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[ CAS No. 1606-67-3 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1606-67-3
Chemical Structure| 1606-67-3
Structure of 1606-67-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1606-67-3 ]

CAS No. :1606-67-3 MDL No. :MFCD00004140
Formula : C16H11N Boiling Point : -
Linear Structure Formula :- InChI Key :YZVWKHVRBDQPMQ-UHFFFAOYSA-N
M.W : 217.27 Pubchem ID :15352
Synonyms :

Calculated chemistry of [ 1606-67-3 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 74.55
TPSA : 26.02 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.57 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.14
Log Po/w (XLOGP3) : 4.31
Log Po/w (WLOGP) : 4.17
Log Po/w (MLOGP) : 3.84
Log Po/w (SILICOS-IT) : 4.04
Consensus Log Po/w : 3.7

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.6
Solubility : 0.00547 mg/ml ; 0.0000252 mol/l
Class : Moderately soluble
Log S (Ali) : -4.57
Solubility : 0.00585 mg/ml ; 0.0000269 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.23
Solubility : 0.000128 mg/ml ; 0.000000587 mol/l
Class : Poorly soluble

Medicinal Chemistry

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

Safety of [ 1606-67-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1606-67-3 ]

* 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 [ 1606-67-3 ]
  • Downstream synthetic route of [ 1606-67-3 ]

[ 1606-67-3 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 5522-43-0 ]
  • [ 1606-67-3 ]
YieldReaction ConditionsOperation in experiment
90% With tin(II) chloride dihdyrate In ethyl acetate for 6 h; Inert atmosphere; Reflux 1-Nitropyrene (1.00 g, 4.0 mmol) and tin(II) chloride dihydrate (4.35 g, 19.2 mmol) were mixed with 60 mL of ethyl acetate in a 250 cm3 three-neck round-bottomed flask, under magnetic stirring and argon atmosphere. The suspension mixture was heated to reflux for 6 h. Subsequently, the solution was cooled at room temperature, a sodium carbonate aqueous solution (20percent; m/v) was added to obtain pH ca. 8.0, and stirring was continued for 1 h. The organic phase was then extracted three times with ethyl acetate and dried with magnesium sulfate. The solid was filtered-off and the solvent was evaporated, resulting in 0.80 g (90percent yield) of a light green product; mp obtained: 115-116 °C (mp lit.:61 115-117 °C); IR (KBr) νmax / cm−1 3345-3387 (N-H), 3036 (C-H aromatic), 1623-1512 (C=C); 1H NMR (400 MHz, DMSO-d6) δ 8.24 (d, 1H, J 9.4 Hz, CH), 7.97 (d, 2H, J 7.8 Hz, 2 × CH), 7.94 (d, 1H, J 7.8 Hz, CH), 7.89 (d, 1H, J 9.0 Hz, CH), 7.86 (d, 1H, J 8.6 Hz, CH), 7.85 (t, 1H, J 7.6 Hz, CH), 7.69 (d, 1H, J 8.6 Hz, CH), 7.34 (d, 1H, J 8.2 Hz, CH), 6.33 (s, 2H, NH2).
Reference: [1] Analytical Chemistry, 1988, vol. 60, # 3, p. 194 - 199
[2] Organic and Biomolecular Chemistry, 2018, vol. 16, # 41, p. 7663 - 7673
[3] Tetrahedron Letters, 1998, vol. 39, # 40, p. 7243 - 7246
[4] Synthetic Communications, 1991, vol. 21, # 2, p. 161 - 165
[5] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 3, p. 593 - 605
[6] Journal of the Brazilian Chemical Society, 2015, vol. 26, # 12, p. 2507 - 2519
[7] Letters in Organic Chemistry, 2010, vol. 7, # 5, p. 399 - 405
[8] Journal of Materials Chemistry, 2010, vol. 20, # 26, p. 5481 - 5492
[9] RSC Advances, 2015, vol. 5, # 56, p. 45201 - 45212
[10] Chemical Communications, 2013, vol. 49, # 8, p. 780 - 782
[11] Chemistry - A European Journal, 2003, vol. 9, # 9, p. 1922 - 1932
[12] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 2, p. 471 - 474
[13] Journal of the Chemical Society - Perkin Transactions 1, 1996, # 2, p. 167 - 174
[14] Chemistry - A European Journal, 2012, vol. 18, # 17, p. 5155 - 5159
[15] Tetrahedron, 2010, vol. 66, # 13, p. 2486 - 2491
[16] Justus Liebigs Annalen der Chemie, 1937, vol. 531, p. 1,109
[17] 1956 2556,
[18] Monatshefte fuer Chemie, 1881, vol. 2, p. 580
[19] Chemical and Pharmaceutical Bulletin, 1983, vol. 31, # 2, p. 776 - 779
[20] Advanced Synthesis and Catalysis, 2011, vol. 353, # 8, p. 1306 - 1316
[21] Journal of Fluorescence, 2010, vol. 20, # 1, p. 315 - 320
[22] Macromolecular Bioscience, 2010, vol. 10, # 8, p. 974 - 982
[23] Electrochimica Acta, 2013, vol. 90, p. 295 - 301
[24] RSC Advances, 2015, vol. 5, # 16, p. 12338 - 12345
[25] RSC Advances, 2018, vol. 8, # 28, p. 15266 - 15281
[26] Chemical Research in Toxicology, 2018, vol. 31, # 8, p. 680 - 687
  • 2
  • [ 129-00-0 ]
  • [ 1606-67-3 ]
Reference: [1] Recueil: Journal of the Royal Netherlands Chemical Society, 1983, vol. 102, # 4, p. 224 - 228
[2] Letters in Organic Chemistry, 2010, vol. 7, # 5, p. 399 - 405
[3] Journal of Materials Chemistry, 2010, vol. 20, # 26, p. 5481 - 5492
[4] Journal of Fluorescence, 2010, vol. 20, # 1, p. 315 - 320
[5] Chemical Communications, 2013, vol. 49, # 8, p. 780 - 782
[6] Electrochimica Acta, 2013, vol. 90, p. 295 - 301
[7] Journal of the Brazilian Chemical Society, 2015, vol. 26, # 12, p. 2507 - 2519
[8] RSC Advances, 2018, vol. 8, # 28, p. 15266 - 15281
[9] Organic and Biomolecular Chemistry, 2018, vol. 16, # 41, p. 7663 - 7673
  • 3
  • [ 36171-39-8 ]
  • [ 1606-67-3 ]
Reference: [1] Journal of the American Chemical Society, 1984, vol. 106, # 18, p. 5234 - 5240
[2] Journal of the American Chemical Society, 1984, vol. 106, # 18, p. 5234 - 5240
  • 4
  • [ 1714-29-0 ]
  • [ 1606-67-3 ]
Reference: [1] Acta Chemica Scandinavica (1947-1973), 1965, vol. 19, p. 520 - 521
[2] Recueil: Journal of the Royal Netherlands Chemical Society, 1983, vol. 102, # 4, p. 224 - 228
  • 5
  • [ 34244-14-9 ]
  • [ 1606-67-3 ]
Reference: [1] Recueil: Journal of the Royal Netherlands Chemical Society, 1983, vol. 102, # 4, p. 224 - 228
  • 6
  • [ 1398531-34-4 ]
  • [ 1606-67-3 ]
Reference: [1] Chemical Communications, 2012, vol. 48, # 76, p. 9540 - 9542
  • 7
  • [ 91110-61-1 ]
  • [ 1606-67-3 ]
Reference: [1] Journal of the American Chemical Society, 1984, vol. 106, # 18, p. 5234 - 5240
  • 8
  • [ 22755-15-3 ]
  • [ 1606-67-3 ]
Reference: [1] Roczniki Chemii, 1937, vol. 17, p. 101,103[2] Chem. Zentralbl., 1937, vol. 108, # II, p. 65
  • 9
  • [ 1714-29-0 ]
  • [ 1606-67-3 ]
  • [ 1732-23-6 ]
Reference: [1] Canadian Journal of Chemistry, 2003, vol. 81, # 6, p. 770 - 776
  • 10
  • [ 129-00-0 ]
  • [ 1606-67-3 ]
  • [ 30269-04-6 ]
  • [ 14923-84-3 ]
  • [ 92821-64-2 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1984, vol. 32, # 5, p. 1992 - 1994
  • 11
  • [ 60-29-7 ]
  • [ 7664-93-9 ]
  • [ 85964-28-9 ]
  • [ 15719-64-9 ]
  • [ 1606-67-3 ]
  • [ 86674-51-3 ]
Reference: [1] Danske Vid. Selsk. Math. fys. Medd., 1941, vol. 19, # 5, p. 3,16, 17
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