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Product Details of [ 1632-83-3 ]

CAS No. :1632-83-3 MDL No. :MFCD00192275
Formula : C8H8N2 Boiling Point : -
Linear Structure Formula :- InChI Key :FGYADSCZTQOAFK-UHFFFAOYSA-N
M.W : 132.16 Pubchem ID :95890
Synonyms :

Safety of [ 1632-83-3 ]

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

Application In Synthesis of [ 1632-83-3 ]

* 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 [ 1632-83-3 ]
  • Downstream synthetic route of [ 1632-83-3 ]

[ 1632-83-3 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 1632-83-3 ]
  • [ 20461-86-3 ]
  • [ 3012-80-4 ]
YieldReaction ConditionsOperation in experiment
40% With ammonium peroxydisulfate; caesium carbonate In dimethyl sulfoxide at 20℃; for 24 h; Inert atmosphere; Irradiation; Green chemistry General procedure: Heterocycle (0.10mmol,1equiv)ammonium persulfate (0.30 mmol, 3 equiv), Cs2CO3(0.20mmol,2 equiv)were placed in a dry glass tube.Then, anhydrous DMSO1 mL) and2,2-diethoxyacetic acid (0.7mmol7equiv), wereinjected into the tube by syringe under a N2atmosphere.The solution was then stirred at roomtemperature under the irradiation of 15W blueLEDs strip for 24h.After completion of the reaction,the mixture was quenched by addition of1.2mL of 3.0 M HCl, stirred for 20hthen saturated Na2CO3solution was added to adjust pH tobasicextract with CH2Cl2,the combined organic layers was washed with brine, then dry overanhydrous Na2SO4. The desired products were obtained in thecorresponding yields afterpurification by flashchromatography on silica gel eluting with petroleum and ethylacetate.
Reference: [1] Synlett, 2018, vol. 29, # 14, p. 1881 - 1886
  • 2
  • [ 1632-83-3 ]
  • [ 68-12-2 ]
  • [ 3012-80-4 ]
Reference: [1] Organic and Biomolecular Chemistry, 2009, vol. 7, # 8, p. 1633 - 1641
[2] Russian Journal of Inorganic Chemistry, 2015, vol. 60, # 7, p. 817 - 822[3] Zh. Neorg. Khim., 2015, vol. 60, # 7, p. 901 - 907,7
[4] European Journal of Organic Chemistry, 2011, # 30, p. 6092 - 6099
[5] ACS Combinatorial Science, 2013, vol. 15, # 2, p. 90 - 100
[6] Dalton Transactions, 2011, vol. 40, # 40, p. 10416 - 10433
[7] Croatica Chemica Acta, 2014, vol. 87, # 2, p. 153 - 160
  • 3
  • [ 85510-65-2 ]
  • [ 1632-83-3 ]
  • [ 3012-80-4 ]
  • [ 3878-69-1 ]
Reference: [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1987, vol. 23, # 2, p. 284 - 287[2] Khimiya Geterotsiklicheskikh Soedinenii, 1987, vol. 23, # 2, p. 339 - 342
[3] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1987, vol. 23, # 2, p. 284 - 287[4] Khimiya Geterotsiklicheskikh Soedinenii, 1987, vol. 23, # 2, p. 339 - 342
[5] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1987, vol. 23, # 2, p. 284 - 287[6] Khimiya Geterotsiklicheskikh Soedinenii, 1987, vol. 23, # 2, p. 339 - 342
  • 4
  • [ 1632-83-3 ]
  • [ 10394-38-4 ]
Reference: [1] Journal of the Chemical Society of Pakistan, 2013, vol. 35, # 5, p. 1343 - 1348
  • 5
  • [ 1632-83-3 ]
  • [ 20572-01-4 ]
YieldReaction ConditionsOperation in experiment
72% With hydrogenchloride; n-butyllithium; carbon dioxide In diethyl ether; water EXAMPLE 375A
1-methyl-1H-benzimidazole-2-carboxylic acid
A suspension of 1-methyl-1H-benzimidazole (5.0 g, 37.83 mmol) in diethyl ether at -78° C. was treated slowly with 1.6M n-butyllithium in hexanes (26 mL, 41.61 mmol) while maintaining the temperature at below -60° C., and stirred at -78° C. for 30 minutes.
Carbon dioxide was bubbled through the reaction solution for 40 minutes.
The dry ice bath was then removed to bring the temperature to -5° C. Concentrated hydrochloric acid (7 mL) was added slowly.
The reaction mixture was stirred at -5° C. for 30 minutes, and then water (10 mL) was added.
The solid was collected by filtration and dried to remove the excess water to provide 4.8 g (72percent) of the desired product which was directly used in the next reaction without further purification or analysis.
Reference: [1] Journal of Organic Chemistry, 1958, vol. 23, p. 1791
[2] Patent: US2005/26944, 2005, A1,
  • 6
  • [ 1632-83-3 ]
  • [ 124-38-9 ]
  • [ 20572-01-4 ]
Reference: [1] Journal of the American Chemical Society, 2010, vol. 132, # 26, p. 8858 - 8859
  • 7
  • [ 1632-83-3 ]
  • [ 109-72-8 ]
  • [ 60-29-7 ]
  • [ 20572-01-4 ]
Reference: [1] Journal of Organic Chemistry, 1958, vol. 23, p. 1791
  • 8
  • [ 1632-83-3 ]
  • [ 124-38-9 ]
  • [ 74-88-4 ]
  • [ 2849-92-5 ]
YieldReaction ConditionsOperation in experiment
50%
Stage #1: With 3-benzyl-1-(1-((2,6-diisopropylphenyl)imino)ethyl)-1H-imidazol-3-ium chloride; potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 80℃; for 24 h; Inert atmosphere
Stage #2: at 65℃; for 1 h; Inert atmosphere
In the reaction flask, Under argon, a catalyst (9.9 mg, 0.025 mmol, 5 molpercent), potassium tert-butoxide (0.0672 g, 0.6 mmol) DMF (3.0 ml), 1-methylbenzimidazole (60.0 μl, 0.5 mmol) was added to the carbon dioxide gas, and the reaction was stirred at 80 ° C for 24 hours under normal pressure. Cooled to 65 ° C, methyl iodide (93 μl, 1.5 mmol) was added, The reaction was stirred at 65 ° C for 1 hour. Cooled to room temperature, the reaction was terminated with deionized water, The reaction product was extracted with ethyl acetate and purified by column chromatography (Using a mixed solvent of ethyl acetate / petroleum ether in a volume ratio of 1:10 as a developing solvent) The yield was 50percent.
Reference: [1] Patent: CN106565623, 2017, A, . Location in patent: Paragraph 0054
  • 9
  • [ 610-17-3 ]
  • [ 1632-83-3 ]
  • [ 2836-03-5 ]
Reference: [1] Chemische Berichte, 1899, vol. 32, p. 1669
[2] Chemische Berichte, 1899, vol. 32, p. 1883,1893
  • 10
  • [ 1632-83-3 ]
  • [ 74-88-4 ]
  • [ 7181-87-5 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 5, p. 1147 - 1152
[2] Organic Letters, 2013, vol. 15, # 17, p. 4410 - 4413
[3] Journal of the American Chemical Society, 2004, vol. 126, # 13, p. 4366 - 4374
[4] Chemische Berichte, 1901, vol. 34, p. 936
[5] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1988, p. 1925 - 1928
[6] Magnetic Resonance in Chemistry, 1986, vol. 24, p. 415 - 420
[7] European Journal of Organic Chemistry, 2000, # 21, p. 3627 - 3631
[8] Organic Letters, 2007, vol. 9, # 26, p. 5401 - 5404
[9] European Journal of Inorganic Chemistry, 2011, # 15, p. 2450 - 2458
[10] Organometallics, 2017, vol. 36, # 10, p. 1981 - 1992
  • 11
  • [ 1632-83-3 ]
  • [ 144701-48-4 ]
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 3, p. 1915 - 1919
[2] Patent: WO2016/89845, 2016, A1,
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