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CAS No. : | 52068-30-1 | MDL No. : | MFCD00137741 |
Formula : | C13H15ClN2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OVNUPJXMCMTQCN-UHFFFAOYSA-N |
M.W : | 250.72 | Pubchem ID : | 3016725 |
Synonyms : |
|
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.08 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 71.59 |
TPSA : | 47.28 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.11 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 3.83 |
Log Po/w (WLOGP) : | 3.01 |
Log Po/w (MLOGP) : | 2.88 |
Log Po/w (SILICOS-IT) : | 1.87 |
Consensus Log Po/w : | 2.32 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.07 |
Solubility : | 0.0216 mg/ml ; 0.000086 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.52 |
Solubility : | 0.0076 mg/ml ; 0.0000303 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -4.76 |
Solubility : | 0.00437 mg/ml ; 0.0000174 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.81 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | 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 |
---|---|---|
96% | Stage #1: With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5 h; Stage #2: With tin(ll) chloride In water at 0℃; for 1 h; |
(4-(Benzyloxy)phenyl)hydrazine hydrochloride (2).; Note: The reaction mixture and all added solutions were maintained at 0 °C during this procedure. 4-Benzyloxyaniline hydrochloride (3.00 g, 12.5 mmol) was added to cone. aq. HC1 (25 mL) and stirred for 10 min at 0 °C, followed by dropwise addition of a solution of NaN02 (852 mg, 12.3 mmol) in water (6 mL) over the course of 15 min. The mixture was stirred for an additional 15 min-period and then a solution of SnCl2 (6.40 g, 33.1 mmol) in cone. aq. HC1 (7.5 mL) was added dropwise. The reaction mixture was stirred for 1 h and filtered to yield an off-white precipitate, which was washed with water and triturated with Et20, to yield 2 (3.01 g, 96percent):IR (ATR, neat) 3232, 2906 (br), 2693, 1568, 1508, 1242, 1177 cm"1; 1H NMR (DMSO-d6, 600 MHz) δ 10.11 (bs, 3 H), 7.44-7.40 (m, 2 H), 7.40-7.35 (m, 2 H), 7.33-7.29 (m, 1 H), 7.01-6.93 (m, 4 H), 5.05 (s, 2 H); 13C NMR (DMSO-d6, 150 MHz) δ 153.7, 139.1, 137.3, 128.5, 128.4, 128.3, 127.9, 127.7, 127.5, 117.1, 116.9, 115.5, 115.3, 69.5; HRMS (EI) m/z calcd for Ci3Hi4N20 214.1106, found 214.1110. |
92% | Stage #1: With hydrogenchloride In water at 0℃; for 0.166667 h; Stage #2: With sodium nitrite In water at 0℃; for 0.5 h; Stage #3: With tin(ll) chloride In water at 0℃; for 1 h; |
Note: The reaction mixture and all added solutions were maintainedat 0 C during this procedure. 4-Benzyloxyanilinehydrochloride (3) (3.0 g, 12.5 mmol) was added to concd aq HCl(25 mL) and stirred for 10 min at 0 C, followed by dropwise additionof NaNO2 (852 mg, 12.3 mmol) in water (6 mL) over the courseof 15 min. The mixture was stirred for additional 15 min and then asolution of SnCl2 (6.4 g, 33.1 mmol) in concd aq HCl (7.5 mL) wasadded dropwise. The reaction mixture was stirred for 1 h and filteredto yield an off-white precipitate, which was washed withwater and triturated with Et2O, to afford an off-white solid (2.9 g,92percent); Mp 179–181 C. IR: mmax (KBr) cm1: 3232, 2907 (br), 1638,1618, 1511, 1246, 1178. 1H NMR (DMSO-d6, 400 MHz) d 10.14(br s, 3H, NH–NH2), 7.35–7.48 (m, 4H, Ar-H), 7.27–7.35 (m, 1H,Ar-H), 6.92–7.05 (m, 4H, Ar-H), 5.06 (s, 2H, CH2). 13C NMR(DMSO-d6, 100 MHz) d 153.7 (ArC–O), 139.1 (ArC–N), 137.3(ArC), 128.5 (ArC), 128.4 (ArC), 128.3 (ArC), 127.9 (ArC), 127.7(ArC), 117.1 (ArC), 116.9 (ArC), 115.5 (ArC), 115.3 (ArC), 69.5(CH2). HRMS (EI): Found 215.1180 (M+H)+, C13H15N2O requires215.1184. |
82% | With hydrogenchloride; stannous chloride; sodium nitrite In diethyl ether; water | (a) 4-Benzyloxyphenylhydrazine hydrochloride To 4-benzyloxyaniline hydrochloride (250 g, 1.56 mol) are added water (355 ml) and con. hydrochloric acid (175 ml), and the mixture is stirred while suspending. A solution of NaNO2 (73.2 g, 1.06 mol) in water (180 ml) is dropwise added at a temperature of 0 - 5°C, followed by stirring at the same temperature for 1 hour (A solution). To con. hydrochloric acid (2.65) is added SnCl2 (604 g), and the A solution is added dropwise at a temperature of 0 - 5°C while stirring. After stirring at the same temperature for 30 minutes, Et2O (2) is further added thereto, followed by further stirring for 30 minutes. The precipitated crystals are filtered off, the crystals are added to methanol (3), and the mixture is stirred for 30 minutes. The crystals are filtered off, and dried to give 220 g of (a) (Yield 82percent). m.p. 187°C (MeOH-H2O) TLC (Merck No. 5714 Sol. CHCl3:MeOH=10:1) Rf=0.49 IR (Nujol) cm-1: 3230, 1585, 1510 1H-NMR (DMSO-D6) δ ppm: 5.03 (2H, s, -CH2-O), 7.35 (5H, s, C-phenyl), 11.0 (3H, br-s, -NH-NH2 * HCl) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With sodium nitrite In hydrogenchloride; water | A. 4-Benzyloxyphenylhydrazine hydrochloride A solution of sodium nitrite (3.8 g, 0.055 mol in 20 mL of H2 O), is added dropwise to an ice cold stirring suspension of 4-benzyloxyaniline (13.0 g, 0.055 mol in 150 mL of concentrated HCl). The reaction mixture is stirred for 90 minutes at -8° to 10° C. A solution of SnCl2.2H2 O (32.0 g, 0142 mol in 50 mL concentrated HCl) is added and stirred for 1 hour at 0° C. The reaction mixture is removed from the ice bath and is stirred at room temperature for 20 hours. The mixture is then filtered and washed with water to give 13.0 g (95percent yield) of product, m.p. 182°-185° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With sodium nitrite In hydrogenchloride; water | A. 4-Benzyloxyphenylhydrazine hydrochloride A solution of sodium nitrite (3.8 g, 0.055 mol in 20 mL of H2 O), is added dropwise to an ice cold stirring suspension of 4-benzyloxyaniline (13.0 g, 0.055 mol in 150 mL of concentrated HCl). The reaction mixture is stirred for 90 minutes at -8° to 10° C. A solution of SnCl2 *2H2 O (32.0 g, 0142 mol in 50 mL concentrated HCl) is added and stirred for i hour at 0° C. The reaction mixture is removed from the ice bath and is stirred at room temperature for 20 hours. The mixture is then filtered and washed with water to give 13.0 g (95percent yield) of product, m.p. 182°-185° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With acetic acid In ethanol at 75 - 80℃; | Example-2 4-Benzyloxy phenyl hydrazine hydrochloride (10 g, 40 mmol), 4-benzyloxy propiophenone (9.6 g, 40 mmol) and acetic acid (0.1 ml, 1.7 mmol) were suspended in 140 ml of ethanol and the mixture was refluxed for 12 hrs at a temperature of 75-80° C. During said period the product precipitates. After cooling the mixture at 10-15° C. the crystallized product was isolated by filtration and washed with chilled ethanol (30 ml) and water (50 ml). 5-Benzyloxy-2-(4-benzyloxy)-3-methyl-1H-indole melting at 152-153° C. was obtained in a yield of 15.7 g (94percent). 1H-NMR (DMSO) δ 10.65 (s, 1H); 7.55 (d, 2H); 7.50 (d, 4H); 7.30-7.45 (m, 6H); 7.21 (d, 1H); 7.10 (d, 1H); 7.10 (d, 1H); 6.91 (dd, 1H); 5.16 (s, 2H); 5.11 (s, 2H); 2.33 (s, 3H) |
94% | at 75 - 80℃; for 12 h; | Example-2 4-Benzyloxy phenyl hydrazine hydrochloride (10 g, 40 mmol), 4-benzyloxy propiophenone (9.6 g, 40 mmol) and acetic acid (0.1 ml, 1.7 mmol) were suspended in 140 ml of ethanol and the mixture was refluxed for 12 hrs at the temperature of 75 to 80°C. During said period the product precipitates. After cooling the mixture at 10 to 15°C the crystallized product was isolated by filtration and washed with chilled ethanol (30 ml) and water (50 ml). 5-Benzyloxy-2-(4-benzyloxy)-3-methyl-1H-indole melting at 152 to 153°C was obtained in a yield of 15.7 g (94percent). 1H-NMR (DMSO) δ 10.65 (s, 1H); 7.55 (d, 2H); 7.50(d, 4H); 7.30-7.45(m, 6H); 7.21(d, 1H); 7.10(d, 1H); 7.10(d, 1H); 6.91(dd, 1H); 5.16(s, 2H); 5.11(s, 2H); 2.33(s, 3H) |
84% | With hydrogenchloride In ethanol for 2 h; Reflux | 1-(4-(Benzyloxy)phenyl)propan-1-one (2) (1.9 g, 8.0 mmol) and1-(4-(benzyloxy)phenyl)hydrazine hydrochloride (4) (2.0 g,8.0 mmol) were dissolved in EtOH (50 mL) and 5 drops of conc.HCl was added and the mixture was refluxed for 2 h. The reaction mixture was then allowed to cool and was stirred for 1 h. The mixturewas filtered to afford an pale pink solid. The solid was washedwith cold EtOH (10 mL) followed by n-hexane (20 mL). (2.8 g, 84percent).Mp: 149–152 C.50 IR: mmax (KBr) cm1: 3470 (N–H), 2880, 2820,1620 (CC). 1H NMR (CDCl3, 400 MHz) d 7.86 (br s, 1H, NH),7.48–7.58 (m, 6H, Ar-H), 7.33–7.47 (m, 6H, Ar-H), 7.25–7.31 (m,1H, Ar-H), 7.14–7.18 (m, 1H, Ar-H), 7.07–7.13 (m, 2H, Ar-H), 6.97(d, J = 7.53 Hz, 1H, Ar-H), 5.18 (s, 2H, CH2), 5.15 (s, 2H CH2), 2.43(s, 3H, CH3) 13C NMR (CDCl3, 100 MHz) d 157.7 (BnO–C), 157.3(BnO–C), 143.6 (Ar-C–CH2), 137.3 (Cq), 136.3 (Cq), 136.0 (Cq),129.9 (ArC), 128.5 (ArC), 128.2 (ArC), 128.2 (ArC), 127.7 (ArC),127.6 (Ar-C), 127.1 (ArC), 120.4 (ArC), 114.7 (ArC), 114.6 (ArC),114.3 (ArC), 112.2 (Cq), 110.8 (CC), 108.8 (ArC), 102.0 (ArC),70.0 (CH2), 69.6 (CH2), 9.3 (CH3). HRMS (EI): Found 442.1797 (M+Na)+, C29H25NNaO2 requires 442.1783. |
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