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Product Details of [ 73635-75-3 ]

CAS No. :73635-75-3
Formula : C7H5NO5
M.W : 183.12
SMILES Code : O=CC1=CC(O)=C(O)C=C1[N+]([O-])=O
MDL No. :MFCD00016645
InChI Key :SDAAKNQPCGUCNH-UHFFFAOYSA-N
Pubchem ID :3782344

Safety of [ 73635-75-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis of [ 73635-75-3 ]

* 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 [ 73635-75-3 ]

[ 73635-75-3 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 712-97-0 ]
  • [ 73635-75-3 ]
References: [1] Journal of the Chemical Society, 1948, p. 1244,1246.
[2] Journal of Organic Chemistry, 1985, vol. 50, # 26, p. 5873 - 5875.
[3] Synthetic Communications, 1985, vol. 15, # 4, p. 321 - 330.
[4] Journal of Organic Chemistry, 1980, vol. 45, # 14, p. 2750 - 2753.
[5] Russian Chemical Bulletin, 2014, vol. 63, # 5, p. 1169 - 1177[6] Izv. Akad. Nauk, Ser. Khim., 2014, # 5, p. 1169 - 1177,9.
[7] Russian Chemical Bulletin, 2016, vol. 65, # 2, p. 507 - 512[8] Izv. Akad. Nauk, Ser. Khim., 2016, # 2, p. 507 - 512,6.
  • 2
  • [ 73635-74-2 ]
  • [ 73635-75-3 ]
YieldReaction ConditionsOperation in experiment
1.79 g With hydrogen bromide In 1,2-dichloro-ethane at 20℃; for 48 h; Inert atmosphere To a solution of pure aluminum chloride (11 g, 82.4 mmol) in anhydrous 1,2-dichloroethane (25 mL) prepared under the argon atmo- sphere and cooled to –5 °C, a solution of compound 1 (5 g, 25.6 mmol) in anhydrous 1,2-dichloroethane (20 mL) was added dropwise with stirring. The reaction was continued for 2 h main- taining the temperature from –5 °C to 5 °C until compound 1 disappeared. To complete the reaction, the mixture was poured into 48percent HBr (60 mL) and stirred for 48 h at room temperature (~20 °C) until the intermediate chloromethyl ether disappeared (TLC control). The reaction mixture was diluted with water (60 mL), extracted with ethyl acetate (3×50 mL), and dried over magnesium sulfate. The solvent was evaporated and the residue was treated with hot hexane. The treatment of the crude product with hot dichloromethane (50 mL) yielded 4,5-dihydroxy- 2-nitrobenzaldehyde (4.3 g, 90percent), which was recrystallized from water (100 mL) to yield the chromatographically homogeneous product (1.79 g) as yellow crystals, m.p. 202—203 °C, Rf 0.25 (acetone—hexane, 1 : 2). 1H NMR (CDCl3), d: 7.21 (s, 1 H, C(6)H); 7.50 (s, 1 H, C(3)H); 10.14 (s, 1 H, CHO); 10.85 (s, 2 H, 2 OH). To a solution of 4,5-dihydroxy-2-nitrobenzaldehyde (0.5 g, 2.7 mmol) in DMF, the anhydrous finely powdered potassium carbonate (0.94 g, 6.8 mmol) and n-bromobutane (1.1 g, 8.1 mmol) were added with stirring in the argon stream with moisture pro- tection. The resulting mixture was heated for 15 h at 60 °C, diluted with water, and extracted with diethyl ether (3×50 mL). The extract was dried with MgSO4and the solvent was evaporat- ed. The residue was recrystallized from diethyl ether to yield the chromatographically homogeneous compound 5 (0.66 g, 83percent) as a crystalline powder, m.p. 80—85 °C, Rf0.62 (acetone—hex- ane, 1 : 2). Found (percent): C, 61.04; H, 7.20; N, 5.71. C15H21NO5. Calculated (percent): C, 61.00; H, 7.17; N, 4.74. 1H NMR (CDCl3), d: 0.98—1.03 (m, 6 H, 2 CH3); 1.47—1.58 (m, 4 H, 2 CH2); 1.82—1.91 (m, 4 H, 2 CH2); 4.13—4.16 (m, 4 H, 2 CH2); 7.38 (s, 1 H, C(6)H); 7.58 (s, 1 H, C(3)H); 10.43 (s, 1 H, CHO).
References: [1] Journal of Organic Chemistry, 1980, vol. 45, # 14, p. 2750 - 2753.
[2] Synthetic Communications, 1985, vol. 15, # 4, p. 321 - 330.
[3] Journal of Organic Chemistry, 1985, vol. 50, # 26, p. 5873 - 5875.
[4] Patent: US4595765, 1986, A, .
[5] Russian Chemical Bulletin, 2016, vol. 65, # 2, p. 507 - 512[6] Izv. Akad. Nauk, Ser. Khim., 2016, # 2, p. 507 - 512,6.
  • 3
  • [ 75-34-3 ]
  • [ 73635-74-2 ]
  • [ 73635-75-3 ]
References: [1] Patent: US4595765, 1986, A, .
  • 4
  • [ 2426-87-1 ]
  • [ 73635-75-3 ]
References: [1] Journal of Materials Chemistry A, 2018, vol. 6, # 15, p. 6667 - 6674.
  • 5
  • [ 121-33-5 ]
  • [ 73635-75-3 ]
References: [1] Journal of Materials Chemistry A, 2018, vol. 6, # 15, p. 6667 - 6674.
  • 6
  • [ 2454-72-0 ]
  • [ 73635-75-3 ]
References: [1] Journal of Materials Chemistry A, 2018, vol. 6, # 15, p. 6667 - 6674.
  • 7
  • [ 331-39-5 ]
  • [ 73635-75-3 ]
References: [1] Tetrahedron Letters, 2001, vol. 42, # 19, p. 3303 - 3305.
  • 8
  • [ 7697-37-2 ]
  • [ 108-24-7 ]
  • [ 73635-75-3 ]
References: [1] Recueil des Travaux Chimiques des Pays-Bas, 1930, vol. 49, p. 33,41.
[2] Journal of the Chemical Society, 1948, p. 2223,2224.
 

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