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[ CAS No. 28443-50-7 ] {[proInfo.proName]}

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Chemical Structure| 28443-50-7
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Product Details of [ 28443-50-7 ]

CAS No. :28443-50-7 MDL No. :MFCD02093863
Formula : C6H6ClNO Boiling Point : -
Linear Structure Formula :ClC6H3(OH)NH2 InChI Key :FZCQMIRJCGWWCL-UHFFFAOYSA-N
M.W : 143.57 Pubchem ID :91591
Synonyms :

Calculated chemistry of [ 28443-50-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 37.88
TPSA : 46.25 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.89 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.2
Log Po/w (XLOGP3) : 1.81
Log Po/w (WLOGP) : 1.64
Log Po/w (MLOGP) : 1.41
Log Po/w (SILICOS-IT) : 1.31
Consensus Log Po/w : 1.47

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.36
Solubility : 0.621 mg/ml ; 0.00433 mol/l
Class : Soluble
Log S (Ali) : -2.4
Solubility : 0.571 mg/ml ; 0.00397 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.06
Solubility : 1.26 mg/ml ; 0.00881 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.09

Safety of [ 28443-50-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 28443-50-7 ]

* 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 [ 28443-50-7 ]
  • Downstream synthetic route of [ 28443-50-7 ]

[ 28443-50-7 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 28443-50-7 ]
  • [ 144-55-8 ]
  • [ 19219-99-9 ]
Reference: [1] Patent: EP318084, 1990, A3,
[2] Patent: EP318084, , A2, [2] Patent: , 1989, ,
  • 2
  • [ 28443-50-7 ]
  • [ 144-55-8 ]
  • [ 19219-99-9 ]
Reference: [1] Patent: US4957932, 1990, A,
  • 3
  • [ 28443-50-7 ]
  • [ 79-04-9 ]
  • [ 27320-99-6 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1984, vol. 23, # 12, p. 1279 - 1283
[2] Patent: WO2007/22257, 2007, A2, . Location in patent: Page/Page column 76
  • 4
  • [ 28443-50-7 ]
  • [ 598-21-0 ]
  • [ 27320-99-6 ]
Reference: [1] ChemMedChem, 2015, vol. 10, # 11, p. 1821 - 1836
  • 5
  • [ 1431459-74-3 ]
  • [ 28443-50-7 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 10, p. 2334 - 2337
  • 6
  • [ 611-07-4 ]
  • [ 28443-50-7 ]
Reference: [1] Journal of the Chemical Society, 1928, p. 2703
[2] Fortsch.Ch.Phys., 1924, vol. 18, p. Heft 2,S.28
[3] Chemical Communications, 2011, vol. 47, # 39, p. 10972 - 10974
  • 7
  • [ 328-50-7 ]
  • [ 932-98-9 ]
  • [ 62558-67-2 ]
  • [ 123-30-8 ]
  • [ 28443-50-7 ]
  • [ 81576-13-8 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, p. 345 - 350
  • 8
  • [ 932-98-9 ]
  • [ 305-72-6 ]
  • [ 62558-67-2 ]
  • [ 123-30-8 ]
  • [ 28443-50-7 ]
  • [ 81576-13-8 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, p. 345 - 350
  • 9
  • [ 932-98-9 ]
  • [ 305-72-6 ]
  • [ 62558-67-2 ]
  • [ 28443-50-7 ]
  • [ 81576-12-7 ]
  • [ 81576-13-8 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, p. 345 - 350
  • 10
  • [ 100-00-5 ]
  • [ 28443-50-7 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1966, p. 1848 - 1858
  • 11
  • [ 16323-09-4 ]
  • [ 28443-50-7 ]
Reference: [1] Journal of Organic Chemistry, 1954, vol. 19, p. 758,762, 765
  • 12
  • [ 5910-69-0 ]
  • [ 28443-50-7 ]
Reference: [1] Journal of Organic Chemistry, 1954, vol. 19, p. 758,762, 765
  • 13
  • [ 74993-54-7 ]
  • [ 108-43-0 ]
  • [ 17609-80-2 ]
  • [ 56962-00-6 ]
  • [ 28443-50-7 ]
Reference: [1] Journal of the American Chemical Society, 1992, vol. 114, # 25, p. 9795 - 9806
  • 14
  • [ 116278-63-8 ]
  • [ 17537-17-6 ]
  • [ 28443-50-7 ]
  • [ 116278-66-1 ]
Reference: [1] Journal of Organic Chemistry, 1995, vol. 60, # 25, p. 8294 - 8304
  • 15
  • [ 139399-68-1 ]
  • [ 28443-50-7 ]
Reference: [1] Chemische Berichte, 1938, vol. 71, p. 2065,2069
  • 16
  • [ 5467-64-1 ]
  • [ 28443-50-7 ]
Reference: [1] Chemische Berichte, 1938, vol. 71, p. 2065,2069
  • 17
  • [ 95-55-6 ]
  • [ 28443-50-7 ]
Reference: [1] Chemische Berichte, 1938, vol. 71, p. 2065,2069
  • 18
  • [ 116278-63-8 ]
  • [ 28443-50-7 ]
  • [ 554-00-7 ]
  • [ 116278-66-1 ]
  • [ 106-51-4 ]
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 20, p. 4762 - 4769
  • 19
  • [ 116278-65-0 ]
  • [ 28443-50-7 ]
  • [ 116278-66-1 ]
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 20, p. 4762 - 4769
  • 20
  • [ 28443-50-7 ]
  • [ 3621-82-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 7, p. 1975 - 1980
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 9, p. 3044 - 3049
[3] Journal of Fluorine Chemistry, 2013, vol. 156, p. 120 - 123
[4] Patent: WO2018/37223, 2018, A1,
  • 21
  • [ 74993-54-7 ]
  • [ 108-43-0 ]
  • [ 17609-80-2 ]
  • [ 56962-00-6 ]
  • [ 28443-50-7 ]
Reference: [1] Journal of the American Chemical Society, 1992, vol. 114, # 25, p. 9795 - 9806
  • 22
  • [ 28443-50-7 ]
  • [ 136808-72-5 ]
YieldReaction ConditionsOperation in experiment
79%
Stage #1: With sulfuric acid; sodium nitrite In water; dimethyl sulfoxide at 0℃; for 1 h;
Stage #2: With potassium iodide In water; dimethyl sulfoxide at 20℃; for 2 h;
Intermediate 15-Chloro-2-iodo-phenol 2-Amino-5-chlorophenol (5.7 g, 40 mmol) is dissolved in DMSO/water/H2SO4 (200/60/140 mL) and cooled to 0° C. To this solution is added sodium nitrite (4.1 g, 60 mmol) in water (20 mL) and the mixture is stirred for 1 h at 0° C. To the mixture is added potassium iodide (19.9 g, 120 mmol) in water (20 mL) and the mixture is stirred at room temperature for 1 h. Another batch of potassium iodide (19.9 g, 120 mmol) in water (20 mL) is added and the mixture is stirred at room temperature for 1 h. The mixture is diluted with ethyl acetate, washed with water, saturated aqueous sodium sulfate, and brine. The organic portion is dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (Biotage.(TM). Si65M, 20percent ethyl acetate/hexane) to yield 8.09 g (79percent) of the title compound as a pink solid. GCMS m/e 254 [M]-.
Reference: [1] Patent: US2010/69425, 2010, A1, . Location in patent: Page/Page column 11-12
[2] Journal of the Chemical Society, 1931, p. 2268,2271
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