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Chemical Structure| 6340-79-0
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Product Details of [ 6340-79-0 ]

CAS No. :6340-79-0 MDL No. :MFCD00016563
Formula : C10H9BrO3 Boiling Point : -
Linear Structure Formula :- InChI Key :ZODFRCZNTXLDDW-UHFFFAOYSA-N
M.W : 257.08 Pubchem ID :80646
Synonyms :

Calculated chemistry of [ 6340-79-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 55.72
TPSA : 54.37 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) : -6.38 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.56
Log Po/w (XLOGP3) : 2.1
Log Po/w (WLOGP) : 2.5
Log Po/w (MLOGP) : 2.02
Log Po/w (SILICOS-IT) : 2.47
Consensus Log Po/w : 2.13

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.81
Solubility : 0.398 mg/ml ; 0.00155 mol/l
Class : Soluble
Log S (Ali) : -2.87
Solubility : 0.345 mg/ml ; 0.00134 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.38
Solubility : 0.106 mg/ml ; 0.000412 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.4

Safety of [ 6340-79-0 ]

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 [ 6340-79-0 ]

* 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 [ 6340-79-0 ]
  • Downstream synthetic route of [ 6340-79-0 ]

[ 6340-79-0 ] Synthesis Path-Upstream   1~31

  • 1
  • [ 6340-79-0 ]
  • [ 35656-89-4 ]
YieldReaction ConditionsOperation in experiment
91.4% With hydrogenchloride; mercury(II) chloride; zinc In water; toluene at 100℃; for 24 h; Zinc (13.0 g, 200 mmol) and mercury chloride (1 .00 g, 480 mmol) were stirred with water (10 mL) and concentrated HCI (0.6 mL) for five minutes. The liquid was decanted off and toluene (20 mL), concentrated HCI (20 mL) and water (8 mL) were added consecutively. 4-(4-bromophenyl)-4-oxobutanoic acid 4 (2.55 g, 10.5 mmol) was added and heated under reflux at 100°C for 24 h adding HCI (1 mL) every 6 h. The reaction was allowed to cool to room temperature, filtered and the solvent removed from the organic layer to give a clear liquid which gave white crystals upon cooling. These were purified with silica gel chromatography (ethyl acetate : hexane, 1 :3) to yield 4-(4- bromophenyl)butanoic acid 5 (2.33 g, 9.63 mmol, 91 .4percent). MS (ESI-QUADRUPOLE) m/z: calc. for CioHn BrO2: 241 .99, 243.99; Found: 244.0 (10), 243.0 (98), 242.0 (1 1 ), 241 .0 (100) (negative ions). HPLC: tr = 27.7 min. 1 H NMR (300 MHz, CDCI3) (δ/ppm) 7.40 (2H, d, J = 8.4 Hz, ArH), 7.06 (2H, d, J = 8.4 Hz, ArH), 2.63 (2H, t, J = 7.8 Hz, CH2), 2.36 (2H, t, J = 7.2 Hz, CH2), 1 .97, (2H, dt, J = 7.2,7.8 Hz, CH2), OH not observed.
89% With potassium hydroxide; hydrazine In diethylene glycol at 120 - 200℃; for 5 h; Dean-Stark 3-(4-Bromobenzoyl)propionic acid (5.142 g, 20 mmols) and potassium hydroxide (2.693 g, 48 mmols) were placed in a round-bottomed flask fitted with a condenser and a Dean-Stark apparatus and suspended in diethylene glycol (50 mL) at room temperature. Hydrazine (1.508 mL, 48 mmol) was slowly added to the reaction which was subsequently heated to 120-130 °C for 2 h upon which the reaction became homogenous. After 2 h, the temperature was increased to 180-200 °C and stirring was continued for 3 h in order to distill off the remaining hydrazine and water byproduct via the Dean-Stark trap. Then, the reaction was allowed to cool to room temperature, diluted with water (20 mL), and carefully poured into 2.5 M hydrochloric acid (40 mL). The precipitate that formed was collected by filtration and residual diethylene glycol was removed by dissolving the precipitate in a saturated, aqueous solution of potassium carbonate (40 mL). This solution was diluted with water (40 mL) and carefully poured into 2.5 M hydrochloric acid (40 mL). A white precipitate formed which was collected by filtration, washed with water (2 x 30 mL), and dried under vacuum to yield the desired product as a white solid (886 mg, 89percent). XH NMR (500 MHz, DMSO-i/6): δ 12.07 (br, 1H), 7.46 (m, 2H), 7.16 (m, 2H), 2.56 (m, 2H), 2.20 (t, J= 7.4 Hz, 2H), 1.77 (quin, J= 7.5 Hz, 2H). C NMR (125 MHz, DMSO-i): δ 174.15, 140.99, 131.11, 130.59, 1 18.82, 33.68, 32.94, 26.05. ESI-HRMS: calcd. for CioHuBr02: [M-H]" = m/z 240.9870, found: [M-H]" = m/z 240.9882.
75% With potassium hydroxide; hydrazine In diethylene glycol at 195℃; for 3 h; Step B: A mixture of the product from Step A (57 g, 223 mmol), potassium hydroxide (43 g, 760 mmol) and hydrazine hydrate (26 ml, 830 mmol) in diethylene glycol (2865 ml) was stirred at 195° C. for 3 hours. After cooling below 40° C., the mixture was diluted with water (300 ml), poured into 3 M NaOH and washed with dichloromethane three times. Brine was added to break up the emulsion. The aqueous layer was acidified to pH 1 with 6 M HCl and extracted with methyl tert-butyl ether three times. The combined organic extracts were dried over magnesium sulfate to give 4-(4-bromophenyl)butyric acid (41 g, 75percent): 1H NMR (300 MHz, DMSO-d6) δ 7.44-7.48 (m, 2H), 7.14-7.20 (m, 2H), 2.56 (t, J=7.2 Hz, 2H), 2.20 (t, J=7.5 Hz, 2H), 1.72-1.82 (m, 2H).
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[3] Patent: WO2016/119017, 2016, A1, . Location in patent: Page/Page column 22; 31
[4] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 22, p. 7434 - 7445
[5] Patent: WO2015/134973, 2015, A1, . Location in patent: Page/Page column 123; 124
[6] Canadian Journal of Chemistry, 2006, vol. 84, # 10, p. 1487 - 1503
[7] Patent: US2006/52378, 2006, A1, . Location in patent: Page/Page column 113
[8] Tetrahedron, 1985, vol. 41, # 8, p. 1509 - 1516
[9] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 13, p. 4345 - 4359
[10] Bulletin de la Societe Chimique de France, 1971, p. 2092 - 2094
[11] Bulletin of the Chemical Society of Japan, 1979, vol. 52, p. 3033 - 3042
[12] Journal of Organic Chemistry, 1964, vol. 29, # 8, p. 2109 - 2116
[13] Chemical Communications, 2016, vol. 52, # 56, p. 8757 - 8760
[14] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 4, p. 395 - 400
[15] Advanced Synthesis and Catalysis, 2018, vol. 360, # 15, p. 2894 - 2899
  • 2
  • [ 6340-79-0 ]
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  • [ 1821-12-1 ]
Reference: [1] Journal of the American Chemical Society, 1938, vol. 60, p. 170,174
  • 3
  • [ 108-30-5 ]
  • [ 108-86-1 ]
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YieldReaction ConditionsOperation in experiment
93.4%
Stage #1: at 0 - 20℃; for 100 h; Inert atmosphere
Stage #2: at 0℃; for 1 h; Inert atmosphere
Succinic anhydride 3 (5.0 g, 50 mmol) and bromobenzene 2 (48 g, 300 mmol) were cooled to 0°C. Aluminium chloride (13.3 g, 100 mmol) was added and the mixture was stirred for 4 h at 0°C under nitrogen atmosphere. The reaction was allowed to warm to room temperature and stirred for 96 h under nitrogen atmosphere. The reaction was cooled to 0°C and concentrated HCI (125 mL) was added and reaction stirred under nitrogen for a further 1 h. The reaction was filtered and washed with water (1 L) to obtain a pale yellow solid which was recrystallised from toluene to yield 4-(4- bromophenyl)-4-oxobutanoic acid 4 (12 g, 46.68 mmol, 93.4percent). MS (ESI-QUADRUPOLE) m/z: calc. for Ci0H9BrO3: 255.97, 257.97; Found : 258.0 (1 1 ), 257.0 (98), 256.0 (12), 255.0 (100), 213.0 (18), 21 1 .0 (17) (negative ions). HPLC: tr = 24.4 min 1 H NMR (500 MHz, ofe-DMSO) δ: 2.59 (2 H, t, J = 6.5 Hz, CH2), 3.21 (2 H, t, J = 6.5 Hz, CH2), 7.88 (2 H, d, J = 8.8 Hz, ArH), 7.96 (2 H, d, J = 8.8 Hz, ArH), 12.19 (1 H, br s, OH).
82% With hydrogenchloride; aluminum (III) chloride In dichloromethane at 0 - 20℃; for 4 h; Step 1: Synthesis of 4-(4-bromophenyl)-4-oxobutanoic acid (37A, R═Br) (0320) Anhydrous aluminum trichloride (29.1 g, 218 mmol) was suspended in dichloromethane (120 mL) and cooled to 0° C. Bromobenzene (35.1 g, 224 mmol) was added carefully. When the addition was complete, succinic anhydride (10.0 g, 100 mmol) was added in ten portions carefully. Then the mixture was warmed to room temperature and stirred for 4 h. TLC showed the reaction was complete, 6N HCl (50 mL) was added dropwise. The solid was filtered, washed with distilled water (10 mL×2) and dried in vacuo to afford 37A, R═Br as a white solid (22 g, yield 82percent).
60% With aluminum (III) chloride In dichloromethane at 20℃; Inert atmosphere General procedure: AlCl3 (1.0 g, 7.5 mmol)was added portion-wise to a solution of succinic anhydride (0.5 g, 5 mmol) and anaromatic compound (6 mmol) in CH2Cl2 (5 mL) at room temperature. The mixture wasstirred at room temperature for overnight, and the mixture was poured into 1N HClsolution (10 mL), extracted with ethyl acetate (15 mL x 3). The organic layer was driedover MgSO4. The solvent was removed under reduced pressure, and the crude productwas purified by recrystallized from ethyl acetate and hexane.
55% With aluminum (III) chloride In cyclohexane at 80℃; for 2 h; Step A: Bromobenzene (150 ml, 1.42 mol) was added in one portion to a mixture of aluminum chloride (109 g, 0.82 mmol) and succinic anhydride (41 g, 0.41 mol) in cyclohexane (200 ml) at 80° C. and the resulting mixture was stirred at 80° C. for 2 hours. After cooling below 40° C., the mixture was slowly poured into 6 M HCl (200 ml) and ice, and yellow solids precipitated. Methyl tert-butyl ether was added to dissolve the solids and the phases were separated. The organic layer was washed with water three times and was extracted into 2 M NaOH. The aqueous extracts were acidified to pH 1 with 6 M HCl, extracted with methyl tert-butyl ether, dried with magnesium sulfate and concentrated to a residue. This material was recrystallized by dissolving the residue in 50:35:15 cyclohexane/toluene/isopropanol at 70° C. followed by cooling to room temperature, filtering and azeotroping the resulting solids with hexanes to give the desired compound (57 g, 55percent) as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 7.89-7.93 (m, 2H), 7.72-7.77 (m, 2H), 3.23 (t, J=6.0 Hz, 2H), 2.58 (t, J=6.6 Hz, 2H).

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[2] Journal of Organic Chemistry, 2001, vol. 66, # 22, p. 7283 - 7286
[3] Organic Syntheses, 2002, vol. 79, p. 204 - 204
[4] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 13, p. 4345 - 4359
[5] Organic Process Research and Development, 2014, vol. 18, # 1, p. 215 - 227
[6] Patent: WO2016/119017, 2016, A1, . Location in patent: Page/Page column 22; 30-31
[7] Canadian Journal of Chemistry, 2006, vol. 84, # 10, p. 1487 - 1503
[8] Journal of the American Chemical Society, 2001, vol. 123, # 17, p. 3940 - 3952
[9] Journal of Materials Chemistry, 2001, vol. 11, # 12, p. 3068 - 3077
[10] Patent: US9138427, 2015, B2, . Location in patent: Page/Page column 268
[11] Organic Letters, 2016, vol. 18, # 3, p. 504 - 507
[12] Synthetic Communications, 2003, vol. 33, # 18, p. 3109 - 3113
[13] Journal of Medicinal Chemistry, 2008, vol. 51, # 24, p. 8088 - 8095
[14] Journal of Chemical Research - Part S, 2003, # 10, p. 650 - 651
[15] Egyptian Journal of Chemistry, 1998, vol. 41, # 1-6, p. 339 - 349
[16] Asian Journal of Chemistry, 2012, vol. 24, # 8, p. 3553 - 3556
[17] Chemistry - A European Journal, 2017, vol. 23, # 40, p. 9501 - 9504
[18] Organic Letters, 2014, vol. 16, # 6, p. 1740 - 1743
[19] Acta Poloniae Pharmaceutica - Drug Research, 2009, vol. 66, # 5, p. 513 - 521
[20] Chemistry Letters, 2015, vol. 44, # 11, p. 1503 - 1505
[21] Patent: US2006/52378, 2006, A1, . Location in patent: Page/Page column 112-113
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[29] Bulletin de la Societe Chimique de France, 1971, p. 2092 - 2094
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[31] Journal of Organic Chemistry, 1964, vol. 29, # 8, p. 2109 - 2116
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[34] Journal of Solution Chemistry, 2007, vol. 36, # 3, p. 345 - 356
[35] Patent: WO2007/96647, 2007, A2, . Location in patent: Page/Page column 101
[36] Patent: US2004/9998, 2004, A1, . Location in patent: Page/Page column 35
[37] Acta Poloniae Pharmaceutica - Drug Research, 2008, vol. 65, # 2, p. 223 - 228
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  • 5
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  • [ 60112-48-3 ]
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Reference: [1] Organic Letters, 2003, vol. 5, # 7, p. 1031 - 1034
  • 6
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  • 7
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[2] Journal of Organic Chemistry, 1948, vol. 13, p. 284,292
[3] Journal of Organic Chemistry, 1948, vol. 13, p. 284,292
[4] Journal of Organic Chemistry, 1948, vol. 13, p. 284,292
  • 8
  • [ 108-30-5 ]
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Reference: [1] Journal of Organic Chemistry, 1992, vol. 57, # 1, p. 366 - 370
  • 9
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  • 10
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[2] Patent: EP885869, 1998, A1,
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[2] Journal of Organic Chemistry, 1984, vol. 49, # 17, p. 3170 - 3173
  • 12
  • [ 2403-27-2 ]
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[2] Journal of the American Chemical Society, 1917, vol. 39, p. 2414
  • 13
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Reference: [1] Journal of the American Chemical Society, 1917, vol. 39, p. 2414
[2] Journal of the American Chemical Society, 1917, vol. 39, p. 2414
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Reference: [1] Journal of the American Chemical Society, 1917, vol. 39, p. 2414
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Reference: [1] Journal of the American Chemical Society, 1917, vol. 39, p. 2414
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[2] Journal of Organic Chemistry, 1948, vol. 13, p. 284,292
[3] Journal of Organic Chemistry, 1948, vol. 13, p. 284,292
  • 17
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Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1983, vol. 32, # 1, p. 190 - 192[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1983, # 1, p. 215 - 218
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Reference: [1] Australian Journal of Chemistry, 2015, vol. 68, # 8, p. 1221 - 1227
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  • [ 35513-39-4 ]
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Reference: [1] Journal of Organic Chemistry, 1948, vol. 13, p. 284,292
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  • [ 6340-79-0 ]
Reference: [1] Journal of Organic Chemistry, 1948, vol. 13, p. 284,292
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  • 22
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  • 27
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  • 28
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YieldReaction ConditionsOperation in experiment
79% With Dimethylphenylsilane; iodine; indium(III) acetate In chloroform at 60℃; for 5 h; Inert atmosphere; Sealed tube General procedure: Freshly distilled chloroform (0.6 mL)was placed into a screw-capped vial under N2, and a magnetic stirrer bar, In(OAc)3(0.0060 mmol, 1.8 mg), I2 (0.600 mmol, 152 mg), a carboxylic acid (0.6 mmol), andMe2PhSiH (3.90 mmol, 600 μL) were successively added. The vial was sealed with acap that contained a PTFE septum. The reaction vial was heated in an oil bath, and thereaction was monitored by GC and TLC until the ester had been completely consumed.After the reaction was complete, the mixture was cooled to room temperature, and wasquenched with HCl aqueous solution (2 mL). The aqueous layer was extracted withhexane (5 mL x 3). The combined organic phases were dried with anhydrous Na2SO4,and the solvent was evaporated under reduced pressure. The crude product was purifiedby silica gel column chromatography (hexane) to give the corresponding tetralinderivatives. If necessary, further purification was performed by gel permeationchromatography (eluent: CHCl3).
Reference: [1] Chemistry Letters, 2015, vol. 44, # 11, p. 1503 - 1505
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Reference: [1] Tetrahedron, 1985, vol. 41, # 8, p. 1509 - 1516
  • 31
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  • [ 1476776-55-2 ]
Reference: [1] Organic Process Research and Development, 2014, vol. 18, # 1, p. 215 - 227
[2] Organic Process Research and Development, 2014, vol. 18, # 1, p. 215 - 227
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Methyl 4-(4-bromophenyl)-4-oxobutanoate

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Chemical Structure| 1208318-08-4

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Ethyl 7-(4-bromophenyl)-4,7-dioxoheptanoate

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Ethyl 4-(4-bromophenyl)-4-oxobutanoate

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1-(4-Bromophenyl)-2-phenylethanone

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Carboxylic Acids

Chemical Structure| 30098-34-1

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