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[ CAS No. 16588-34-4 ]

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2D
Chemical Structure| 16588-34-4
Chemical Structure| 16588-34-4
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Product Details of [ 16588-34-4 ]

CAS No. :16588-34-4MDL No. :MFCD00007078
Formula : C7H4ClNO3 Boiling Point : 299.8±25.0°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :185.57Pubchem ID :85505
Synonyms :

Computed Properties of [ 16588-34-4 ]

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

Safety of [ 16588-34-4 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P280-P305+P351+P338UN#:N/A
Hazard Statements:H315-H317-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 16588-34-4 ]

  • Upstream synthesis route of [ 16588-34-4 ]
  • Downstream synthetic route of [ 16588-34-4 ]

[ 16588-34-4 ] Synthesis Path-Upstream   1~12

  • 1
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  • [ 32863-33-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 4, p. 657 - 667
  • 2
  • [ 16588-34-4 ]
  • [ 6287-38-3 ]
Reference: [1] Journal of the Chemical Society, 1927, p. 25
  • 3
  • [ 66399-01-7 ]
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Reference: [1] Journal of Organic Chemistry, 2010, vol. 75, # 2, p. 484 - 486
  • 4
  • [ 104-88-1 ]
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YieldReaction ConditionsOperation in experiment
97% for 2 h; Cooling To the mixture of nitrosonitric acid (55 mL) and sulfuric acid (55 mL) was added 4-chlorobenzaldehyde (70 g, 0.5 mol) in batches at 5 °C and stirred for 2 h.
Then the mixture was poured slowly to ice water (1 L) while stirring constantly.
The resulting precipitate was filtered and recrystallized from ethanol/water to give product 13 (90 g, 97percent) as white acicular crystal. Mp: 62-63 °C
94% at 0 - 20℃; for 0.5 h; Inert atmosphere General procedure: 10 mmol of the desired p-substituted benzaldehyde was dissolved in 5 mL of conc. sulfuric acid, and cooled to 0 °C, and then 1.2 equiv. of nitric acid was dissolved in 1 mL of conc. sulfuric acid, and then slowly added to the reaction mixture. The reaction was allowed to warmgradually to room temperature and stirred for 30 min at room temperature. It was then poured into 50 mL of ice-cold water. The produced precipitate was filtered and washed with cold water. The product was purified on reverse phase column chromatography with gradient increase of methanol in water containing 0.1percent of formic acid as eluent.
75% at 150℃; for 0.025 h; Microwave irradiation General procedure: The microwave (MW) reactor used was of CEM make, which was equipped with temperature, pressure, and MW power control units. An oven-dried MW vial was charged with a mixture containing aromatic compound, V2O5 (9 mg, 0.005 mmol) and 69percent HNO3 (0.063 mL, 1 mmol) and silica gel slurry, and irradiated in a MW (power input 140 W) at 150 °C for few minutes. After completion of the reaction, as as certained by TLC, the reaction mixture was treated with sodium bicarbonate; the organic layer was diluted with dichloromethane (DCM) and separated from aqueous layer. The crude product mixture was purified with ethyl acetate DCM mixture. The purity was checked with TLC. The products were identified by characteristic spectroscopic data.
70% at 0 - 40℃; for 1 h; General procedure: The nitration of aldehydes was carried out in a three-neckedflask of 50 ml with magnetic stirrer. H2SO4 25 ml (0.47 M)were cooled to 0 °C, 3.1 ml (0.070 M) of HNO3 were added,and then the aldehyde (0.06 M) was slowly added. Thereaction was carried out at a temperature of 0–5 °C. Then,the mixture was heated at 40 °C for 1 h. The reaction waspoured into ice water and filtered under a vacuum; thenitrobenzaldehydes were purified by recrystallization. Thescheme of reaction is showed in Fig. 1 (Furniss et al. 1989).The spectrums of 1H NMR of nitrobenzaldehydes wereobtained in CDCl3 and TMS as reference. 4-chloro-3-nitrobenzaldehyde: Yellow solid; mp 60–62 °C; yield: 70percent; 1H NMR (600MHz, CDCl3), 7.89(d, J = 8.16, 1H Ar–H), 8.25 (d, J = 8.16, 1H, Ar–H), 8.98(t, J = 8.16, 1H, Ar–H), 10.01 (s, 1H, –CHO).

Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 4, p. 657 - 667
[2] European Journal of Medicinal Chemistry, 2014, vol. 77, p. 361 - 377
[3] Journal of Chemical Research, 2008, # 12, p. 722 - 724
[4] Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 2013, vol. 43, # 8, p. 977 - 983
[5] Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 2014, vol. 44, # 7, p. 921 - 926
[6] Medicinal Chemistry Research, 2018, vol. 27, # 7, p. 1782 - 1791
[7] Supramolecular Chemistry, 2011, vol. 23, # 5, p. 407 - 410
[8] Journal of the Chemical Society, 1927, p. 25
[9] Justus Liebigs Annalen der Chemie, 1897, vol. 294, p. 380
[10] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 3, p. 65
[11] Recueil des Travaux Chimiques des Pays-Bas, 1926, vol. 45, p. 694[12] Recueil des Travaux Chimiques des Pays-Bas, 1929, vol. 48, p. 1137
[13] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 3, p. 63
[14] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 3, p. 63
[15] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 3, p. 64
[16] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 3, p. 63
  • 5
  • [ 55912-20-4 ]
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Reference: [1] Synthetic Communications, 2008, vol. 38, # 15, p. 2638 - 2645
[2] Tetrahedron Letters, 2006, vol. 47, # 1, p. 13 - 17
[3] Angewandte Chemie - International Edition, 2018, vol. 57, # 33, p. 10535 - 10539[4] Angew. Chem., 2018, vol. 130, # 33, p. 10695 - 10699,5
  • 6
  • [ 662165-72-2 ]
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Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 10, p. 2635 - 2637
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  • [ 85152-60-9 ]
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Reference: [1] Journal of the American Chemical Society, 1983, vol. 105, # 9, p. 2718 - 2725
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  • [ 42860-04-8 ]
Reference: [1] Journal of the Chemical Society, 1927, p. 25
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  • [ 42860-10-6 ]
Reference: [1] Journal of the Chemical Society, 1927, p. 25
  • 10
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  • [ 86265-88-5 ]
Reference: [1] Journal of the Chemical Society, 1927, p. 25
[2] Journal of Medicinal Chemistry, 2004, vol. 47, # 12, p. 3163 - 3179
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  • [ 276866-90-1 ]
Reference: [1] Journal of the Chemical Society, 1927, p. 25
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  • [ 42564-51-2 ]
YieldReaction ConditionsOperation in experiment
92.5% With potassium fluoride In thiophene; water EXAMPLE 5
18.6 g (0.1 mol) of 4-chloro-3-nitrobenzaldehyde and 8.7 g (0.15 mol) of potassium fluoride in 100 ml of sulpholane are stirred for 1 hour at 180° C.
The mixture is stirred with 300 ml of water and the aldehyde is extracted with methylene chloride.
After the customary working-up, 17.1 g of 92percent strength 4-fluoro-3-nitrobenzaldehyde are obtained.
Yield:
92.5percent of the theoretical yield.
Reference: [1] Patent: US4456772, 1984, A,
[2] Patent: US4456772, 1984, A,
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