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Chemical Structure| 145691-59-4
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Product Details of [ 145691-59-4 ]

CAS No. :145691-59-4 MDL No. :MFCD01632143
Formula : C7H6Br2O Boiling Point : -
Linear Structure Formula :- InChI Key :ZQNSHKZQTZSNTB-UHFFFAOYSA-N
M.W :265.93 Pubchem ID :7009423
Synonyms :

Calculated chemistry of [ 145691-59-4 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.97
TPSA : 20.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.37
Log Po/w (XLOGP3) : 3.03
Log Po/w (WLOGP) : 2.55
Log Po/w (MLOGP) : 3.03
Log Po/w (SILICOS-IT) : 3.03
Consensus Log Po/w : 2.8

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.78
Solubility : 0.0446 mg/ml ; 0.000168 mol/l
Class : Soluble
Log S (Ali) : -3.12
Solubility : 0.202 mg/ml ; 0.000758 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.93
Solubility : 0.031 mg/ml ; 0.000117 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.36

Safety of [ 145691-59-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 145691-59-4 ]

* 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 [ 145691-59-4 ]
  • Downstream synthetic route of [ 145691-59-4 ]

[ 145691-59-4 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 67-56-1 ]
  • [ 145691-59-4 ]
  • [ 51329-15-8 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 29, p. 10776 - 10782
  • 2
  • [ 145691-59-4 ]
  • [ 56990-02-4 ]
Reference: [1] Synlett, 2002, # 2, p. 251 - 254
  • 3
  • [ 145691-59-4 ]
  • [ 56908-88-4 ]
YieldReaction ConditionsOperation in experiment
2.5 g With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 1 h; General procedure: 3,5-Di-t-butylbenzoic acid (5.00 g, 0.021 mol) was dissolved in anhydrous THF (250 mL) under argon atmosphere and the solution cooled to 0 °C. Lithium aluminum hydride (1.62 g, 0.043 mol) was added in small portions and the solution stirred at room temperature overnight. The reaction was quenched with water, Et2O (100 mL) was added and the mixture acidified with concentrated HCl solution until the solid residue was dissolved. The medium was extracted with Et2O and the organic phase dried over MgSO4, filtered and concentrated to yield 4.31g of 5a. 1H NMR δ (CDCl3) 1.34 (s, 18H, di-t-butyl), 4.70 (s, 2H, PhCH2OH), 7.23 (d, 2H, J = 1.8 Hz, 2-CH and 6-CH), 7.38 (t, 1H, J = 1.8 Hz, 4-CH). Crude alcohol 5a (4.25 g) was dissolved in anhydrous CH2Cl2 (500 mL) and cooled at 0 °C. Triphenylphosphine (10.23 g, 0.039 mol) and carbon tetrabromide (12.93 g, 0.039 mol) were added and the mixture was stirred at room temperature for 1 h. The reaction mixture was quenched with water and extracted with CH2Cl2. The organic phase was dried over MgSO4, filtered and concentrated. The product was purified by flash chromatography on silica gel with hexanes to yield 4.62 g (86percent) of bromide 5b.
Reference: [1] Chemistry - A European Journal, 2012, vol. 18, # 24, p. 7473 - 7485
[2] European Journal of Organic Chemistry, 2007, # 16, p. 2700 - 2712
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 3, p. 1215 - 1227
[4] European Journal of Medicinal Chemistry, 2011, vol. 46, # 9, p. 4227 - 4237
  • 4
  • [ 56990-02-4 ]
  • [ 145691-59-4 ]
YieldReaction ConditionsOperation in experiment
84% With sodium tetrahydroborate In methanol at 0 - 20℃; for 1 h; Example 15
[4-[3,5-Bis-[(4-trifluoromethylphenyl)ethynyl]benzyloxy]-2-methylphenoxy]acetic acid
3,5-Dibromobenzaldehyde (1.7 g, 6.3 mmol) was dissolved in methanol (100 mL) and sodium borohydride (0.250 g, 6.3 mmol) was added at 0° C.
The reaction mixture was stirred for 0.5 h at 0° C. and then at 20° C. for another 0.5 h.
The reaction mixture was concentrated in vacuo, diluted with brine (250 mL), acidified with hydrochloric acid and extracted with dichloromethane (3*50 mL).
Evaporation of the organic solution gave 3,5-dibromo-benzyl alcohol as a white crystalline compound.
Yield: 1.4 g (84percent).
RF (SiO2, hexanes/ethyl acetate 9:1) 0.25.
1H NMR spectrum (300 MHz, CDCl3, A) 7.59 (d, J=1.5 Hz, 1H); 7.47 (d, J=1.5 Hz, 2H); 4.36 (s, 2H); 1.55 (s, 1H).
84% With sodium tetrahydroborate In methanol at 0 - 20℃; for 1 h; Example 15; [4-[3,5-Bis-[(4-trifluoromethylphenyl)ethynyl]benzyloxy]-2-methylphenoxy]acetic acid; 3,5-Dibromobenzaldehyde (1.7 g, 6.3 mmol) was dissolved in methanol (100 mL) and sodium borohydride (0.250 g, 6.3 mmol) was added at 0 °C. The reaction mixture was stirred for 0.5 h at 0 °C and then at 20 °C for another 0.5 h. The reaction mixture was con- centrated in vacuo, diluted with brine (250 mL), acidified with hydrochloric acid and extracted with dichloromethane (3 x 50 mL). Evaporation of the organic solution gave 3,5-dibromo- benzyl alcohol as a white crystalline compound. Yield: 1.4 g (84 percent). RF (Si02, hexanes/ethyl acetate 9:1) 0.25. 1H NMR spectrum (300 MHz, CDCl3, No.H) : 7.59 (d, J=1.5 Hz, 1 H) ; 7.47 (d, J=1.5 Hz, 2 H); 4.36 (s, 2 H); 1.55 (s, 1 H).
Reference: [1] Chemistry - A European Journal, 2012, vol. 18, # 24, p. 7473 - 7485
[2] Journal of Medicinal Chemistry, 1997, vol. 40, # 21, p. 3442 - 3452
[3] Organic Letters, 2004, vol. 6, # 16, p. 2765 - 2767
[4] Patent: US2009/209588, 2009, A1, . Location in patent: Page/Page column 25
[5] Patent: WO2005/105726, 2005, A1, . Location in patent: Page/Page column 62
[6] Chemical Communications, 2004, # 14, p. 1582 - 1583
[7] Patent: US5457118, 1995, A,
[8] Patent: WO2009/42694, 2009, A1, . Location in patent: Page/Page column 114
[9] Journal of Polymer Science, Part A: Polymer Chemistry, 2014, vol. 52, # 5, p. 707 - 718
  • 5
  • [ 618-58-6 ]
  • [ 145691-59-4 ]
YieldReaction ConditionsOperation in experiment
94% With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃; Step 1 : To a stirred solution of 3,5-dibromobenzoic acid (2 g, 7.168 mmol) in tetrahydrofuran (20 mL) was added borane dimethylsulfide (3.4 mL, 35.842 mmol, 5 eq.) at 0 °C, and the reaction mixture was stirred at room temperature for overnight. The reaction mixture was quenched with methanol at 0 °C and concentrated under vacuo to obtain (3,5- dibromophenyl)methanol as an off white solid (1.8 g, 94percent). H NMR (400 MHz, DMSO-d6) δ ppm 4.47 (d, J = 6 Hz, 2H), 5.39 (t, J = 6 Hz, 1 H), 7.49 (s, 2H), 7.65 (s, 1 H).
Reference: [1] Patent: WO2017/46739, 2017, A1, . Location in patent: Page/Page column 60
[2] Patent: JP2005/120047, 2005, A, . Location in patent: Page/Page column 165
[3] Synlett, 2002, # 2, p. 251 - 254
[4] European Journal of Medicinal Chemistry, 2011, vol. 46, # 9, p. 4227 - 4237
  • 6
  • [ 67973-33-5 ]
  • [ 145691-59-4 ]
Reference: [1] European Journal of Organic Chemistry, 2009, # 18, p. 2953 - 2955
  • 7
  • [ 626-39-1 ]
  • [ 145691-59-4 ]
Reference: [1] Australian Journal of Chemistry, 1997, vol. 50, # 4, p. 425 - 434
[2] Journal of Polymer Science, Part A: Polymer Chemistry, 2014, vol. 52, # 5, p. 707 - 718
  • 8
  • [ 56908-88-4 ]
  • [ 145691-59-4 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1926, vol. 45, p. 303
  • 9
  • [ 56990-02-4 ]
  • [ 145691-59-4 ]
  • [ 193408-02-5 ]
Reference: [1] Australian Journal of Chemistry, 1997, vol. 50, # 4, p. 425 - 434
  • 10
  • [ 145691-59-4 ]
  • [ 188347-48-0 ]
Reference: [1] Patent: WO2014/15054, 2014, A1,
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 3, p. 1215 - 1227
[3] Patent: WO2018/132268, 2018, A1,
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