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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 : |
|
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 |
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 |
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 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
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 |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280 | UN#: | N/A |
Hazard Statements: | H302+H312+H332 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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). |
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