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Chemical Structure| 38186-51-5
Chemical Structure| 38186-51-5
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Product Details of [ 38186-51-5 ]

CAS No. :38186-51-5 MDL No. :MFCD05663693
Formula : C11H16BrO3P Boiling Point : -
Linear Structure Formula :- InChI Key :IPTXXSZUISGKCJ-UHFFFAOYSA-N
M.W : 307.12 Pubchem ID :11077666
Synonyms :

Calculated chemistry of [ 38186-51-5 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.45
Num. rotatable bonds : 6
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 69.17
TPSA : 45.34 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.35 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.0
Log Po/w (XLOGP3) : 2.57
Log Po/w (WLOGP) : 4.06
Log Po/w (MLOGP) : 2.79
Log Po/w (SILICOS-IT) : 2.65
Consensus Log Po/w : 3.02

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.24
Solubility : 0.175 mg/ml ; 0.000569 mol/l
Class : Soluble
Log S (Ali) : -3.17
Solubility : 0.208 mg/ml ; 0.000676 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.72
Solubility : 0.00581 mg/ml ; 0.0000189 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.33

Safety of [ 38186-51-5 ]

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 [ 38186-51-5 ]

* 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 [ 38186-51-5 ]
  • Downstream synthetic route of [ 38186-51-5 ]

[ 38186-51-5 ] Synthesis Path-Upstream   1~11

  • 1
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YieldReaction ConditionsOperation in experiment
72%
Stage #1: at 0℃; Inert atmosphere
Stage #2: With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 2 h; Inert atmosphere
A solution of benzophenone (1.82g, 10 mmol) and diethyl 4-bromobenzylphosphonate (3.1 g, 10 mmol) in anhydrous THF (40 mL) was stirred under argon atmosphere at 0 ºC. Potassium tert-butoxide (1.1 g, 10 mmol) was added quickly and the mixture was stirred for 2 h at room temperature. The reaction mixture was poured into ethanol and a solid precipitated out. The precipitate was filtered and washed with ethanol (3×10 mL) to afford product 6 as a white powder (2.41g, 72percent). Mp 52−54 ºC; IR (KBr, cm-1): 3032, 1610, 1484; 1H NMR (300 MHz, CDCl3): δ 7.25−7.18 (m, 3H), 7.16–7.06 (m, 5H), 7.05−6.94 (m, 4H), 6.92−6.82 (m, 3H); MS (EI): m/z 335, 337 (M+, M++2, 95, 100percent).
72% With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 20℃; for 2 h; Inert atmosphere A solution of benzophenone (1.82 g, 10 mmol) and diethyl 4-bromobenzylphosphonate (3.1 g, 10 mmol) in anhydrous THF (40 mL) was stirred under argon atmosphere at 0°C. Potassium tert-butoxide (1.1 g, 10 mmol) was added quickly and the mixture was stirred for 2 h at room temperature. The reaction mixture was poured into ethanol (10 mL) and a solid precipitated out. The precipitate was filtered and washed with ethanol (310 mL) to afford 1 as a white powder (2.41 g, 72percent). Mp 52-54 °C; IR (KBr, cm-1): 3032, 1610, 1484; 1H NMR (300 MHz, CDCl3): δ 7.25-7.18 (m, 3H), 7.16-7.06 (m, 5H), 7.05-6.94 (m, 4H), 6.92-6.82 (m, 3H); LCMS(EI): m/z 335 (MH+, 100percent).
Reference: [1] Journal of the American Chemical Society, 2000, vol. 122, # 24, p. 5695 - 5709
[2] Tetrahedron Letters, 2012, vol. 53, # 50, p. 6838 - 6842
[3] Dyes and Pigments, 2013, vol. 99, # 3, p. 740 - 747
[4] Patent: WO2009/51390, 2009, A2, . Location in patent: Page/Page column 64-65; 70-72
[5] Journal of Materials Chemistry, 2012, vol. 22, # 35, p. 18505 - 18513
[6] Chemistry - An Asian Journal, 2011, vol. 6, # 6, p. 1470 - 1478
  • 2
  • [ 19350-68-6 ]
  • [ 762-04-9 ]
  • [ 38186-51-5 ]
YieldReaction ConditionsOperation in experiment
73% With copper(l) iodide; caesium carbonate In 1,2-dimethoxyethane at 85℃; for 3 h; Inert atmosphere General procedure: Under an argon atmosphere, the carbonyl compounds (0.40 mmol), TsNHNH2 (0.42 mmol, 1.05 eq) and DME (1.0 mL) were successively added to a flame-dried Schlenk flask. The reaction was heated at 60 ºC with stirring for 30 minutes. After the solution cooled down to room temperature H-Phosphonate 1b (0.40 mmol, 1.0 eq), Cs2CO3 (0.60 mmol, 1.5 eq), and CuI (0.04 mmol, 10 mol percent) were sequentially added to the system. The mixture was stirred to 85oC. When the reaction was considered complete, as determined by TLC analysis, the reaction mixture was cooled to room temperature and filtered through a short plug of silica gel [washed with EtOAc]. Solvent was then removed in vacuo to provide a crude mixture, which was purified by silica gel column chromatography to afford pure product.
Reference: [1] Advanced Synthesis and Catalysis, 2012, vol. 354, # 14-15, p. 2659 - 2664
[2] Tetrahedron, 2013, vol. 69, # 3, p. 1065 - 1068
[3] Angewandte Chemie - International Edition, 2018, vol. 57, # 22, p. 6624 - 6628[4] Angew. Chem., 2018, vol. 130, # 22, p. 6734 - 6738,5
  • 3
  • [ 873-75-6 ]
  • [ 122-52-1 ]
  • [ 38186-51-5 ]
YieldReaction ConditionsOperation in experiment
90% at 120℃; for 24 h; Inert atmosphere To a 20 mL tubular reactor was added 4-bromobenzyl alcohol (93.0 mg, 0.50 mmol)(3.8 mg, 0.01 mmol, 2 molpercent), protected by vacuum nitrogen and then heated to 120 ° C under solvent-free conditions 24h After the TLC monitoring reaction was complete, the product was purified by column chromatography and the yield was 90percent.
Reference: [1] Patent: CN106543221, 2017, A, . Location in patent: Paragraph 0030; 0031; 0032; 0033
[2] Green Chemistry, 2018, vol. 20, # 15, p. 3408 - 3413
  • 4
  • [ 589-15-1 ]
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  • [ 38186-51-5 ]
YieldReaction ConditionsOperation in experiment
100% at 100℃; for 24 h; A solution of 25 g (0.1 mol) of 4-bromobenzyl bromide and 19 ml (0.11 mol) of triethylphosphite is heated at 100° C. for 24 hours. At room temperature, the residue is purified on a silica column (dichloromethane and then ethyl acetate). [00400] Yellow oil. m=31 g. Y=100percent. 1H NMR (CDCl3): 1.22-1.28 (6H, t), 3.05-3.13 (2H, d), 3.96-4.08 (4H, q), 7.15-7.19 (2H, dd, J=6 Hz, J'=2.4 Hz), 7.42-7.45 (2H, d, J=8 Hz).
99% at 150℃; for 12 h; Inert atmosphere Preparing Example 2
Preparation Of Diethyl 4-Bromobenzyl-Phosphonate (Compound A)
1-bromo-4-(bromomethyl)benzene (5.00 g, 20.0 mmol) was in a two-neck bottle. after introducing nitrogen gas by vacuum pumping, anhydrous toluene (80.0 mL) and triethyl phosphite (10.4 mL, 60.0 mmol) were added and heated to 150° C. for twelve hours.
After the reaction finished, the solvent was removed by the rotary concentrator to obtain yellow liquid of 6.08 g (compound A) with a yield of 99percent.
1H NMR (400 MHz, CDCl3, δ): 7.39-7.37 (m, 2H), 7.12 (dd, J=8.4 Hz, J=2.4 Hz, 2H), 3.99-3.94 (m, 4H), 3.04 (d, J=21.6 Hz, 2H), 1.21-1.18 (m, 6H)13C NMR (100 MHz, CDCl3, 5): 131.5, 131.5, 131.4, 131.3, 130.7, 130.6, 120.8, 120.8, 62.2, 62.1, 33.8, 32.4, 16.3, 16.2.
98% at 90℃; for 19 h; Example lj. Diethyl 4-bromobenzylphosphonate (16).; l-bromo-4-(bromomethyl) benzene (5.0 g, 20 mmol) and triethyl phosphite (51 mL, 300 mmol) were mixed in a round bottom flask and refluxed at 90 °C for 19 hours. Excess triethyl phosphite was removed under reduced pressure and the product purified by flash chromatography (1 : 1 Hexane/ EtOAc) to give compound 16. 16: 98 percent yield ; colorless liquid; 1H NMR (400 MHz, CDC13) δ 7.30 (d, 2H, J= 7.5 Hz), 7.05 (d, 2H, J= 7.6 Hz), 3.99- 3.88 (m, 4H), 2.99 (s, IH), 2.94 (s, IH), 1.12 (t, 6H, J= 6.9 Hz); 13C NMR (100 MHz, CDC13) δ 131.7, 131.6, 131.5, 121.0, 62.3, 34.0, 32.0, 16.5; HRMS Calc for CnHi6Br03P ( M+H)+ 307.0097 found 307.0093.
98% at 160 - 170℃; Inert atmosphere General procedure: Organohalogen compound and anhydrous NiBr2(5–10 molpercent) as catalyst were charged into a two-necked round bottom flask equipped with a dropping funnel and short distillation column (no catalyst was used in the cases of benzyl derivatives). The mixture was degassed by bubbling the solution with dry N2gas for 30 min and then heated at 160–170°C. P(OEt)3(1.2 equiv. relative to the organohalogen compound) was slowly added through the dropping funnel. The mixture was stirred and heated at 160–170°Covernight. The crude product was purified by silica gel column chromatography using dichloromethane as an eluent. The product was dried at 70°Cunder reduced pressure for 2 h.Benzyl derivatives were purified by distillation under reduced pressure without column chromatography. Diethyl organophosphonate (ArP(O)(OEt)2) was obtained as colorless liquid.
92% at 160℃; for 2 h; A mixture of triethyl phosphite (2.54 g, 15.3 mmol) and 4-bromobenzyl bromide (2.00 g, 10.2 mmol) was stirred at 160° C. for 2 h. During this period ethyl bromide was distilled from the reaction mixture. Subsequently, the mixture was cooled to 70° C. and the excess of triethyl phosphite was removed by distillation under reduced pressure. The product was used without further purification, yielded 92percent product. 1H NMR (400 MHz, CDCl3): δ 1.25 (t, 6H, J=7.2 Hz), 3.06, 3.11 (s, 2H), 4.01 (m, 4H), 7.16 (d, 2H, J=8.4 Hz), 7.42 (d, 2H, I=8.4 Hz).
92.5% at 140℃; for 2 h; General procedure: Diethyl benzylphosphonate as the basis compound for thesynthesis of the t-APE isomers was prepared according to literature[18,19]. Benzyl bromide (1.50 g, 8.8 mmol) was suspended in 5 mLof toluene, containing triethylphosphite (6.00 g, 35 mmol). The mixture was refluxed at 140 °C for 2 h. Excess triethylphosphite and toluene were removed by distillation to give the required product as a yellow oil (1.80 g, 89.9percent).
91% at 150℃; for 3 h; Intermediate 1 Diethyl 4-bromobenzylphosphonate 4-Bromoben2yl bromide (22.5g, 90mmol) and triethylphosphite (16.45g, 99mmol) were heated to 150°C for 3 h. The mixture was purifed by flash chromatography (1/4 EtOAc/hexane) to give diethyl 4-bromobenzylphosphonate (25.2g, 91percent). Ή NMR (300 MHz, CDCI3) δ ?7.45 (m, 2H), 7.15 (m, 2H), 4.00 (m, 4H), 3.05 (m, 2H), 1.25 (m, 6H)
81% for 24 h; Heating / reflux 4-bromobenzylbromide (10. Og, 40.0mmol) was dissolved in triethylphosphite (8.4mL, 48.0mmol) under a nitrogen atmosphere, and the reaction solution was refluxed and stirred for 24 hours. The reaction solution was passed through a silica gel column by using hexane-ethylacetate 7:3 as an eluant. After the solvent was removed, the residue material was dried in vacuum to thereby obtain pale yellow oil (10. Og, yield: 81percent) .

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  • 5
  • [ 1067-71-6 ]
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Reference: [1] Advanced Synthesis and Catalysis, 2011, vol. 353, # 18, p. 3340 - 3346
  • 6
  • [ 78-40-0 ]
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[3] Patent: CN105712917, 2016, A, . Location in patent: Paragraph 0021
  • 7
  • [ 1122-91-4 ]
  • [ 122-52-1 ]
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  • 8
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  • 9
  • [ 1122-91-4 ]
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[2] Tetrahedron, 2013, vol. 69, # 3, p. 1065 - 1068
[3] Angewandte Chemie - International Edition, 2018, vol. 57, # 22, p. 6624 - 6628[4] Angew. Chem., 2018, vol. 130, # 22, p. 6734 - 6738,5
  • 10
  • [ 106-38-7 ]
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  • 11
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