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CAS No. : | 206201-64-1 | MDL No. : | MFCD13189079 |
Formula : | C7H4N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DMDMMMFMXWZSLM-UHFFFAOYSA-N |
M.W : | 132.12 | Pubchem ID : | 21364144 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 34.34 |
TPSA : | 53.75 Ų |
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) : | -6.84 cm/s |
Log Po/w (iLOGP) : | 0.62 |
Log Po/w (XLOGP3) : | 0.37 |
Log Po/w (WLOGP) : | 0.77 |
Log Po/w (MLOGP) : | -0.84 |
Log Po/w (SILICOS-IT) : | 1.46 |
Consensus Log Po/w : | 0.47 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.27 |
Solubility : | 7.09 mg/ml ; 0.0537 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.06 |
Solubility : | 11.4 mg/ml ; 0.0863 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.02 |
Solubility : | 1.25 mg/ml ; 0.00946 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.37 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H319 | 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 |
---|---|---|
50% | Stage #1: at 150℃; for 0.333333 h; Stage #2: at 20℃; |
Preparation 18 6-FormylnicotinonitrileA mixture of 6-methylnicotinonitrile (10.0 g, 84.6 mmol) and iodine (20.0 g, 78.8 mmol) in dimethylsulfoxide (150 mL) was heated at 15O0C under nitrogen for 20 minutes (reaction exhaust was scrubbed with bleach to remove dimethyl sulfide). After cooling to room temperature saturated aqueous sodium bicarbonate (200 mL) was added carefully and the resulting mixture was extracted with toluene (3 x 100 mL). The combined organic extracts were washed with brine, dried (MgSO4) and evaporated to give the desired product as an orange oil (5.65 g, 50percent) which was used without further purification. 1H NMR (CDCI3, 400 MHz) δ 8.06 (1H, d), 8.17 (1H, dd), 9.05 (1H, d), 10.12 (1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | Stage #1: With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 0.333333 h; Cooling with acetone-dry ice Stage #2: at -78℃; for 2 h; Cooling with acetone-dry ice |
Oxalyl chloride (936 mg, 7.38 mmol) is dissolved in dichlormethane (8 ml) under an argon atmosphere and cooled to-78 C in an acetone dry-ice bath. Dimethylsulfoxide (1. 153 g, 14. 76 mmol) is added dropwise and the mixture is stirred for 20 minutes at - 78 C. The compound of Example 32A (900 mg, 6.71 mmol) is added dropwise as a dichloromethane (7 ml) solution. The reaction is stirred for an additional two hours at - 78 C. Triethylamine (3.05 g, 30.19 mmol) is added and the reaction is kept at-78 C for 10 minutes, then allowed to warm to room temperature. The reaction is quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The ethyl acetate phase is washed with bicarbonate and brine, dried over magnesium <Desc/Clms Page number 48>sulphate monohydrate, filtered and concentrated to afford a yellow oil. The crude oil is purified by column chromatography on silica gel with dichloromethane as eluent. Yield: 424 mg (48percent of th.) HPLC (method 8): Rt1. 19 min MS(EI) :m/z= 132 (M) +IH-NMR (200 MHz,DMSO-d6) :6 = 5.69 (t, 1H); 7.65 (d, 1H); 8.31 (dd, 1H); 8.93 (d, 1H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With sodium periodate In tetrahydrofuran; water for 2 h; | To a stirred solution of the enamine (6.16g, 35.6mmol) in THF (130mL) was added a solution of sodium periodate (23.0g, 107mmol) in water (130mL). The mixture was stirred for 2h and filtered (Celite). The filtrate was diluted with water and extracted into CH2Cl2. Extracts were washed with brine, dried (MgSO4) and evaporated. The product was purified by flash chromatography on silica eluting with hexanes/ethyl acetate (7:3) to give the aldehyde (2.94g, 63percent): mp 91–92°C; 1H NMR δ 10.03 (d, J=0.7Hz, 1H), 9.28 (dd, J1=2.0Hz, J2=0.9Hz, 1H), 8.58 (ddd, J1=8.1Hz, J2=2.0Hz, J3=0.7Hz, 1H), 8.07 (dd, J1=8.1Hz, J2=0.9Hz, 1H). Anal. Calcd for C7H4N2O: C, 63.64; H, 3.05; N, 21.20. Found: C, 63.57; H, 3.00; N, 21.11. |
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