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[ CAS No. 331-25-9 ] {[proInfo.proName]}

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Chemical Structure| 331-25-9
Chemical Structure| 331-25-9
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Product Details of [ 331-25-9 ]

CAS No. :331-25-9 MDL No. :MFCD00004331
Formula : C8H7FO2 Boiling Point : -
Linear Structure Formula :- InChI Key :YEAUYVGUXSZCFI-UHFFFAOYSA-N
M.W : 154.14 Pubchem ID :67617
Synonyms :

Calculated chemistry of [ 331-25-9 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 37.94
TPSA : 37.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.07 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.38
Log Po/w (XLOGP3) : 1.65
Log Po/w (WLOGP) : 1.87
Log Po/w (MLOGP) : 2.09
Log Po/w (SILICOS-IT) : 1.96
Consensus Log Po/w : 1.79

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.11
Solubility : 1.21 mg/ml ; 0.00782 mol/l
Class : Soluble
Log S (Ali) : -2.05
Solubility : 1.38 mg/ml ; 0.00898 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.44
Solubility : 0.561 mg/ml ; 0.00364 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.39

Safety of [ 331-25-9 ]

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 [ 331-25-9 ]

* 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 [ 331-25-9 ]
  • Downstream synthetic route of [ 331-25-9 ]

[ 331-25-9 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 201230-82-2 ]
  • [ 456-42-8 ]
  • [ 331-25-9 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: With C28H22CoN4O6 In butan-1-ol at 60℃; for 2 h; Glovebox; High pressure; Green chemistry
Stage #2: With tetra-(n-butyl)ammonium iodide; sodium hydroxide In butan-1-ol at 60℃; for 22 h; Glovebox; High pressure; Green chemistry
General procedure: A 100 mL reactor equipped with Teflon-coated magnetic stir bars was charged with n-Butyl alcohol (20 mL) and the catalyst (0.5 mmol). The reactor was then taken out of the glove box and pressured with carbon monoxide (1 atm). The mixture was stirred 2 h at 60 °C, cooled to ambient temperature and slowly vented. After benzyl chloride (10 mmol), NaOH (15 mL, 15percent), and TBAI (0.25 mmol) were added, the reactor was sealed and the reaction mixtures were stirred for 22 h at 60 °C under carbon monoxide (1 atm). After the reaction, the water phase was detached and washing the organic phase three times with H2O (3×5 mL), the combined water layer was washed with Et2O, then the resulting solution was cooled to 0 °C and adjusted to pH=1–2 with HCl (6 mol/L). The product was filtered, dried in RT, and then recrystallized.
Reference: [1] Tetrahedron, 2013, vol. 69, # 35, p. 7264 - 7268
  • 2
  • [ 372-20-3 ]
  • [ 75-36-5 ]
  • [ 331-25-9 ]
Reference: [1] Patent: US4578387, 1986, A,
  • 3
  • [ 124-38-9 ]
  • [ 456-42-8 ]
  • [ 331-25-9 ]
Reference: [1] ChemCatChem, 2015, vol. 7, # 23, p. 3972 - 3977
  • 4
  • [ 350-51-6 ]
  • [ 331-25-9 ]
Reference: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 12, p. 2132 - 2141
  • 5
  • [ 352-70-5 ]
  • [ 331-25-9 ]
Reference: [1] Journal of the American Chemical Society, 1963, vol. 85, p. 709 - 724
[2] Australian Journal of Chemistry, 1970, vol. 23, p. 1921 - 1937
  • 6
  • [ 501-00-8 ]
  • [ 331-25-9 ]
Reference: [1] Journal of the American Chemical Society, 1948, vol. 70, p. 2837,2842
[2] Chemicke Zvesti, 1960, vol. 14, p. 119,120, 122[3] Chem.Abstr., 1960, # 21003,
[4] Australian Journal of Chemistry, 1970, vol. 23, p. 1921 - 1937
[5] Journal of the American Chemical Society, 1963, vol. 85, p. 709 - 724
  • 7
  • [ 456-42-8 ]
  • [ 331-25-9 ]
Reference: [1] Journal of the American Chemical Society, 1963, vol. 85, p. 709 - 724
  • 8
  • [ 1121-86-4 ]
  • [ 64-19-7 ]
  • [ 331-25-9 ]
Reference: [1] ChemCatChem, 2014, vol. 6, # 6, p. 1589 - 1593
  • 9
  • [ 6929-49-3 ]
  • [ 331-25-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 15, p. 1723 - 1727
  • 10
  • [ 455-38-9 ]
  • [ 331-25-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 15, p. 1723 - 1727
  • 11
  • [ 1711-07-5 ]
  • [ 331-25-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 15, p. 1723 - 1727
  • 12
  • [ 163733-96-8 ]
  • [ 331-25-9 ]
Reference: [1] Patent: CN106928044, 2017, A,
  • 13
  • [ 456-41-7 ]
  • [ 331-25-9 ]
Reference: [1] Australian Journal of Chemistry, 1970, vol. 23, p. 1921 - 1937
  • 14
  • [ 67-56-1 ]
  • [ 143659-28-3 ]
  • [ 5903-23-1 ]
  • [ 331-25-9 ]
Reference: [1] Canadian Journal of Chemistry, 1992, vol. 70, # 3, p. 992 - 999
[2] Canadian Journal of Chemistry, 1992, vol. 70, # 3, p. 992 - 999
  • 15
  • [ 331-25-9 ]
  • [ 52059-53-7 ]
YieldReaction ConditionsOperation in experiment
84% With sodium hydroxide In methanol; diethyl ether a
3-(Fluoro)phenethyl alcohol
To a stirred solution of 3-fluorophenylacetic acid (5.0 g, 32.0 mmol) in diethyl ether (100 ml), at -10° C., was added lithium aluminium hydride (32.4 ml of a 1M solution in diethyl ether, 32.4 mmol), dropwise.
The reaction mixture was allowed to warm to +25° C. and stirred for 1 h, before again cooling to -10° C., and quenching by addition of methanol (20 ml) and 4M sodium hydroxide (20 ml).
The resulting slurry was filtered and the filtrate evaporated in vacuo.
The crude product was chromatographed on silica gel eluding with CH2 Cl2 /MeOH/NH3 (80:8:1) to give 3-(fluoro)phenethyl alcohol (3.80 g, 84percent), δ (250 MHz, CDCl3) 2.87 (3H, t, J=6.5 Hz, CH2), 3.87 (3H, t, J=6.5 Hz, CH2), 6.89-7.02 (3H, m, Ar--H), 7.23-7.33 (1H, m, Ar--H).
Reference: [1] Journal of Organic Chemistry, 2005, vol. 70, # 14, p. 5528 - 5535
[2] Tetrahedron Asymmetry, 2001, vol. 12, # 4, p. 585 - 596
[3] Patent: US5889008, 1999, A,
[4] Helvetica Chimica Acta, 1973, vol. 56, p. 2460 - 2479
[5] Journal of the American Chemical Society, 1978, vol. 100, p. 228 - 246
[6] Journal of Medicinal Chemistry, 2002, vol. 45, # 19, p. 4321 - 4335
[7] Patent: US5877317, 1999, A,
[8] Patent: US5087635, 1992, A,
[9] Journal of the American Chemical Society, 2011, vol. 133, # 43, p. 17142 - 17145
[10] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 131 - 134
[11] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 14, p. 3719 - 3735
[12] Journal of Enzyme Inhibition and Medicinal Chemistry, 2018, vol. 33, # 1, p. 1460 - 1471
  • 16
  • [ 331-25-9 ]
  • [ 52059-53-7 ]
Reference: [1] Patent: US5204333, 1993, A,
  • 17
  • [ 917-54-4 ]
  • [ 331-25-9 ]
  • [ 1737-19-5 ]
Reference: [1] Journal of Medicinal Chemistry, 1986, vol. 29, # 6, p. 924 - 939
  • 18
  • [ 331-25-9 ]
  • [ 458-45-7 ]
Reference: [1] Tetrahedron Asymmetry, 2001, vol. 12, # 4, p. 585 - 596
  • 19
  • [ 331-25-9 ]
  • [ 29640-98-0 ]
YieldReaction ConditionsOperation in experiment
87%
Stage #1: With ammonium nitrate In chloroform at 0℃;
Stage #2: at 0℃; for 3 h;
3-Fluoro phenyl acetic acid (5 g, 36.7 mmol) was diluted in 30 mL of chloroform and ammonium nitrate (3.12 g, 38.9 mmol) was added. The reaction mixture was cooled to 0° C. and trifluoro acetic acid anhydride (16.02 mL, 113 mmol) was added dropwise. The reaction stirred at 0° C. for 3 h before water was added to slowly quench the reaction. The chloroform layer was washed with water, collected and dried over Na2SO4, and concentrated. The desired isomer crystallized out of the crude solution in ethyl acetate and was then triturated with acetonitrile to afford 5.25 g of the desired isomer as a brown solid. Yield 87percent; MS (APCI): 199 [M-H]+.
Reference: [1] Journal of Organic Chemistry, 1995, vol. 60, # 20, p. 6389 - 6396
[2] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 20, p. 4560 - 4563
[3] Patent: US2004/67960, 2004, A1, . Location in patent: Page/Page column 19
[4] Patent: US4160032, 1979, A,
  • 20
  • [ 67-56-1 ]
  • [ 331-25-9 ]
  • [ 64123-77-9 ]
YieldReaction ConditionsOperation in experiment
97% at 0 - 20℃; for 3 h; General procedure: 5.1.57.1. Step 1. To a solution of 3-fluorophenylacetic acid (24.85 g,158 mmol) in MeOH (200 mL) was added SOCl2 (4.00 mL,52.2 mmol) at 0 C with silica gel blue tube. After stirring at rtfor 3 h, the reaction mixture was concentrated under reduced pressure.The residue was partitioned between 1 N NaOH (250 mL) andEtOAc (250 mL). The separable organic layer was washed withbrine (100 mL), dried over MgSO4, filtered, concentrated underreduced pressure to obtain methyl (3-fluorophenyl)acetate(25.81 g, 97percent) as colorless oil. 1H NMR (CDCl3) d 3.62 (2H, s),3.71 (3H, s), 6.92–7.09 (3H, m), 7.29 (1H, ddd, J = 7.9, 7.7, 6.0 Hz);IR (KBr) cm1 3065, 3024, 3001, 2955, 2845, 1740, 1616, 1593,1489, 1450, 1437, 1342, 1258, 1200, 1165, 1144, 1076, 1015,955, 930.
65% Reflux General procedure: To an appropriately substituted phenylacetic acid (10 mmol) dissolved in dried methanol (50 mL), concentrated sulfuric acid (0.5 mL) was added dropwise.The mixture was refluxed from 7 to 9 h. Next, the solvent was evaporated, and residue was dissolved in 40 mL of ethyl acetate, washed with 0.5percent NaOH andbrine. Organic layer was dried over anhydrous Na2SO4 and filtered. The solvent was evaporated to give the products as colorless oils.
Reference: [1] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 13, p. 2843 - 2866
[2] Advanced Synthesis and Catalysis, 2012, vol. 354, # 4, p. 751 - 756
[3] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 14, p. 3719 - 3735
[4] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 15, p. 4694 - 4703
[5] Tetrahedron, 2002, vol. 58, # 51, p. 10113 - 10126
[6] European Journal of Medicinal Chemistry, 2017, vol. 135, p. 117 - 124
[7] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 16, p. 1893 - 1895
[8] Patent: WO2006/123639, 2006, A1, . Location in patent: Page/Page column 172
[9] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 12, p. 3943 - 3949
[10] Russian Journal of Bioorganic Chemistry, 2015, vol. 41, # 2, p. 170 - 177
[11] Journal of Chemistry, 2017, vol. 2017,
  • 21
  • [ 331-25-9 ]
  • [ 18107-18-1 ]
  • [ 64123-77-9 ]
Reference: [1] Patent: WO2005/27837, 2005, A2, . Location in patent: Page/Page column 46
[2] Patent: WO2003/87037, 2003, A1, . Location in patent: Page/Page column 62
[3] Patent: WO2005/44785, 2005, A1, . Location in patent: Page/Page column 47-48
[4] Patent: WO2005/27837, 2005, A2, . Location in patent: Page/Page column 46
  • 22
  • [ 331-25-9 ]
  • [ 1532533-67-7 ]
  • [ 1532533-69-9 ]
Reference: [1] Patent: US2015/290317, 2015, A1,
[2] Patent: US2015/290317, 2015, A1,
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