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[ CAS No. 4254-67-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 4254-67-5
Chemical Structure| 4254-67-5
Chemical Structure| 4254-67-5
Structure of 4254-67-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 4254-67-5 ]

CAS No. :4254-67-5 MDL No. :MFCD07367994
Formula : C15H13BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :IAPCKPXQFYWNDN-UHFFFAOYSA-N
M.W : 305.17 Pubchem ID :10542593
Synonyms :

Calculated chemistry of [ 4254-67-5 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.13
Num. rotatable bonds : 5
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 75.49
TPSA : 26.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.13 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.73
Log Po/w (XLOGP3) : 4.27
Log Po/w (WLOGP) : 3.69
Log Po/w (MLOGP) : 3.23
Log Po/w (SILICOS-IT) : 4.31
Consensus Log Po/w : 3.65

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.59
Solubility : 0.00793 mg/ml ; 0.000026 mol/l
Class : Moderately soluble
Log S (Ali) : -4.53
Solubility : 0.00891 mg/ml ; 0.0000292 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.25
Solubility : 0.000171 mg/ml ; 0.00000056 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.03

Safety of [ 4254-67-5 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P264-P270-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501 UN#:3261
Hazard Statements:H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 4254-67-5 ]

* 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 [ 4254-67-5 ]
  • Downstream synthetic route of [ 4254-67-5 ]

[ 4254-67-5 ] Synthesis Path-Upstream   1~12

  • 1
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YieldReaction ConditionsOperation in experiment
83% With phenyltrimethylammonium tribromide In tetrahydrofuran at 0℃; To a clear solution of 1-(4-(benzyloxy)phenyl)-2-bromoethanone To a clear solution of l-(4-(benzyloxy)phenyl)ethanone (16.1 g, 71.2 mmol) in tetrahydrofuran (200 mL) was added dropwise a solution of phenyltrimethylammonium tribromide (29.4 g, 78 mmol) in tetrahydrofuran (150 mL) at 0°C. After completion of the reaction, the insoluble material was filtered off and washed with tetrahydrofuran. The filtrate was evaporated and the yellow oil was crystallized from isopropanol. (Yield: 17.99 g, 83percent).
78% With pyridinium hydrobromide perbromide In methanol; dichloromethane at 20℃; for 3 h; Inert atmosphere Pyridinium tribromide (9.5 g, 29.8 mmol) was added to a solution of 4-benzyloxy- acetophenone (6.1 g, 27.1 mmol) in CH2CI2 (275 mL) and MeOH (100 mL) at rt. After 3 h at rt the mixture was concentrated and the residue partitioned between water and EtOAc.The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic phases were washed with brine, dried over Na2SO4 and filtered. Concentration of the filtrate and crystallization of the residue from hexane/EtOAc gave the sub-title compound (6.4 g, 21.1 mmol, 78 percent).
65% With tetra-N-butylammonium tribromide In tetrahydrofuran; methanol for 49 h; A solution of tetrabutylammonium tribromide (53g, 110mm) in tetrahydrofuran (70mL) was added dropwise to a suspension of 4-benzyloxyacetophenone (27.38g, 121mmol) in tetrahydrofuran (100mL) and methanol (25mL) over 1 hour. The reaction mixture was then left to stir for 48 hours and the solvent removed in vacuo. The residue was dissolved in ethyl acetate (250mL) and washed with water (250mL). The phases were separated and the aqueous layer was extracted with ethyl acetate (2 x 100mL). The organic layers were combined, dried over magnesium sulfate and concentrated in vacuo to give a solid. The crude residue was recrystallised using cyclohexane to afford the desired product, 22g (65percent). 1H NMR (400 MHz, CDCI3) 6 4.38 (2H, s), 5.10 (2H, s), 7.00 (2H, m), 7.21-7. 40 (5H, m), 7.9 (2H, m). LRMS: m/z APCI+ 305 [MH+].
34.6% With bromine; sodium sulfate In chloroform; water (2)
4'-Benzyloxy-2-bromoacetophenone
4'-Benzyloxyacetophenone (55.0 g) was stirred in chloroform (500 ml), and bromine (13.0 ml) was added dropwise thereto at room temperature in 30 minutes.
The mixture was stirred for 10 minutes, and the reaction mixture was washed with aqueous solution of sodium sulfate, water and saturated saline in turn, dried with anhydrous sodium sulfate and then concentrated.
The precipitating crystals were recrystallized from acetone-diisopropyl ether to give 4'-benzyloxy-2-bromoacetophenone (25.7 g, 34.6percent).
m.p. 81°-82° C.
NMR(CDCl3)δ: 4.4(2H,s), 5.1(2H,s),
16 g With bromine In methanol at 0 - 20℃; for 4.5 h; Step 2: Synthesis of l-(4-(benzyloxy)phenyl)-2-bromoethan-l-one: [0247] To the stirred solution of l-(4-(benzyloxy)phenyl)ethan-l-one (step 1, 25 g, 110.5 mmol) in 200 ml of MeOH at 0°C was added Bromine (4.5 ml, 28.5 mmol) (dropwise addition), stirred for about 30 minutes and stirred for about 4 hours at room temperature. After completion of the reaction (monitored by TLC), the reaction mixture was concentrated and the crude product was dissolved in n-hexane and stirred for about 30 minutes. The obtained solid was filtered and washed with n-hexane then dried and proceeded for next step (wt: 16.0g). M.Wt: 305.

Reference: [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 7, p. 1376 - 1383
[2] Journal of the Indian Chemical Society, 2002, vol. 79, # 5, p. 469 - 471
[3] Patent: WO2015/16728, 2015, A1, . Location in patent: Page/Page column 36; 37; 62
[4] Australian Journal of Chemistry, 2008, vol. 61, # 12, p. 991 - 999
[5] Marine Drugs, 2012, vol. 10, # 6, p. 1412 - 1421
[6] Patent: WO2017/153737, 2017, A1, . Location in patent: Page/Page column 47
[7] Journal of the American Chemical Society, 2010, vol. 132, # 40, p. 14002 - 14003
[8] Patent: WO2005/92841, 2005, A1, . Location in patent: Page/Page column 74
[9] RSC Advances, 2014, vol. 4, # 99, p. 56489 - 56501
[10] Chemical and Pharmaceutical Bulletin, 1984, vol. 32, # 8, p. 3066 - 3074
[11] Patent: US5106732, 1992, A,
[12] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1979, vol. 17, p. 305 - 306
[13] Chemistry of Natural Compounds, 1975, vol. 11, p. 71 - 75[14] Khimiya Prirodnykh Soedinenii, 1975, vol. 11, # 1, p. 73 - 77
[15] Analytical chemistry, 1980, vol. 52, # 12, p. 1815 - 1820
[16] Bioscience, Biotechnology, and Biochemistry, 1992, vol. 56, # 12, p. 1943 - 1948
[17] Journal of Labelled Compounds and Radiopharmaceuticals, 1997, vol. 39, # 12, p. 973 - 985
[18] Synthetic Communications, 1999, vol. 29, # 12, p. 2069 - 2078
[19] Patent: US6080754, 2000, A,
[20] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 13, p. 3434 - 3438
[21] Synlett, 2012, vol. 23, # 12, p. 1797 - 1800
[22] Heterocycles, 2012, vol. 85, # 8, p. 1941 - 1948
[23] Journal of Organic Chemistry, 2013, vol. 78, # 12, p. 6276 - 6280
[24] Archiv der Pharmazie, 2014, vol. 347, # 2, p. 89 - 95
[25] Patent: WO2014/105926, 2014, A1, . Location in patent: Paragraph 0247
[26] Journal of Agricultural and Food Chemistry, 2017, vol. 65, # 19, p. 3965 - 3974
[27] Chemical Communications (Cambridge, United Kingdom), 2018, vol. 54, # 86, p. 12182 - 12185
[28] Chemistry - A European Journal, 2018, vol. 24, # 72, p. 19156 - 19161
  • 2
  • [ 2491-38-5 ]
  • [ 100-39-0 ]
  • [ 4254-67-5 ]
YieldReaction ConditionsOperation in experiment
43% With silver carbonate In tetrahydrofuran at 0 - 20℃; for 16 h; Step 1: Preparation of l-(4-(benzyloxy)phenyl)-2-bromoethanone [00170] To a solution of 2-bromo- 1 -(4-hydroxyphenyl)ethanone (2 g, 9.3 mmol) in tetrahydrofuran (70 mL) was added silver carbonate (5.128 g, 18.6 mmol) and the reaction mixture was cooled to 0 °C. Benzyl bromide (1.32 m L, 11.16 mmol) was added drop wise and the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was filtered through celite, the filtrate was diluted with ethyl acetate (200 mL) and washed with water (60 mL x 2). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The crude was purified by column chromatography using 6percent ethyl acetate in hexane to afford title l-(4-(benzyloxy)phenyl)-2-bromoethanone (1.22 g, 43percent yield) as a white solid. Calculated M+H: 306.17; Found M+H: 306.
Reference: [1] Patent: WO2016/49165, 2016, A1, . Location in patent: Paragraph 00170
  • 3
  • [ 123-91-1 ]
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Reference: [1] Patent: US4933344, 1990, A,
  • 4
  • [ 84284-70-8 ]
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Reference: [1] Green Chemistry, 2017, vol. 19, # 8, p. 1983 - 1989
  • 5
  • [ 99-93-4 ]
  • [ 4254-67-5 ]
Reference: [1] Journal of the Indian Chemical Society, 2002, vol. 79, # 5, p. 469 - 471
[2] Chemistry of Natural Compounds, 1975, vol. 11, p. 71 - 75[3] Khimiya Prirodnykh Soedinenii, 1975, vol. 11, # 1, p. 73 - 77
[4] Marine Drugs, 2012, vol. 10, # 6, p. 1412 - 1421
[5] Patent: WO2015/16728, 2015, A1,
[6] Journal of Organic Chemistry, 2015, vol. 80, # 19, p. 9713 - 9721
[7] Patent: WO2017/153737, 2017, A1,
[8] Journal of Agricultural and Food Chemistry, 2017, vol. 65, # 19, p. 3965 - 3974
[9] Advanced Synthesis and Catalysis, 2018, vol. 360, # 7, p. 1376 - 1383
  • 6
  • [ 100-39-0 ]
  • [ 4254-67-5 ]
Reference: [1] Marine Drugs, 2012, vol. 10, # 6, p. 1412 - 1421
[2] Patent: WO2015/16728, 2015, A1,
[3] Patent: WO2017/153737, 2017, A1,
[4] Journal of Agricultural and Food Chemistry, 2017, vol. 65, # 19, p. 3965 - 3974
[5] Advanced Synthesis and Catalysis, 2018, vol. 360, # 7, p. 1376 - 1383
  • 7
  • [ 54696-05-8 ]
  • [ 7789-45-9 ]
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Reference: [1] Patent: US6037362, 2000, A,
[2] Patent: US6051577, 2000, A,
  • 8
  • [ 54696-05-8 ]
  • [ 4254-67-5 ]
Reference: [1] ChemMedChem, 2010, vol. 5, # 9, p. 1541 - 1555
  • 9
  • [ 2491-38-5 ]
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Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 19, p. 9713 - 9721
[2] Journal of Organic Chemistry, 2015, vol. 80, # 19, p. 9713 - 9721
  • 10
  • [ 15028-44-1 ]
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Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 19, p. 9713 - 9721
  • 11
  • [ 92850-54-9 ]
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Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 19, p. 9713 - 9721
  • 12
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Reference: [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 7, p. 1376 - 1383
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