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CAS No. : | 26735-20-6 | MDL No. : | MFCD06446874 |
Formula : | C10H22N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 170.30 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P260-P264-P271-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P403+P233-P405-P501 | UN#: | 2735 |
Hazard Statements: | H335-H314 | Packing Group: | Ⅱ |
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 |
---|---|---|
With phenol at 100℃; |
Yield | Reaction Conditions | Operation in experiment |
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With diethyl ether; ammonia; nickel at 125℃; Hydrogenation; |
Yield | Reaction Conditions | Operation in experiment |
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3-<Methyl-cyclohexylamino>-propionsaeure-nitril, H2 (Rh-Al2O3); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: N-methylcyclohexylamine; 3-(N-phthaloyl)propionaldehyde With sodium tris(acetoxy)borohydride at 20℃; Stage #2: With methanol; ammonia | 4 Description 4: λ/-Cyclohexyl-λ/-methyl-1,3-propanediamine; To a suspension of 3-(1 ,3-dioxo-1 ,3-dihydro-2H-isoindol-2-yl)propanal (200 mg, 0.98 mmol) in dichloromethane (5 mL) was added λ/-methylcyclohexanamine (88 mg, 0.78 mmol) in dichloromethane (5 mL) followed by sodium triacetoxyborohydride (311 mg, 1.47 mmol) and the reaction stirred at room temperature overnight. The reaction mixture was added to an SCX column, washed with methanol and eluted with 2M ammonia in methanol and the solvent removed in vacuo to give a yellow viscous oil (168 mg). An attempt to purify by SCX failed, so the mixture was separated between diethyl ether (10 mL) and aqueous sodium hydroxide (2M, 10 mL). The organic phase was concentrated in vacuo to give the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: trimethyl-benzyl-ammonium hydroxide 2: Raney nickel; diethyl ether; ammonia / 125 °C / 73550.8 - 91938.4 Torr / Hydrogenation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With calcium hydride; carbon dioxide; hydrogen In tetrahydrofuran at 50℃; for 16h; | 104 Example 104(4-Amino-3-(r3-(cvclohexvl-methvl-amino)-propylamino1-methvl>-phenvl)-phenyl-methanoneO; A mixture of 5-benzoyl-2-nitrobenzaldehyde (0.0058 mol) in THF (100ml) was hydrogenated with 10% Pd/C (1 g) as a catalyst in the presence of 4%thiophene solution (1 ml_). After uptake of H2 (3 equiv), the mixture was put inan autoclave. /V-cyclohexyl, A/-methyl-propane-1,3-diamine (0.01 mol) andCaH2 (0.5 g) were added and the mixture was reacted under 10 atm of CO2and 50 atm of H2 at 50°C for 16 hours. When the reaction was complete, themixture was purified over silica gel on a glass filter (eluent: 90:10CH2CI2:(CH3OH:NH3)). The product fractions were collected and the solventwas evaporated to yield the title compound as a residue. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 5-benzoyl-2-nitro-benzaldehyde With hydrogen In tetrahydrofuran Stage #2: N<SUP>1</SUP>-cyclohexyl-N<SUP>1</SUP>-methylpropane-1,3-diamine With calcium hydride; carbon dioxide; hydrogen In tetrahydrofuran at 50℃; for 16h; | 104 Example 104; (4-Amino-3-fr3-(cvclohexvl-methvl-amino)-propvlamino1-methvl>-phenyl)-phenyl-methanone; A mixture of 5-benzoyl-2-nitrobenzaldehyde (0.0058 mol) in THF (100ml) was hydrogenated with 10% Pd/C (1 g) as a catalyst in the presence of 4%thiophene solution (1 mL). After uptake of H2 (3 equiv), the mixture was put inan autoclave. A/-cyclohexyl, A/-methyl-propane-1,3-diamine (0.01 mol) andCaH2 (0.5 g) were added and the mixture was reacted under 10 atm of CO2and 50 atm of H2 at 50°C for 16 hours. When the reaction was complete, themixture was purified over silica gel on a glass filter (eluent: 90:10CH2Cl2:(CH3OH:NH3)). The product fractions were collected and the solventwas evaporated to yield the title compound as a residue. | |
Stage #1: 5-benzoyl-2-nitro-benzaldehyde With thiophene; hydrogen In tetrahydrofuran Stage #2: N<SUP>1</SUP>-cyclohexyl-N<SUP>1</SUP>-methylpropane-1,3-diamine With calcium hydride; carbon dioxide at 50℃; for 16h; | 104 A mixture of 5-benzoyl-2-nitrobenzaldehyde (0.0058 mol) in THF (100 ml) was hydrogenated with 10% Pd/C (1 g) as a catalyst in the presence of 4% thiophene solution (1 ml_). After uptake of H2 (3 equiv), the mixture was put in an autoclave. /V-cyclohexyl, Λ/-methyl-propane-1 ,3-diamine (0.01 mol) and CaH2 (0.5 g) were added and the mixture was reacted under 10 atm of CO2 and 50 atm of H2 at 50°C for 16 hours. When the reaction was complete, the mixture was purified over silica gel on a glass filter (eluent: 90:10 CH2CI2:(CH3OH:NH3)). The product fractions were collected and the solvent was evaporated to yield the title compound as a residue. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5.68 g | With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 18h; | 4.2.5. 10-(3-Chlorobenzyl)-N-(3-(cyclohexyl(methyl)amino)-propyl)-11-oxo-10,11 dihydrodibenzo[b,f][1,4]thiazepine-8-carboxamide (52) Ester 51 (16.12 g, 0.0393 mol) was dissolved in THF (170 mL) containing H2O (30 mL). After cooling to 0 °C, LiOH·H2O (4.95 g, 0.117 mol) was added in one portion. After 2 h at 0 °C, the reaction was warmed to rt. HPLC or TLC indicated that hydrolysis was complete after 23 h at which point the pH was adjusted to 7.0 by the addition of 2 M HCl. The remaining mixture was dried by sequential rotary evaporation followed by lyophilization with MeOH (6 × 100 mL) resulting in yellow wax. The wax was further dried by rotary evaporation of toluene (3 × 120 mL). The resulting material was suspended in EtN(iPr)2 (20.55 mL, 0.117 mmol) in DMF (150 mL). After cooling to 0 °C, HATU (22.42 g, 0.0590 mol) was in three portions over 15 min. The reaction was warmed to rt over 1 h. After an additional 2 h at rt, N-1-cyclohexyl-N-1-methylpropane-1,3-diamine (7.00 g, 0.0411 mmol) was added in 10 mL DMF. After 18 h of vigorous stirring at rt, the mixture was diluted in EtOAc (200 mL) and filtered with a mixture of 1:5 MeOH/EtOAc (1 L) through a DCVC column charged with 100 g of Celite (packed at top of column) and 100 g of silica gel (packed at bottom of column). The elutant was concentrated on a rotary evaporator. Flash chromatography (2:1 Hx/EtOAc to 10:1 MeOH/EtOAc) afforded 5.68 g (81%) of clear wax 52. 1H NMR (500 MHz, CD3OD) δ 7.96 (d, J = 1.9 Hz, 1H), 7.65 (m, 2H); 7.56 (dd, J = 1.9, 8.1 Hz, 1H), 7.48 (m, 1H), 7.40 (m, 1H), 7.38 (m, 2H), 7.29 (dd, J = 1.5, 7.4 Hz, 1H), 7.22 (t, J = 7.6 Hz, 1H), 7.18 (m, 1H) 5.84 (d, J = 15.5 Hz, 1H), 4.95 (d, J = 15.5 Hz, 1H), 3.44 (td, J = 1.7, 6.4 Hz, 2H), 3.20 (ddt, J = 3.4, 11.9, 14.3 Hz, 2H), 3.13 (t, J = 7.5 Hz, 2H), 2.76 (s, 3H), 1.98 (m, 4H), 1.88 (m, 2H), 1.67 (m, 1H), 1.47 (dq, J = 2.8, 12.9 Hz, 2H), 1.34 (tq, J = 2.8, 12.1 Hz, 2H), 1.17 (tq, J = 3.6, 13.0 Hz, 2H 1H); 13C NMR (125 MHz, CD3OD) δ 171.1, 169.1, 144.4, 141.7, 140.5, 139.7, 138.9, 137.0, 135.4, 134.6, 132.8, 132.5, 132.4, 131.1, 130.4, 129.2, 128.7, 127.5, 126.6, 126.4, 66.5, 54.6, 52.5, 38.9, 37.1, 36.6, 31.8, 27.8, 26.3, 26.2, 26.1; HREIMS [M+Na]+ m/z: 570.1917 (calcd for C31H34ClN3NaO2S, 570.1958). |