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[ CAS No. 1746-28-7 ] {[proInfo.proName]}

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Chemical Structure| 1746-28-7
Chemical Structure| 1746-28-7
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Product Details of [ 1746-28-7 ]

CAS No. :1746-28-7 MDL No. :MFCD00045052
Formula : C8H8Br2 Boiling Point : -
Linear Structure Formula :- InChI Key :APTDRDYSJZQPPI-UHFFFAOYSA-N
M.W : 263.96 Pubchem ID :11010825
Synonyms :

Calculated chemistry of [ 1746-28-7 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.79
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.66
Log Po/w (XLOGP3) : 3.76
Log Po/w (WLOGP) : 3.39
Log Po/w (MLOGP) : 4.12
Log Po/w (SILICOS-IT) : 3.84
Consensus Log Po/w : 3.55

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.16
Solubility : 0.0184 mg/ml ; 0.0000696 mol/l
Class : Moderately soluble
Log S (Ali) : -3.45
Solubility : 0.093 mg/ml ; 0.000352 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.91
Solubility : 0.00323 mg/ml ; 0.0000122 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.62

Safety of [ 1746-28-7 ]

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 [ 1746-28-7 ]

* 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 [ 1746-28-7 ]
  • Downstream synthetic route of [ 1746-28-7 ]

[ 1746-28-7 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 1746-28-7 ]
  • [ 693-04-9 ]
  • [ 23703-22-2 ]
YieldReaction ConditionsOperation in experiment
94 %Chromat. With cobalt(II) chloride; lithium iodide; isoprene In tetrahydrofuran at -78 - 50℃; for 5 h; Inert atmosphere General procedure: Coupling of Alkyl Halides with t-BuMgCl; Procedure 1 (P1)An alkyl halide (1.0 mmol), decane (63 mg as an internal standard)and LiI (5.3 mg, 0.04 mmol) were added to a dry, nitrogen-flushedtest tube equipped with a rubber septum and a magnetic stir bar.THF (0.8 mL) was added and the solution was cooled to –78 °C usinga dry ice/EtOH bath. t-BuMgCl (2a) (1.5 mL, 0.81 M in THF,1.2 mmol) was added slowly followed by isoprene (136.2 mg, 2.0mmol). To this mixture was added CoCl2 [2.6 mg, 0.02 mmol, as apowder or as a THF solution (0.5 mL, 0.04 M)]. (Note 1: CoCl2should be added after isoprene, otherwise the catalytic performancedecreases significantly). The cold bath was removed and the mixturewas warmed to r.t. (ca. over 10 min), and then heated for 5 h bysuspending the reaction vessel in an oil bath kept at 50 °C. (Note 2:when the reaction mixture was heated at 30 °C during this stage, unidentifiedside reactions occurred resulting in low yields of couplingproducts). The resulting mixture was cooled to 0 °C in an ice bathand the reaction was quenched with aq HCl (5 mL, 1 M). The productwas extracted with Et2O (3 × 20 mL). The combined organiclayer dried over Na2SO4, concentrated and analyzed by gas chromatographyto determine the GC yield. The residue was purified by silicagel column chromatography or by GPC. 1.0 mmol) and n-BuMgCl (2j) (1.0 M in THF, 1.2 mmol) were reactedunder standard conditions.Yield: 94percent (determined by GC using decane as an internal standard).
Reference: [1] Journal of the American Chemical Society, 2002, vol. 124, # 16, p. 4222 - 4223
[2] Journal of the American Chemical Society, 2013, vol. 135, # 26, p. 9604 - 9607
[3] Synthesis (Germany), 2014, vol. 46, # 12, p. 1583 - 1592
[4] Journal of Organic Chemistry, 2014, vol. 79, # 18, p. 8522 - 8532
  • 2
  • [ 1746-28-7 ]
  • [ 143-33-9 ]
  • [ 57775-08-3 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1977, p. 2357 - 2364
  • 3
  • [ 30089-00-0 ]
  • [ 1746-28-7 ]
  • [ 106418-67-1 ]
YieldReaction ConditionsOperation in experiment
97 mg With [((Me)NN2)NiCl]; isopropyl alcohol; sodium iodide; sodium hydroxide In 1,4-dioxane; isopropyl alcohol at 80℃; for 24 h; Inert atmosphere General procedure: To a solution of NaOH (32 mg, 0.8 mmol, 1.6 equiv), catalyst 1 (8.4mg, 0.025 mmol, 5 molpercent), NaI (37 mg, 0.25 mmol, 0.5 equiv), and i-PrOH (76 μL, 1 mmol, 2 equiv) in dry 1,4-dioxane (2.4 mL), were added alkyl halide (0.5 mmol) and the alkyl-(9-BBN) (1.6 mL, 0.8mmol, 1.6 equiv) under a N2 atmosphere. The mixture was stirred at 80 °C for 24 h. The solution was diluted in Et2O (10 mL), filtered on a short pad of silica, washed with Et2O (3 × 10 mL), and concentrated to dryness under reduced pressure. The residue was purified with a flash purification system to give the coupling product (Tables 1 and 2).
Reference: [1] Synthesis (Germany), 2013, vol. 45, # 21, p. 2949 - 2958
  • 4
  • [ 1746-28-7 ]
  • [ 364794-81-0 ]
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8267 - 8276
  • 5
  • [ 110-91-8 ]
  • [ 1746-28-7 ]
  • [ 736991-39-2 ]
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8267 - 8276
[2] MedChemComm, 2013, vol. 4, # 11, p. 1501 - 1507
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