.70 (m, 1H), 7.94 (m, 1H) 13.22 (s, 1H).
 

Historical Records