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[ CAS No. 14191-95-8 ] {[proInfo.proName]}

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Chemical Structure| 14191-95-8
Chemical Structure| 14191-95-8
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Product Details of [ 14191-95-8 ]

CAS No. :14191-95-8 MDL No. :MFCD00002383
Formula : C8H7NO Boiling Point : -
Linear Structure Formula :- InChI Key :AYKYOOPFBCOXSL-UHFFFAOYSA-N
M.W : 133.15 Pubchem ID :26548
Synonyms :

Calculated chemistry of [ 14191-95-8 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 37.99
TPSA : 44.02 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) : -6.05 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.14
Log Po/w (XLOGP3) : 1.49
Log Po/w (WLOGP) : 1.46
Log Po/w (MLOGP) : 1.12
Log Po/w (SILICOS-IT) : 1.65
Consensus Log Po/w : 1.37

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.98
Solubility : 1.39 mg/ml ; 0.0104 mol/l
Class : Very soluble
Log S (Ali) : -2.02
Solubility : 1.27 mg/ml ; 0.00951 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.28
Solubility : 0.7 mg/ml ; 0.00526 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 14191-95-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302+H312+H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 14191-95-8 ]

* 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 [ 14191-95-8 ]
  • Downstream synthetic route of [ 14191-95-8 ]

[ 14191-95-8 ] Synthesis Path-Upstream   1~35

  • 1
  • [ 14191-95-8 ]
  • [ 108-46-3 ]
  • [ 17720-60-4 ]
Reference: [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 39, p. 5460 - 5463
[2] Monatshefte fuer Chemie, 1938, vol. 71, p. 215,226
[3] Justus Liebigs Annalen der Chemie, 1931, vol. 489, p. 118,127, 140
  • 2
  • [ 104-47-2 ]
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YieldReaction ConditionsOperation in experiment
95.41%
Stage #1: With aluminum (III) chloride In toluene at 20 - 70℃; for 4.33 - 6.5 h;
Stage #2: With hydrogenchloride; water In toluene at 20℃;
Example 1:; 2-(4-Hydroxyphenyl)acetonitrile (Formula III):; To the stirred slurry of aluminum chloride (1358.86g, 10.19 moles) in toluene (2100ml) was added 2-(4-methoxyphenyl)acetonitrile (50Og5 3.397 moles) slowly over a period of 20-30 minutes at room temperature. Reaction mixture was gradually heated to 70°C was maintained at the same temperature for 4-6 hrs. Reaction progress was monitored by TLC (5percent Ethyl acetate / Hexane). After heating for 4-6 hrs, reaction was quenched into cooled aqueous hydrochloric acid (Water = 3000 ml; cone. HCl = 667 ml) by maintaining temperature below 2O0C. Organic layer was separated out & aqueous layer was extracted with ethyl acetate (3 x 500ml). Combined organic layer was washed with water (2 x 500ml), dried over anhydrous sodium sulphate (5Og). Solvent was evaporated under reduced pressure to obtain crude residue. Crude product was stirred with mixture of hexane (800 ml) & ethyl acetate (40 ml) for 1.0 hr. Solid product was then filtered out & washed with hexane (300ml). Light brown colored product was dried under vacuum at 35-4O0C. Yield: 431.6g (95.41percent); HPLC purity: 99.56 percent; MP: 70-71.60C1H NMR in DMSO d&6 (δppm): 9.55 (s, IH, ArOH)5 7.15 (d, 2H, ArH)5 6.80 (d, 2H, ArH)5 3.84 (s, 2H5 CH2) 13C NMR in DMSO-d6 (δppm): 156.99, 129.40, 121.21, 119.80, 115.85, 21.73 <n="21"/>IR (KBr): 3340.71, 2268.29, 19.9, 1614.42, 1516.05, 1446.61, 1408.04, 1263.37, 1222.87, 1105.21, 943.19, 819.75, 759.95, 707.88, 578.64 cm"1. GCMS: 133 (base peak), 106, 90, 78.
Reference: [1] Patent: WO2009/84037, 2009, A2, . Location in patent: Page/Page column 7; 8; 18-19
[2] European Journal of Organic Chemistry, 2007, # 21, p. 3449 - 3462
[3] Letters in Organic Chemistry, 2011, vol. 8, # 1, p. 48 - 52
[4] Journal of Chemical Research, 2004, # 10, p. 693 - 694
[5] Journal fuer Praktische Chemie (Leipzig), 1987, vol. 329, # 6, p. 963 - 974
[6] Journal of Medicinal Chemistry, 1964, vol. 7, p. 511 - 518
  • 3
  • [ 107-31-3 ]
  • [ 623-05-2 ]
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YieldReaction ConditionsOperation in experiment
96% With sulfuric acid In methanol; dichloromethane; water EXAMPLE 1
Preparation of para-hydroxybenzyl cyanide
A mixture of 4.96 para-hydroxybenzyl alcohol 2.8 g. sodium cyanide 18 ml. methanol and 6 ml. of methyl formate is heated with stirring under reflux for a period of 70 minutes.
The reaction mixture is distilled under partial vacuum to recover starting material, and the residue stirred with 20 ml. water and sulphuric acid added until the mixture is no longer alkaline.
The product is now isolated by extracting 3 times each time with 15 ml. methylene chloride.
The combined solvent extracts are washed with 10 ml. aqueous sodium bicarbonate and solvent evaporated finally under vacuum at a temperature of 60° C.
There is obtained 5.11 g. of crude para-hydroxybenzyl cyanide corresponding to a weight yield of 96percent of theory.
On simple distillation under oil pump vacuum there is obtained a pale yellow fraction m.pt.
65° C. corresponding to a weight yield equivalent to 93percent of theory.
Melting point data indicates that this material has an absolute purity of 97percent.
Reference: [1] Patent: US4378319, 1983, A,
  • 4
  • [ 122-87-2 ]
  • [ 14191-95-8 ]
YieldReaction ConditionsOperation in experiment
80% With sodium hydroxide In water; N,N-dimethyl-formamide EXAMPLE 1
Sodium cyanide (3.0 g.) is added to a stirred solution of p-hydroxyphenylglycine (10.0 g.) and sodium hydroxide (2.4 g.) in N,N-dimethylformamide (20 ml.) at 80° C., and the mixture is then stirred and heated at 130° C. for 1 hour and cooled to 20° C. Water (25 ml.) is added and the mixture is acidified to pH 5 with concentrated aqueous hydrochloric acid and extracted four times with diethyl ether (40 ml. each time).
The combined extracts are dried and evaporated to dryness and the residue is distilled at a pressure of 0.05 mm. Hg.
There is thus obtained as distillate, which solidifies on cooling, p-hydroxybenzyl cyanide, m.p. 68°-69° C. (6.37 g.; 80percent yield).
Reference: [1] Patent: US4154758, 1979, A,
  • 5
  • [ 623-05-2 ]
  • [ 109-94-4 ]
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Reference: [1] Patent: US4378319, 1983, A,
  • 6
  • [ 35421-08-0 ]
  • [ 14191-95-8 ]
Reference: [1] Patent: US4069340, 1978, A,
[2] Patent: US3983178, 1976, A,
  • 7
  • [ 91983-26-5 ]
  • [ 14191-95-8 ]
Reference: [1] Polymer, 2017, vol. 126, p. 291 - 295
  • 8
  • [ 838-96-0 ]
  • [ 14191-95-8 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 19, p. 3729 - 3732
  • 9
  • [ 16532-79-9 ]
  • [ 14191-95-8 ]
Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 7, p. 1968 - 1972[2] Angew. Chem., 2018, vol. 130, p. 1986 - 1990,5
  • 10
  • [ 110-74-7 ]
  • [ 623-05-2 ]
  • [ 14191-95-8 ]
Reference: [1] Patent: US4317781, 1982, A,
  • 11
  • [ 60-18-4 ]
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Reference: [1] Journal of the Chemical Society, Chemical Communications, 1985, # 14, p. 974 - 975
[2] Green Chemistry, 2018, vol. 20, # 18, p. 4217 - 4223
  • 12
  • [ 4985-46-0 ]
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Reference: [1] Journal of the Chemical Society, Chemical Communications, 1985, # 14, p. 974 - 975
  • 13
  • [ 773837-37-9 ]
  • [ 150-76-5 ]
  • [ 14191-95-8 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 2, p. 158 - 160
  • 14
  • [ 773837-37-9 ]
  • [ 623-05-2 ]
  • [ 14191-95-8 ]
Reference: [1] Organic Process Research and Development, 1998, vol. 2, # 4, p. 274 - 276
[2] Journal of Natural Medicines, 2010, vol. 64, # 3, p. 245 - 251
[3] Organic Process Research and Development, 2016, vol. 20, # 7, p. 1354 - 1362
  • 15
  • [ 623-05-2 ]
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Reference: [1] Patent: US3983160, 1976, A,
  • 16
  • [ 3544-25-0 ]
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Reference: [1] Chemische Berichte, 1900, vol. 33, p. 165
[2] Chemische Berichte, 1884, vol. 17, p. 506[3] Chemische Berichte, 1889, vol. 22, p. 2139
[4] Journal of Biological Chemistry, 1919, vol. 39, p. 592
[5] Justus Liebigs Annalen der Chemie, 1925, vol. 444, p. 89
  • 17
  • [ 1050-28-8 ]
  • [ 14191-95-8 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1985, # 14, p. 974 - 975
  • 18
  • [ 1252085-64-5 ]
  • [ 14191-95-8 ]
Reference: [1] Journal of Natural Medicines, 2010, vol. 64, # 3, p. 245 - 251
  • 19
  • [ 55-21-0 ]
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Reference: [1] Patent: US3983178, 1976, A,
  • 20
  • [ 937-62-2 ]
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Reference: [1] Journal of Organic Chemistry, 1968, vol. 33, # 3, p. 1084 - 1087
  • 21
  • [ 15451-04-4 ]
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Reference: [1] Journal of Organic Chemistry, 1968, vol. 33, # 3, p. 1084 - 1087
[2] Patent: US3983178, 1976, A,
  • 22
  • [ 123-08-0 ]
  • [ 14191-95-8 ]
Reference: [1] Organic Process Research and Development, 2016, vol. 20, # 7, p. 1354 - 1362
  • 23
  • [ 61661-14-1 ]
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Reference: [1] Journal of Organic Chemistry, 1968, vol. 33, # 3, p. 1084 - 1087
  • 24
  • [ 35421-08-0 ]
  • [ 143-33-9 ]
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Reference: [1] Journal of Organic Chemistry, 1968, vol. 33, # 3, p. 1084 - 1087
  • 25
  • [ 56401-28-6 ]
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Reference: [1] Proceedings of the Iowa Academy of Science, 1954, vol. 61, p. 271,275
  • 26
  • [ 267877-40-7 ]
  • [ 14191-95-8 ]
  • [ 103-90-2 ]
  • [ 767-00-0 ]
Reference: [1] Australian Journal of Chemistry, 1999, vol. 52, # 11, p. 1029 - 1033
  • 27
  • [ 14191-95-8 ]
  • [ 17194-82-0 ]
Reference: [1] Organic Process Research and Development, 1998, vol. 2, # 4, p. 274 - 276
[2] Chemische Berichte, 1889, vol. 22, p. 2138
  • 28
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  • [ 17194-82-0 ]
Reference: [1] Patent: US4154757, 1979, A,
[2] Patent: US4154757, 1979, A,
  • 29
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  • [ 17194-82-0 ]
Reference: [1] Patent: US4154757, 1979, A,
  • 30
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Reference: [1] Patent: US4154757, 1979, A,
  • 31
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Reference: [1] Tetrahedron, 1993, vol. 49, # 44, p. 10099 - 10102
  • 32
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  • [ 6343-93-7 ]
Reference: [1] Journal of the American Chemical Society, 1984, vol. 106, # 11, p. 3344 - 3353
[2] Chemische Berichte, 1889, vol. 22, p. 2138
  • 33
  • [ 75-91-2 ]
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  • [ 25804-49-3 ]
Reference: [1] RSC Advances, 2016, vol. 6, # 104, p. 102023 - 102027
  • 34
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  • [ 17138-28-2 ]
Reference: [1] Chemische Berichte, 1889, vol. 22, p. 2138
  • 35
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  • [ 29122-68-7 ]
Reference: [1] Organic Process Research and Development, 1998, vol. 2, # 4, p. 274 - 276
[2] Organic Process Research and Development, 1998, vol. 2, # 4, p. 274 - 276
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