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Chemical Structure| 120-21-8
Chemical Structure| 120-21-8
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Product Details of [ 120-21-8 ]

CAS No. :120-21-8 MDL No. :
Formula : C11H15NO Boiling Point : -
Linear Structure Formula :- InChI Key :MNFZZNNFORDXSV-UHFFFAOYSA-N
M.W : 177.24 Pubchem ID :67114
Synonyms :

Safety of [ 120-21-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H312-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 120-21-8 ]

* 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 [ 120-21-8 ]
  • Downstream synthetic route of [ 120-21-8 ]

[ 120-21-8 ] Synthesis Path-Upstream   1~16

  • 1
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YieldReaction ConditionsOperation in experiment
92% With Aliquat 336; potassium carbonate In dimethyl sulfoxide at 95℃; for 72 h; 4-fluorobenzaldehyde (2.5 g, 0.02 mol), diethyl amine(5.12 g, 0.07 mol), K2CO3 (4.15 g), DMSO (25.0 mL) and Aliquat-336 (0.05 mL) were added into a one-necked flask (100 mL) fitted with a stirrer and a condenser. The mixture was stirred for 72 h at 95C, and then cooled to room temperature. The yellow precipitation was obtained after ice water wasintroduced into the flask. The crude product was washed with cool water for 2-3 times, and thenrecrystallized from ethanol. Yellow solid (4-diethylaminobenzaldehyde) was obtained. Yield: 92percent.Anal. Calcd. for C11H15NO: C, 74.54; H, 8.53; N, 7.90; Found: C, 74.67; H, 8.58; N, 7.85; 1H NMR(500 MHz, CDCl3, ppm) δ 9.71(s, 1H), 7.72(q, 2H), 6.69 (d, J = 8.8 Hz, 2H), 1.24 (t, 6H), 3.46 (q,4H). The second step: The potassium (0.78 g, 0.02 mol) was introduced into tert-butanol (11.3 mL,0.12 mol) in a 50 mL one-necked flask fitted with a condenser. After fully reaction, 4-picoline (0.975mL, 10 mmol) and 4-diethylaminobenzaldehyde (1.77 g, 10 mmol) were added. The mixture washeated for 2 hours at 80°C under stirring; tert-butanol was evaporated, then added to 200 mLdichloromethane and washed once with 200 mL ice water, stirred. The water phase was extracted withdichloromethane for 3 times. The organic phase was dried on sodium sulfate, solvent was evaporated,and the crude solid was recrystallized in toluene. Yield: 86percent. 1H NMR (500 MHz, DMSO, ppm) δ8.43 (d, J = 5.2 Hz, 2H), 7.42 (t, J = 8.8 Hz, 2H), 7.23 (d, J = 5.4 Hz, 2H), 7.04 (d, J = 8.7 Hz, 2H),6.27-6.66 (m, 2H), 3.39 (m, 4H), 1.13 (t, 6H). 13C NMR (500 MHz, CDCl3, ppm) δ 148.56-146.96 (m,py), 134.57 (s, py), 128.86 (s, benzene) 120.51-119.95 (d, benzene), 111.56 (s, CH=CH), 44.47 (s,CH2), 12.62 (s, CH3). Anal. Calcd. for C17H20N2 (EI-MS: 253.3): C, 80.91; H, 7.99; N, 11.10. Found: C,80.76; H, 7.91; N, 11.01. IR data (KBr, cm−1): 3026 w, 2974 m, 1581 s, 1520 vs, 1408 m, 1355 m,1329 w, 1272 m, 1185 m, 1158 m, 1074 w, 972 w, 818 m, 795 m, 518 w. m.p. 258 °C.
Reference: [1] Dyes and Pigments, 2015, vol. 120, p. 175 - 183
[2] Journal of Molecular Structure, 2007, vol. 829, # 1-3, p. 202 - 207
[3] Journal of Materials Chemistry, 2012, vol. 22, # 33, p. 16927 - 16932
[4] Journal of Medicinal Chemistry, 2012, vol. 55, # 19, p. 8483 - 8492,10
[5] Journal of Medicinal Chemistry, 2012, vol. 55, # 19, p. 8483 - 8492
[6] European Journal of Medicinal Chemistry, 2014, vol. 87, p. 429 - 439
[7] ChemMedChem, 2017, vol. 12, # 13, p. 1022 - 1032
  • 2
  • [ 1535-67-7 ]
  • [ 91-66-7 ]
  • [ 120-21-8 ]
YieldReaction ConditionsOperation in experiment
42%
Stage #1: With tin(IV) chloride In dichloromethane at 20℃; for 2 h; Inert atmosphere
Stage #2: With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In water; dimethyl sulfoxide at 20℃; for 2 h;
General procedure: In a round-bottomed flask equipped with a stirring bar and rubber septum was placed a 1 M solution of SnCl4 in anhydrous CH2Cl2 (1 mL, 1 mmol). To this solution was added PhSCF2H (1; 240.2 mg, 1.5 mmol) in anhydrous CH2Cl2 (1.5 mL), followed by a solution of an aromatic compound (0.5 mmol) in anhydrous CH2Cl2 (1 mL). The reaction was allowed to proceed for 2 h before it was quenched with a solution of IBX (140 mg, 0.5 mmol) in DMSO/H2O (4 mL; 3:1 v:v). After 2 h of stirring at rt, the reaction mixture was quenched by addition of a saturated aqueous solution of sodium thiosulfate (10 mL), then basified with a saturated aqueous solution of sodium hydrogen carbonate (10 mL), followed by stirring and extraction with CH2Cl2 (3 × 10 mL). The combined organic layers were washed with water (3 × 10 mL) and brine (10 mL), dried (anhydrous MgSO4), filtered and concentrated (aspirator). The residue was purified by PTLC, radial chromatography or column chromatography to furnish analytically pure product.
Reference: [1] Synthesis (Germany), 2018, vol. 50, # 10, p. 2033 - 2040
  • 3
  • [ 68-12-2 ]
  • [ 91-66-7 ]
  • [ 120-21-8 ]
Reference: [1] Journal of Materials Chemistry C, 2016, vol. 4, # 48, p. 11474 - 11481
[2] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 5, p. 1555 - 1566
[3] Patent: CN104341347, 2018, B, . Location in patent: Paragraph 0130; 0131
  • 4
  • [ 91-66-7 ]
  • [ 149-73-5 ]
  • [ 120-21-8 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 11, p. 1955 - 1958
  • 5
  • [ 74974-49-5 ]
  • [ 120-21-8 ]
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 51, p. 7035 - 7039
  • 6
  • [ 56542-00-8 ]
  • [ 68-12-2 ]
  • [ 120-21-8 ]
Reference: [1] Russian Chemical Bulletin, 1993, vol. 42, # 3, p. 584 - 585[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1993, # 3, p. 615
  • 7
  • [ 1054451-35-2 ]
  • [ 120-21-8 ]
Reference: [1] Synthetic Communications, 2008, vol. 38, # 16, p. 2748 - 2752
  • 8
  • [ 62-53-3 ]
  • [ 120-21-8 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 5, p. 558 - 561
  • 9
  • [ 149796-22-5 ]
  • [ 120-21-8 ]
Reference: [1] Patent: DE108026, , ,
[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 5, p. 117
  • 10
  • [ 121-69-7 ]
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Reference: [1] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 5, p. 558 - 561
  • 11
  • [ 91-66-7 ]
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Reference: [1] Chemische Berichte, 1904, vol. 37, p. 862
[2] Chemische Berichte, 1886, vol. 19, p. 366
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Reference: [1] Chemische Berichte, 1904, vol. 37, p. 862
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Reference: [1] Chemische Berichte, 1927, vol. 60, p. 121
  • 14
  • [ 100-97-0 ]
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Reference: [1] Journal of the Chemical Society, 1945, p. 276
  • 15
  • [ 50-00-0 ]
  • [ 82529-61-1 ]
  • [ 64-19-7 ]
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Reference: [1] Chemische Berichte, 1904, vol. 37, p. 862
  • 16
  • [ 120-21-8 ]
  • [ 41876-70-4 ]
Reference: [1] Chemistry - A European Journal, 1997, vol. 3, # 11, p. 1765 - 1773
[2] Chemical Communications, 2011, vol. 47, # 16, p. 4685 - 4687
[3] Patent: WO2012/120141, 2012, A1,
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