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Product Details of [ 6358-06-1 ]

CAS No. :6358-06-1 MDL No. :MFCD01707858
Formula : C6H6ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :JSCNCRWPXOTDDZ-UHFFFAOYSA-N
M.W : 143.57 Pubchem ID :80676
Synonyms :

Calculated chemistry of [ 6358-06-1 ]      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) : -6.13 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.37
Log Po/w (XLOGP3) : 1.47
Log Po/w (WLOGP) : 1.64
Log Po/w (MLOGP) : 1.41
Log Po/w (SILICOS-IT) : 1.31
Consensus Log Po/w : 1.44

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.15
Solubility : 1.02 mg/ml ; 0.00709 mol/l
Class : Soluble
Log S (Ali) : -2.05
Solubility : 1.29 mg/ml ; 0.00896 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 : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.11

Safety of [ 6358-06-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H312-H315-H319-H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6358-06-1 ]

* 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 [ 6358-06-1 ]
  • Downstream synthetic route of [ 6358-06-1 ]

[ 6358-06-1 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 619-10-3 ]
  • [ 6358-06-1 ]
YieldReaction ConditionsOperation in experiment
96% With water; iron; ammonium chloride In ethanol for 2 h; Reflux Step 1
5-Amino-2-chloro-phenol
To a solution of 2-chloro-5-nitrophenol (20.0 g, 115.2 mmol) in ethanol (150 ml) and water (150 ml) was added iron powder (32.2 g, 576.2 mmol) and ammonium chloride (32.1 g, 599.3 mmol).
The mixture was heated at reflux for two hours, then cooled to room temperature and filtered.
The filtrate was concentrated to dryness under reduced pressure.
Purification of the residue by flash chromatography (hex:EtOAc/9:1) gave 5-amino-2-chloro-phenol (15.85 g, 96percent) as a white solid.
96% With water; iron; ammonium chloride In ethanol for 2 h; Reflux Step 1
5-Amino-2-chloro-phenol
To a solution of 2-chloro-5-nitrophenol (20.0 g, 115.2 mmol) in ethanol (150 ml) and water (150 ml) was added iron powder (32.2 g, 576.2 mmol) and ammonium chloride (32.1 g, 599.3 mmol).
The mixture was heated at reflux for two hours, then cooled to room temperature and filtered.
The filtrate was concentrated to dryness under reduced pressure.
Purification of the residue by flash chromatography (hex:EtOAc/9:1) gave 5-amino-2-chloro-phenol (15.85 g, 96percent) as a white solid.
96% With iron; ammonium chloride In ethanol; water for 2 h; Reflux To a solution of 2-chloro-5-nitrophenol (20.0 g, 115.2 mmol) in ethanol (150 ml) and water (150 ml) was added iron powder (32.2 g, 576.2 mmol) and ammonium chloride (32.1 g, 599.3 mmol).
The mixture was heated at reflux for two hours, then cooled to room temperature and filtered.
The filtrate was concentrated to dryness under reduced pressure.
Purification of the residue by flash chromatography (hex:EtOAc/9:1) gave 5-amino-2-chloro-phenol (15.85 g, 96percent) as a white solid.
96% With iron; ammonium chloride In ethanol; water for 2 h; Reflux Step 1 5-Amino-2-chloro-phenolTo a solution of 2-chloro-5-nitrophenol (20.0 g, 115.2 mmol) in ethanol (150 ml) and water (150 ml) was added iron powder (32.2 g, 576.2 mmol) and ammonium chloride (32.1 g, 599.3 mmol). The mixture was heated at reflux for two hours, then cooled to room temperature and filtered. The filtrate was concentrated to dryness under reduced pressure. Purification of the residue by flash chromatography (hex:EtOAc/9:1) gave 5-amino-2-chloro-phenol (15.85 g, 96percent) as a white solid.
70% With tin(II)chloride dihydrate In ethanol at 60℃; for 3 h; Compound 3 (1.0 g, 5.7 mmol, 1 equiv) was dissolved in 5 mlethanol, followed by addition of SnCl22H2O (14 g, 63.5 mmol,11 equiv). The reaction mixture stirred at 60 C for 3 h. After coolingto room temperature, the reaction mixture was neutralizedwith 2percent aqueous NaOH solution and adjusted to pH 7. The resultingprecipitate was filtered and dried under vacuum at 40 C. Further, this dried solid was stirred in EtOAc for 4 h, and then evaporatedthe solvent under reduced pressure to give compound 4 asan off white powder (0.58 g) with the yield of 70percent. Mp: 166–168 C, 1H NMR (400 DMSO-d6) d ppm: 5.12 (br s, 2H, NH2), 6.02(dd, 1H, J = 2.5 Hz, 2.4 Hz, Ph-H), 6.20 (d, 1H, J = 2.5 Hz, Ph-H),6.86 (d, 1H, J = 8.5 Hz, Ph-H), 9.51 (s, 1H, Ph-OH); ESI-MS: 142.1[MH]. C6H6ClNO [143.57].

Reference: [1] Patent: US2003/100580, 2003, A1,
[2] Patent: US2010/160388, 2010, A1, . Location in patent: Page/Page column 58
[3] Patent: US2010/160389, 2010, A1, . Location in patent: Page/Page column 49
[4] Patent: US2011/28502, 2011, A1, . Location in patent: Page/Page column 44-45
[5] Patent: US2011/71143, 2011, A1, . Location in patent: Page/Page column 36
[6] Journal of Medicinal Chemistry, 2015, vol. 58, # 21, p. 8413 - 8426
[7] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 3, p. 668 - 671
[8] Environmental Toxicology and Chemistry, 2001, vol. 20, # 7, p. 1381 - 1389
[9] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 23, p. 7398 - 7405
[10] Patent: WO2007/38387, 2007, A2, . Location in patent: Page/Page column 24; 25
[11] Przemysl Chemiczny, 1951, vol. 30, p. 647[12] Chem.Abstr., 1952, p. 11141
[13] Biochemical Journal, 1956, vol. 64, p. 38,39
[14] Patent: WO2004/85425, 2004, A1, . Location in patent: Page 110-111
  • 2
  • [ 13726-14-2 ]
  • [ 6358-06-1 ]
Reference: [1] Patent: US3948596, 1976, A,
  • 3
  • [ 1009-36-5 ]
  • [ 6358-06-1 ]
Reference: [1] Environmental Toxicology and Chemistry, 2001, vol. 20, # 7, p. 1381 - 1389
  • 4
  • [ 97-52-9 ]
  • [ 6358-06-1 ]
Reference: [1] Environmental Toxicology and Chemistry, 2001, vol. 20, # 7, p. 1381 - 1389
  • 5
  • [ 121-88-0 ]
  • [ 6358-06-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 3, p. 668 - 671
[2] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 23, p. 7398 - 7405
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