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CAS No. : | 5041-09-8 | MDL No. : | MFCD00060199 |
Formula : | C4H12ClN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BSMNBEHEFWDHJD-UHFFFAOYSA-N |
M.W : | 109.60 | Pubchem ID : | 12206183 |
Synonyms : |
|
Num. heavy atoms : | 6 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 1.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 31.01 |
TPSA : | 26.02 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.88 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.53 |
Log Po/w (WLOGP) : | 1.4 |
Log Po/w (MLOGP) : | 1.16 |
Log Po/w (SILICOS-IT) : | 0.03 |
Consensus Log Po/w : | 0.82 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 3.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.42 |
Solubility : | 4.19 mg/ml ; 0.0382 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.69 |
Solubility : | 2.26 mg/ml ; 0.0206 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.61 |
Solubility : | 26.8 mg/ml ; 0.244 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319 | 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 |
---|---|---|
79% | Stage #1: With (R)-Carvone In propan-1-ol at 20 - 190℃; for 0.0833333 h; Sealed tube; Microwave irradiation Stage #2: With hydrogenchloride In propan-1-ol; water at 190℃; for 0.0833333 h; Microwave irradiation |
General procedure: General “One-Pot” Procedure for the Decarboxylation of Amino Acids [0045] A magnetic stir bar, 3 mL of n-PrOH, 10 mmol of R-Carvone, and 5 mmol of amino acid were charged to a pressure vessel. The vessel was heated from room temperature to 190° C. over 5 min with stirring. If necessary the reaction vessel was maintained at 190° C. for additional time until the slurry became clear. The vessel was allowed to cool to below the solvent boiling point, carefully vented to release evolved CO2, and 10 mL of 2M HCl was added. The vessel was heated to 190° C. over 5 min with stirring and allowed to cool. The aqueous reaction mixture was washed three times with 25 mL of ether and water solvent distilled off from the hydrochloride salt. The hydrochloride salt was transferred to a vacuum oven and dried overnight at 150° C. and 10 Torr. The hydrochloride salt was then weighed and analyzed via IR and NMR.; 2-methylpropan-1-amine hydrochloride, δH 0.83 6H d J=4, 1.79 1H m J=8, 2.69 2H d J=8; δC 18.8, 26.2, 46.3 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 130 - 140℃; in einem indifferenten Loesungsmittel; |
Yield | Reaction Conditions | Operation in experiment |
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With phenol at 120℃; |
Yield | Reaction Conditions | Operation in experiment |
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With nitrobenzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water at 60℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With chloroform; sulfur dioxide; chlorine Irradiation.UV-Licht und Behandeln des Reaktionsprodukts mit wss. NaOH; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With calcium chloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hypochlorite |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trichlorophosphate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trichlorophosphate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 150℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(i) MeOH, (ii) aq. HCl; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In toluene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane | ||
In dichloromethane with soln. of anhydrousa alkylammonium chloride in CH2Cl2, 5°C; filtering off, drying in vac.; | ||
In dichloromethane with soln. of anhydrousa alkylammonium chloride in CH2Cl2, 5°C; filtering off, drying in vac.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chlorobenzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide In methanol at 100℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With phosphorus pentachloride In chlorobenzene at 150 - 160℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuryl dichloride In acetonitrile |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With phosphorus pentachloride In benzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(i) NaOMe, MeOH, (ii) /BRN= 3606922/; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With N,N-dimethyl-cyclohexanamine; phosphorus pentoxide at 180℃; for 1.16667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With N,N-dimethyl-cyclohexanamine; phosphorus pentoxide at 220℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With N,N-dimethyl-cyclohexanamine; phosphorus pentoxide at 220℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With N,N-dimethyl-cyclohexanamine; phosphorus pentoxide at 220℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With N,N-dimethyl-cyclohexanamine; phosphorus pentoxide at 220℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium cyanoborohydride In methanol for 36h; Ambient temperature; pH neutral (12N HCl); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; formic acid; iodosylbenzene 1.) CH3CN, H2O, 15 h, room temp.; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In ethanol for 12h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With triethylamine In diethyl ether; ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With N,N-dimethyl-cyclohexanamine; phosphorus pentoxide at 150℃; for 1.25h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In benzene for 2h; Ambient temperature; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With magnesium sulfate; triethylamine In dichloromethane for 24h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With hydrogenchloride In benzene for 12h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With N,N-dimethyl-cyclohexanamine; phosphorus pentoxide at 240℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With N,N-dimethyl-cyclohexanamine; phosphorus pentoxide at 180℃; for 0.75h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 55% 2: 8% 3: 0.8 g | With N,N-dimethyl-cyclohexanamine; phosphorus pentoxide at 180℃; for 0.75h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With diphenyl-phosphinic acid; triethylamine In N,N-dimethyl-formamide at 0℃; for 10h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With diphenyl-phosphinic acid; triethylamine In N,N-dimethyl-formamide at 0℃; for 10h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In ethanol Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With butan-1-ol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 150℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dimethyl sulfoxide at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70.3% | With phosphorus pentachloride In chlorobenzene at 90 - 100℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: N-isobutyl-N-triphenylmethylamine With trifluoroacetic acid In dichloromethane at 20℃; for 0.166667h; Stage #2: With hydrogenchloride In methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42.3% | at 140℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In diethyl ether for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With triethylamine In ethanol at 150℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 1,3-dihydroxyacetone dimer; potassium thioacyanate; isobutylamine hydrochloride With acetic acid In butan-1-ol at 20℃; for 24h; Stage #2: With water In acetic acid; butan-1-ol for 0.5h; | 275 Reference Example 275 A mixture of potassium thiocyanate (25.9 g), dihydroxyacetone dimer (16.0 g), and isobutylamine hydrochloride (25.0 g) was added by portions to a mixed solution of acetic acid (19.2 ml) and 1-butanol (128 ml). The mixture was stirred for 1 day at room temperature, water (26 ml) was added to the mixture, and the mixture was stirred for 30 minutes. The precipitated solid was collected by filtration, and further washed with water (40 ml) twice and diisopropyl ether once. The obtained solid was dried under reduced pressure, to give 5-hydroxymethyl-1-isobutyl-2-mercaptoimidazole (15.1 g) as colorless crystals. 1H-NMR (200 MHz, DMSO-d6) δ 0.85 (6H, d, J = 6.6 Hz), 2.29 to 2.43 (1H, m), 3.80 (2H, d, J = 7.2 Hz), 4.33 (2H, d, J = 4.8 Hz), 5.21 (1H, t, J = 4.8 Hz), 6.81 (1H, s), 12.00 (1H, br) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With hydrogenchloride In ethanol at 110℃; for 9h; | 4 3-(Isobutylamino)-1-(thiophen-2-yl)propan-1-one · HCl (II, X = S, R = isobutyl) Example 4 3-(Isobutylamino)-1-(thiophen-2-yl)propan-1-one · HCl (II, X = S, R = isobutyl) 2-Acetylthiophene (6.3 g, 50 mmol); isobutylamine hydrochloride (8.3 g, 75 mmol, 1.5 eq); paraformaldehyde (2.1 g, 75 mmol, 1.5 eq); HCl conc. (0.3 g); ethanol (35 mL); 110 °C for 9 hours; ca. 2 to 2.5 bar; removing of ethanol (35 mL) in vacuo; addition of ethyl acetate (50 mL); ca. 56 % yield. 1H-NMR δ (DMSO-d6, 400 MHz): 9.0 (2 H, s, br), 8.08 (1 H, dd), 7.99 (1 H, dd), 7.29 (1 H, dd), 3.55 (2 H, t), 3.22 (2 H, t), 2.78 (2 H, d), 2.03 (1 H, m), 0.96 (6 H, d). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | 33-1) 5-Hydroxymethyl-1-isobutylimidazole The title compound was obtained in a yield of 45percent according to the same procedure as Preparation 31-1) using dihydroxyacetone and isobutylamine hydrochloride as starting materials. 1H NMR(CDCl3) delta0.90(d, 6H), 1.76(m, 1H), 3.62(d, 2H), 4.24(brs, 1H), 4.60(s, 2H), 6.85(s, 1H), 7.45(s, 1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol byproducts: water; mixt. in aq. alcoholic soln., under N2; pptn. (cooling), washed (EtOH/ether), evapn.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; water mixing of stoich. amts. of the amine hydrochloride and FeCl2*4H2O in aq. alc. soln. under N2, crystn. upon cooling; washing (ethanol/ether), drying (vac.); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In hydrogenchloride; water addn. of stoichiometric amounts of aq. soln. of alkanaminium chloride to aq. HCl soln. of SnCl4*5H2O; filtration, washing with aq. HCl, drying in a vac. desiccator over NaOH and P2O5; | ||
In hydrogenchloride concd. by heating; | ||
In hydrogenchloride concd. by heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In not given An excess of the chloride of the base is added to a freshly prepd. soln. of RuO4 in concd. HCl;; crystn.; recrystn. from dild. HCl, dried over H2SO4 in a desiccator;; | ||
In not given An excess of the chloride of the base is added to a freshly prepd. soln. of RuO4 in concd. HCl;; crystn.; recrystn. from dild. HCl, dried over H2SO4 in a desiccator;; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water addn. of the freshly prepared chloride to an aq. solution of Na2{OsCl6};; recrystn. from dild. HCl;; | ||
In water addn. of the freshly prepared chloride to an aq. solution of Na2{OsCl6};; recrystn. from dild. HCl;; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water evapn. of aq. soln. over H2SO4, recrystn. (dild. HCl);; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water evapn. of aq. soln. over H2SO4, recrystn. (dild. HCl);; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | ||
69% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With 18-crown-6 ether In diethyl ether refluxing under Ar for 5 h; cooling, evapn. of solvent, sublimating residue under vac.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With NaOH In water addn. of tungstate soln. (pH = 6.5) to ammonium salt soln. at 60°C;; pptn. recrystallized from water while addn. of ammonium salt at 80°C; pptn. washed with water and dried on air;; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol satn. of soln. with HCl; addn. of ether;; pptn.;; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; water heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; water dissoln. of RhCl3 in excess of aq. alkylammonium chloride, addn. of EtOHand large excess of amine (stirring; crystn.); cooling in ice, collection (filtration), washing (EtOH), drying in air, recrystn. (aq. EtOH); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water mixing stoich. amts. of satd. Zn-salt soln. and org. compd., pptn. on slow cooling; twice recrystn. from same solvent, suction filtration, washing (Et2O), drying; DSC; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 20°C;; | ||
at 20°C;; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | Stage #1: 5,7-dinitro-quinolin-8-ol With sodium tetrahydroborate In ethanol; N,N-dimethyl-formamide Cooling; Stage #2: formaldehyd; isobutylamine hydrochloride With phosphoric acid In ethanol; water; N,N-dimethyl-formamide at 5℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine In butan-1-ol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
529 mg | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; | |
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | Stage #1: L-valine With (R)-Carvone In propan-1-ol at 20 - 190℃; for 0.0833333h; Sealed tube; Microwave irradiation; Stage #2: With hydrogenchloride In propan-1-ol; water at 190℃; for 0.0833333h; Microwave irradiation; | General “One-Pot” Procedure for the Decarboxylation of Amino Acids General procedure: General “One-Pot” Procedure for the Decarboxylation of Amino Acids [0045] A magnetic stir bar, 3 mL of n-PrOH, 10 mmol of R-Carvone, and 5 mmol of amino acid were charged to a pressure vessel. The vessel was heated from room temperature to 190° C. over 5 min with stirring. If necessary the reaction vessel was maintained at 190° C. for additional time until the slurry became clear. The vessel was allowed to cool to below the solvent boiling point, carefully vented to release evolved CO2, and 10 mL of 2M HCl was added. The vessel was heated to 190° C. over 5 min with stirring and allowed to cool. The aqueous reaction mixture was washed three times with 25 mL of ether and water solvent distilled off from the hydrochloride salt. The hydrochloride salt was transferred to a vacuum oven and dried overnight at 150° C. and 10 Torr. The hydrochloride salt was then weighed and analyzed via IR and NMR.; 2-methylpropan-1-amine hydrochloride, δH 0.83 6H d J=4, 1.79 1H m J=8, 2.69 2H d J=8; δC 18.8, 26.2, 46.3 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: cellulose With sodium periodate; lithium chloride at 75℃; for 3h; Stage #2: isobutylamine hydrochloride With hydrogenchloride; 2-picoline borane complex In water at 20℃; for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53.4 mg | With hydrogenchloride; water In diethyl ether at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 130 - 150℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With hydrogenchloride In propan-1-ol at 190℃; for 0.0833333h; Microwave irradiation; Green chemistry; | General Decarboxylation Procedure General procedure: Ten mL of 2M HCl was then added in a one-pot fashion, and, in all cases but threonine, the reaction vessel was heated to 190°Cover 5 min with stirring and then allowed to cool. In the case of the temperature-sensitive threonine, soxhlet extraction with toluene was performed at 80°C to remove R-carvone from the reaction mixture. The aqueous reaction mixture was washed three times with 25 mL of ether, and then water solvent was distilled off from the hydrochloride salt. The hydrochloride salt was transferred to a vacuum oven and dried overnight at 150 °C and 10 Torr. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2-(diphenylphosphanyl)-1-(2-methoxyphenyl)-1H-pyrrole; palladium dichloride In tetrahydrofuran at 125℃; for 24h; Inert atmosphere; Autoclave; Overall yield = 74 %; Overall yield = 157.3 mg; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With hydrogenchloride; hydrogen In propan-1-ol; water at 60 - 70℃; for 18h; Flow reactor; | |
98% | Stage #1: Isobutyronitrile With cobalt pivalate; 1,1,3,3-Tetramethyldisiloxane; tert-butylisonitrile at 80℃; for 24h; Stage #2: With hydrogenchloride In diethyl ether at 20℃; for 0.5h; | |
55% | Stage #1: Isobutyronitrile With potassium <i>tert</i>-butylate In tetrahydrofuran at 80℃; for 12h; Glovebox; Inert atmosphere; Sealed tube; Stage #2: With sodium hydroxide In tetrahydrofuran; water at 20℃; Glovebox; Inert atmosphere; Sealed tube; Stage #3: With hydrogenchloride In methanol; diethyl ether at 20℃; for 0.333333h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: cyclohexanedione monoethylene ketal; isobutylamine hydrochloride With titanium(IV) isopropylate; triethylamine In ethanol at 20℃; for 10h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In ethanol at 20℃; for 8h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | Stage #1: ISOPROPYLAMIDE With [(aNHC)KN(SiMe3)2]2; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In toluene at 40℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Stage #2: With water; sodium hydroxide In diethyl ether; toluene at 40℃; for 1h; Inert atmosphere; Glovebox; Schlenk technique; Stage #3: With hydrogenchloride In diethyl ether; water Inert atmosphere; Glovebox; Schlenk technique; | |
62% | Stage #1: ISOPROPYLAMIDE With phenylsilane; C28H18ClMnN2O2; potassium <i>tert</i>-butylate In tetrahydrofuran at 50℃; for 12h; Inert atmosphere; Glovebox; Stage #2: With sodium hydroxide In tetrahydrofuran for 3h; Inert atmosphere; Glovebox; Stage #3: With hydrogenchloride In methanol; diethyl ether Glovebox; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | Stage #1: C13H14F4N2O; 4-Nitrophenyl chloroformate With triethylamine In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere; Stage #2: isobutylamine hydrochloride With dmap; triethylamine In methanol; dichloromethane at 0 - 20℃; for 36h; | 181 To a precooled (0 °C) solution of intermediate 2.132 (150 mg, 0.571 mmol) and p-nitrophenylchloroformate (156 mg, 0.775 mmol) in CH2Cl2 (4 mL) under N2 atmosphere was added dropwise triethylamine (22 µL, 1.6 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 16 h, then quenched with NaHCO3 (sat. aq.). The layers were separated, and the aqueous phase was extracted with CH2Cl2 (3x). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo. Flash chromatography (SiO2, 70:30 hexanes:ethyl acetate) afforded the product, which was carried forward. (0636) [00214] To a precooled (0 °C) vial charged with iso-butylamine ^HCl (13 µL, 0.13 mmol) was added a solution of intermediate (30. mg, 0.066 mmol), triethylamine (20 µL, 0.1 mmol) and 4-dimethylaminopyridine (2 mg, 0.002 mmol) in CH2Cl2 (0.5 mL) and MeOH (0.5 mL). The resulting mixtures were allowed to warm to room temperature and stirred for 36 h, then diluted with wet DMSO (0.5 mL), filtered through Celite, and purified via mass- directed isolation using ultra-performance liquid chromatography (4.6 mg, 18% yield).1H NMR (500 MHz, Acetonitrile-d3) d 9.29 (s, 1H), 7.81 (d, J = 13.5 Hz, 1H), 7.59 (t, J = 8.3 Hz, 1H), 7.40 (d, J = 9.2 Hz, 1H), 5.37 (s, 1H), 3.85 (d, J = 13.8 Hz, 1H), 3.71- 3.55 (m, 1H), 3.26 (dd, J = 13.7, 8.9 Hz, 1H), 3.03- 2.85 (m, 2H), 2.52- 2.42 (m, 2H), 1.88-1.76 (m, 1H), 1.76- 1.66 (m, 1H), 1.61 (t, J = 8.9 Hz, 1H), 1.54- 1.37 (m, 1H), 0.92- 0.74 (m, 3H); AMM 412.1631 (ESI) m/z [calc for C18H23F4N3O2Na (M+Na)+ 412.1624]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In ethanol Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | Stage #1: 1-nitroisobutane With C36H56Cl3CrN2O; magnesium; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In tetrahydrofuran at 60℃; for 24h; Inert atmosphere; Schlenk technique; Stage #2: With hydrogenchloride In tetrahydrofuran; water; ethyl acetate at 20℃; | |
83% | Stage #1: 1-nitroisobutane With triethyl borane; potassium <i>tert</i>-butylate; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In tetrahydrofuran at 100℃; for 24h; Inert atmosphere; Sealed tube; Green chemistry; Stage #2: With hydrogenchloride In water at 20℃; for 6h; Green chemistry; | 5 In a nitrogen environment, the aliphatic nitro derivatives (0.6mmol), pinacol borane (3.6mmol, 6.0equiv), tetrahydrofuran (2mL), triethylboron (5mol%), potassium tert-butoxide (5mol %) into a 10mL sealed tube, and place it in a 100 oil bath with heating and stirring for 24 hours. At the end of the reaction, add 2mL of 1M hydrochloric acid aqueous solution to the reaction solution under the air environment, and stir at room temperature for 6h, and finally filter the solid The aliphatic amine hydrochloride product was obtained by draining it out, and the yield was 83%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19 mg | Stage #1: N-isobutyl-4,4,5,5-tetramethyl-N-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolan-2-amine With sodium hydroxide In diethyl ether; water monomer for 1h; Stage #2: With hydrogenchloride In methanol | |
With hydrogenchloride In diethyl ether Inert atmosphere; |
Tags: 5041-09-8 synthesis path| 5041-09-8 SDS| 5041-09-8 COA| 5041-09-8 purity| 5041-09-8 application| 5041-09-8 NMR| 5041-09-8 COA| 5041-09-8 structure
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Code | Phrase |
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P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
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P272 | Contaminated work clothing should not be allowed out of the workplace. |
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Code | Phrase |
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P304 | IF INHALED: |
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P306 | IF ON CLOTHING: |
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P322 | |
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P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
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P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
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P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
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P405 | Store locked up. |
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P422 | |
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Disposal | |
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Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
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H220 | Extremely flammable gas |
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H226 | Flammable liquid and vapour |
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H229 | Pressurized container: may burst if heated |
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H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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