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[ CAS No. 138500-85-3 ] {[proInfo.proName]}

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Chemical Structure| 138500-85-3
Chemical Structure| 138500-85-3
Structure of 138500-85-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 138500-85-3 ]

CAS No. :138500-85-3 MDL No. :MFCD02179493
Formula : C13H18BBrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :CBUOGMOTDGNEAW-UHFFFAOYSA-N
M.W : 297.00 Pubchem ID :3734506
Synonyms :

Calculated chemistry of [ 138500-85-3 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.54
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 75.75
TPSA : 18.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.65 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 3.47
Log Po/w (WLOGP) : 2.73
Log Po/w (MLOGP) : 2.41
Log Po/w (SILICOS-IT) : 2.87
Consensus Log Po/w : 2.3

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.0
Solubility : 0.0299 mg/ml ; 0.000101 mol/l
Class : Soluble
Log S (Ali) : -3.54
Solubility : 0.0857 mg/ml ; 0.000289 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.24
Solubility : 0.00169 mg/ml ; 0.0000057 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.03

Safety of [ 138500-85-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 138500-85-3 ]

* 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 [ 138500-85-3 ]
  • Downstream synthetic route of [ 138500-85-3 ]

[ 138500-85-3 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 302348-51-2 ]
  • [ 138500-85-3 ]
YieldReaction ConditionsOperation in experiment
92% With carbon tetrabromide; triphenylphosphine In tetrahydrofuran at 20℃; for 4 h; Cooling with ice 4-hydroxymethylphenylboronic acid, pinacol ester (1.08 g, 4.61 mmol) was dissolved in THF (20 ml) together with triphenylphosphine (2.42 g, 9.23mmol). The reaction mixture was cooled in an ice-water bath, and carbon tetrabromide (3.06 g, 9.23 mmol) was added portion wise. After stirring for 4 hours at room temperature, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was combined and dried by sodium sulfate. After filtration, the solvent was evaporated, and the residue was purified by flash chromatography to give the product as a white solid (1.72 g, 92percent). 1H NMR (300 MHz, CD2C12, δ): 7.62 (d, J = 6.0 Hz, 2H), 7.32 (d, J = 6.0 Hz, 2H), 4.58 (d, 2H), 1.34 (s, 9H); MS (ESI) m/z 297.0.
Reference: [1] Patent: WO2013/25885, 2013, A1, . Location in patent: Paragraph 0086
[2] Synthetic Communications, 2002, vol. 32, # 17, p. 2669 - 2676
[3] Patent: EP2450354, 2012, A1,
  • 2
  • [ 195062-57-8 ]
  • [ 138500-85-3 ]
YieldReaction ConditionsOperation in experiment
82% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 12 h; Reflux Scheme 1. Synthesis of 4-(4,4,5,5-tetrarnethyl- 1,3,2 -dioxaboratophenyl)-methyl triphenylphosphonium bromide 4. [00120] Compound 6 (8) was prepared starting from 4,4,5,5-tetramethyl-2-p-tolyl- 1 ,2>,2- dioxaborolane 7, NBS and A1BN in carbon tetrachloride were refluxed for 12 hours. In an initial attempt 4-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaboratophenyl)-methyl triphenylphosphonium bromide 4 was isolated as a white solid in 92percent yield. The minor excess of PPh3 was removed from the product by trituration with ether 2-3 times and the product was found to be stable under normal atmospheric conditions. Subsequently, the Wittig reaction of the ylide derived from this salt using benzaldehyde (Scheme 2) was optimized.
Reference: [1] Synlett, 2006, # 3, p. 475 - 477
[2] Patent: WO2006/81807, 2006, A2, . Location in patent: Page/Page column 20; 32
[3] Tetrahedron Letters, 2009, vol. 50, # 25, p. 3031 - 3034
[4] Tetrahedron Letters, 2012, vol. 53, # 11, p. 1316 - 1318
[5] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 18, p. 5638 - 5641
[6] Patent: WO2012/112670, 2012, A1, . Location in patent: Page/Page column 31-32
[7] Journal of Organometallic Chemistry, 2015, vol. 798, p. 51 - 59
[8] Journal of the American Chemical Society, 2017, vol. 139, # 29, p. 10157 - 10163
[9] Angewandte Chemie - International Edition, 2018, vol. 57, # 21, p. 6324 - 6328[10] Angew. Chem., 2018, vol. 130, p. 6432 - 6436,5
[11] Chemistry - A European Journal, 2009, vol. 15, # 46, p. 12627 - 12635
[12] Tetrahedron Letters, 2010, vol. 51, # 30, p. 3913 - 3917
[13] Organic Letters, 2013, vol. 15, # 4, p. 917 - 919
[14] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 1, p. 59 - 62
[15] Patent: WO2017/8743, 2017, A1, . Location in patent: Paragraph 112
[16] Patent: US6335451, 2002, B1, . Location in patent: Page column 36
  • 3
  • [ 128-08-5 ]
  • [ 195062-57-8 ]
  • [ 138500-85-3 ]
YieldReaction ConditionsOperation in experiment
76.1% With 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 14 h; Reflux P-toluene boronic acid pinacol ester (10.91 g, 50.0 mmol),Bromosuccinimide (NBS, 9.91 g, 55.0 mmol),Azobisisobutyronitrile (AIBN, 0.44 g, 2.0 mmol) was dissolved in dry carbon tetrachloride (CCl4, 200 mL).It was stirred at reflux for 14 hours, filtered, the solvent was removed by rotary evaporation, and the ethyl acetate (200 mL) was dissolved.After washing once with distilled water (100 mL) and saturated aqueous sodium chloride solution (100 mL), it was dried over anhydrous sodium sulfate.Spin-steaming, finally using petroleum ether as eluent to cross the column,4-Bromomethylphenylboronic acid pinacol ester (11.30 g, yield 76.1percent) was isolated.
Reference: [1] Patent: CN107417714, 2017, A, . Location in patent: Paragraph 0056; 0057; 0061
[2] Dalton Transactions, 2016, vol. 45, # 35, p. 13726 - 13741
  • 4
  • [ 5720-05-8 ]
  • [ 138500-85-3 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 4, p. 917 - 919
[2] Patent: WO2017/8743, 2017, A1,
[3] Angewandte Chemie - International Edition, 2018, vol. 57, # 21, p. 6324 - 6328[4] Angew. Chem., 2018, vol. 130, p. 6432 - 6436,5
[5] Patent: US6335451, 2002, B1,
  • 5
  • [ 76-09-5 ]
  • [ 138500-85-3 ]
Reference: [1] Synlett, 2006, # 3, p. 475 - 477
[2] Patent: WO2017/8743, 2017, A1,
[3] Angewandte Chemie - International Edition, 2018, vol. 57, # 21, p. 6324 - 6328[4] Angew. Chem., 2018, vol. 130, p. 6432 - 6436,5
[5] Patent: US6335451, 2002, B1,
  • 6
  • [ 76-09-5 ]
  • [ 68162-47-0 ]
  • [ 138500-85-3 ]
Reference: [1] Organic Preparations and Procedures International, 1991, vol. 23, # 6, p. 729 - 734
  • 7
  • [ 40881-45-6 ]
  • [ 138500-85-3 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 4, p. 917 - 919
  • 8
  • [ 106-38-7 ]
  • [ 138500-85-3 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 4, p. 917 - 919
  • 9
  • [ 73183-34-3 ]
  • [ 138500-85-3 ]
Reference: [1] Patent: EP2450354, 2012, A1,
  • 10
  • [ 18282-51-4 ]
  • [ 138500-85-3 ]
Reference: [1] Patent: EP2450354, 2012, A1,
  • 11
  • [ 5084-80-0 ]
  • [ 138500-85-3 ]
Reference: [1] Synlett, 2006, # 3, p. 475 - 477
  • 12
  • [ 87199-17-5 ]
  • [ 138500-85-3 ]
Reference: [1] Synthetic Communications, 2002, vol. 32, # 17, p. 2669 - 2676
  • 13
  • [ 128376-64-7 ]
  • [ 138500-85-3 ]
Reference: [1] Synthetic Communications, 2002, vol. 32, # 17, p. 2669 - 2676
  • 14
  • [ 624-31-7 ]
  • [ 138500-85-3 ]
Reference: [1] Dalton Transactions, 2016, vol. 45, # 35, p. 13726 - 13741
  • 15
  • [ 25015-63-8 ]
  • [ 138500-85-3 ]
Reference: [1] Dalton Transactions, 2016, vol. 45, # 35, p. 13726 - 13741
  • 16
  • [ 76-09-5 ]
  • [ 5720-05-8 ]
  • [ 138500-85-3 ]
Reference: [1] Patent: CN107417714, 2017, A,
  • 17
  • [ 110-91-8 ]
  • [ 138500-85-3 ]
  • [ 364794-79-6 ]
YieldReaction ConditionsOperation in experiment
100% at 20℃; 2-(4-Bromomethyl-phenyl)-4,4,5,5-tetramethyl-[ 1,3,2]dioxaborolane (200mg, 0.673mmol) was dissolved in THF (5mL) and morpholine (0.088mL, 1.01 mmol) was added. The mixture stirred overnight at room temperature and was then filtered and concentrated to afford the title compound (223mg, 100percent). lH NMR (300 MHz, CDCI3): 8 7.79 (d, 2H), 7.36 (d, 2H), 3.73 (t, 4H), 3.55 (s, 2H), 2.47 (t, 4H).
72.6% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 4 h; 4-bromomethylphenylboronic acid pinacol ester (5.00 g, 1.68 mmol),Morpholine (1.74 g, 2.00 mmol),Potassium carbonate (2.80g, 2.OOmmol) was added to the reaction flask,Add 50 mL of N,N-dimethylformamide,The reaction was stirred at 80° C. for 4 hours.Cool to room temperature,Pour the reaction solution into 250mL ice water,Stir for 30 minutes,The title product was filtered by suction to give 3.7 g of a white solid. The yield was 72.6percent.
Reference: [1] Patent: WO2006/20879, 2006, A1, . Location in patent: Page/Page column 108
[2] ACS Combinatorial Science, 2011, vol. 13, # 1, p. 24 - 31
[3] Patent: CN107759587, 2018, A, . Location in patent: Paragraph 0245-0246
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 17, p. 5133 - 5138
[5] RSC Advances, 2016, vol. 6, # 87, p. 83864 - 83869
  • 18
  • [ 109-01-3 ]
  • [ 138500-85-3 ]
  • [ 938043-30-2 ]
Reference: [1] ACS Combinatorial Science, 2011, vol. 13, # 1, p. 24 - 31
[2] Patent: WO2007/78523, 2007, A2, . Location in patent: Page/Page column 58
[3] Patent: WO2009/10488, 2009, A1, . Location in patent: Page/Page column 57
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 17, p. 5133 - 5138
  • 19
  • [ 110-89-4 ]
  • [ 138500-85-3 ]
  • [ 859833-22-0 ]
Reference: [1] Patent: WO2009/10488, 2009, A1, . Location in patent: Page/Page column 57-58
  • 20
  • [ 138500-85-3 ]
  • [ 57260-71-6 ]
  • [ 936694-19-8 ]
Reference: [1] ACS Combinatorial Science, 2011, vol. 13, # 1, p. 24 - 31
[2] Patent: WO2008/139161, 2008, A1, . Location in patent: Page/Page column 97-98
  • 21
  • [ 123-75-1 ]
  • [ 138500-85-3 ]
  • [ 884507-39-5 ]
Reference: [1] Patent: US2011/281842, 2011, A1, . Location in patent: Page/Page column 75
  • 22
  • [ 138500-85-3 ]
  • [ 1206161-97-8 ]
Reference: [1] Patent: US2015/224199, 2015, A1,
[2] Patent: US2015/225398, 2015, A1,
[3] Patent: WO2016/165952, 2016, A1,
[4] Patent: CN107759587, 2018, A,
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