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[ CAS No. 6280-88-2 ] {[proInfo.proName]}

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Chemical Structure| 6280-88-2
Chemical Structure| 6280-88-2
Structure of 6280-88-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 6280-88-2 ]

CAS No. :6280-88-2 MDL No. :MFCD00007214
Formula : C7H4ClNO4 Boiling Point : -
Linear Structure Formula :Cl(NO2)C6H3COOH InChI Key :JAHIPDTWWVYVRV-UHFFFAOYSA-N
M.W : 201.56 Pubchem ID :80475
Synonyms :

Calculated chemistry of [ 6280-88-2 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.23
TPSA : 83.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.05 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.81
Log Po/w (XLOGP3) : 2.08
Log Po/w (WLOGP) : 1.95
Log Po/w (MLOGP) : 1.11
Log Po/w (SILICOS-IT) : -0.26
Consensus Log Po/w : 1.14

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.61
Solubility : 0.495 mg/ml ; 0.00246 mol/l
Class : Soluble
Log S (Ali) : -3.46
Solubility : 0.0707 mg/ml ; 0.000351 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.77
Solubility : 3.4 mg/ml ; 0.0169 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.75

Safety of [ 6280-88-2 ]

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

Application In Synthesis of [ 6280-88-2 ]

* 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 [ 6280-88-2 ]
  • Downstream synthetic route of [ 6280-88-2 ]

[ 6280-88-2 ] Synthesis Path-Upstream   1~24

  • 1
  • [ 6280-88-2 ]
  • [ 31374-18-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 147, p. 227 - 237
  • 2
  • [ 6280-88-2 ]
  • [ 89-77-0 ]
Reference: [1] Chemical Biology and Drug Design, 2016, p. 710 - 723
[2] Journal of the American Chemical Society, 1954, vol. 76, p. 6336,6337
[3] Journal of the American Chemical Society, 1923, vol. 45, p. 1028
[4] Collection of Czechoslovak Chemical Communications, 1968, vol. 33, # 6, p. 1852 - 1872
[5] European Journal of Medicinal Chemistry, 2018, vol. 147, p. 227 - 237
  • 3
  • [ 6280-88-2 ]
  • [ 53449-14-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 147, p. 227 - 237
  • 4
  • [ 6280-88-2 ]
  • [ 5900-58-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 8, p. 1743 - 1754
[2] Journal of the American Chemical Society, 1923, vol. 45, p. 1028
  • 5
  • [ 6280-88-2 ]
  • [ 34662-32-3 ]
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 7, p. 2794 - 2803
  • 6
  • [ 6280-88-2 ]
  • [ 34662-32-3 ]
Reference: [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 21, p. 4394 - 4404
[2] Tetrahedron, 1994, vol. 50, # 18, p. 5515 - 5525
  • 7
  • [ 6280-88-2 ]
  • [ 41513-04-6 ]
YieldReaction ConditionsOperation in experiment
96% With trichloroisocyanuric acid; bromine In tetrachloromethane at 10 - 100℃; for 18 h; Photolysis General procedure: A 25 mL round bottom flask equipped with Dimroth condenser (chilled to 10 °C) was charged with nitroarenecarboxylic acid ArC02H (1.8 mmol), chloroisocyanurate, brominating agent and solvent (8 mL). The mixture was stirred and heated in an oil bath under fluorescent room light irradiation (FL). The cooled reaction mixture was filtered through short silica gel pad, washed with 1 M aq Na2S03, dried over Na2S04, filtered and concentrated in vacuo to obtain bromonitroarene ArBr. The obtained product contained between 1-5percent of the corresponding chloronitroarene ArCl as a by-product. The results are presented in Table 2. Table 2. Bromodecarboxylation of nitroarenecarboxylic acids ArC02H a
Reference: [1] Patent: WO2017/60906, 2017, A1, . Location in patent: Paragraph 00122
[2] Journal of Organic Chemistry, 2016, vol. 81, # 7, p. 2794 - 2803
[3] Organic and Biomolecular Chemistry, 2018, vol. 16, # 30, p. 5416 - 5421
  • 8
  • [ 6280-88-2 ]
  • [ 5446-05-9 ]
YieldReaction ConditionsOperation in experiment
72% With 2.9-dimethyl-1,10-phenanthroline; oxygen; copper (I) acetate; silver sulfate; sodium iodide In dimethyl sulfoxide at 160℃; for 24 h; Schlenk technique Silak reaction tube equipped with a magnetic stirrer was added6.2 mg of silver sulfate,21.8 mg of copper acetate,2,9-dimethyl-1,10-phenanthroline12.5mg,40.3 mg of 2-nitro-4-chlorobenzoic acid and 45 mg of sodium iodide4 mL of dimethyl sulfoxide.The reaction was heated at 160 ° C for 24 hours in the presence of oxygen.After the reaction was completed, distilled water was added to quench the reaction,Extraction with ethyl acetate 3 times, each time 10mL,The combined organic phases are concentrated to give2-nitro-4-chloroiodobenzene 40.8 mg,The yield is 72percent.
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 7, p. 2794 - 2803
[2] Patent: CN107325002, 2017, A, . Location in patent: Page/Page column 6; 7
[3] Organic and Biomolecular Chemistry, 2018, vol. 16, # 30, p. 5416 - 5421
  • 9
  • [ 74-11-3 ]
  • [ 6280-88-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 147, p. 227 - 237
  • 10
  • [ 34662-32-3 ]
  • [ 6280-88-2 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1888, vol. <2> 37, p. 197
[2] Journal of the Chemical Society, 1947, p. 232,236
[3] Journal of the American Chemical Society, 1923, vol. 45, p. 1028
[4] Chemische Berichte, 1916, vol. 49, p. 547
  • 11
  • [ 89-63-4 ]
  • [ 6280-88-2 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1888, vol. <2> 37, p. 197
[2] Journal of the American Chemical Society, 1923, vol. 45, p. 1028
[3] Journal of the Chemical Society, 1947, p. 232,236
  • 12
  • [ 89-59-8 ]
  • [ 6280-88-2 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1887, vol. <2> 36, p. 22
[2] Chemische Berichte, 1891, vol. 24, p. 3814
[3] Monatshefte fuer Chemie, 1901, vol. 22, p. 474
[4] Journal of the Chemical Society, 1905, vol. 87, p. 1271
[5] Journal of the Chemical Society, 1947, p. 232,236
[6] Journal of Organic Chemistry, 1946, vol. 11, p. 405,412
[7] Journal of the Chemical Society, 1891, vol. 59, p. 1017
  • 13
  • [ 2001-16-3 ]
  • [ 6280-88-2 ]
Reference: [1] Journal of Organic Chemistry, 1957, vol. 22, p. 639,641
  • 14
  • [ 622-98-0 ]
  • [ 6280-88-2 ]
Reference: [1] Journal of Organic Chemistry, 1957, vol. 22, p. 639,641
  • 15
  • [ 119-32-4 ]
  • [ 6280-88-2 ]
Reference: [1] Journal of the Chemical Society, 1891, vol. 59, p. 1017
[2] Journal fuer Praktische Chemie (Leipzig), 1887, vol. <2> 36, p. 22
  • 16
  • [ 88-72-2 ]
  • [ 6280-88-2 ]
Reference: [1] Monatshefte fuer Chemie, 1901, vol. 22, p. 474
  • 17
  • [ 41994-91-6 ]
  • [ 6280-88-2 ]
Reference: [1] Chemische Berichte, 1916, vol. 49, p. 547
  • 18
  • [ 89-59-8 ]
  • [ 7697-37-2 ]
  • [ 6280-88-2 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1887, vol. <2> 36, p. 22
[2] Journal of the Chemical Society, 1905, vol. 87, p. 1271
[3] Chemische Berichte, 1891, vol. 24, p. 3814
  • 19
  • [ 6280-88-2 ]
  • [ 13421-13-1 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1968, vol. 33, # 6, p. 1852 - 1872
  • 20
  • [ 6280-88-2 ]
  • [ 105-53-3 ]
  • [ 23082-51-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 24, p. 7381 - 7387
  • 21
  • [ 6280-88-2 ]
  • [ 23082-51-1 ]
Reference: [1] Journal of the Chemical Society, 1947, p. 232,236
[2] Patent: WO2015/54572, 2015, A1,
  • 22
  • [ 6280-88-2 ]
  • [ 39061-72-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 24, p. 7381 - 7387
[2] Patent: WO2015/54572, 2015, A1,
  • 23
  • [ 6280-88-2 ]
  • [ 123158-76-9 ]
YieldReaction ConditionsOperation in experiment
73% With copper(I) oxide; potassium phosphate; bismuth (III) nitrate pentahydrate; palladium(II) trifluoroacetate; oxygen; sodium iodide In dimethyl sulfoxide at 170℃; for 20 h; Schlenk technique In a Schlenk reaction tube equipped with a magnetic stirrer, 6.7 mg of palladium trifluoroacetate was added.Cuprous oxide 28.6 mg, phosphorusPotassium 6.4mg,4-chloro-2-nitrobenzoic acid 40.3 mg,Sodium iodide 36mg,bismuth nitrate pentahydrate 194mg and 2mL of dimethyl Sulfoxide.The reaction was heated at 170°C for 20 hours in the presence of oxygen. After the reaction is completed, distilled water is added to quench the reaction.useEthyl acetate was extracted 3 times.10 mL each, the combined organic phases are concentrated to give 1-chloro-3-iodo-5-nitrobenzene41.4 mg, yield 73percent.
Reference: [1] Patent: CN107513020, 2017, A, . Location in patent: Paragraph 0069-0070
  • 24
  • [ 6280-88-2 ]
  • [ 1393803-55-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 15, p. 5031 - 5034
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