Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 65169-38-2 | MDL No. : | MFCD07082888 |
Formula : | C7H5ClN2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BXUFVXSRHLSIMN-UHFFFAOYSA-N |
M.W : | 152.58 | Pubchem ID : | 12387736 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 38.93 |
TPSA : | 36.68 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) : | -5.88 cm/s |
Log Po/w (iLOGP) : | 1.65 |
Log Po/w (XLOGP3) : | 1.9 |
Log Po/w (WLOGP) : | 1.92 |
Log Po/w (MLOGP) : | 0.73 |
Log Po/w (SILICOS-IT) : | 2.4 |
Consensus Log Po/w : | 1.72 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.43 |
Solubility : | 0.571 mg/ml ; 0.00374 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.29 |
Solubility : | 0.777 mg/ml ; 0.00509 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.1 |
Solubility : | 0.122 mg/ml ; 0.0008 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.72 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
85% | at 50 - 55℃; for 2 h; | 1. After enamine formation was complete as above in Step 1 B, HC1 gas was slowly charged at room temperature while stirring. After charging was completed the reaction mixture was heated to 50-55°C and held until the reaction was complete. Completion was checked by HPLC.2. If the reaction was not complete, step 1 was repeated. The reaction was typically complete in about 2 hours.3. After completion of reaction, the reaction mixture was distilled to remove approximately 75percent of solvent, followed by the addition of water (150-200ml) to the residue with stirring.4. The product was filtered and washed with water (3xSOml). 5. The product was dried at around 3 0-40°C under vacuum to a constant weight. The average telescope yield for the three steps (Steps lA, lB and 1C) is 85percent. The purity was 98Apercent by HPLC. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98.2% | With phosphorus pentachloride In water | (c) Preparation of 2-chloro-3-cyano-4-methylpyridine (Chlorination) The product of the preceding step, 4-methyl-3-cyano-2-pyridone (40.7 g, 0.304 moles) was added to a stirred solution of POCL3 (140 g, 0.912 moles) and PCl5 (19.0 g, 0.091 moles). The reaction was heated to reflux (approximately 115° C.) and held under those conditions for two hours. Excess POCL3 was removed by distillation. The reaction mixture was then cooled followed by the addition of water (30 mL) water. The aqueous mixture was extracted with 30 mL methylene chloride. The extracts were concentrated and 43.2 g was recovered as a tan solid, which was determined to be 2-chloro-3-cyano-4-methylpyridine (4). mp: 102-104° C. Yield: 98.2percent 1H NMR: 8.03 (d, J=2 Hz, 1H), 7.6 (d, J=2 Hz, 1H), 2.5 (s, 3H); 13C NMR 156.1, 152.6, 151.8, 124.9, 114.4, 111.8, 20.6 Mass spectrum m/z: 155, 154, 152, 117, 116, 90, 89, 76, 64, 63, 62 FTIR (KBr): 3144, 2979, 2834, 2228, 1653, 1616, 1540, 1484, 1242, 1218, 1173, 819, 607 cm-1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89.2% | for 1 h; Heating / reflux | Example 9 Synthesis of 2-chloro-4-methylpyridine-3-carbonitrile (9) To a 250 ML flask equipped with a magnetic stirrer was added 10g of 2-hydroxy-4-methyl-3-pyridinylcarbonitrile (8) and 60 ML of phosphorous oxychloride.. The mixture was refluxed for one hour.. The excess POCl3 was distilled under reduced pressure.. The residue was poured into water.. The crystalline material was filtered and dried at to give 10.2g (89.2percent) of (9).. m.p.: 109-110°C, NMR (DMSO); ppm: 2.56 (s,3H); 7.6 (bs,1H); 8.56 (m,1H). MS: (EI) m/z M+ 152, 146 |
88% | for 2 h; Reflux | A mixture of 2-hydroxy-4-methylpyridine-3-carbonitrile (3.0 g, 22.38 mmol; obtained as described in WO 2011/088201), phosphoryl chloride (6.26 mL, 67.16 mmol) and phosphorus pentachloride (1.4 g, 6.71 mmol) was refluxed for 2 hours. The reaction mixture was cooled to room temperature, and then concentrated under vacuo to dryness. The obtained residue was diluted with aqueous sodium bicarbonate solution. The precipitate thus obtained was collected by filtration and dried to give the title compound as an off-white solid (3.0 g, 88percent). MS(ESI)m/z: 153.1 (M+l) ; 1H NMR CDC13: δ 8.43 (d, J = 5.2 Hz, 1H), 7.22 (d, J = 4.8 Hz, 1H) , 2.8 ( s, 3H |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
180.1 g | Stage #1: at 20℃; for 4 h; Stage #2: at 20℃; for 5 h; Stage #3: With hydrogenchloride In isopropyl alcohol at 10℃; for 10 h; Cooling with ice |
Under ice-cooling, add to the reaction flask30percent by weight of hydrogen chloride in isopropanol 1.2 L,The reddish brown oil obtained in Example 1 was slowly added,After completion of the addition, hydrogen chloride gas was continuously introduced at 10 ° C,Keep the reaction for 10 hours;The reaction mixture was added dropwise to 6 L of water,Keeping stirring for 1 hour; filtering,The filter cake was washed with ice water, dried in vacuo,To obtain 180.1 g of 2-chloro-3-cyano-4-methylpyridine, and the HPLC purity was 99.8percent. |
[ 1195189-83-3 ]
2-Chloro-3-methylisonicotinonitrile
Similarity: 0.96
[ 14237-71-9 ]
2-Chloro-4,6-dimethylnicotinonitrile
Similarity: 0.95
[ 28900-10-9 ]
2-Chloro-6-methylnicotinonitrile
Similarity: 0.87
[ 875-35-4 ]
2,6-Dichloro-4-methylnicotinonitrile
Similarity: 0.85
[ 1195189-83-3 ]
2-Chloro-3-methylisonicotinonitrile
Similarity: 0.96
[ 14237-71-9 ]
2-Chloro-4,6-dimethylnicotinonitrile
Similarity: 0.95
[ 28900-10-9 ]
2-Chloro-6-methylnicotinonitrile
Similarity: 0.87
[ 875-35-4 ]
2,6-Dichloro-4-methylnicotinonitrile
Similarity: 0.85
[ 1195189-83-3 ]
2-Chloro-3-methylisonicotinonitrile
Similarity: 0.96
[ 14237-71-9 ]
2-Chloro-4,6-dimethylnicotinonitrile
Similarity: 0.95
[ 28900-10-9 ]
2-Chloro-6-methylnicotinonitrile
Similarity: 0.87
[ 875-35-4 ]
2,6-Dichloro-4-methylnicotinonitrile
Similarity: 0.85