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[ CAS No. 64080-15-5 ] {[proInfo.proName]}

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Chemical Structure| 64080-15-5
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Product Details of [ 64080-15-5 ]

CAS No. :64080-15-5 MDL No. :MFCD01593653
Formula : C8H9BrO Boiling Point : -
Linear Structure Formula :- InChI Key :XAVFMOSJCDSLCQ-UHFFFAOYSA-N
M.W : 201.06 Pubchem ID :16641252
Synonyms :

Calculated chemistry of [ 64080-15-5 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.94
TPSA : 20.23 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) : -5.36 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.3
Log Po/w (XLOGP3) : 3.05
Log Po/w (WLOGP) : 2.72
Log Po/w (MLOGP) : 2.88
Log Po/w (SILICOS-IT) : 2.81
Consensus Log Po/w : 2.75

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.39
Solubility : 0.0827 mg/ml ; 0.000411 mol/l
Class : Soluble
Log S (Ali) : -3.14
Solubility : 0.145 mg/ml ; 0.000723 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.47
Solubility : 0.068 mg/ml ; 0.000338 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.22

Safety of [ 64080-15-5 ]

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 [ 64080-15-5 ]

* 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 [ 64080-15-5 ]
  • Downstream synthetic route of [ 64080-15-5 ]

[ 64080-15-5 ] Synthesis Path-Upstream   1~4

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YieldReaction ConditionsOperation in experiment
34% With oxygen; cobalt(II) diacetate tetrahydrate; sodium hydroxide In ethylene glycol at 100℃; for 10 h; General procedure: A mixture of substrate 1 (2.0 mmol), Co(OAc)24H2O (40 mg, 0.16 mmol) andNaOH (160 mg, 4.0 mmol) in EG (9.0 ml) was stirred with molecular oxygen(1 atm) being bubbled, under 100 C for specified time. After completion ofreaction, diluted hydrochloric acid (15 ml, 2 percent) and chloroform (15 ml) weresuccessively added to the reaction mixture. The organic layer was separated, and theaqueous phase was extracted with chloroform (15 ml 9 2). The combined organicphase was dried over anhydrous sodium sulfate and concentrated to give a residue,which was purified by column chromatography on silica gel (eluents: petroleumether:ethyl acetate = 10:1) providing the desired products 2.
Reference: [1] Research on Chemical Intermediates, 2015, vol. 41, # 10, p. 7115 - 7124
  • 2
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YieldReaction ConditionsOperation in experiment
98% With bromine In dichloromethane at 0℃; Bromine (11. 6mL, 0. 23MOL) was added slowly to a cooled 0 C of 4-ethylphenol (25g, 0. 21 mol) dissolved IN CH2CI2 (125mL). After the addition was complete the reaction mixture was stirred for 5 mins and then quenched with 1 N NAOH. The reaction mixture was diluted with H20 and the layers separated. The organic layer was concentrated to an orange oil. Purification by flash column chromatography (0percent to 5percent EtOAc in hexanes) gave the title compound as a clear oil (42g, 98percent). 1H NMR (400 MHz, CDCl3) : 5 1.20 (t, J=7. 6 Hz, 3 H), 2.58 (q, J=7. 5 Hz, 2 H), 5.36 (s, 1 H), 6.93 (d, J=8. 3 Hz, 1 H), 7.03 (d, J=8. 3 Hz, 1 H), 7.28 (s, 1 H).
98% With bromine In dichloromethane at 0℃; for 0.0833333 h; Bromine (11.6 mL, 0.23 mol) was added slowly to a cooled 0° C. of 4-ethylphenol (2 g, 0.21 mol) dissolved in CH2Cl2 (125 mL). After the addition was complete the reaction mixture was stirred for 5 mins and then quenched with 1N NaOH. The reaction mixture was diluted with H2O and the layers separated. The organic layer was concentrated to an orange oil. Purification by flash column chromatography (0percent to 5percent EtOAc in hexanes) gave the title compound as a clear oil (4 g, 98percent). 1H NMR (400 MHz, CDCl3): δ 1.20 (t, J=7.6 Hz, 3H), 2.58 (q, J=7.5 Hz, 2H), 5.36 (s, 1H), 6.93 (d, J=8.3 Hz, 1H), 7.03 (d, J=8.3 Hz, 1H), 7.28 (s, 1H).
79.2% With bromine; sodium hydrogencarbonate In chloroform at 0℃; General procedure: To a solution of 4-alkylphenol (20 mmol) in chloroform (20 mL), sodium hydrogencarbonate (2 g, 24 mmol) was added. The resulting suspension was cooled to 0°C. While a solution of elementary bromine (1.12 mL, 22 mmol) in chloroform (8 mL) was slowly added, the suspension was vigorously stirred. After completion of the reaction, monitored by TLC the suspension was filtered. The filter with the solid residue was rinsed once with 50 mL of chloroform. The combined organic solutions were evaporated under reduced pressure. The final workup of the product was done either by distillation or by column chromatography (petroleum ether : ethyl acetate, 9 : 1).
61% With N-Bromosuccinimide In acetonitrile for 24 h; Example 30 3-F 4- [3- ()- (4-ETHYL-2-THIOPHEN-2-YL-PHENOXY)-BUTOXY]-2-METHYL-PHENYL}-PROPIONIC ACID Step A 2-BROMO-4-ETHYL-PHENOL; N-bromosuccinimide (1. 58 g, 8.92 mmol) is added to a solution of 4-ethyl phenol (1.0 g, 8.19 mmol) in ACN (35 mL), and the mixture is stirred under N2 at ambient temperature. After 24 h, the mixture is concentrated under reduced pressure and diluted with water. The mixture is extracted with EtOAc, and organic phases are washed with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification by flash chromatography, silica, hexanes: EtOAc (95: 5) yields title compound (1.01 g, 4.9 mmol, 61percent): RF 0.34 hexanes: EtOAc (90: 10), 1H NMR (400 MHz, CDC13) 7.28 (d, 1H, J= 2. 4 Hz), 7.03 (dd, 1H, JL= 2.4 Hz, J2= 8.4 Hz), 6. 92 (d, 1H, J= 8. 4 Hz), 5.34 (s, 1H), 2.56 (q, 2H, J = 7.6 Hz), 1.20 (t, 3H, J= 7. 6 Hz).
52% With N-Bromosuccinimide In acetonitrile at 20℃; for 2 h; To a solution of 4-ethylphenol (1.0 g, 8.2 mmol, 1.0 eq) in dry acetonitrile (40 mL) was added NBS (1.46 g, 8.2 mmol, 1.0 eq). The mixture was allowed to stir at RT for 2 h followed by removal of acetonitrile. The residue was redissolved in Et20 and washed with H20. The organic extracts were dried over Na2S04, filtered, and concentrated. The crude material was purified by flash chromatography (Biotage FLASH 40S KP-Sil silica, 5percent Et20/hexanes) to yield 1.0 g (52percent) of 16 as a clear oil. 1H NMR (CD2Cl2, 300 MHz) : 7.33 (s, 1H), 7.07 (d, J= 8.1 Hz, 1H), 6.93 (d, J= 8.1 Hz, 1H), 2.58 (m, J= 7.5 Hz, 2H), 1.20 (t, J= 7.5 Hz, 3H).

Reference: [1] Patent: WO2004/74270, 2004, A2, . Location in patent: Page 348
[2] Patent: US2005/176701, 2005, A1, . Location in patent: Page/Page column 169-170
[3] Australian Journal of Chemistry, 2003, vol. 56, # 11, p. 1099 - 1106
[4] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 24, p. 6908 - 6917
[5] Chemistry - A European Journal, 2018, vol. 24, # 62, p. 16516 - 16520
[6] Chemische Berichte, 1986, vol. 119, # 11, p. 3507 - 3514
[7] Patent: WO2005/19151, 2005, A1, . Location in patent: Page/Page column 146
[8] Angewandte Chemie - International Edition, 2018, vol. 57, # 24, p. 7200 - 7204[9] Angew. Chem., 2018, vol. 130, p. 7318 - 7322,5
[10] Patent: WO2005/108406, 2005, A1, . Location in patent: Page/Page column 118-119
[11] Journal of the Chemical Society, 1941, p. 358,359
[12] Journal of the Chemical Society, 1943, p. 525
[13] Tetrahedron Letters, 2007, vol. 48, # 13, p. 2271 - 2274
[14] Patent: US2001/1799, 2001, A1,
[15] Patent: US5053548, 1991, A,
[16] Organic and Biomolecular Chemistry, 2016, vol. 14, # 10, p. 2819 - 2823
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  • [ 123-07-9 ]
  • [ 7726-95-6 ]
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Reference: [1] Journal of the Chemical Society, 1943, p. 525
[2] Journal of the Chemical Society, 1941, p. 358,359
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  • [ 7726-95-6 ]
  • [ 64-19-7 ]
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Reference: [1] Journal of the Chemical Society, 1943, p. 525
[2] Journal of the Chemical Society, 1941, p. 358,359
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