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CAS No. : | 3843-97-8 | MDL No. : | MFCD20694404 |
Formula : | C8H10ClN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GXMFLLVURQXDPD-UHFFFAOYSA-N |
M.W : | 155.62 | Pubchem ID : | 12465045 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 45.63 |
TPSA : | 26.02 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) : | -5.35 cm/s |
Log Po/w (iLOGP) : | 1.99 |
Log Po/w (XLOGP3) : | 2.67 |
Log Po/w (WLOGP) : | 2.49 |
Log Po/w (MLOGP) : | 2.72 |
Log Po/w (SILICOS-IT) : | 2.54 |
Consensus Log Po/w : | 2.48 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.86 |
Solubility : | 0.212 mg/ml ; 0.00136 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.87 |
Solubility : | 0.211 mg/ml ; 0.00135 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.43 |
Solubility : | 0.0577 mg/ml ; 0.000371 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.07 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
100% | With iron(III) chloride; amino aminoalcohol In methanol at 20 - 80℃; for 5 h; Sealed tube | Step 3:ο a mixture of 4-chloro-l-ethyl-2-nitrobenzene (0.9 g, 4.9 mmol), iron (III) chloride (0.13 g, 0.49 mmol), and charcoal (80 mg, 6.6 mmol) in methanol (17 ml) was added hydrazine hydrate (0.95 ml, 20 mmol) in methanol (7 ml). The reaction mixture was stirred at rt as gas was evolved. When gas evolution ceased, the vial was sealed and heated at 80 deg C for 5 h (**pressure builds over time and vial needed to be vented frequently). The mixture was cooled to rt and filtered through celite washing with methanol, concentrated, and purified by silica gel chromatography (gradient 0 to 50percent EtOAc/hexanes). The product, aniline 4, is a light yellow oil (quant.); 1H NMR (400 MHz, DMSO-d6) δ 6.86 (dd, = 8.0, 0.7 Hz, 1H), 6.59 (d, = 2.2 Hz, 1H), 6.44 (dd, 7 = 8.0, 2.2 Hz, 1H), 5.11 (s, 2H), 2.43 - 2.31 (m, 2H), 1.06 (t, J = 7.5 Hz, 3H). |
97% | With iron(III) chloride; hydrazine hydrate In methanol for 13 h; Reflux | Step 3 : 5-Chloro-2-ethylanilineA solution of hydrazine hydrate (6.95 mL, 134.7 mmol) in MeOH (50 mL) was added dropwise to a solution of 4- chloro-1-ethyl-2-nitrobenzene (6.25 g, 33.7 mmol) in MeOH (120 mL), in the presence of iron(lll) chloride (547 mg, 3.4 mmol) and activated charcoal (547 mg), and the reaction mixture was stirred under reflux for 13 h. The solids were filtered over celite, the filtrate concentrated and purified by flash chromatography (hexane:AcOEt 9:1) to obtain the title compound as a light-pink oil (5.09 g, 97percent).1H NMR (400 MHz, DMSO-d6) δ ppm 1.09 (t, J =7.51 Hz, 3 H), 2.39 (q, J =7.49 Hz, 2 H), 5.13 (s, 2 H), 6.47 (dd, J =8.06, 2.20 Hz, 1 H), 6.62 (d, J =2.20 Hz, 1 H), 6.89 (d, J =8.06 Hz, 1 H). |
97% | With iron(III) chloride; hydrazine hydrate In methanol for 13 h; Reflux | Step 3: 5-Chloro-2-ethylanilineA solution of hydrazine hydrate (6.95 mL, 134.7 mmol) in methanol (50 mL) was added drop wise to a solution of 4- chloro-1-ethyl-2-nitrobenzene (6.25 g, 33.7 mmol) in methanol (120 mL), in the presence of iron (III) chloride (547 mg, 3.4 mmol) and activated charcoal (547 mg) and the reaction mixture was stirred under reflux for 13 h. The solids were filtered over celite, the filtrate concentrated and purified by flash chromatography (hexane/EtOAc 9/1) to obtain the title compound as a light-pink oil (5.09 g, 97percent).1H NMR (400 MHz, DMSO- /6) δ ppm 1.09 (t, J=7.51 Hz, 3 H), 2.39 (q, J=7A9 Hz, 2 H), 5.13 (s, 2 H), 6.47 (dd, J=8.06, 2.20 Hz, 1 H), 6.62 (d, J=2.20 Hz, 1 H), 6.89 (d, J=8.06 Hz, 1 H). |
97% | With iron(III) chloride; hydrazine hydrate In methanol for 14 h; Reflux | Step 3: 5’Chloro.2.ethylenlllne A solution of hydrazine hydrate (6.95 itt, 134.7 mmd) In methand (50 nt) was added drop wise to a sdudon of 4-chloro-1-ethyl-2-nlb’cbenzene (6.25 g, 33.7 mmd) In methanol (120 nt), In the presence of Iron (Ill) chloride (547mg,3Ammd)andacdedcftm&(M7mg)andthereadionmbcbirewasstirredunderrefiuxtrl4h.Thesolidswere removed by filtration through Celite, the titrate concentrated and purified by flash chromatography(hexanelEtOAc WI) to obtain the dUe compound as a light-pink 01(5.099,97percent).1H NMR (400 MHz, DM8O.) 86.89 (d, J= 8.0 Hz, IH), 6.62 (d, J= 22Hz, IH), 6.47 (dd, J=2.2, 8.0 Hz, IH), 5.12(s, 2H), 2.39 (q, J= 7.5 Hz, 2H), 1.09 (t, J= 7.4Hz, 3H). |
97% | With iron(III) chloride; pyrographite; hydrazine hydrate In methanol for 13 h; Reflux | Step 3: 5-Chloro-2-ethylaniline A solution of hydrazine hydrate (6.95 mL, 134.7 mmol) in MeOH (50 mL) was added dropwise to a solution of 4-chloro-1-ethyl-2-nitrobenzene (6.25 g, 33.7 mmol) in MeOH (120 mL), in the presence of iron(III) chloride (547 mg, 3.4 mmol) and activated charcoal (547 mg), and the reaction mixture was stirred under reflux for 13 h. The solids were filtered over celite, the filtrate concentrated and purified by flash chromatography (hexane:AcOEt 9:1) to obtain the title compound as a light-pink oil (5.09 g, 97percent). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.09 (t, J=7.51 Hz, 3H), 2.39 (q, J=7.49 Hz, 2H), 5.13 (s, 2H), 6.47 (dd, J=8.06, 2.20 Hz, 1H), 6.62 (d, J=2.20 Hz, 1H), 6.89 (d, J=8.06 Hz, 1H). |
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