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[ CAS No. 21745-41-5 ] {[proInfo.proName]}

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Chemical Structure| 21745-41-5
Chemical Structure| 21745-41-5
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Product Details of [ 21745-41-5 ]

CAS No. :21745-41-5 MDL No. :MFCD09881742
Formula : C6H7ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :SAIXZIVDXDTYCH-UHFFFAOYSA-N
M.W : 142.59 Pubchem ID :3462489
Synonyms :

Calculated chemistry of [ 21745-41-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 2.0
Molar Refractivity : 40.26
TPSA : 52.04 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 : No
Log Kp (skin permeation) : -6.07 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.29
Log Po/w (XLOGP3) : 1.55
Log Po/w (WLOGP) : 1.52
Log Po/w (MLOGP) : 1.41
Log Po/w (SILICOS-IT) : 1.07
Consensus Log Po/w : 1.37

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.19
Solubility : 0.912 mg/ml ; 0.0064 mol/l
Class : Soluble
Log S (Ali) : -2.25
Solubility : 0.797 mg/ml ; 0.00559 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.27
Solubility : 0.766 mg/ml ; 0.00537 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.2

Safety of [ 21745-41-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 21745-41-5 ]

* 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 [ 21745-41-5 ]
  • Downstream synthetic route of [ 21745-41-5 ]

[ 21745-41-5 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 64-18-6 ]
  • [ 21745-41-5 ]
  • [ 16931-35-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 3, p. 1357 - 1369
[2] Bollettino Scientifico della Facolta di Chimica Industriale di Bologna, 1953, vol. 11, p. 42
  • 2
  • [ 21745-41-5 ]
  • [ 1339789-49-9 ]
  • [ 16931-35-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 4, p. 1218 - 1221
  • 3
  • [ 131543-46-9 ]
  • [ 21745-41-5 ]
  • [ 62163-09-1 ]
YieldReaction ConditionsOperation in experiment
97% With 10 wtpercent sulfated polyborate In neat (no solvent) at 100℃; for 0.05 h; Green chemistry General procedure: To a mixture of substituted o-phenylenediamines derivative(2.0 mmol) and 1,2-diketone / α-hydroxy ketone (2.0 mmol),was added sulfated polyborate (10 wtpercent). The reaction mixture was stirred at 100 °C in an oil bath. The reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the mixture was cooled to room temperature and quenched by water. The resultant product was filtered/extracted with EtOAc to get the product. Crude products were either recrystallized from ethanol or purified by column chromatography using silica as the stationary phase and EtOAc: pet. ether as mobile phase. The products obtained were known compounds and were identified by melting point and 1H and 13C NMR spectroscopy. The spectral data were compared with the literature values.
Reference: [1] Journal of Chemical Sciences, 2017, vol. 129, # 2, p. 141 - 148
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, p. 357 - 364
[3] Organic Magnetic Resonance, 1980, vol. 14, # 4, p. 300 - 304
  • 4
  • [ 21745-41-5 ]
  • [ 517-21-5 ]
  • [ 62163-09-1 ]
Reference: [1] Bulletin des Societes Chimiques Belges, 1986, vol. 95, # 8, p. 663 - 670
[2] Journal of the Chemical Society, 1953, p. 2816,2819
  • 5
  • [ 21745-41-5 ]
  • [ 67130-04-5 ]
Reference: [1] Bollettino Scientifico della Facolta di Chimica Industriale di Bologna, 1958, vol. 16, p. 1
  • 6
  • [ 21745-41-5 ]
  • [ 55687-05-3 ]
Reference: [1] Journal of Medicinal Chemistry, 1981, vol. 24, # 1, p. 93 - 101
[2] Journal of the American Chemical Society, 1949, vol. 71, p. 6,7
  • 7
  • [ 769-11-9 ]
  • [ 21745-41-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2009, vol. 52, # 14, p. 4454 - 4465
[2] Applied Organometallic Chemistry, 2017, vol. 31, # 12,
[3] Bulletin des Societes Chimiques Belges, 1986, vol. 95, # 8, p. 663 - 670
[4] Bulletin des Societes Chimiques Belges, 1992, vol. 101, # 6, p. 491 - 496
[5] Patent: US4134978, 1979, A,
[6] Patent: WO2008/42282, 2008, A2, . Location in patent: Page/Page column 213
[7] Patent: EP1988091, 2008, A1, . Location in patent: Page/Page column 57
  • 8
  • [ 59483-54-4 ]
  • [ 21745-41-5 ]
YieldReaction ConditionsOperation in experiment
97% With ammonium chloride; zinc In ethanol; water at 20℃; for 18 h; Step 1:
3-chloro-2-nitroaniline (5.0 g, 29 mmol), zinc dust (18.9 g, 290 mmol) and ammonium chloride (31.0 g, 579 mmol) were stirred in 100 mL of a 1:1 solution of ethanol and water, at room temperature for 18 hours.
The reaction was filtered and the filtrate concentrated to give a brown solid, which was transferred to a separatory funnel and partitioned between methylene chloride and water.
The organic extracts were separated, combined, dried (MgSO4), filtered and the solvent removed, in vacuo, to give 3-chlorobenzene-1,2-diamine as a brown solid (4.00 g, 97percent Yield).
79.09%
Stage #1: With hydrogenchloride; tin(ll) chloride In ethanol; water for 3 h; Heating / reflux
Stage #2: With potassium hydroxide; water In ethanol
Example 81: Preparation of N-((5-Chloro-3-(2-chlorophenyl)quinoxalin-2- yl)methyl)-9H-purin-6-amine; 3-Chlorobenzene-l ,2-diamine; To s aolution of 3-chloro-2-nitroaniline (10.00 g, 57.95 mmol), 3 N aq. HCl (96.58 mL, 289.7 mmol), and ethyl alcohol (148.6 mL, 57.95 mmol) was added Tin(II) chloride dihydrate (65.96 g, 289.7 mmol) and the mixture was heated under reflux with stirring. After 3 h, the mixture was cooled to room temperature and concentrated under reduced pressure to give a brown syrup. The mixture was cautiously treated with an excess of 10 M KOH (115.9 mL, 1159 mmol, 20 eqv.). The mixture was diluted with EtOAc (200 mL), filtered through Celite.(TM). pad, and washed the pad well with EtOAc (100 mL x 2). The filtrate was extracted with EtOAc (100 mL x 2). The combined organic layers were washed with water (100 mL xl), dried over MgSO4, filtered, and concentrated under reduced pressure to give 3-chlorobenzene-l,2-diamine as a red oil: 1H NMR (400 MHz, DMSO-dβ) δ ppm 6.43 - 6.53 (2 H, m), 6.38 (1 H, t, J=7.8 Hz), 4.80 (2 H, s), 4.60 (2 H, s); LC- MS (ESI) m/z 142.9 [M+H]+. The crude product was carried on crude without purification for the next step.
70% With ammonium chloride; zinc In water; acetone at 0 - 23℃; To a solution of 3-chloro-2-nit.ro- phenylamine (1.73 g, 10.0 mmol), NH4CI (2.68 g, 50.0 mmol), acetone (40 ml_) and water (10 ml_), was added zinc powder portion-wise (three equal portions over 5 minutes) (3.26 g, 50.0 mmol) at 0 0C. The mixture was stirred for 2 h then warmed to 23 0C. The mixture was filtered through Celite.(R). and the solvents were concentrated under reduced pressure. The mixture was re-dissolved in EtOAc/DCM and filtered a second time through Celite.(R). and the solvents were evaporated. The crude mixture was diluted with EtOAc (100 ml_), washed with brine (40 ml_), dried, filtered, and concentrated under reduced pressure. The residue was purified (FCC) (10-50percent EtOAc/hexanes) to yield the titled compound (1.00 g, 70percent). MS (ESI/CI): mass calcd. for C6H7CIN2, 142.0; m/z found, 143.1 [M+H]+. 1H NMR (500 MHz, CDCI3): 6.86-6.78 (m, 1 H), 6.65-6.58 (m, 2H), 3.74 (br s, 2H), 3.46 (br s, 2H)
Reference: [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 3, p. 1357 - 1369
[2] Patent: US2010/120778, 2010, A1, . Location in patent: Page/Page column 29
[3] Patent: WO2008/118468, 2008, A1, . Location in patent: Page/Page column 132
[4] Patent: WO2009/134750, 2009, A1, . Location in patent: Page/Page column 72
[5] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 5, p. 543 - 548
[6] Journal of Heterocyclic Chemistry, 2009, vol. 46, # 5, p. 936 - 948
[7] Patent: EP2102201, 2010, B1, . Location in patent: Page/Page column 38
[8] Patent: US2007/32475, 2007, A1, . Location in patent: Page/Page column 33
[9] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 12, p. 933 - 937
[10] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 3, p. 252 - 256
[11] Patent: US8138168, 2012, B1, . Location in patent: Page/Page column 241
[12] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 3, p. 252 - 256
[13] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 17, p. 4790 - 4793
[14] Patent: US2014/315963, 2014, A1, . Location in patent: Paragraph 0226
[15] Patent: WO2014/169832, 2014, A1, . Location in patent: Page/Page column 118; 119; 125; 126
[16] Journal of Medicinal Chemistry, 2017, vol. 60, # 14, p. 6289 - 6304
[17] Patent: WO2008/118454, 2008, A2, . Location in patent: Page/Page column 51
  • 9
  • [ 769-11-9 ]
  • [ 7440-02-0 ]
  • [ 21745-41-5 ]
Reference: [1] Patent: US6204249, 2001, B1,
  • 10
  • [ 3209-22-1 ]
  • [ 21745-41-5 ]
Reference: [1] Bulletin des Societes Chimiques Belges, 1986, vol. 95, # 8, p. 663 - 670
  • 11
  • [ 602-02-8 ]
  • [ 21745-41-5 ]
Reference: [1] Gazzetta Chimica Italiana, 1957, vol. 87, p. 329,339
[2] Bollettino Scientifico della Facolta di Chimica Industriale di Bologna, 1953, vol. 11, p. 42
  • 12
  • [ 5228-61-5 ]
  • [ 21745-41-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 17, p. 4790 - 4793
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