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[ CAS No. 74316-55-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 74316-55-5
Chemical Structure| 74316-55-5
Chemical Structure| 74316-55-5
Structure of 74316-55-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 74316-55-5 ]

CAS No. :74316-55-5 MDL No. :MFCD04966995
Formula : C10H8BrN Boiling Point : -
Linear Structure Formula :- InChI Key :REIFWJGDIKRUSB-UHFFFAOYSA-N
M.W : 222.08 Pubchem ID :4715022
Synonyms :

Calculated chemistry of [ 74316-55-5 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.1
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 54.41
TPSA : 12.89 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) : -5.35 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.33
Log Po/w (XLOGP3) : 3.25
Log Po/w (WLOGP) : 3.31
Log Po/w (MLOGP) : 2.85
Log Po/w (SILICOS-IT) : 3.6
Consensus Log Po/w : 3.07

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.88
Solubility : 0.0292 mg/ml ; 0.000132 mol/l
Class : Soluble
Log S (Ali) : -3.19
Solubility : 0.142 mg/ml ; 0.000639 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.95
Solubility : 0.00251 mg/ml ; 0.0000113 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.38

Safety of [ 74316-55-5 ]

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 [ 74316-55-5 ]

* 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 [ 74316-55-5 ]
  • Downstream synthetic route of [ 74316-55-5 ]

[ 74316-55-5 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 611-32-5 ]
  • [ 74316-55-5 ]
YieldReaction ConditionsOperation in experiment
71% at 20℃; for 5 h; Step 1: 5-bromo-8-methylquinolineA solution (0.3 M) of 8-methylquinoline in H2SO4 (cone.) was treated with Ag2SC^ (1.5 eq.) and bromine (1.0 eq.) were added. The reaction mixture was stirred at RT for 5 h and then poured into ice. The precipitate was filtrated and discarded. The remaining solution was basified with aqueous Na2CO3 (saturated solution) and the aqueous phase was extracted with EtOAc. The combined organic layers were dried and evaporated affording (71percent) the title compound as a solid; MS (ES+) m/z 222, 224 (M+H)+.
Reference: [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1980, vol. 16, # 3, p. 275 - 277[2] Khimiya Geterotsiklicheskikh Soedinenii, 1980, vol. 16, # 3, p. 366 - 368
[3] Tetrahedron, 2005, vol. 61, # 41, p. 9696 - 9704
[4] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 8, p. 2836 - 2848
[5] Patent: WO2007/28789, 2007, A1, . Location in patent: Page/Page column 34
[6] Journal of the American Chemical Society, 2014, vol. 136, # 11, p. 4141 - 4144
[7] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1988, vol. 24, # 8, p. 892 - 897[8] Khimiya Geterotsiklicheskikh Soedinenii, 1988, # 8, p. 1084 - 1090
[9] Patent: WO2013/96194, 2013, A1, . Location in patent: Page/Page column 31-32
[10] Advanced Synthesis and Catalysis, 2017, vol. 359, # 17, p. 2912 - 2917
[11] Patent: WO2009/141386, 2009, A1, . Location in patent: Page/Page column 162; 163
  • 2
  • [ 39478-78-9 ]
  • [ 56-81-5 ]
  • [ 74316-55-5 ]
Reference: [1] Yakugaku Zasshi, 1928, vol. 48, p. 74[2] Chem. Zentralbl., 1928, vol. 99, # II, p. 53
[3] Patent: WO2011/67272, 2011, A1, . Location in patent: Page/Page column 81
[4] Patent: US2012/238517, 2012, A1, . Location in patent: Page/Page column 38
[5] Journal of Organic Chemistry, 2014, vol. 79, # 11, p. 5379 - 5385
[6] Chemistry - A European Journal, 2016, vol. 22, # 32, p. 11165 - 11169
[7] Organic Letters, 2017, vol. 19, # 8, p. 2086 - 2089
  • 3
  • [ 611-32-5 ]
  • [ 74316-55-5 ]
  • [ 98786-47-1 ]
Reference: [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1988, vol. 24, # 8, p. 892 - 897[2] Khimiya Geterotsiklicheskikh Soedinenii, 1988, # 8, p. 1084 - 1090
  • 4
  • [ 7726-95-6 ]
  • [ 74316-55-5 ]
Reference: [1] Yakugaku Zasshi, 1931, vol. 51, p. 73[2] Chem. Zentralbl., 1931, vol. 102, # II, p. 2330
  • 5
  • [ 74316-55-5 ]
  • [ 928839-62-7 ]
YieldReaction ConditionsOperation in experiment
62% With chromium(VI) oxide; sulfuric acid In water at 90℃; for 2 h; Step 2: S-bromoquinoline-S-carboxylic acidA solution (0.1 M) of 5-bromo-8-methylquinoline (from Step 1) in H2SOzrH2O (3:2) was treated with Cr?3 (10 eq.) at 900C. The reaction mixture was heated at 900C for 2 h. Then, the mixture was poured into ice and the precipitate was filtered affording (62percent) the title compound as an orange solid; MS (ES+) m/z 252, 254 (M+H)+.
Reference: [1] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 8, p. 2836 - 2848
[2] Patent: WO2007/28789, 2007, A1, . Location in patent: Page/Page column 34
[3] Patent: WO2013/96194, 2013, A1,
[4] Patent: WO2015/84842, 2015, A1, . Location in patent: Paragraph 0089
[5] Patent: WO2009/141386, 2009, A1, . Location in patent: Page/Page column 162; 163
  • 6
  • [ 74316-55-5 ]
  • [ 1445781-45-2 ]
Reference: [1] Patent: WO2013/96194, 2013, A1,
[2] Patent: WO2015/84842, 2015, A1,
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