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bromobenzene
3,5-Dibromophenyl acetate
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bromobenzene
benzyl dibromobenzene

[ CAS No. 909389-74-8 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 909389-74-8
Chemical Structure| 909389-74-8
Chemical Structure| 909389-74-8
Structure of 909389-74-8 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 909389-74-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
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Product Details of [ 909389-74-8 ]

CAS No. :909389-74-8 MDL No. :MFCD08445663
Formula : C8H6Br2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :QPXGHGNAEBFULS-UHFFFAOYSA-N
M.W : 293.94 Pubchem ID :26967130
Synonyms :

Calculated chemistry of [ 909389-74-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 53.34
TPSA : 26.3 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) : -5.92 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.62
Log Po/w (XLOGP3) : 3.06
Log Po/w (WLOGP) : 3.14
Log Po/w (MLOGP) : 3.38
Log Po/w (SILICOS-IT) : 3.05
Consensus Log Po/w : 3.05

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.83
Solubility : 0.0437 mg/ml ; 0.000149 mol/l
Class : Soluble
Log S (Ali) : -3.28
Solubility : 0.155 mg/ml ; 0.000526 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.17
Solubility : 0.0199 mg/ml ; 0.0000676 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.85

Safety of [ 909389-74-8 ]

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 [ 909389-74-8 ]

* 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.

  • Downstream synthetic route of [ 909389-74-8 ]

[ 909389-74-8 ] Synthesis Path-Downstream   1~39

  • 1
  • [ 909389-74-8 ]
  • 4-ethynylpyridine hydrochloride [ No CAS ]
  • [ 909389-75-9 ]
YieldReaction ConditionsOperation in experiment
66% With triethylamine In tetrahydrofuran at 60℃; for 16h;
66% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 60℃; for 16h;
65.3% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 60℃;
Reference： [1]Yang, Hai-Bo; Das, Neeladri; Huang, Feihe; Hawkridge, Adam M.; Muddiman, David C.; Stang, Peter J. [Journal of the American Chemical Society, 2006, vol. 128, # 31, p. 10014 - 10015]
[2]Yang, Hai-Bo; Hawkridge, Adam M.; Huang, Songping D.; Das, Neeladri; Bunge, Scott D.; Muddiman, David C.; Stang, Peter J. [Journal of the American Chemical Society, 2007, vol. 129, # 7, p. 2120 - 2129]
[3]Jia, Pei-Pei; Xu, Lin; Hu, Yi-Xiong; Li, Wei-Jian; Wang, Xu-Qing; Ling, Qing-Hui; Shi, Xueliang; Yin, Guang-Qiang; Li, Xiaopeng; Sun, Haitao; Jiang, Yanrong; Yang, Hai-Bo [Journal of the American Chemical Society, 2021, vol. 143, # 1, p. 399 - 408]
  • 2
  • [ 626-41-5 ]
  • [ 108-24-7 ]
  • [ 909389-74-8 ]
YieldReaction ConditionsOperation in experiment
95% at 70℃; for 2h;
93% With dmap In toluene at 20℃; Inert atmosphere;
92% at 70℃; for 2h;
92% at 70℃; for 2h;
92% at 70℃;

Reference： [1]Yang, Hai-Bo; Hawkridge, Adam M.; Huang, Songping D.; Das, Neeladri; Bunge, Scott D.; Muddiman, David C.; Stang, Peter J. [Journal of the American Chemical Society, 2007, vol. 129, # 7, p. 2120 - 2129]
[2]Swain, Jonathan A.; Iadevaia, Giulia; Hunter, Christopher A. [Journal of the American Chemical Society, 2018, vol. 140, # 36, p. 11526 - 11536]
[3]Yang, Hai-Bo; Das, Neeladri; Huang, Feihe; Hawkridge, Adam M.; Muddiman, David C.; Stang, Peter J. [Journal of the American Chemical Society, 2006, vol. 128, # 31, p. 10014 - 10015]
[4]Zhou, Fengyan; Li, Shijun; Cook, Timothy R.; He, Zuoli; Stang, Peter J. [Organometallics, 2014, vol. 33, # 24, p. 7019 - 7022]
[5]Jia, Pei-Pei; Xu, Lin; Hu, Yi-Xiong; Li, Wei-Jian; Wang, Xu-Qing; Ling, Qing-Hui; Shi, Xueliang; Yin, Guang-Qiang; Li, Xiaopeng; Sun, Haitao; Jiang, Yanrong; Yang, Hai-Bo [Journal of the American Chemical Society, 2021, vol. 143, # 1, p. 399 - 408]
  • 3
  • [ 909389-74-8 ]
  • [ 909389-76-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 66 percent / Pd(PPh3)4; CuI; Et3N / tetrahydrofuran / 16 h / 60 °C 2: 99 percent / aq. NaHCO3 / methanol / 2 h / 20 °C
Multi-step reaction with 2 steps 1: 66 percent / Et3N / Pd(PPh3)4; CuI / tetrahydrofuran / 16 h / 60 °C 2: 95 percent / aq. NaHCO3 / methanol / 2 h / 20 °C
Reference： [1]Yang, Hai-Bo; Hawkridge, Adam M.; Huang, Songping D.; Das, Neeladri; Bunge, Scott D.; Muddiman, David C.; Stang, Peter J. [Journal of the American Chemical Society, 2007, vol. 129, # 7, p. 2120 - 2129]
[2]Yang, Hai-Bo; Das, Neeladri; Huang, Feihe; Hawkridge, Adam M.; Muddiman, David C.; Stang, Peter J. [Journal of the American Chemical Society, 2006, vol. 128, # 31, p. 10014 - 10015]
  • 4
  • [ 909389-74-8 ]
  • [ 909389-77-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 66 percent / Pd(PPh3)4; CuI; Et3N / tetrahydrofuran / 16 h / 60 °C 2.1: 99 percent / aq. NaHCO3 / methanol / 2 h / 20 °C 3.1: NaH / dimethylformamide / 0.5 h 3.2: 85 percent / dimethylformamide / 2 h / 65 °C
Reference： [1]Yang, Hai-Bo; Hawkridge, Adam M.; Huang, Songping D.; Das, Neeladri; Bunge, Scott D.; Muddiman, David C.; Stang, Peter J. [Journal of the American Chemical Society, 2007, vol. 129, # 7, p. 2120 - 2129]
  • 5
  • [ 909389-74-8 ]
  • [ 909389-78-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 66 percent / Pd(PPh3)4; CuI; Et3N / tetrahydrofuran / 16 h / 60 °C 2.1: 99 percent / aq. NaHCO3 / methanol / 2 h / 20 °C 3.1: NaH / dimethylformamide / 0.5 h 3.2: 89 percent / dimethylformamide / 2 h / 65 °C
Reference： [1]Yang, Hai-Bo; Hawkridge, Adam M.; Huang, Songping D.; Das, Neeladri; Bunge, Scott D.; Muddiman, David C.; Stang, Peter J. [Journal of the American Chemical Society, 2007, vol. 129, # 7, p. 2120 - 2129]
  • 6
  • [ 909389-74-8 ]
  • [ 909389-79-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 66 percent / Pd(PPh3)4; CuI; Et3N / tetrahydrofuran / 16 h / 60 °C 2.1: 99 percent / aq. NaHCO3 / methanol / 2 h / 20 °C 3.1: NaH / dimethylformamide / 0.5 h 3.2: 87 percent / dimethylformamide / 2 h / 65 °C
Reference： [1]Yang, Hai-Bo; Hawkridge, Adam M.; Huang, Songping D.; Das, Neeladri; Bunge, Scott D.; Muddiman, David C.; Stang, Peter J. [Journal of the American Chemical Society, 2007, vol. 129, # 7, p. 2120 - 2129]
  • 7
  • [ 909389-74-8 ]
  • C28H20N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 66 percent / Et3N / Pd(PPh3)4; CuI / tetrahydrofuran / 16 h / 60 °C 2: 95 percent / aq. NaHCO3 / methanol / 2 h / 20 °C 3: 85 percent / NaH / dimethylformamide / 65 °C
Reference： [1]Yang, Hai-Bo; Das, Neeladri; Huang, Feihe; Hawkridge, Adam M.; Muddiman, David C.; Stang, Peter J. [Journal of the American Chemical Society, 2006, vol. 128, # 31, p. 10014 - 10015]
  • 8
  • [ 909389-74-8 ]
  • C42H32N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 66 percent / Et3N / Pd(PPh3)4; CuI / tetrahydrofuran / 16 h / 60 °C 2: 95 percent / aq. NaHCO3 / methanol / 2 h / 20 °C 3: 89 percent / NaH / dimethylformamide / 65 °C
Reference： [1]Yang, Hai-Bo; Das, Neeladri; Huang, Feihe; Hawkridge, Adam M.; Muddiman, David C.; Stang, Peter J. [Journal of the American Chemical Society, 2006, vol. 128, # 31, p. 10014 - 10015]
  • 9
  • [ 909389-74-8 ]
  • C70H56N2O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 66 percent / Et3N / Pd(PPh3)4; CuI / tetrahydrofuran / 16 h / 60 °C 2: 95 percent / aq. NaHCO3 / methanol / 2 h / 20 °C 3: 87 percent / NaH / dimethylformamide / 65 °C
Reference： [1]Yang, Hai-Bo; Das, Neeladri; Huang, Feihe; Hawkridge, Adam M.; Muddiman, David C.; Stang, Peter J. [Journal of the American Chemical Society, 2006, vol. 128, # 31, p. 10014 - 10015]
  • 10
  • [ 909389-74-8 ]
  • [ 1066-54-2 ]
  • [ 1020182-87-9 ]
YieldReaction ConditionsOperation in experiment
86% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In toluene at 110℃; for 0.5h; Microwave irradiation; Inert atmosphere;
80% With triethylamine In tetrahydrofuran at 20℃; for 16h;
Reference： [1]Swain, Jonathan A.; Iadevaia, Giulia; Hunter, Christopher A. [Journal of the American Chemical Society, 2018, vol. 140, # 36, p. 11526 - 11536]
[2]Ghosh, Koushik; Yang, Hai-Bo; Northrop, Brian H.; Lyndon, Matthew M.; Zheng, Yao-Rong; Muddiman, David C.; Stang, Peter J. [Journal of the American Chemical Society, 2008, vol. 130, # 15, p. 5320 - 5334]
  • 11
  • [ 626-41-5 ]
  • [ 75-36-5 ]
  • [ 909389-74-8 ]
YieldReaction ConditionsOperation in experiment
92% With pyridine; In dichloromethane; at 0 - 20℃;Inert atmosphere; To a stirred solution of compound XLVIII-1 (10.00 g, 39.69 mmol) in DCM (20 mL) and Py (50 mL) was added dropwise acetyl chloride (3.73 g, 47.51 mmol) at 0 °C under argon. After the addition, the solution was stirred overnight at room temperature. TLC monitored the reaction. After completion of the reaction, the mixture was poured into ice/water (100 mL), extract with DCM (50 mL x 3), the combined organic layers were dried over Na2S04, concentrated in vacuo. The residue was purified by column chromatography (PE:EA = 100: 1) to afford compound XLVIII-2 (11.67 g , yield: 92percent).
Reference： [1]Patent: WO2013/25733,2013,A1 .Location in patent: Paragraph 0574
  • 12
  • [ 909389-74-8 ]
  • [ 669767-20-8 ]
YieldReaction ConditionsOperation in experiment
81.25% With aluminum (III) chloride at 160℃; for 3h; Inert atmosphere; XLVIII A stirred solution of compound XLVIII-2 (8.00 g, 54.43 mmol) and A1C13 (7.26 g, 54.43 mmol) was heated to 160 °C for 3 hours under argon. The solution was quenched with water, extract with EtOAc (60 mL x 3), the combined organic layers were dried over Na2S04, concentrated in vacuo, and purified by chromatography (PE:EA = 50: 1) to afford compound XLVIII-3 (6.5 g, yield 81.25%). 1H NMR (400MHz, DMSO-d6) ^10.94 (s, 1 H), 7.32 (s, 1H), 7.07 (s, 1 H), 2.43 (s, 3 H).
Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2013/25733, 2013, A1 Location in patent: Paragraph 0575
  • 13
  • [ 909389-74-8 ]
  • [ 1423702-17-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 3 h / 160 °C / Inert atmosphere 2: sodium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2013/25733, 2013, A1
  • 14
  • [ 909389-74-8 ]
  • [ 1423702-20-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: aluminum (III) chloride / 3 h / 160 °C / Inert atmosphere 2: sodium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 3: pyridine; hydroxylamine hydrochloride / 6 h / 130 °C / Inert atmosphere
Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2013/25733, 2013, A1
  • 15
  • [ 909389-74-8 ]
  • [ 1423702-22-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: aluminum (III) chloride / 3 h / 160 °C / Inert atmosphere 2: sodium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 3: pyridine; hydroxylamine hydrochloride / 6 h / 130 °C / Inert atmosphere 4: N,N`-dimethylethylenediamine; sodium t-butanolate; copper(l) iodide / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2013/25733, 2013, A1
  • 16
  • [ 909389-74-8 ]
  • [ 1423702-25-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: aluminum (III) chloride / 3 h / 160 °C / Inert atmosphere 2: sodium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 3: pyridine; hydroxylamine hydrochloride / 6 h / 130 °C / Inert atmosphere 4: N,N`-dimethylethylenediamine; sodium t-butanolate; copper(l) iodide / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 5: boron tribromide / dichloromethane / 0 °C / Inert atmosphere
Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2013/25733, 2013, A1
  • 17
  • [ 909389-74-8 ]
  • [ 1423702-28-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: aluminum (III) chloride / 3 h / 160 °C / Inert atmosphere 2: sodium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 3: pyridine; hydroxylamine hydrochloride / 6 h / 130 °C / Inert atmosphere 4: N,N`-dimethylethylenediamine; sodium t-butanolate; copper(l) iodide / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 5: boron tribromide / dichloromethane / 0 °C / Inert atmosphere 6: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,2-dimethoxyethane / 80 °C / Inert atmosphere
Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2013/25733, 2013, A1
  • 18
  • [ 909389-74-8 ]
  • [ 1423702-31-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: aluminum (III) chloride / 3 h / 160 °C / Inert atmosphere 2: sodium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 3: pyridine; hydroxylamine hydrochloride / 6 h / 130 °C / Inert atmosphere 4: N,N`-dimethylethylenediamine; sodium t-butanolate; copper(l) iodide / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 5: boron tribromide / dichloromethane / 0 °C / Inert atmosphere 6: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,2-dimethoxyethane / 80 °C / Inert atmosphere 7: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2013/25733, 2013, A1
  • 19
  • [ 909389-74-8 ]
  • [ 1423702-34-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: aluminum (III) chloride / 3 h / 160 °C / Inert atmosphere 2: sodium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 3: pyridine; hydroxylamine hydrochloride / 6 h / 130 °C / Inert atmosphere 4: N,N`-dimethylethylenediamine; sodium t-butanolate; copper(l) iodide / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 5: boron tribromide / dichloromethane / 0 °C / Inert atmosphere 6: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,2-dimethoxyethane / 80 °C / Inert atmosphere 7: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere 8: palladium diacetate; caesium carbonate; Benzophenone imine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tetrahydrofuran / 80 °C / Inert atmosphere
Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2013/25733, 2013, A1
  • 20
  • [ 909389-74-8 ]
  • [ 1423690-66-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: aluminum (III) chloride / 3 h / 160 °C / Inert atmosphere 2.1: sodium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 3.1: pyridine; hydroxylamine hydrochloride / 6 h / 130 °C / Inert atmosphere 4.1: N,N`-dimethylethylenediamine; sodium t-butanolate; copper(l) iodide / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 5.1: boron tribromide / dichloromethane / 0 °C / Inert atmosphere 6.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,2-dimethoxyethane / 80 °C / Inert atmosphere 7.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere 8.1: palladium diacetate; caesium carbonate; Benzophenone imine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tetrahydrofuran / 80 °C / Inert atmosphere 9.1: pyridine / 1,2-dichloro-ethane / 1 h / 0 - 20 °C / Inert atmosphere 9.2: 80 °C / Inert atmosphere
Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2013/25733, 2013, A1
  • 21
  • [ 909389-74-8 ]
  • [ 1423684-81-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: aluminum (III) chloride / 3 h / 160 °C / Inert atmosphere 2.1: sodium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 3.1: pyridine; hydroxylamine hydrochloride / 6 h / 130 °C / Inert atmosphere 4.1: N,N`-dimethylethylenediamine; sodium t-butanolate; copper(l) iodide / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 5.1: boron tribromide / dichloromethane / 0 °C / Inert atmosphere 6.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,2-dimethoxyethane / 80 °C / Inert atmosphere 7.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere 8.1: palladium diacetate; caesium carbonate; Benzophenone imine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tetrahydrofuran / 80 °C / Inert atmosphere 9.1: pyridine / 1,2-dichloro-ethane / 1 h / 0 - 20 °C / Inert atmosphere 9.2: 80 °C / Inert atmosphere 10.1: lithium hydroxide; water / methanol / 60 °C / Inert atmosphere 10.2: Acidic conditions
Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2013/25733, 2013, A1
  • 22
  • [ 909389-74-8 ]
  • [ 1066-54-2 ]
  • C12H8O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 60℃;
Reference： [1]Zhou, Fengyan; Li, Shijun; Cook, Timothy R.; He, Zuoli; Stang, Peter J. [Organometallics, 2014, vol. 33, # 24, p. 7019 - 7022]
  • 23
  • [ 909389-74-8 ]
  • C34H30N2O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / tetrahydrofuran / 60 °C 2.1: potassium hydroxide / methanol / 24 h 3.1: dichloromethane / 0.5 h / Molecular sieve; Inert atmosphere 3.2: 3 h / 0 °C / Molecular sieve; Inert atmosphere 4.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / tetrahydrofuran / 24 h / 60 °C / Schlenk technique; Inert atmosphere
Reference： [1]Zhou, Fengyan; Li, Shijun; Cook, Timothy R.; He, Zuoli; Stang, Peter J. [Organometallics, 2014, vol. 33, # 24, p. 7019 - 7022]
  • 24
  • [ 909389-74-8 ]
  • C26H22N2O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / tetrahydrofuran / 60 °C 2.1: potassium hydroxide / methanol / 24 h 3.1: dichloromethane / 0.5 h / Molecular sieve; Inert atmosphere 3.2: 3 h / 0 °C / Molecular sieve; Inert atmosphere 4.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / tetrahydrofuran / 16 h / 60 °C / Schlenk technique; Inert atmosphere 5.1: sodium methylate / methanol / 12 h / 20 °C
Reference： [1]Zhou, Fengyan; Li, Shijun; Cook, Timothy R.; He, Zuoli; Stang, Peter J. [Organometallics, 2014, vol. 33, # 24, p. 7019 - 7022]
  • 25
  • [ 909389-74-8 ]
  • C26H22N2O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / tetrahydrofuran / 60 °C 2.1: potassium hydroxide / methanol / 24 h 3.1: dichloromethane / 0.5 h / Molecular sieve; Inert atmosphere 3.2: 3 h / 0 °C / Molecular sieve; Inert atmosphere 4.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / tetrahydrofuran / 24 h / 60 °C / Schlenk technique; Inert atmosphere 5.1: sodium methylate / methanol / 12 h / 20 °C
Reference： [1]Zhou, Fengyan; Li, Shijun; Cook, Timothy R.; He, Zuoli; Stang, Peter J. [Organometallics, 2014, vol. 33, # 24, p. 7019 - 7022]
  • 26
  • [ 909389-74-8 ]
  • C26H22N2O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / tetrahydrofuran / 60 °C 2.1: potassium hydroxide / methanol / 24 h 3.1: dichloromethane / 0.5 h / Molecular sieve; Inert atmosphere 3.2: 3 h / 0 °C / Molecular sieve; Inert atmosphere 4.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / tetrahydrofuran / 24 h / 60 °C / Schlenk technique; Inert atmosphere 5.1: sodium methylate / methanol / 12 h / 20 °C
Reference： [1]Zhou, Fengyan; Li, Shijun; Cook, Timothy R.; He, Zuoli; Stang, Peter J. [Organometallics, 2014, vol. 33, # 24, p. 7019 - 7022]
  • 27
  • [ 909389-74-8 ]
  • [ 918826-08-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / tetrahydrofuran / 60 °C 2: potassium hydroxide / methanol / 24 h
Reference： [1]Zhou, Fengyan; Li, Shijun; Cook, Timothy R.; He, Zuoli; Stang, Peter J. [Organometallics, 2014, vol. 33, # 24, p. 7019 - 7022]
  • 28
  • [ 909389-74-8 ]
  • C24H24O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / tetrahydrofuran / 60 °C 2.1: potassium hydroxide / methanol / 24 h 3.1: dichloromethane / 0.5 h / Molecular sieve; Inert atmosphere 3.2: 3 h / 0 °C / Molecular sieve; Inert atmosphere
Reference： [1]Zhou, Fengyan; Li, Shijun; Cook, Timothy R.; He, Zuoli; Stang, Peter J. [Organometallics, 2014, vol. 33, # 24, p. 7019 - 7022]
  • 29
  • [ 909389-74-8 ]
  • C24H24O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / tetrahydrofuran / 60 °C 2.1: potassium hydroxide / methanol / 24 h 3.1: dichloromethane / 0.5 h / Molecular sieve; Inert atmosphere 3.2: 3 h / 0 °C / Molecular sieve; Inert atmosphere
Reference： [1]Zhou, Fengyan; Li, Shijun; Cook, Timothy R.; He, Zuoli; Stang, Peter J. [Organometallics, 2014, vol. 33, # 24, p. 7019 - 7022]
  • 30
  • [ 909389-74-8 ]
  • C24H24O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / tetrahydrofuran / 60 °C 2.1: potassium hydroxide / methanol / 24 h 3.1: dichloromethane / 0.5 h / Molecular sieve; Inert atmosphere 3.2: 3 h / 0 °C / Molecular sieve; Inert atmosphere
Reference： [1]Zhou, Fengyan; Li, Shijun; Cook, Timothy R.; He, Zuoli; Stang, Peter J. [Organometallics, 2014, vol. 33, # 24, p. 7019 - 7022]
  • 31
  • [ 909389-74-8 ]
  • C36H40O18 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / tetrahydrofuran / 60 °C 2.1: potassium hydroxide / methanol / 24 h 3.1: dichloromethane / 0.5 h / Molecular sieve; Inert atmosphere 3.2: 3 h / 0 °C / Molecular sieve; Inert atmosphere
Reference： [1]Zhou, Fengyan; Li, Shijun; Cook, Timothy R.; He, Zuoli; Stang, Peter J. [Organometallics, 2014, vol. 33, # 24, p. 7019 - 7022]
  • 32
  • [ 909389-74-8 ]
  • C34H30N2O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / tetrahydrofuran / 60 °C 2.1: potassium hydroxide / methanol / 24 h 3.1: dichloromethane / 0.5 h / Molecular sieve; Inert atmosphere 3.2: 3 h / 0 °C / Molecular sieve; Inert atmosphere 4.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / tetrahydrofuran / 16 h / 60 °C / Schlenk technique; Inert atmosphere
Reference： [1]Zhou, Fengyan; Li, Shijun; Cook, Timothy R.; He, Zuoli; Stang, Peter J. [Organometallics, 2014, vol. 33, # 24, p. 7019 - 7022]
  • 33
  • [ 909389-74-8 ]
  • C34H30N2O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / tetrahydrofuran / 60 °C 2.1: potassium hydroxide / methanol / 24 h 3.1: dichloromethane / 0.5 h / Molecular sieve; Inert atmosphere 3.2: 3 h / 0 °C / Molecular sieve; Inert atmosphere 4.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / tetrahydrofuran / 24 h / 60 °C / Schlenk technique; Inert atmosphere
Reference： [1]Zhou, Fengyan; Li, Shijun; Cook, Timothy R.; He, Zuoli; Stang, Peter J. [Organometallics, 2014, vol. 33, # 24, p. 7019 - 7022]
  • 34
  • [ 3240-34-4 ]
  • [ 108-36-1 ]
  • [ 36914-79-1 ]
  • [ 28165-72-2 ]
  • [ 909389-74-8 ]
YieldReaction ConditionsOperation in experiment
Stage #1: [bis(acetoxy)iodo]benzene With palladium diacetate; acetic anhydride; acetic acid at 20℃; for 0.00416667h; Stage #2: 1,3-dibromobenzene at 100℃; for 14h; Sealed tube; Overall yield = 86 %Chromat.;
Reference： [1]Valderas, Carolina; Naksomboon, Kananat; Fernández-Ibáñez, M. Ángeles [ChemCatChem, 2016, vol. 8, # 20, p. 3213 - 3217]
  • 35
  • [ 3240-34-4 ]
  • [ 108-36-1 ]
  • [ 36914-79-1 ]
  • [ 909389-74-8 ]
YieldReaction ConditionsOperation in experiment
Stage #1: [bis(acetoxy)iodo]benzene With 6-fluoropyridine-2-carboxylic acid; palladium diacetate; acetic anhydride; acetic acid at 20℃; for 0.00416667h; Stage #2: 1,3-dibromobenzene at 100℃; for 14h; Sealed tube; Overall yield = 86 %Chromat.;
Reference： [1]Valderas, Carolina; Naksomboon, Kananat; Fernández-Ibáñez, M. Ángeles [ChemCatChem, 2016, vol. 8, # 20, p. 3213 - 3217]
  • 36
  • [ 108-22-5 ]
  • [ 626-41-5 ]
  • [ 909389-74-8 ]
YieldReaction ConditionsOperation in experiment
99% With iron(III) trifluoromethanesulfonate at 20℃; for 5h; Schlenk technique;
Reference： [1]Zhu, Xiaotao; Qian, Bo; Wei, Rongbiao; Huang, Jian-Dong; Bao, Hongli [Green Chemistry, 2018, vol. 20, # 7, p. 1444 - 1447]
  • 37
  • [ 909389-74-8 ]
  • [ 1066-54-2 ]
  • [ 918826-08-1 ]
YieldReaction ConditionsOperation in experiment
98% Stage #1: acetic acid 3,5-dibromo-phenyl ester; trimethylsilylacetylene With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 60℃; for 12h; Inert atmosphere; Stage #2: With potassium hydroxide In tetrahydrofuran; methanol; water at 20℃; for 12h;
Stage #1: acetic acid 3,5-dibromo-phenyl ester; trimethylsilylacetylene With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In tetrahydrofuran at 40℃; for 24h; Stage #2: With sodium hydroxide In tetrahydrofuran; methanol; water for 5h; Inert atmosphere;
Reference： [1]Zhang, Xu; Moku, Balakrishna; Leng, Jing; Rakesh; Qin, Hua-Li [European Journal of Organic Chemistry, 2019, vol. 2019, # 8, p. 1763 - 1769]
[2]Chen, Yu; Tan, Ying; Tan, Chunyan; Lu, Yunpeng; Chen, Yuzong; Jiang, Yuyang [Organic and Biomolecular Chemistry, 2019, vol. 17, # 10, p. 2635 - 2639]
  • 38
  • [ 626-41-5 ]
  • [ 909389-74-8 ]
YieldReaction ConditionsOperation in experiment
94% With acetic anhydride at 70℃; for 2h;
Reference： [1]Zhang, Xu; Moku, Balakrishna; Leng, Jing; Rakesh; Qin, Hua-Li [European Journal of Organic Chemistry, 2019, vol. 2019, # 8, p. 1763 - 1769]
  • 39
  • [ 909389-74-8 ]
  • C13H11O4S(1-)*K(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine / tetrahydrofuran / 24 h / 40 °C 1.2: 5 h / Inert atmosphere 2.1: potassium hydroxide / ethanol / 24 h / 20 °C
Reference： [1]Chen, Yu; Tan, Ying; Tan, Chunyan; Lu, Yunpeng; Chen, Yuzong; Jiang, Yuyang [Organic and Biomolecular Chemistry, 2019, vol. 17, # 10, p. 2635 - 2639]

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Technical Information

• Acid-Catalyzed α -Halogenation of Ketones • Addition of a Hydrogen Halide to an Internal Alkyne • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • Alcohols React with PX3 • Alkyl Halide Occurrence • Alkylation of an Alkynyl Anion • An Alkane are Prepared from an Haloalkane • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Conversion of Amino with Nitro • Convert Haloalkanes into Alcohols by SN2 • Deprotonation of Methylbenzene • Directing Electron-Donating Effects of Alkyl • Electrophilic Chloromethylation of Polystyrene • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation of Benzene with Haloalkanes • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Alkenes • Halogenation of Benzene • Hiyama Cross-Coupling Reaction • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Methylation of Ammonia • Methylation of Ammonia • Nitration of Benzene • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Preparation of Alkylbenzene • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Dihalides • Reductive Removal of a Diazonium Group • Reverse Sulfonation——Hydrolysis • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Sulfonation of Benzene • Suzuki Coupling • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Nitro Group Conver to the Amino Function • Vilsmeier-Haack Reaction • Williamson Ether Syntheses
Historical Records
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