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[ CAS No. 149817-62-9 ] {[proInfo.proName]}

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Chemical Structure| 149817-62-9
Chemical Structure| 149817-62-9
Structure of 149817-62-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 149817-62-9 ]

CAS No. :149817-62-9 MDL No. :MFCD06796965
Formula : C15H10BrN3 Boiling Point : -
Linear Structure Formula :- InChI Key :CJRRILXBSCRHKN-UHFFFAOYSA-N
M.W : 312.16 Pubchem ID :10614995
Synonyms :

Calculated chemistry of [ 149817-62-9 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 78.4
TPSA : 38.67 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.99
Log Po/w (XLOGP3) : 2.65
Log Po/w (WLOGP) : 3.97
Log Po/w (MLOGP) : 1.8
Log Po/w (SILICOS-IT) : 4.12
Consensus Log Po/w : 3.11

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.01
Solubility : 0.0302 mg/ml ; 0.0000968 mol/l
Class : Moderately soluble
Log S (Ali) : -3.11
Solubility : 0.241 mg/ml ; 0.000771 mol/l
Class : Soluble
Log S (SILICOS-IT) : -7.15
Solubility : 0.0000222 mg/ml ; 0.000000071 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.57

Safety of [ 149817-62-9 ]

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 [ 149817-62-9 ]

* 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 [ 149817-62-9 ]
  • Downstream synthetic route of [ 149817-62-9 ]

[ 149817-62-9 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 865-34-9 ]
  • [ 149817-62-9 ]
  • [ 201733-56-4 ]
  • [ 128143-86-2 ]
  • [ 1692-25-7 ]
  • [ 181866-50-2 ]
  • [ 381218-94-6 ]
Reference: [1] Journal of the Chemical Society. Perkin Transactions 2, 2002, # 10, p. 1669 - 1681
  • 2
  • [ 128143-88-4 ]
  • [ 149817-62-9 ]
YieldReaction ConditionsOperation in experiment
86%
Stage #1: at 100℃; for 12 h;
Stage #2: With potassium carbonate In water
Example 5
4'-Bromo-2,2';6',2"-terpyridine (5)
A 500 mL flask was charged with 2,6-bis-pyridyl-4-(1H)-pyridone (2.47 g, 9.9 mmol), phosphorus pentabromide (6.6 g, 15.4 mmol), and phosphorus oxybromide (30 g) and heated to 100° C. with stirring for 12 h, giving a black oily residue.
The reaction was cooled to room temperature; ice was added cautiously to the reaction until the evolution of gas subsided.
The reaction mixture was neutralized with K2CO3 (aq), extracted with CH2Cl2 (3*300 mL), dried over MgSO4, and filtered.
Removal of solvent gave a tan colored solid which was purified by column chromatography on neutral alumina using 2:1 CH2Cl2:hexanes as the eluant, providing 2.65 g of pure 4'-bromo-2,2';6',2"-terpyridine (86percent yield, based on 2.47 g of the 2,6-bis-pyridyl-4-(1H)-pyridone starting material).
Reference: [1] Journal of the American Chemical Society, 2002, vol. 124, # 46, p. 13806 - 13813
[2] Patent: US7445845, 2008, B2, . Location in patent: Page/Page column 22-23; sheet 3
[3] Journal of the Chemical Society, Chemical Communications, 1995, # 1, p. 65 - 66
[4] Journal of the Chemical Society - Dalton Transactions, 1996, # 22, p. 4249 - 4255
[5] Dalton Transactions, 2007, # 41, p. 4659 - 4665
[6] Journal of the American Chemical Society, 2011, vol. 133, # 9, p. 2884 - 2896
[7] Inorganica Chimica Acta, 2017, vol. 454, p. 27 - 39
[8] Inorganic Chemistry, 2018, vol. 57, # 3, p. 1017 - 1028
  • 3
  • [ 1148-79-4 ]
  • [ 149817-62-9 ]
YieldReaction ConditionsOperation in experiment
91% With hydrogen bromide; dihydrogen peroxide In methanol; water at 20℃; for 20 h; A stirred solution of terpyridine (3.0 g, 0.013 mmol) and HBr (1.04 g, 0.7 mL, 0.013 mmol) in CH3OH (60 mL) was added to a 47percent aqueous solution of H2O2 (0.44 g, 0.4 mL, 0.013 mmol) slowly, over a period of 15 min at room temperature. The mixture was stirred for 20 h whilst monitoring the reaction progress by TLC. After completion, the solvent was removed under reduced pressure and the residue dissolved in EtOAc (150 mL), washed with brine (3 .x. 100 mL) and dried over anhydrous Na2SO4. The product was isolated by careful column chromatography on silica gel using CH2Cl2-EtOAc (4:1, v/v, 200 mL) to give a yellow-red viscous liquid which was allowed to air dry, and finally recrystallized from Et2O-EtOH to afford the title compound 1 (2.74 g, 91percent) as a bright yellow solid. Found: C, 57.94; H, 3.54; N, 13.27; C15H10N3Br requires C, 57.71; H, 3.23; N, 13.46; mp 209-211 °C; IR (KBr): 3475, 3407, 3039, 2806, 1606, 1583, 1562, 1524, 1454, 1442, 1423, 1355, 1289, 1172, 1153, 1078, 1039, 991, 857, 833, 784, 764, 547 cm-1.
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 2, p. 274 - 277
  • 4
  • [ 134653-69-3 ]
  • [ 149817-62-9 ]
Reference: [1] Chemistry - A European Journal, 2013, vol. 19, # 16, p. 5088 - 5096
[2] Inorganica Chimica Acta, 2017, vol. 454, p. 27 - 39
[3] Journal of the Chemical Society. Perkin Transactions 2, 2002, # 10, p. 1669 - 1681
  • 5
  • [ 193944-66-0 ]
  • [ 149817-62-9 ]
Reference: [1] Synthesis, 2008, # 10, p. 1514 - 1516
  • 6
  • [ 2524-52-9 ]
  • [ 149817-62-9 ]
Reference: [1] Inorganica Chimica Acta, 2017, vol. 454, p. 27 - 39
[2] Inorganic Chemistry, 2018, vol. 57, # 3, p. 1017 - 1028
  • 7
  • [ 22109-63-3 ]
  • [ 149817-62-9 ]
Reference: [1] European Journal of Organic Chemistry, 1999, # 1, p. 313 - 321
  • 8
  • [ 1005-02-3 ]
  • [ 149817-62-9 ]
Reference: [1] European Journal of Organic Chemistry, 1999, # 1, p. 313 - 321
  • 9
  • [ 128143-87-3 ]
  • [ 149817-62-9 ]
Reference: [1] Inorganica Chimica Acta, 2017, vol. 454, p. 27 - 39
  • 10
  • [ 994-89-8 ]
  • [ 214215-03-9 ]
  • [ 149817-62-9 ]
Reference: [1] European Journal of Organic Chemistry, 1999, # 1, p. 313 - 321
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