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[ CAS No. 168823-76-5 ] {[proInfo.proName]}

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Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
Accessible (Haz class 3, 4, 5 or 8), International USD 200+
3d Animation Molecule Structure of 168823-76-5
Chemical Structure| 168823-76-5
Chemical Structure| 168823-76-5
Structure of 168823-76-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 168823-76-5 ]

CAS No. :168823-76-5 MDL No. :MFCD10697592
Formula : C6H5BrClN Boiling Point : -
Linear Structure Formula :- InChI Key :YESFMWFCJUGBLH-UHFFFAOYSA-N
M.W : 206.47 Pubchem ID :11401501
Synonyms :

Calculated chemistry of [ 168823-76-5 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.7
TPSA : 12.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.16 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.97
Log Po/w (XLOGP3) : 1.97
Log Po/w (WLOGP) : 2.43
Log Po/w (MLOGP) : 1.91
Log Po/w (SILICOS-IT) : 3.01
Consensus Log Po/w : 2.26

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.79
Solubility : 0.336 mg/ml ; 0.00163 mol/l
Class : Soluble
Log S (Ali) : -1.87
Solubility : 2.81 mg/ml ; 0.0136 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.9
Solubility : 0.0258 mg/ml ; 0.000125 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.73

Safety of [ 168823-76-5 ]

Signal Word:Danger Class:8
Precautionary Statements:P501-P260-P270-P271-P264-P280-P362+P364-P303+P361+P353-P301+P330+P331-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P405 UN#:3261
Hazard Statements:H302+H312+H332-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 168823-76-5 ]

* 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 [ 168823-76-5 ]
  • Downstream synthetic route of [ 168823-76-5 ]

[ 168823-76-5 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 88139-91-7 ]
  • [ 168823-76-5 ]
YieldReaction ConditionsOperation in experiment
92% With thionyl chloride In dichloromethane at 0 - 20℃; for 3 h; Part B: Compound 413A (500 mg, 2.7 mmol) was dissolved in methylene chloride (5 mL) and cooled in an ice bath. Thionyl chloride (480 mg, 4.05 mmol) was added dropwise and stirred at room temperature for 3 hours. The reaction was quenched with saturated sodium bicarbonate. The organic layer was dried over sodium sulfate and concentrated to provide the desired product (510 mg, 92percent).
0.8 g With thionyl chloride In dichloromethane at 0℃; for 4 h; Step 1
Preparation of 5-Bromo-2-chloromethyl-pyridine
To a stirred solution of (5-Bromo-pyridin-2-yl)-methanol (1 g, 5.319 mmol) in CH2Cl2 (20 mL) is added drop wise thionyl chloride (0.57 mL, 7.979 mmol) at 0° C. then stirred for another 4 hours.
Reaction mixture is diluted with saturated sodium bicarbonate solution and extracted with CH2Cl2.
Organic layer is dried over sodium sulphate, solvent is evaporated in vacuo and purified by column chromatography using 7percent ethyl acetate in hexane as an eluent to afford the title compound (0.8 g).
1HNMR (400 MHz, DMSO-d6) δ: 4.7 (s, 2H), 7.53 (d, 8.36 Hz, 1H), 8.09-8.11 (dd, J1=2.44 Hz, J2=8.23 Hz, 1H), 8.69 (d, J=2.4 Hz, 1H), LC-MS (m/z): [M+H]=206.0.
4 g With thionyl chloride In dichloromethane at 0 - 20℃; for 4 h; To the stirred solution of (5-Bromo-pyridin-2-yl)-Methanol (5gm, 26.59mmol, 1 eq) in DCM (50mL) at 0°C is added Thionyl chloride (3ml_) drop wise at RT then stirred at RT for 4h. After completion, the reaction mixture quenched with saturated sodium bicarbonate solution and extracted with DCM (3X100ml_). The combined organic layer dried over sodium sulphate and evaporated under reduced pressure. The crude is purified by column chromatography using silica 100-200 mesh using 10percent EtOAc: Hexane as eluent to afford title compound (4g) as brown colored liquid. 1 NMR (400 MHz, DMSO) δ: 4.77 (s, 2H), 7.54 (d, J = 8.64Hz, 1 H), 8.09-8.12 (dd, J1 = 2.4Hz, J2 = 8.32Hz, 1 H), 8.70 (d, J = 5.96Hz, 1 H).
Reference: [1] Journal of Porphyrins and Phthalocyanines, 2010, vol. 14, # 6, p. 469 - 480
[2] Patent: WO2007/84451, 2007, A1, . Location in patent: Page/Page column 147
[3] Chemistry - A European Journal, 2011, vol. 17, # 38, p. 10670 - 10681
[4] Journal of Organic Chemistry, 2004, vol. 69, # 2, p. 250 - 262
[5] Patent: WO2006/76415, 2006, A2, . Location in patent: Page/Page column 46
[6] Patent: US2008/4449, 2008, A1, . Location in patent: Page/Page column 13-14
[7] Patent: WO2011/14774, 2011, A1, . Location in patent: Page/Page column 29
[8] Journal of Medicinal Chemistry, 2011, vol. 54, # 13, p. 4721 - 4734
[9] Patent: US2013/237502, 2013, A1, . Location in patent: Paragraph 0323
[10] Patent: WO2014/172443, 2014, A1, . Location in patent: Page/Page column 21
  • 2
  • [ 900186-88-1 ]
  • [ 168823-76-5 ]
Reference: [1] Journal of Organic Chemistry, 2004, vol. 69, # 2, p. 250 - 262
  • 3
  • [ 3430-13-5 ]
  • [ 168823-76-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 13, p. 4721 - 4734
[2] Patent: WO2007/84451, 2007, A1,
  • 4
  • [ 31181-90-5 ]
  • [ 168823-76-5 ]
Reference: [1] Journal of Porphyrins and Phthalocyanines, 2010, vol. 14, # 6, p. 469 - 480
  • 5
  • [ 31181-64-3 ]
  • [ 168823-76-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 13, p. 4721 - 4734
  • 6
  • [ 29682-15-3 ]
  • [ 168823-76-5 ]
Reference: [1] Chemistry - A European Journal, 2011, vol. 17, # 38, p. 10670 - 10681
  • 7
  • [ 145218-19-5 ]
  • [ 168823-76-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 23, p. 8421 - 8439
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