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[ CAS No. 26830-96-6 ]

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Chemical Structure| 26830-96-6
Chemical Structure| 26830-96-6
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CAS No. :26830-96-6 MDL No. :MFCD00173706
Formula : C8H8N2 Boiling Point : 301.2°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :132.16 g/mol Pubchem ID :2801276
Synonyms :

Safety of [ 26830-96-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 26830-96-6 ]

  • Upstream synthesis route of [ 26830-96-6 ]
  • Downstream synthetic route of [ 26830-96-6 ]

[ 26830-96-6 ] Synthesis Path-Upstream   1~13

  • 1
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  • [ 75844-40-5 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1889, vol. <2> 40, p. 12
[2] Patent: WO2013/100632, 2013, A1,
[3] Patent: US2014/371219, 2014, A1,
  • 2
  • [ 64-18-6 ]
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Reference: [1] Journal of the American Chemical Society, 1905, vol. 27, p. 1301
  • 3
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YieldReaction ConditionsOperation in experiment
83% With hydrogen In 1,4-dioxane a)
2-Amino-4-methylbenzonitrile
A mixture of 4-methyl-2-nitrobenzonitrile (4.9 g, 30 mmol) and 10percent palladium on carbon (500 mg) in 1,4-dioxane (60 mL) was stirred under hydrogen (balloon) overnight.
The catalyst was removed by filtration through the Celite, and the filtrate was concentrated in vacuo.
The residue was purified by flash chromatography (dichloromethane) to give the title compound as a pale yellow solid (3.3 g, 83percent).
1H-NMR (300 MHz, CDCl3) δ 7.26 (d, J = 8.3 Hz, 1H), 6.56 (s, 1H), 6.55 (s, 1H), 4.32 (br s, 2H), 2.29 (s, 3H).
Reference: [1] Chemical Communications, 2011, vol. 47, # 31, p. 8808 - 8810
[2] Journal of the Chemical Society, Perkin Transactions 2, 2001, # 2, p. 214 - 228
[3] Patent: US5891909, 1999, A,
[4] Patent: EP906091, 2006, B1, . Location in patent: Page/Page column 46
[5] Journal fuer Praktische Chemie (Leipzig), 1889, vol. <2> 40, p. 12
[6] Journal of the American Chemical Society, 1905, vol. 27, p. 1301
[7] Chemische Berichte, 1888, vol. 21, p. 2652
[8] Journal of the Chemical Society, 1929, p. 2557
[9] Journal of Organic Chemistry, 1978, vol. 43, # 2, p. 220 - 224
[10] Patent: US2009/54395, 2009, A1, . Location in patent: Page/Page column 39
  • 4
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Reference: [1] Justus Liebigs Annalen der Chemie, 1941, vol. 546, p. 277,291
[2] Journal of the Chemical Society, 1929, p. 2557
[3] Justus Liebigs Annalen der Chemie, 1941, vol. 546, p. 277,291
  • 5
  • [ 24920-35-2 ]
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Reference: [1] Journal of the Chemical Society, 1929, p. 2557
[2] Journal of the Chemical Society, 1929, p. 2557
  • 6
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  • [ 2305-36-4 ]
Reference: [1] Chemische Berichte, 1888, vol. 21, p. 1539[2] Journal fuer Praktische Chemie (Leipzig), 1889, vol. <2> 40, p. 15
  • 7
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  • [ 63089-50-9 ]
Reference: [1] Chemische Berichte, 1888, vol. 21, p. 2652
[2] Monatshefte fuer Chemie, 1891, vol. 12, p. 625
  • 8
  • [ 26830-96-6 ]
  • [ 1829-21-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1973, p. 2940 - 2948
  • 9
  • [ 75-16-1 ]
  • [ 26830-96-6 ]
  • [ 122710-21-8 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 12, p. 2748 - 2752
[2] Organic Letters, 2017, vol. 19, # 19, p. 5344 - 5347
  • 10
  • [ 676-58-4 ]
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  • [ 122710-21-8 ]
Reference: [1] Organic Letters, 2018, vol. 20, # 13, p. 4052 - 4056
  • 11
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  • [ 42872-73-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1941, vol. 546, p. 277,291
  • 12
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YieldReaction ConditionsOperation in experiment
53% With sulfuric acid In water at 120℃; for 0.333333 h; Concentrated sulfuric acid (3 mL) was carefully added to a suspension of 2- amino-4-methylbenzonitrile (800 mg, 6.1 mmol) in H2O (1 mL). The solution was then placed into an oil bath, pre-heated to 120 0C, the reaction stirred for 20 min and then immediately cooled in an ice bath. The solution was made basic via the addition of 5 percent NaOH and the resulting solid collected via vacuum filtration. 484.4 mg (53 percent) of the title compound as a light brown solid were obtained. 1H NMR (DMSO-dβ) δ 7.63 (br s, 1 H), 7.42 (d, 1 H), 6.95 (br s, 1 H), 6.55 (br s, 2 H), 6.45 - 6.48 (m, 1 H), 6.29 (ddd, 1 H), 2.16 (s, 3 H). MS (ES) 134 (M - 16).
43% With potassium hydroxide In ethanol for 8 h; Reflux 2-amino-4-methylbenzonitrile (10 g, 75.7 mmol) was dissolved in ethanol, added with potassium hydroxide (21.2 g, 378 mmol), followed by refluxing for 8 hours. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and dissolved in ethyl acetate. The organic layer formed was washed with a saturated aqueous solution of sodium bicarbonate and brine. The obtained organic layer is dried over anhydrous sodium sulfate, concentrated under reduced pressure, and recrystallized from ethanol to obtain the title compound (4.9 g, 43percent). 1H-NMR Spectrum (300 MHz, DMSO- 6): δ 7.40 (d, 1H), 6.52 (s, 2H), 6.45 (s, 1H), 6.28 (d, lH), 2.14 (s, 3H)
43% With potassium hydroxide In ethanol for 8 h; Reflux 2-amino-4-methylbenzonitrile (10 g, 75.7 mmol) was dissolved in ethanol, added with potassium hydroxide (21.2 g, 378 mmol), followed by refluxing for 8 hours. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and dissolved in ethyl acetate. The organic layer formed was washed with a saturated aqueous solution of sodium bicarbonate and brine. The obtained organic layer is dried over anhydrous sodium sulfate, concentrated under reduced pressure, and recrystallized from ethanol to obtain the title compound (4.9 g, 43percent). 1H-NMR Spectrum (300 MHz, DMSO-d6): δ 7.40 (d, 1H), 6.52 (s, 2H), 6.45 (s, 1H), 6.28 (d, 1H), 2.14 (s, 3H)
Reference: [1] Journal of the American Chemical Society, 2008, vol. 130, # 47, p. 15786 - 15787
[2] Journal of Organic Chemistry, 2006, vol. 71, # 1, p. 382 - 385
[3] Patent: WO2006/74223, 2006, A2, . Location in patent: Page/Page column 51
[4] Patent: WO2013/100632, 2013, A1, . Location in patent: Page/Page column 49; 50
[5] Patent: US2014/371219, 2014, A1, . Location in patent: Paragraph 0342; 0343
[6] Journal fuer Praktische Chemie (Leipzig), 1889, vol. <2> 40, p. 12
  • 13
  • [ 26830-95-5 ]
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Reference: [1] Justus Liebigs Annalen der Chemie, 1941, vol. 546, p. 277,291
[2] Journal of the Chemical Society, 1929, p. 2557
[3] Justus Liebigs Annalen der Chemie, 1941, vol. 546, p. 277,291
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