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[ CAS No. 94-67-7 ]

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2D
Chemical Structure| 94-67-7
Chemical Structure| 94-67-7
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Product Details of [ 94-67-7 ]

CAS No. :94-67-7MDL No. :MFCD00002120
Formula : C7H7NO2 Boiling Point : 256.492°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :137.14Pubchem ID :-
Synonyms :

Computed Properties of [ 94-67-7 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 94-67-7 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P273-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335-H401Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 94-67-7 ]

  • Upstream synthesis route of [ 94-67-7 ]
  • Downstream synthetic route of [ 94-67-7 ]

[ 94-67-7 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 22755-24-4 ]
  • [ 108-95-2 ]
  • [ 94-67-7 ]
  • [ 699-06-9 ]
Reference: [1] Tetrahedron Letters, 1989, vol. 30, # 42, p. 5763 - 5766
  • 2
  • [ 90-02-8 ]
  • [ 94-67-7 ]
YieldReaction ConditionsOperation in experiment
98% With hydroxylamine hydrochloride; sodium carbonate In ethanol; water at 20℃; for 2 h; At room temperature,30 mmol of 2-hydroxybenzaldehyde, 60 mmol of sodium bicarbonate,45 mmol of hydroxylamine hydrochloride were mixed in ethanol / water (50/5 mL)The reaction mixture was stirred for two hours and concentrated to remove most of the solvent.The residue was diluted with ethyl acetate and filtered directly. The filtrate was concentrated to give 3.99 g (98percent) of a colorless oil.
95% With zinc(II) oxide; hydroxylamine hydrochloride; silica gel In neat (no solvent) at 20℃; for 0.0666667 h; Green chemistry General procedure: Hydroxylamine hydrochloride (0.138 g, 2 mmol), ZnO nanotubes (0.071 g, 0.8 mmol), silica gel (0.43 g) and aldehyde (ketone) (1 mmol) were ground together in a mortar with a pestle at room temperature for a period of time as indicated in Tables 1 and 2. The progress of the reaction was monitored by TLC. After complete disappearance of the starting materials, the reaction mixture was poured with diethyl ether (2×10 mL) and filtered to remove silica gel and ZnO nanotubes, The filtrate mixed with water and extracted. The solvent was removed in vaccuo to give the product which was recrystallized from suitable solvent and afforded the TLC and 1H-NMR pure products in 75-98 percent isolated yields.
92% With acetylhydroxamic acid; boron trifluoride diethyl etherate In methanol for 0.1 h; Microwave irradiation; Sealed tube General procedure: Benzaldehyde 1a (1.0 g, 9.4 mmol), acetohydroxamic acid (1.1 g, 14.1 mmol), methanol (1 ml) were taken in a 10 ml pressure tube and to this, BF3.OEt2 (135 μl, 0.94 mmol) was added and the mixture was subjected to microwave heating (CEM discover, 360 W, 70 °C, 25 psi) for 6 min. The crude product obtained was purified as mentioned above to afford benzaldoxime 2a (1.1 g, 95percent), which gave spectral data same as above.
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1989, vol. 331, # 5, p. 870 - 872
[2] Journal of the Iranian Chemical Society, 2010, vol. 7, # 1, p. 114 - 118
[3] Patent: CN103864754, 2016, B, . Location in patent: Paragraph 0378; 0379
[4] Chemical Communications, 2014, vol. 50, # 56, p. 7531 - 7534
[5] Revue Roumaine de Chimie, 2015, vol. 60, # 9, p. 875 - 880
[6] Tetrahedron Letters, 2011, vol. 52, # 36, p. 4701 - 4704
[7] Journal of the Indian Chemical Society, 2013, vol. 90, # 4, p. 529 - 532
[8] Synthetic Communications, 1999, vol. 29, # 10, p. 1697 - 1701
[9] Tetrahedron Letters, 2012, vol. 53, # 51, p. 6877 - 6880
[10] Catalysis Communications, 2012, vol. 29, p. 53 - 57
[11] Chemical Communications (Cambridge, United Kingdom), 2012, vol. 48, # 92, p. 11289 - 11291,3
[12] Chemical Communications, 2017, vol. 53, # 76, p. 10512 - 10515
[13] Chemistry - A European Journal, 2016, vol. 22, # 43, p. 15328 - 15339
[14] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1993, # 7, p. 1291 - 1294
[15] Chemische Berichte, 1883, vol. 16, p. 1786
[16] European Journal of Medicinal Chemistry, 2010, vol. 45, # 9, p. 4331 - 4338
[17] Monatshefte fur Chemie, 2010, vol. 141, # 4, p. 461 - 469
[18] Beilstein Journal of Organic Chemistry, 2012, vol. 8, p. 1105 - 1111
[19] Organometallics, 2012, vol. 31, # 17, p. 6482 - 6490
[20] ChemMedChem, 2013, vol. 8, # 7, p. 1210 - 1223
[21] Chemical Communications, 2015, vol. 51, # 19, p. 4085 - 4088
[22] European Journal of Medicinal Chemistry, 2015, vol. 101, p. 836 - 842
[23] Chinese Journal of Chemistry, 2015, vol. 33, # 9, p. 1011 - 1014
[24] Synthetic Communications, 2017, vol. 47, # 3, p. 232 - 237
[25] Journal of the Serbian Chemical Society, 2017, vol. 82, # 1, p. 1 - 12
[26] Catalysis Letters, 2017, vol. 147, # 2, p. 602 - 611
[27] Chemical Communications, 2017, vol. 53, # 71, p. 9886 - 9889
[28] Molecules, 2017, vol. 22, # 11,
[29] Applied Organometallic Chemistry, 2018, vol. 32, # 6,
  • 3
  • [ 90-02-8 ]
  • [ 273-53-0 ]
  • [ 94-67-7 ]
YieldReaction ConditionsOperation in experiment
28% With acetylhydroxamic acid; sulfuric acid In acetonitrile at 80℃; for 0.133333 h; Microwave irradiation General procedure: 2-Hydroxy acetophenone 4a (1.0 g, 7.4 mmol), acetohydroxamic acid (0.83 g, 11.0 mmol), acetonitrile (3 ml), and conc. H2SO4 (0.2 ml) were taken into a 10 ml pressure tube and subjected to microwave heating (CEM discover, 360 W, 80 °C, 25 psi) for 8 min. Next, the reaction mixture was diluted with ethyl acetate (3 ml) and to this; saturated sodium bicarbonate solution (5 ml) was added drop-wise. The mixture was extracted with ethyl acetate (2 .x. 10 ml) and the combined organic layer was washed with saturated NaCl solution, dried over anhy. Na2SO4, and concentrated under reduced pressure. Purification of the mixture by normal column chromatography (silica gel 60-120 mesh, ethyl acetate/hexane: 1:9) gave benzoxazole 5a (0.67 g, 70percent) in the form of a yellow oil and 2-hydroxy acetophenone oxime 6a (68 mg, 6percent, mp 104-107 °C) in the form of a white powder.
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 46, p. 6103 - 6107
  • 4
  • [ 90-01-7 ]
  • [ 94-67-7 ]
YieldReaction ConditionsOperation in experiment
96% With hydroxylamine; oxygen In ethanol at 20℃; for 0.5 h; Green chemistry General procedure: In an oven-dried 10-mL round-bottom flask, 10 mg catalyst 4 (3.2 molpercent) along with 1 mmol amine or hydroxyl amine was added to 7 mL absolute ethanol at ambient temperature.Then, 1 mmol of alcohol was added to the reaction mixture and stirred under O2 atmosphere (~1 atm.). After 14–60 min,yellow to red sediments were appeared which show successful oxidation of alcohols followed by imine formation. The product was filtered and added to 20 mL of hot methanol which just dissolved the imine compound. The filtration of the reaction mixture left a solid on the filter that was the catalyst 4. The remained solution set a side overnight for crystallization, and the recovered catalyst was reused for the next run (Scheme 2).
Reference: [1] Journal of the Iranian Chemical Society, 2017, vol. 14, # 9, p. 1917 - 1933
[2] Phosphorus, Sulfur and Silicon and the Related Elements, 2004, vol. 179, # 9, p. 1809 - 1812
  • 5
  • [ 89-95-2 ]
  • [ 94-67-7 ]
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 49, p. 8665 - 8668
[2] Russian Journal of Applied Chemistry, 2002, vol. 75, # 3, p. 511 - 512
[3] Phosphorus, Sulfur and Silicon and the Related Elements, 2004, vol. 179, # 6, p. 1193 - 1196
[4] Synthetic Communications, 2000, vol. 30, # 15, p. 2785 - 2791
[5] Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 2003, vol. 59, # 4, p. 755 - 760
[6] Bioorganic Chemistry, 2003, vol. 31, # 2, p. 129 - 135
[7] Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy, 2004, vol. 60, # 11, p. 2601 - 2610
[8] Journal of the Indian Chemical Society, 2004, vol. 81, # 3, p. 203 - 206
[9] Synthesis, 2005, # 5, p. 787 - 790
  • 6
  • [ 95-48-7 ]
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Reference: [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 27, p. 7397 - 7401
[2] Organic and Biomolecular Chemistry, 2015, vol. 13, # 27, p. 7397 - 7401
  • 7
  • [ 90-02-8 ]
  • [ 611-20-1 ]
  • [ 94-67-7 ]
Reference: [1] Catalysis Communications, 2014, vol. 49, p. 47 - 51
  • 8
  • [ 5470-11-1 ]
  • [ 90-02-8 ]
  • [ 94-67-7 ]
Reference: [1] Dalton Transactions, 2015, vol. 44, # 33, p. 14918 - 14924
  • 9
  • [ 22755-24-4 ]
  • [ 108-95-2 ]
  • [ 94-67-7 ]
  • [ 699-06-9 ]
Reference: [1] Tetrahedron Letters, 1989, vol. 30, # 42, p. 5763 - 5766
  • 10
  • [ 30866-43-4 ]
  • [ 94-67-7 ]
  • [ 30866-42-3 ]
  • [ 75586-62-8 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1335 - 1337
  • 11
  • [ 50-00-0 ]
  • [ 108-95-2 ]
  • [ 2467-02-9 ]
  • [ 94-67-7 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1994, # 13, p. 1823 - 1832
  • 12
  • [ 14363-30-5 ]
  • [ 94-67-7 ]
Reference: [1] Soumen Kemistilehti B, 1959, vol. 32, p. 203 - 207
[2] Suomen Kemistilehti B, [3] Suomen Kemistilehti B, 1959, vol. 32, p. 261 - 265
[4] , Gmelin Handbook: Ni: MVol.C2, 8.1, page 805 - 813,
  • 13
  • [ 59417-52-6 ]
  • [ 94-67-7 ]
  • [ 271-95-4 ]
  • [ 64-19-7 ]
Reference: [1] Tetrahedron, 1981, vol. 37, # 17, p. 2977 - 2982
  • 14
  • [ 80277-94-7 ]
  • [ 94-67-7 ]
  • [ 271-95-4 ]
  • [ 142-62-1 ]
Reference: [1] Tetrahedron, 1981, vol. 37, # 17, p. 2977 - 2982
  • 15
  • [ 80289-35-6 ]
  • [ 143-07-7 ]
  • [ 94-67-7 ]
  • [ 271-95-4 ]
Reference: [1] Tetrahedron, 1981, vol. 37, # 17, p. 2977 - 2982
  • 16
  • [ 94-67-7 ]
  • [ 938-73-8 ]
Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1983, vol. 32, # 10, p. 2153 - 2155[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1983, # 10, p. 2389 - 2391
[3] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1983, vol. 32, # 10, p. 2153 - 2155[4] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1983, # 10, p. 2389 - 2391
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