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[ CAS No. 1821-12-1 ] {[proInfo.proName]}

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Chemical Structure| 1821-12-1
Chemical Structure| 1821-12-1
Structure of 1821-12-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1821-12-1 ]

CAS No. :1821-12-1 MDL No. :MFCD00004403
Formula : C10H12O2 Boiling Point : -
Linear Structure Formula :- InChI Key :OBKXEAXTFZPCHS-UHFFFAOYSA-N
M.W : 164.20 Pubchem ID :4775
Synonyms :
4-PBA;Benzenebutyric acid

Calculated chemistry of [ 1821-12-1 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.6
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) : -5.58 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.69
Log Po/w (XLOGP3) : 2.42
Log Po/w (WLOGP) : 2.09
Log Po/w (MLOGP) : 2.29
Log Po/w (SILICOS-IT) : 2.23
Consensus Log Po/w : 2.14

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.49
Solubility : 0.533 mg/ml ; 0.00325 mol/l
Class : Soluble
Log S (Ali) : -2.85
Solubility : 0.234 mg/ml ; 0.00143 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.98
Solubility : 0.174 mg/ml ; 0.00106 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 1821-12-1 ]

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 [ 1821-12-1 ]

* 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 [ 1821-12-1 ]
  • Downstream synthetic route of [ 1821-12-1 ]

[ 1821-12-1 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 1821-12-1 ]
  • [ 1370290-52-0 ]
  • [ 4521-22-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 7, p. 3285 - 3306
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 7, p. 3285 - 3306
  • 2
  • [ 1821-12-1 ]
  • [ 583-53-9 ]
Reference: [1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 15, p. 5431 - 5435
  • 3
  • [ 1821-12-1 ]
  • [ 40353-34-2 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1927, vol. 451, p. 53
  • 4
  • [ 1821-12-1 ]
  • [ 16503-46-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 21, p. 2765 - 2770
  • 5
  • [ 1821-12-1 ]
  • [ 26673-32-5 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1927, vol. 451, p. 53
  • 6
  • [ 6340-79-0 ]
  • [ 35656-89-4 ]
  • [ 1821-12-1 ]
Reference: [1] Journal of the American Chemical Society, 1938, vol. 60, p. 170,174
  • 7
  • [ 1821-12-1 ]
  • [ 15118-60-2 ]
Reference: [1] Journal of the American Chemical Society, 1949, vol. 71, p. 779
[2] Journal of the American Chemical Society, 1934, vol. 56, p. 744
[3] Justus Liebigs Annalen der Chemie, 1955, vol. 596, p. 1,219
  • 8
  • [ 1821-12-1 ]
  • [ 27913-58-2 ]
YieldReaction ConditionsOperation in experiment
42% With sulfuric acid; iodine; acetic acid; periodic acid In water at 70℃; for 19 h; A mixture of 4-phenylbutanoic acid (20.0 g, 121.8 mmol), H5IO6 (5.56 g, 24.4 mmol), iodine (13.30 g, 52.4 mmol), 10 M H2SO4 (5.0 mL), water (36 mL) and acetic acid (166 mL) was heated at 70° C. for 19 h.
The reaction mixture was cooled and evaporated to dryness.
The residue was dissolved in EtOAc (300 mL) and washed with aqueous Na2S2O3 (2*200 mL), brine (2*200 mL), dried over Na2SO4, filtered, and evaporated to leave a yellow solid.
The crude product was precipitated from EtOAc/hexane at 0° C. to afford product as light yellow solid (15.0 g, 42percent).
1H NMR (400 MHz, CDCl3) δ 11.0 (brs, 1H), 7.61 (d, J=8.4 Hz, 2H), 6.95 (d, J=8.0 Hz, 2H), 2.63 (t, J=7.6 Hz, 2H), 2.38 (t, J=7.6 Hz, 2H).
Reference: [1] Mendeleev Communications, 2015, vol. 25, # 2, p. 111 - 113
[2] European Journal of Organic Chemistry, 2015, vol. 2015, # 27, p. 5919 - 5924
[3] Patent: US2018/66298, 2018, A1, . Location in patent: Paragraph 0172; 0173; 0174
[4] Journal of the American Chemical Society, 1943, vol. 65, p. 1273,1274
[5] Patent: US2348231, 1940, ,
[6] Patent: US2348231, 1940, ,
  • 9
  • [ 1821-12-1 ]
  • [ 27913-58-2 ]
Reference: [1] Tetrahedron, 2004, vol. 60, # 32, p. 6945 - 6958
[2] Phytochemistry, 2013, vol. 96, p. 223 - 234
  • 10
  • [ 1821-12-1 ]
  • [ 22009-40-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1927, vol. 451, p. 53
  • 11
  • [ 1821-12-1 ]
  • [ 1716-12-7 ]
YieldReaction ConditionsOperation in experiment
96% With sodium hydroxide In water 0.40 g (2.436 mmol) of 4-phenylbutyric acid are suspended in 30 ml of H2O, and then 0.097 g (2.436 mmol) of sodium hydroxide is added. After the acid has been dissolved, the solution is concentrated by rotary evaporation and twice dewatered azeotropically with toluene. This gives 0.44 g (96.0percent) of sodium 4-phenylbutyrate in solid form.
88.2% With sodium hydroxide In ethanol for 4 h; Industrial scale As shown in Fig. 5, 6000 ml of anhydrous ethanol and 243.6 g of sodium hydroxide were successively charged into 10 L of a four-necked reaction flask. After heating and stirring, 1000 g of phenylbutyric acid prepared in Example 3 was added thereto, stirred and heated to dissolve, (TLC developing solvent: methanol: dichloromethane = 1: 2, Rf = 0.2 for phenylbutyric acid, Rf = 0.1 for sodium phenylbutyrate), and the reaction was terminated for about 4 hours. Add 30g of activated carbon reflux 10 minutes, slightly cold, filter to remove activated carbon. Collect the liquid at 50 ° C. Distillation to remove most of the solvent. A large amount of white solid precipitated. After cooling the residue to 15 ° C, the solid was collected by filtration and washed with 100 ml of absolute ethanol. The solid was dried at 40 ° C for 4 hours and then dried at 60 ° C for 12 hours to give 1000 g of white sodium phenylbutyrate in 88.2percent yield, HPLC purity of 99.77percent (octadecyl silane bonded silica as stationary phase, Glacial acetic acid-methanol-water (1:49:50) as the mobile phase; detection wavelength of 245nm), high-performance liquid chromatography shown in Figure 5, the results shown in Table 8, we can see that a single impurity control Within 0.1percent.
Reference: [1] Patent: US2012/77677, 2012, A1, . Location in patent: Page/Page column 3
[2] Patent: CN105924345, 2016, A, . Location in patent: Paragraph 0084; 0089
[3] Patent: US2007/4805, 2007, A1, . Location in patent: Page/Page column 5
[4] Patent: US2008/171792, 2008, A1, . Location in patent: Page/Page column 7
[5] Crystal Growth and Design, 2010, vol. 10, # 4, p. 1990 - 2003
[6] Langmuir, 2012, vol. 28, # 25, p. 9332 - 9340
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