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[ CAS No. 99-60-5 ] {[proInfo.proName]}

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Chemical Structure| 99-60-5
Chemical Structure| 99-60-5
Structure of 99-60-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 99-60-5 ]

CAS No. :99-60-5 MDL No. :MFCD00007209
Formula : C7H4ClNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :QAYNSPOKTRVZRC-UHFFFAOYSA-N
M.W : 201.56 Pubchem ID :7448
Synonyms :

Calculated chemistry of [ 99-60-5 ]

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) : 0.86
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 : 1.14

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.58
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 : 1.68

Safety of [ 99-60-5 ]

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 [ 99-60-5 ]

* 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 [ 99-60-5 ]
  • Downstream synthetic route of [ 99-60-5 ]

[ 99-60-5 ] Synthesis Path-Upstream   1~18

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  • [ 23687-26-5 ]
Reference: [1] Patent: US9840468, 2017, B1,
  • 2
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  • [ 46004-37-9 ]
Reference: [1] Patent: WO2013/68467, 2013, A1,
[2] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 17, p. 4377 - 4381
[3] Patent: WO2018/68296, 2018, A1,
  • 3
  • [ 5568-33-2 ]
  • [ 99-60-5 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 40, p. 20636 - 20640
[2] Chemische Berichte, 1891, vol. 24, p. 706
  • 4
  • [ 121-86-8 ]
  • [ 99-60-5 ]
Reference: [1] Journal of the American Chemical Society, 1949, vol. 71, p. 4154
[2] Chemische Berichte, 1932, vol. 65, p. 999,1003
[3] Journal of the Indian Chemical Society, 1941, vol. 18, p. 25,26
[4] Zhurnal Obshchei Khimii, 1933, vol. 3, p. 615,618
[5] Farmaco (1946-1952), 1948, vol. 3, p. 509,523
[6] Zhurnal Obshchei Khimii, 1945, vol. 15, p. 962,964[7] Chem.Abstr., 1946, p. 6443
[8] Yakugaku Zasshi, 1934, vol. 54, p. 557-559; dtsch. Ref. S. 95[9] Chem.Abstr., 1937, p. 97
[10] Justus Liebigs Annalen der Chemie, 1907, vol. 355, p. 366[11] Justus Liebigs Annalen der Chemie, 1909, vol. 371, p. 388
[12] Justus Liebigs Annalen der Chemie, 1877, vol. 185, p. 281
[13] Journal of the Chemical Society, 1905, vol. 87, p. 1271
[14] Chemische Berichte, 1891, vol. 24, p. 706
  • 5
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  • [ 52301-88-9 ]
Reference: [1] Patent: CN105237317, 2016, A, . Location in patent: Paragraph 0081; 0082
  • 6
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Reference: [1] Farmaco (1946-1952), 1948, vol. 3, p. 509,523
  • 7
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  • [ 99-60-5 ]
Reference: [1] Chemische Berichte, 1891, vol. 24, p. 706
  • 8
  • [ 99-99-0 ]
  • [ 99-60-5 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1877, vol. 185, p. 281
  • 9
  • [ 42533-63-1 ]
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Reference: [1] Chemische Berichte, 1891, vol. 24, p. 706
  • 10
  • [ 99-55-8 ]
  • [ 99-60-5 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1907, vol. 355, p. 366[2] Justus Liebigs Annalen der Chemie, 1909, vol. 371, p. 388
  • 11
  • [ 121-86-8 ]
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Reference: [1] Chemische Berichte, 1932, vol. 65, p. 999,1003
  • 12
  • [ 10026-13-8 ]
  • [ 22952-26-7 ]
  • [ 99-60-5 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1906, vol. 25, p. 63
  • 13
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  • [ 52301-88-9 ]
YieldReaction ConditionsOperation in experiment
98%
Stage #1: With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 1 h;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water at 20℃; for 16 h;
λ/,iV'-Carbonyldiimidazole (19.91 g, 122 mmol) is added batchwise to 2-chloro-4- nitrobenzoic acid (25 g, 90 percent purity, 111 mmol) in anhydrous THF (420 mL) at RT and stirred for 1 h. At 15 - 20 0C, NaBH (13.09 g, 346 mmol) in water (85 mL) is added dropwise thereto and the mixture is stirred for 16 h at RT. The reaction mixture is adjusted to pH 1 with 6 N HCl and exhaustively extracted with EtOAc. The combined organic <n="26"/>phases are washed with 15 percent potassium carbonate solution (2 x 150 mL) and saturated saline solution (150 mL), dried, filtered and evaporated down. Yield: 20.60 g (98 percent
97%
Stage #1: With borane In tetrahydrofuran at 20℃; for 16 h;
Stage #2: With water; potassium carbonate In tetrahydrofuran
Starting with acid 52: a solution of 2-chloro-4-nitrobenzoic acid (15.95 g, 79 mmol, 1.0 equiv.) in THF (200 mL) was cooled to 0 0C. BH3 (118.7 mL, 118.7 mmol, 1 M solution in THF, 1.5 equiv.) was added dropwise. Reaction mixture was allowed to warm to room temperature and stirred for 16 h. A sat'd solution OfK2CO3 in water was added dropwise untill gas evolution stopped. After precipitation of a white solid, the r.m. was filtered and washed with EtOAc. Filtrate and washings were combined and concentrated in vacuo. The product was redissolved in EtOAc, washed with IN HCl (2x), sat'd NaHCO3 and brine and dried on Na2SO4. After filtration and concentration in vacuo, compound 53 was obtained as a yellowish solid in 97percent yield (14.45 g)-
Reference: [1] Patent: WO2005/63239, 2005, A1, . Location in patent: Page/Page column 154
[2] Patent: WO2008/152013, 2008, A1, . Location in patent: Page/Page column 24
[3] Patent: WO2008/51826, 2008, A2, . Location in patent: Page/Page column 57; 58
[4] Patent: WO2007/122219, 2007, A1, . Location in patent: Page/Page column 18
[5] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 13, p. 3986 - 3991
  • 14
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Reference: [1] Patent: CN105237317, 2016, A, . Location in patent: Paragraph 0081; 0082
  • 15
  • [ 99-60-5 ]
  • [ 3011-89-0 ]
Reference: [1] Chemische Berichte, 1891, vol. 24, p. 3814
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 5, p. 1424 - 1427
  • 16
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  • [ 2457-76-3 ]
YieldReaction ConditionsOperation in experiment
88% at 20℃; for 2.5 h; First, NaBH4 (1 mmol) was used as a reducing agent forthe conversion of Ag (+ 1) to Ag (0) in methanol at roomtemperature for 2 h. After that, the Ag/MMT was filtered andused as a catalyst. Then, in a typical procedure, a mixtureof 4-nitrophenol (0.1 mmol), KOH (0.15 mmol), isopropylalcohol (3 mL), and Ag/MMT catalyst (50 mg) 1.01 wtpercentwas stirred at room temperature for an appropriate time(Scheme 2). After the completion of the reaction (monitoredby GC), the catalyst was separated by filtration. The ensuingproduct was extracted with ethyl acetate and repeatedlywashed with water (3–4 times) to remove KOH. The resultingsolvent was evaporated to dryness in vacuum.
24% With iron; ammonium chloride In ethanol; water for 2 h; Reflux Step 5a.
4-Amino-2-chlorobenzoic acid (compound 3002)
A mixture of 2-chloro-4-nitrobenzoic acid (5.0 g, 24.8 mmol), iron powder (8.0 g, 142.9 mmol) and NH4Cl (7.6 g, 142.9 mmol) in EtOH/water (50/50 mL) was heated at reflux for 2 h.
The hot mixture was filtered through Celite and washed with ethyl acetate.
The mixture was separated and extracted with ethyl acetate.
The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate.
The crude product was purified by column chromatography (hexanes/ethyl acetate: 5/1, 3/1, 1/1) to afford compound 3002 as a white solid (1.0 g, 24percent yield).
1H NMR (400 MHz, DMSO-d6): δ 6.04 (s, 2H), 6.49 (dd, J=8.4 Hz, 2.0 Hz, 1H), 6.61 (d, J=2.0 Hz, 1H), 6.63 (d, J=8.8 Hz, 1H), 12.21 (br, 1H).
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 27, p. 6730 - 6739
[2] Journal of the Iranian Chemical Society, 2018, vol. 15, # 2, p. 281 - 291
[3] Patent: US2014/18368, 2014, A1, . Location in patent: Paragraph 0162; 0187
[4] Journal of the American Chemical Society, 1949, vol. 71, p. 4154
[5] Chemische Berichte, 1891, vol. 24, p. 706
[6] Journal of the Indian Chemical Society, 1941, vol. 18, p. 25,26
[7] Bulletin of the Chemical Society of Japan, 1983, vol. 56, # 11, p. 3517 - 3518
[8] Patent: EP1182200, 2002, A1, . Location in patent: Referential example 1
  • 17
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  • [ 67818-41-1 ]
Reference: [1] Patent: WO2015/31650, 2015, A1,
[2] Patent: US2018/28518, 2018, A1,
  • 18
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  • [ 56363-84-9 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1983, vol. 56, # 11, p. 3517 - 3518
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