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Chemical Structure| 776-75-0 Chemical Structure| 776-75-0

Structure of 776-75-0

Chemical Structure| 776-75-0

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Product Details of [ 776-75-0 ]

CAS No. :776-75-0
Formula : C12H15NO
M.W : 189.25
SMILES Code : O=C(C1=CC=CC=C1)N2CCCCC2
MDL No. :MFCD00023702
InChI Key :YXTROGRGRSPWKL-UHFFFAOYSA-N
Pubchem ID :69892

Safety of [ 776-75-0 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H318
Precautionary Statements:P264-P270-P280-P301+P312-P305+P351+P338-P310-P330-P501
Class:8
UN#:1760
Packing Group:

Application In Synthesis of [ 776-75-0 ]

* 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 [ 776-75-0 ]

[ 776-75-0 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 776-75-0 ]
  • [ 2905-56-8 ]
YieldReaction ConditionsOperation in experiment
84% General procedure: In a nitrogen-filled glovebox, to a 15 mL reaction tube equipped with a magnetic stirrer, were added Cp2ZrH2 (0.01mmol, 2.2 mg) as the catalyst, and the appropriate amide (0.2mmol); solvent was added when necessary. HBpin (3 equiv. peramide functional group) was then added, and the reaction tube was taken out from the glovebox and stirred at room temperature for 12-48 h. The resultant crude amines were either isolated using silica gel flash chromatography, or acidified by stirring with HCl in Et2O (2 mL, 1N) for 2 h, after which time precipitation was observed. Then, the reaction solution was transferred to a centrifuge tube and centrifuged three times. The supernatant was removed and the resulting solid was dried inan oven at 80 C for several hours to obtain the HCl salt of the amine.
References: [1]Angewandte Chemie - International Edition,2009,vol. 48,p. 9507 - 9510.
[2]Organic Letters,2015,vol. 17,p. 446 - 449.
[3]Journal of Organic Chemistry,2014,vol. 79,p. 7728 - 7733.
[4]Chemical Communications,2018,vol. 54,p. 5855 - 5858.
[5]Advanced Synthesis and Catalysis,2013,vol. 355,p. 3358 - 3362.
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[7]Chemical Communications,2013,vol. 49,p. 9758 - 9760.
[8]Advanced Synthesis and Catalysis,2016,vol. 358,p. 452 - 458.
[9]Organometallics,2013,vol. 32,p. 7440 - 7444.
[10]Chemical Communications,2021,vol. 57,p. 9204 - 9207.
[11]European Journal of Organic Chemistry,2013,p. 2066 - 2070.
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[13]Journal of Organic Chemistry,2021,vol. 86,p. 15992 - 16000.
[14]Tetrahedron,1998,vol. 54,p. 10899 - 10914.
[15]Journal of the American Chemical Society,2010,vol. 132,p. 1770 - 1771.
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[17]Advanced Synthesis and Catalysis,2019,vol. 361,p. 4817 - 4824.
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[19]ChemCatChem,2017,vol. 9,p. 2009 - 2017.
[20]Chemistry - A European Journal,2011,vol. 17,p. 12186 - 12192.
[21]Advanced Synthesis and Catalysis,2013,vol. 355,p. 2775 - 2780.
[22]ChemCatChem,2019,vol. 11,p. 3818 - 3827.
[23]Tetrahedron Letters,2008,vol. 49,p. 6873 - 6875.
[24]European Journal of Organic Chemistry,2014,vol. 2014,p. 5144 - 5148.
[25]Chemische Berichte,1899,vol. 32,p. 74.
[26]Archiv der Pharmazie,1927,p. 390,400.
    Chemisches Zentralblatt,1924,vol. 95,p. 1404.
[27]Journal of Organic Chemistry,1953,vol. 18,p. 1190,1196.
[28]Journal of Organic Chemistry,1981,vol. 46,p. 3730 - 3732.
[29]Journal of the American Chemical Society,2008,vol. 130,p. 933 - 944.
[30]Journal of the American Chemical Society,2012,vol. 134,p. 640 - 653.
[31]New Journal of Chemistry,2014,vol. 38,p. 1694 - 1700.
[32]Chemical Communications,2014,vol. 50,p. 9349 - 9352.
[33]Chemical Communications,2016,vol. 52,p. 1855 - 1858.
[34]Angewandte Chemie - International Edition,2017,vol. 56,p. 15901 - 15904.
    Angew. Chem.,2017,vol. 129,p. 16117 - 16120,4.
[35]Patent: DE164365,1904,C .
    Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 8,p. 1053.
    Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 8,p. 1053.
[36]Patent: DE164365,1904,C .
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    Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 8,p. 1053.
[37]Journal of the American Chemical Society,2020,vol. 142,p. 8019 - 8028.
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    Angew. Chem.,2021,vol. 133,p. 16171 - 16179.
  • 2
  • [ 776-75-0 ]
  • [ 7664-93-9 ]
  • lead cathode [ No CAS ]
  • [ 2905-56-8 ]
  • 3
  • [ 776-75-0 ]
  • [ 60-29-7 ]
  • lithium alanate [ No CAS ]
  • [ 2905-56-8 ]
  • 4
  • [ 110-89-4 ]
  • [ 100-52-7 ]
  • [ 776-75-0 ]
  • [ 2905-56-8 ]
  • 6
  • [ 110-89-4 ]
  • [ 100-51-6 ]
  • [ 776-75-0 ]
  • [ 2905-56-8 ]
  • 7
  • [ 776-75-0 ]
  • [ 120942-83-8 ]
  • [ 2905-56-8 ]
  • [ 110023-85-3 ]
  • 8
  • [ 776-75-0 ]
  • [ 381-98-6 ]
  • C16H18F3NO3 [ No CAS ]
  • 9
  • [ 776-75-0 ]
  • [ 2905-56-8 ]
  • [ 100-51-6 ]
YieldReaction ConditionsOperation in experiment
86%Spectr.; 13%Spectr. With 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; In neat (no solvent); at 120℃; for 24h;Inert atmosphere; Sealed tube; General procedure: N,N-dimethylbenzamide (0.0746 g,0.5 mmol), or N-methylbenzamide (0.0676 g, 0.5 mmol) was taken in culture tube (11 ml) at 25 C, sealed with septum, the air in culture tube was replaced with argon gas. After adding pinacolborane (0.36 ml, 2.5 mmol 5 equiv), the screw cap was closed, stirred at 120 C for 24 h. Afterthis time, it was cooled to room temperature, excess HBpin was quenched by adding water (0.1 ml). After adding 2 ml of 5 N NaOH (aq), reaction mixture was extracted with ether (20 ml). The organic part was dried over MgSO4, filtered and dried under high vacuum to remove volatile organic impurities. The yield was analyzed by 1HNMR (using acetonitrile [8μl, 0.33 eq] as an internal standard).
 

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