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CAS No. : | 1142197-14-5 | MDL No. : | MFCD11869551 |
Formula : | C8H8BrN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WCHBRVOAPMMHIR-UHFFFAOYSA-N |
M.W : | 198.06 | Pubchem ID : | 45788476 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.38 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 44.4 |
TPSA : | 12.89 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) : | -5.53 cm/s |
Log Po/w (iLOGP) : | 2.25 |
Log Po/w (XLOGP3) : | 2.79 |
Log Po/w (WLOGP) : | 2.66 |
Log Po/w (MLOGP) : | 2.22 |
Log Po/w (SILICOS-IT) : | 3.12 |
Consensus Log Po/w : | 2.61 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.2 |
Solubility : | 0.124 mg/ml ; 0.000626 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.72 |
Solubility : | 0.38 mg/ml ; 0.00192 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.48 |
Solubility : | 0.0656 mg/ml ; 0.000331 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.91 |
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: |
* 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 |
---|---|---|
76% | at 25℃; for 24 h; Inert atmosphere | General procedure: Aminopyridine (1 mmol) and corresponding Cu(II) halide (0.5 mmol) were dissolveddibromo(chloro)methane (6 mL) at 25 °C under an argon atmosphere. Alkyl nitrite (1.1 mmol)was added dropwise over 5 min and reaction mixture stirred at the appropriate temperature(Table 1 and 2) until GC-MS analysis of the reaction mixture indicated full consumption the of starting material. The reaction mixture was poured into 1 N NaOH (20 mL), stirred for 1 h andextracted with CH2Cl2 (3 × 20 mL). The combined organic extracts were dried (Na2SO4) andevaporated to dryness. The crude product was purified by column chromatography on silica gel,eluting with CH2Cl2. 2-Bromo-5-cyclopropylpyridine (2a): yield 76percent. Rf = 0.49. 1H NMR (400MHz, CDCl3) δ 8.17 (d, J = 2.4 Hz, 1H), 7.34 (d, J = 8.2 Hz, 1H), 7.15 (dd, J =8.2, 2.4 Hz, 1H), 1.89 – 1.82 (m, 1H), 1.10 – 0.98 (m, 2H), 0.75 – 0.64 (m,2H). 13C NMR (100 MHz, CDCl3) δ 148.6, 138.8, 138.7, 135.4, 127.5, 12.5,9.1. GC-MS: tR= 7.031 min (m/z (rel. in.)) 197 (43.52percent), 199 (41.85percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42 %Chromat. | With copper(ll) bromide; isopentyl nitrite In acetonitrile at 25℃; for 16 h; Inert atmosphere | General procedure: Aminopyridine (1 mmol) and corresponding Cu(II) halide (0.5 mmol) were dissolved dibromo(chloro)methane (6 mL) at 25 °C under an argon atmosphere. Alkyl nitrite (1.1 mmol)was added dropwise over 5 min and reaction mixture stirred at the appropriate temperature(Table 1 and 2) until GC-MS analysis of the reaction mixture indicated full consumption the of starting material. The reaction mixture was poured into 1 N NaOH (20 mL), stirred for 1 h and extracted with CH2Cl2 (3 × 20 mL). The combined organic extracts were dried (Na2SO4) andevaporated to dryness. The crude product was purified by column chromatography on silica gel,eluting with CH2Cl2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45 %Chromat. | With copper(ll) bromide; isopentyl nitrite In acetonitrile at 25℃; for 3 h; Inert atmosphere | General procedure: Aminopyridine (1 mmol) and corresponding Cu(II) halide (0.5 mmol) were dissolved dibromo(chloro)methane (6 mL) at 25 °C under an argon atmosphere. Alkyl nitrite (1.1 mmol)was added dropwise over 5 min and reaction mixture stirred at the appropriate temperature(Table 1 and 2) until GC-MS analysis of the reaction mixture indicated full consumption the of starting material. The reaction mixture was poured into 1 N NaOH (20 mL), stirred for 1 h and extracted with CH2Cl2 (3 × 20 mL). The combined organic extracts were dried (Na2SO4) andevaporated to dryness. The crude product was purified by column chromatography on silica gel,eluting with CH2Cl2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17 %Chromat. | With copper(ll) bromide; isopentyl nitrite In acetonitrile at 25℃; for 16 h; Inert atmosphere | General procedure: Aminopyridine (1 mmol) and corresponding Cu(II) halide (0.5 mmol) were dissolved dibromo(chloro)methane (6 mL) at 25 °C under an argon atmosphere. Alkyl nitrite (1.1 mmol)was added dropwise over 5 min and reaction mixture stirred at the appropriate temperature(Table 1 and 2) until GC-MS analysis of the reaction mixture indicated full consumption the of starting material. The reaction mixture was poured into 1 N NaOH (20 mL), stirred for 1 h and extracted with CH2Cl2 (3 × 20 mL). The combined organic extracts were dried (Na2SO4) andevaporated to dryness. The crude product was purified by column chromatography on silica gel,eluting with CH2Cl2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80 %Chromat. | at 25℃; for 72 h; Inert atmosphere | General procedure: Aminopyridine (1 mmol) and corresponding Cu(II) halide (0.5 mmol) were dissolveddibromo(chloro)methane (6 mL) at 25 °C under an argon atmosphere. Alkyl nitrite (1.1 mmol)was added dropwise over 5 min and reaction mixture stirred at the appropriate temperature(Table 1 and 2) until GC-MS analysis of the reaction mixture indicated full consumption the of starting material. The reaction mixture was poured into 1 N NaOH (20 mL), stirred for 1 h andextracted with CH2Cl2 (3 × 20 mL). The combined organic extracts were dried (Na2SO4) andevaporated to dryness. The crude product was purified by column chromatography on silica gel,eluting with CH2Cl2. 2-Bromo-5-cyclopropylpyridine (2a): yield 76percent. Rf = 0.49. 1H NMR (400MHz, CDCl3) δ 8.17 (d, J = 2.4 Hz, 1H), 7.34 (d, J = 8.2 Hz, 1H), 7.15 (dd, J =8.2, 2.4 Hz, 1H), 1.89 – 1.82 (m, 1H), 1.10 – 0.98 (m, 2H), 0.75 – 0.64 (m,2H). 13C NMR (100 MHz, CDCl3) δ 148.6, 138.8, 138.7, 135.4, 127.5, 12.5,9.1. GC-MS: tR= 7.031 min (m/z (rel. in.)) 197 (43.52percent), 199 (41.85percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21 %Chromat. | at 65℃; for 72 h; Inert atmosphere | General procedure: Aminopyridine (1 mmol) and corresponding Cu(II) halide (0.5 mmol) were dissolveddibromo(chloro)methane (6 mL) at 25 °C under an argon atmosphere. Alkyl nitrite (1.1 mmol)was added dropwise over 5 min and reaction mixture stirred at the appropriate temperature(Table 1 and 2) until GC-MS analysis of the reaction mixture indicated full consumption the of starting material. The reaction mixture was poured into 1 N NaOH (20 mL), stirred for 1 h andextracted with CH2Cl2 (3 × 20 mL). The combined organic extracts were dried (Na2SO4) andevaporated to dryness. The crude product was purified by column chromatography on silica gel,eluting with CH2Cl2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80 %Chromat. | at 65℃; for 1 h; Inert atmosphere | General procedure: Aminopyridine (1 mmol) and corresponding Cu(II) halide (0.5 mmol) were dissolveddibromo(chloro)methane (6 mL) at 25 °C under an argon atmosphere. Alkyl nitrite (1.1 mmol)was added dropwise over 5 min and reaction mixture stirred at the appropriate temperature(Table 1 and 2) until GC-MS analysis of the reaction mixture indicated full consumption the of starting material. The reaction mixture was poured into 1 N NaOH (20 mL), stirred for 1 h andextracted with CH2Cl2 (3 × 20 mL). The combined organic extracts were dried (Na2SO4) andevaporated to dryness. The crude product was purified by column chromatography on silica gel,eluting with CH2Cl2. 2-Bromo-5-cyclopropylpyridine (2a): yield 76percent. Rf = 0.49. 1H NMR (400MHz, CDCl3) δ 8.17 (d, J = 2.4 Hz, 1H), 7.34 (d, J = 8.2 Hz, 1H), 7.15 (dd, J =8.2, 2.4 Hz, 1H), 1.89 – 1.82 (m, 1H), 1.10 – 0.98 (m, 2H), 0.75 – 0.64 (m,2H). 13C NMR (100 MHz, CDCl3) δ 148.6, 138.8, 138.7, 135.4, 127.5, 12.5,9.1. GC-MS: tR= 7.031 min (m/z (rel. in.)) 197 (43.52percent), 199 (41.85percent). |
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