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Chemical Structure| 60577-34-6
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Product Details of [ 60577-34-6 ]

CAS No. :60577-34-6 MDL No. :MFCD04037125
Formula : C7H8IN Boiling Point : -
Linear Structure Formula :- InChI Key :IZVRDZGBMDYYQT-UHFFFAOYSA-N
M.W : 233.05 Pubchem ID :6454006
Synonyms :

Safety of [ 60577-34-6 ]

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:

Application In Synthesis of [ 60577-34-6 ]

* 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.

  • Upstream synthesis route of [ 60577-34-6 ]
  • Downstream synthetic route of [ 60577-34-6 ]

[ 60577-34-6 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 100-61-8 ]
  • [ 60577-34-6 ]
YieldReaction ConditionsOperation in experiment
91% With 1,4-dibenzyl-1,4-diazoniabicyclo[2.2.2]octane dichloroiodate In neat (no solvent) at 20℃; for 0.166667 h; General procedure: General procedure for the iodination of aryl amines under solvent-free conditions.DBDABCODCI (0.5 mmol) and aryl amine (1 mmol) were triturated together in a porcelainmortar at room temperature. After completing reaction which monitored by TLC, the ethylacetate added to mixture and filtered, the organic layer washed with 5percent aqueous sodiumthiosulfate, and dried over MgSO4. The solvent was removed in vacuum and the crude mixturewas purified by column chromatography using ethyl acetate and hexane mixture and analyzedby m.p. and 1H NMR spectroscopy.
80% With iodine; sodium carbonate In cyclohexane; water at 20℃; for 2 h; General procedure: To a clean 50 mL round bottomed flask equipped with a large stir bar was added the substrate (10 mmol) followed by cyclohexane (ca. 6.0 mL to maintain the reaction concentration of 1.67 M) and an aqueous saturated solution of sodium carbonate (2.8 mL). Finally, iodine beads (11 mmol) were added as a solid and the flask was sealed with a septum and vented with a needle to the open atmosphere. The reaction was allowed to stir for the specified time at room temperature unless otherwise noted (see refPreviewPlaceHolderTable 1). The reaction mixture was poured into a separatory funnel with the aid of ethyl acetate or MTBE (2-3 mL) with additional aqueous saturated sodium carbonate (1 mL). The organic layer was washed twice with an aqueous saturated solution of sodium bisulfite (4 mL) and brine (5 mL), dried over sodium sulfate, and concentrated in vacuo to provide crude iodinated product. The products were purified by crystallization (if crystalline) from hexanes. Column chromatography (ethyl acetate/hexanes) was performed on the oils.
Reference: [1] Organic Letters, 2001, vol. 3, # 7, p. 991 - 992
[2] Journal of Organic Chemistry, 2018, vol. 83, # 15, p. 7606 - 7621
[3] Bulletin of the Chemical Society of Ethiopia, 2015, vol. 29, # 1, p. 157 - 162
[4] Bulletin of the Chemical Society of Japan, 1988, vol. 61, # 2, p. 600 - 602
[5] Bulletin of the Chemical Society of Japan, 2012, vol. 85, # 11, p. 1239 - 1243
[6] Canadian Journal of Chemistry, 2009, vol. 87, # 12, p. 1675 - 1681
[7] Advanced Synthesis and Catalysis, 2009, vol. 351, # 11-12, p. 1925 - 1932
[8] Tetrahedron Letters, 2011, vol. 52, # 52, p. 7141 - 7145
[9] Tetrahedron, 1994, vol. 50, # 17, p. 5139 - 5146
[10] Organic and Biomolecular Chemistry, 2011, vol. 9, # 8, p. 2987 - 2991
[11] Journal of the Chinese Chemical Society, 1996, vol. 43, # 1, p. 95 - 99
[12] Molecules, 2004, vol. 9, # 7, p. 617 - 621
[13] Molecules, 2002, vol. 7, # 12, p. 867 - 870
[14] Synthesis, 2004, # 3, p. 441 - 445
[15] Journal of Materials Chemistry, 2004, vol. 14, # 3, p. 292 - 295
[16] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1988, vol. 42, # 7, p. 448 - 454
[17] Synthetic Communications, 2004, vol. 34, # 19, p. 3579 - 3585
[18] Patent: US2003/201429, 2003, A1, . Location in patent: Page/Page column 4-5
[19] Journal of the American Chemical Society, 2011, vol. 133, # 18, p. 6868 - 6870
[20] Asian Journal of Chemistry, 2011, vol. 23, # 1, p. 465 - 466
[21] Journal of Medicinal Chemistry, 2015, vol. 58, # 8, p. 3548 - 3571
[22] Organic and Biomolecular Chemistry, 2017, vol. 15, # 10, p. 2246 - 2252
[23] Journal of the American Chemical Society, 2018, vol. 140, # 33, p. 10553 - 10561
  • 2
  • [ 62404-59-5 ]
  • [ 60577-34-6 ]
YieldReaction ConditionsOperation in experiment
90% With triethyl borane; sodium hydroxide In hexane at 80℃; for 6 h; Inert atmosphere; Sealed tube Under argon atmosphere, NaOH and triethyl boron were first stirred at room temperature to form a clear clear solution at a concentration of 1 M / L; Subsequently, 20 mmol (4 molpercent) of the above-mentioned triethylboron solution, 5 mmol of amide substrate, 15 mmol of silane, 2 mL of solvent Into a 10 mL sealed tube and placed in an oil bath at 80 ° C for 6 hours with heating. The reaction was completed and the reaction was exposed to air quenching, followed by The yield was determined by column chromatography and gas chromatography and a pure product was obtained. When using polymethylhydrogensiloxane (PMHS) and When the tetrahydrofuran was used as the silane and the solvent, the yields of the products A and B were 90percent and 0percent, respectively. When the triethoxysilane And n-hexane as silane and solvent, respectively, the yield of products A, B were: 94percent, 4percent
Reference: [1] Patent: CN107235845, 2017, A, . Location in patent: Paragraph 0034; 0035; 0036; 0037
[2] Organic and Biomolecular Chemistry, 2017, vol. 15, # 10, p. 2246 - 2252
  • 3
  • [ 62404-59-5 ]
  • [ 60577-34-6 ]
YieldReaction ConditionsOperation in experiment
94% With triethyl borane; Triethoxysilane; sodium hydroxide In hexane at 80℃; for 6 h; Inert atmosphere; Sealed tube Under argon atmosphere, NaOH and triethyl boron were first stirred at room temperature to form a clear clear solution at a concentration of 1 M / L; Subsequently, 20 mmol (4 molpercent) of the above-mentioned triethylboron solution, 5 mmol of amide substrate, 15 mmol of silane, 2 mL of solvent Into a 10 mL sealed tube and placed in an oil bath at 80 ° C for 6 hours with heating. The reaction was completed and the reaction was exposed to air quenching, followed by The yield was determined by column chromatography and gas chromatography and a pure product was obtained. When using polymethylhydrogensiloxane (PMHS) and When the tetrahydrofuran was used as the silane and the solvent, the yields of the products A and B were 90percent and 0percent, respectively. When the triethoxysilane And n-hexane as silane and solvent, respectively, the yield of products A, B were: 94percent, 4percent
Reference: [1] Patent: CN107235845, 2017, A, . Location in patent: Paragraph 0034; 0035; 0036; 0037
  • 4
  • [ 698-70-4 ]
  • [ 60577-34-6 ]
YieldReaction ConditionsOperation in experiment
59%
Stage #1: With tert.-butylhydroperoxide In toluene for 0.0333333 h; Inert atmosphere
Stage #2: With triethylamine In toluene at 110℃; for 3 h; Inert atmosphere
General procedure: A round-bottom flask was chargedwith N,N-dialkyl aniline dissolved in toluene solution, under N2 condition. TBHP was added drop wise and reaction was stirred for 2 min. Triethylamine was added thereafter, and then the contents of the reaction were stirred for 3 h at 110 °C under inert N2 condition. The reaction mixture was washed 2–3 times with H2O and ethyl acetate. The upper organic layer was separated and dried over sodium sulphate and then subjected to rotavapour. The crude mixture was purified by column chromatography on silica gel (60–120).
Reference: [1] Journal of Chemical Sciences, 2016, vol. 128, # 9, p. 1469 - 1473
  • 5
  • [ 616-38-6 ]
  • [ 540-37-4 ]
  • [ 60577-34-6 ]
YieldReaction ConditionsOperation in experiment
76% With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1-methyl-pyrrolidin-2-one at 250℃; for 0.2 h; Flow reactor General procedure: Selective N-monomethlyation reactions were performed in a Vapourtec E-series continuous flow system equipped with a high temperature tube reactor (10 mL, stainless steel, 0.03'' i.d., Fig. 2 ) and a membrane back pressure regulator (Zaiput). Stock solutions of aniline (20 mmol, 1.0 equiv, 2 M), DMC (5.05 mL, 60 mmol, 3.0 equiv, 6 M), and DBU (4.47 mL, 30 mmol, 1.5 equiv, 3 M) were prepared in oven-dried 10 mL volumetric flasks using NMP as the solvent. The solutions were transferred to screw-thread vials with septum caps and reagents were pumped directly from the vials. After the high temperature coiled tube reactor was heated to 250 °C, peristaltic pumps (Vapourtec V-3) were used to pump the reactant solutions into the system (0.277 mL/min each for a 12 min residence time). The solutions were mixed with a cross-mixer (0.4″ i.d.), passed though the high temperature coiled tube reactor. Upon exiting the reactor, the reaction stream was passed through a short segment of stainless steel tubing to enable the reaction to cool and then exited the system by passage through the back pressure regulator (Note: PFA fittings should not be used at the exit of the reactor as they will deform due to the high temperature of the reaction stream and cause leaks in the system. Stainless steel connectors and tubing (12'') were used in our system.). After the flow system was equilibrated for 18 min, the product stream was collected for 5 min (2.77 mmol of aniline). The crude mixture was dissolved in ethyl acetate and washed with brine. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (Biotage 25 g Ultra-sil, 3–15percent ethyl acetate in hexanes) to afford the desired product.
Reference: [1] Tetrahedron, 2018, vol. 74, # 25, p. 3124 - 3128
  • 6
  • [ 67-56-1 ]
  • [ 540-37-4 ]
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Reference: [1] ACS Catalysis, 2015, vol. 5, # 7, p. 4082 - 4088
[2] Organic Letters, 2018, vol. 20, # 19, p. 5985 - 5990
[3] RSC Advances, 2012, vol. 2, # 23, p. 8645 - 8652
[4] Journal of Catalysis, 2017, vol. 347, p. 57 - 62
  • 7
  • [ 641612-91-1 ]
  • [ 60577-34-6 ]
Reference: [1] Patent: US2004/6062, 2004, A1, . Location in patent: Page/Page column 48
  • 8
  • [ 540-37-4 ]
  • [ 74-88-4 ]
  • [ 60577-34-6 ]
Reference: [1] Organic Letters, 2009, vol. 11, # 6, p. 1225 - 1228
  • 9
  • [ 540-37-4 ]
  • [ 74-88-4 ]
  • [ 60577-34-6 ]
  • [ 698-70-4 ]
Reference: [1] Chemical Communications, 2010, vol. 46, # 20, p. 3538 - 3540
  • 10
  • [ 100-61-8 ]
  • [ 60577-34-6 ]
  • [ 57056-93-6 ]
Reference: [1] Synlett, 2012, # 2, p. 208 - 214
  • 11
  • [ 579-10-2 ]
  • [ 60577-34-6 ]
Reference: [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 10, p. 2246 - 2252
  • 12
  • [ 6393-17-5 ]
  • [ 60577-34-6 ]
Reference: [1] Tetrahedron Letters, 1982, vol. 23, # 33, p. 3315 - 3318
  • 13
  • [ 540-37-4 ]
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Reference: [1] Chemical Communications, 2014, vol. 50, # 49, p. 6523 - 6525
  • 14
  • [ 540-37-4 ]
  • [ 74-88-4 ]
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  • [ 698-70-4 ]
Reference: [1] Chemical Communications, 2010, vol. 46, # 20, p. 3538 - 3540
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