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[ CAS No. 84459-33-6 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 84459-33-6
Chemical Structure| 84459-33-6
Chemical Structure| 84459-33-6
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Product Details of [ 84459-33-6 ]

CAS No. :84459-33-6 MDL No. :MFCD09056792
Formula : C7H4BrClO Boiling Point : -
Linear Structure Formula :- InChI Key :AJOAHIKYBSZIEV-UHFFFAOYSA-N
M.W : 219.46 Pubchem ID :13154710
Synonyms :

Calculated chemistry of [ 84459-33-6 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.54
TPSA : 17.07 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) : -5.3 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.93
Log Po/w (XLOGP3) : 3.29
Log Po/w (WLOGP) : 2.92
Log Po/w (MLOGP) : 2.79
Log Po/w (SILICOS-IT) : 3.3
Consensus Log Po/w : 2.85

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.65
Solubility : 0.049 mg/ml ; 0.000223 mol/l
Class : Soluble
Log S (Ali) : -3.32
Solubility : 0.104 mg/ml ; 0.000475 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.82
Solubility : 0.0331 mg/ml ; 0.000151 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.33

Safety of [ 84459-33-6 ]

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 [ 84459-33-6 ]

* 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 [ 84459-33-6 ]
  • Downstream synthetic route of [ 84459-33-6 ]

[ 84459-33-6 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 84459-33-6 ]
  • [ 57381-49-4 ]
Reference: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 42, p. 7959 - 7963
  • 2
  • [ 84459-33-6 ]
  • [ 52864-54-7 ]
Reference: [1] Patent: US2017/275282, 2017, A1,
[2] Patent: WO2009/158426, 2009, A1,
  • 3
  • [ 84459-33-6 ]
  • [ 825-40-1 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 22, p. 5566 - 5569
[2] Tetrahedron Letters, 2017, vol. 58, # 4, p. 285 - 288
[3] Chemistry - An Asian Journal, 2018, vol. 13, # 15, p. 1897 - 1901
  • 4
  • [ 84459-33-6 ]
  • [ 59236-37-2 ]
Reference: [1] Chemical Biology and Drug Design, 2015, vol. 85, # 6, p. 743 - 755
  • 5
  • [ 143888-84-0 ]
  • [ 84459-33-6 ]
YieldReaction ConditionsOperation in experiment
85% With pyridinium chlorochromate In dichloromethane for 2 h; Add pyridinium chlorochromate (432 mg, 2 mmol) to a solution of 2-bromo-4- chlorobenzyl alcohol (200 mg, 0.9 mmol) in dichloromethane (4 mL). Stir the resulting mixture for 2 h. Add diethyl ether (4 mL) and stir for 20 "min. Decant the diethyl ether solution. Wash the remaining solids with diethyl ether twice. Combine the diethyl ether solutions and concentrate. Chromatograph on silica gel, eluting with 20:80 to 1:1 ethyl acetate:dichloromethane to give 2-bromo-4-chlorobenzaldehyde as a white solid (167 mg, 85percent).
81% With sulfur trioxide pyridine complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 1 h; To a 0 °C solution of (2-bromo-4-chloro-phenyl)-methanol (5.57 g, 0.025 mol), dichloromethane (250 ml_), diisopropylethylamine (22 ml_, 0.126 mol), and dimethyl sulfoxide (15 ml_, 0.211 mol) was added sulfur thoxide-pyhdine (12.0 g, 0.075 mol), in portions, over 15 minutes. The resulting solution was stirred at 0 °C for 45 minutes. The reaction mixture was diluted with 250 ml_ dichloromethane, then washed with saturated aqueous NaHCO3 (500 ml_). The organic phase was washed with saturated aqueous sodium thiosulfate (500 ml_) to reduce excess oxidant. The organic phase was dried over Na2SO4, filtered and concentrated to afford a yellow oily solid. A solution of this crude product and CH2CI2 (200 ml_) was evaporated onto silica gel, and the dry silica gel-supported product was loaded onto a 120 g silica gel column. Flash chromatography was carried out using an ISCO purification system (95:5 hexanes-ethyl acetate). 2-Bromo-4-chloro-benzaldehyde was isolated as 4.43 g (81percent yield) of a white solid. 1H NMR (300 MHz, CDCI3) δ ppm 10.31 (s, 1 H), 7.88 (d, J = 8.2 Hz, 1 H), 7.69 (d, J = 1.6 Hz, 1 H), 7.44 (dd, J = 8.2, 1.6 Hz, 1 H).
Reference: [1] Patent: WO2006/44454, 2006, A1, . Location in patent: Page/Page column 47
[2] Patent: WO2010/55005, 2010, A1, . Location in patent: Page/Page column 72-73
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 23, p. 6463 - 6466
  • 6
  • [ 1202889-66-4 ]
  • [ 84459-33-6 ]
Reference: [1] Patent: WO2009/158426, 2009, A1, . Location in patent: Page/Page column 63-64
  • 7
  • [ 57381-49-4 ]
  • [ 84459-33-6 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 9, p. 2473 - 2477[2] Angew. Chem., 2017, vol. 129, p. 2513 - 2517,5
  • 8
  • [ 936-08-3 ]
  • [ 84459-33-6 ]
Reference: [1] Patent: WO2016/168098, 2016, A1,
[2] Patent: WO2017/74832, 2017, A1,
  • 9
  • [ 623-03-0 ]
  • [ 84459-33-6 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 9, p. 2473 - 2477[2] Angew. Chem., 2017, vol. 129, p. 2513 - 2517,5
  • 10
  • [ 27139-97-5 ]
  • [ 84459-33-6 ]
Reference: [1] Patent: WO2009/158426, 2009, A1,
  • 11
  • [ 84459-33-6 ]
  • [ 1135531-73-5 ]
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 8, p. 2789 - 2792
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