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[ CAS No. 2516-96-3 ] {[proInfo.proName]}

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Chemical Structure| 2516-96-3
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Product Details of [ 2516-96-3 ]

CAS No. :2516-96-3 MDL No. :MFCD00007294
Formula : C7H4ClNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :QUEKGYQTRJVEQC-UHFFFAOYSA-N
M.W : 201.56 Pubchem ID :17287
Synonyms :

Calculated chemistry of [ 2516-96-3 ]      Expand+

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) : -6.09 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.73
Log Po/w (XLOGP3) : 2.03
Log Po/w (WLOGP) : 1.95
Log Po/w (MLOGP) : 1.11
Log Po/w (SILICOS-IT) : -0.26
Consensus Log Po/w : 1.11

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.58
Solubility : 0.532 mg/ml ; 0.00264 mol/l
Class : Soluble
Log S (Ali) : -3.4
Solubility : 0.0796 mg/ml ; 0.000395 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 : 1.78

Safety of [ 2516-96-3 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 2516-96-3 ]

* 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 [ 2516-96-3 ]
  • Downstream synthetic route of [ 2516-96-3 ]

[ 2516-96-3 ] Synthesis Path-Upstream   1~25

  • 1
  • [ 2516-96-3 ]
  • [ 474799-41-2 ]
Reference: [1] Patent: WO2008/152014, 2008, A2,
  • 2
  • [ 118-91-2 ]
  • [ 2516-96-3 ]
  • [ 3970-35-2 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1900, vol. 19, p. 55
[2] Recueil des Travaux Chimiques des Pays-Bas, 1901, vol. 20, p. 215,225
[3] Justus Liebigs Annalen der Chemie, 1884, vol. 222, p. 195
  • 3
  • [ 7697-37-2 ]
  • [ 118-91-2 ]
  • [ 2516-96-3 ]
  • [ 3970-35-2 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1926, vol. 45, p. 531
[2] Justus Liebigs Annalen der Chemie, 1884, vol. 222, p. 195
[3] Recueil des Travaux Chimiques des Pays-Bas, 1900, vol. 19, p. 55
[4] Recueil des Travaux Chimiques des Pays-Bas, 1901, vol. 20, p. 215,225
  • 4
  • [ 2516-96-3 ]
  • [ 34595-33-0 ]
Reference: [1] Patent: EP1176140, 2002, A1,
  • 5
  • [ 2516-96-3 ]
  • [ 32188-75-3 ]
Reference: [1] Patent: EP1176140, 2002, A1,
  • 6
  • [ 2516-96-3 ]
  • [ 506-77-4 ]
  • [ 16588-02-6 ]
Reference: [1] Patent: US4189580, 1980, A,
  • 7
  • [ 2516-96-3 ]
  • [ 16588-02-6 ]
Reference: [1] Patent: EP1176140, 2002, A1,
  • 8
  • [ 2516-96-3 ]
  • [ 2965-22-2 ]
Reference: [1] Canadian Journal of Chemistry, 1971, vol. 49, p. 583 - 587
  • 9
  • [ 2516-96-3 ]
  • [ 3898-66-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 3, p. 1068 - 1072
[2] Patent: WO2018/208132, 2018, A1,
  • 10
  • [ 2516-96-3 ]
  • [ 20246-81-5 ]
Reference: [1] Journal of the American Chemical Society, 1923, vol. 45, p. 1914
  • 11
  • [ 2516-96-3 ]
  • [ 26513-20-2 ]
  • [ 20246-81-5 ]
Reference: [1] Journal of the American Chemical Society, 1923, vol. 45, p. 1914
  • 12
  • [ 2516-96-3 ]
  • [ 16588-26-4 ]
Reference: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 30, p. 5416 - 5421
  • 13
  • [ 2516-96-3 ]
  • [ 89-54-3 ]
YieldReaction ConditionsOperation in experiment
95.1% With iron; ammonium chloride In ethanol; water at 78 - 80℃; for 5 h; To the reaction flask was added 75 g of 2-chloro-5-nitrobenzoic acid, 59 g of iron powder, 800 ml of ethanol, 150 ml of water, 115 g of ammonium chlorideHeated to 78 ~ 80° C reflux 5h,TLC (PE / EA: 1/3) After the reaction was monitored, the filtrate was filtered while hot, washed with 150 ml of hot ethanol, and the filtrate was reduced to dryness at 60 ° C to obtain a crude product,Add 400ml ethyl acetate heating reflux beating 2h,Naturally dropped to room temperature after the salt bath cooling to 0 ~ 5° C crystallization more than 30min,Centrifuged, washed with 50 ml of ethyl acetate and dried at 50 ° C under reduced pressure to give a yellow solid 60.7 g of 2-chloro-5-aminobenzoic acid, 99.1percent purity and 95.1percent yield.
Reference: [1] Arzneimittel-Forschung/Drug Research, 1982, vol. 32, # 3, p. 183 - 186
[2] Chemical and Pharmaceutical Bulletin, 1988, vol. 36, # 9, p. 3462 - 3467
[3] Patent: CN106748721, 2017, A, . Location in patent: Paragraph 0029; 0030
[4] Angewandte Chemie - International Edition, 1999, vol. 38, # 18, p. 2777 - 2779
[5] Justus Liebigs Annalen der Chemie, 1868, vol. 147, p. 258
[6] Justus Liebigs Annalen der Chemie, 1884, vol. 222, p. 198
[7] Journal of the Indian Chemical Society, 1941, vol. 18, p. 25,26
[8] Helvetica Chimica Acta, 1938, vol. 21, p. 51,55
[9] Patent: US2100242, 1936, ,
[10] Journal of the Chemical Society, 1946, p. 102,107
[11] Grundlegende Operationen der Farbenchemie, 5. Aufl. <Wien 1943>, S. 162,
[12] Journal of Organic Chemistry, 1954, vol. 19, p. 357,362
[13] Journal of the American Chemical Society, 1954, vol. 76, p. 6336,6337
[14] Monatshefte fuer Chemie, 1921, vol. 42, p. 80[15] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1924, vol. 54, p. 832[16] Chem. Zentralbl., 1925, vol. 96, # I, p. 227
[17] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1924, vol. 54, p. 675[18] Chem. Zentralbl., 1924, vol. 95, # I, p. 905
[19] Bulletin de la Societe Chimique de France, 1966, p. 1848 - 1858
[20] Journal of Organic Chemistry, 1961, vol. 26, p. 919 - 923
[21] European Journal of Organic Chemistry, 2018, vol. 2018, # 2, p. 209 - 214
  • 14
  • [ 2516-96-3 ]
  • [ 74534-15-9 ]
Reference: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 30, p. 5416 - 5421
  • 15
  • [ 2516-96-3 ]
  • [ 23082-50-0 ]
Reference: [1] Arzneimittel-Forschung/Drug Research, 1989, vol. 39, # 9, p. 1073 - 1080
[2] Organic Process Research and Development, 2016, vol. 20, # 8, p. 1509 - 1519
  • 16
  • [ 2516-96-3 ]
  • [ 2252-50-8 ]
Reference: [1] Journal of Organic Chemistry, 1961, vol. 26, p. 919 - 923
  • 17
  • [ 2516-96-3 ]
  • [ 62-53-3 ]
  • [ 22978-25-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 12, p. 4113 - 4124
  • 18
  • [ 2516-96-3 ]
  • [ 42122-75-8 ]
Reference: [1] Patent: WO2013/22766, 2013, A1,
  • 19
  • [ 2516-96-3 ]
  • [ 56961-30-9 ]
Reference: [1] Arzneimittel-Forschung/Drug Research, 1982, vol. 32, # 3, p. 183 - 186
[2] Monatshefte fuer Chemie, 1921, vol. 42, p. 80[3] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1924, vol. 54, p. 832[4] Chem. Zentralbl., 1925, vol. 96, # I, p. 227
  • 20
  • [ 2516-96-3 ]
  • [ 719282-11-8 ]
Reference: [1] Journal of the Chemical Society, 1946, p. 102,107
  • 21
  • [ 504-24-5 ]
  • [ 2516-96-3 ]
  • [ 313516-66-4 ]
YieldReaction ConditionsOperation in experiment
58%
Stage #1: With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2 h;
Stage #2: With triethylamine In dichloromethane at 20℃; for 16 h;
To a solution of 2-chloro-5-nitrobenzoic acid (0.500 g, 2.48 mmol) in dichloromethane (8.3 mL) was added oxalyl chloride (0.239 mL, 2.73 mmol) slowly, followed by /V,N-dimethylformamide ( 1 drop). The reaction was stirred at room temperature for 2 hours. To the solution was added triethylamine (0.691 mL, 4.96 mmol) followed by pyridin-4-amine (0.467 g, 4.96 mmol) in dichloromethane ( 1 mL). The reaction was allowed to stir at room temperature for 16 hours. Purification by flash column chromatography using 0-100percent ethyl acetate/hexanes as eluent provided the title compound as a tan solid (0.401 g, 58percent) : ' H NMR (400 MHz, DMSO-de) δ 11.10 (s, 1H), 8.64 - 8.45 (m, 3H), 8.37 (dd, J = 8.9, 2.8 Hz, 1 H), 7.92 (d, J = 8.8 Hz, 1H), 7.73 - 7.61 (m, 2H) ; 13C NMR ( 101 MHz, DMSO-de) δ 163.67, 150.56, 146.14, 145.04, 136.95, 131.40, 126.06, 124.00, 113.68 ; ESIMS m/z 278 ( [M + H ]+ ).
Reference: [1] Patent: WO2016/168059, 2016, A1, . Location in patent: Page/Page column 160
  • 22
  • [ 2516-96-3 ]
  • [ 915095-86-2 ]
Reference: [1] Patent: CN106699570, 2017, A,
  • 23
  • [ 2516-96-3 ]
  • [ 288251-82-1 ]
Reference: [1] Patent: EP1176140, 2002, A1,
  • 24
  • [ 2516-96-3 ]
  • [ 288251-85-4 ]
Reference: [1] Patent: EP1176140, 2002, A1,
  • 25
  • [ 2516-96-3 ]
  • [ 288251-87-6 ]
Reference: [1] Patent: EP1176140, 2002, A1,
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