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CAS No. : | 115-70-8 | MDL No. : | MFCD00004680 |
Formula : | C5H13NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IOAOAKDONABGPZ-UHFFFAOYSA-N |
M.W : | 119.16 | Pubchem ID : | 8282 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 1.0 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 31.22 |
TPSA : | 66.48 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.95 cm/s |
Log Po/w (iLOGP) : | 1.26 |
Log Po/w (XLOGP3) : | -1.3 |
Log Po/w (WLOGP) : | -0.92 |
Log Po/w (MLOGP) : | -0.65 |
Log Po/w (SILICOS-IT) : | -0.68 |
Consensus Log Po/w : | -0.46 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | 0.44 |
Solubility : | 327.0 mg/ml ; 2.74 mol/l |
Class : | Highly soluble |
Log S (Ali) : | 0.4 |
Solubility : | 301.0 mg/ml ; 2.52 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | 0.03 |
Solubility : | 127.0 mg/ml ; 1.07 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: | 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 |
---|---|---|
With propylamine; hydrogen;molybdenum promoted RANEY type nickel catalyst; In methanol; at 35℃; under 36961.4 Torr;Autoclave; Industry scale;Product distribution / selectivity; | Examples 1-82-Amino-2-Ethyl-1,3-PropanediolExamples 1-8 relate to 2-amino-2-ethyl-1,3-propanediol (AEPD), which may be prepared from 1-nitropropane and formaldehyde).The analytical (characterization) methods used in the examples are as follows.GC Analysis. An HP 5890 Series II Gas Chromatograph with a J&W DB-5 column, 30 m*0.25 mm*1.0 mum is used to monitor effects of process changes on GC area %. The FID detector is set at 250 C. and the injector at 180 C. Oven temperature program: 60 C. for 4 minutes, ramp at 30 C./min to 220 C., hold 7 minutes, ramp at 20 C./min to 280 C., and hold 2 minutes. The injection volume was 1 muL with split ratio of 100:1 and helium as carrier gas.HPLC Analysis. The concentration of 2-nitrobutanol (2-NB), an undesired side product of the condensation reaction, and 2-nitro-2-ethyl-1,3-propanediol (NEPD) are determined by HPLC analysis. Using Waters 2695 Separations Module, HPLC analysis is performed with Alltech OA-1000 size exclusion column. The mobile phase is 0.01 N H2SO4 solution. Detection is achieved using Waters 996 Photodiode Array Detector at wave length of 273 nm. Five standard solutions containing both 2-NB and NEPD are prepared for calibration.Titration Parameters-Percent Free Formaldehyde. The amount of free formaldehyde is determined by reaction and titration. Hydroxylammonium chloride (NH2OH.HCl) reacts with formaldehyde to form hydrochloric acid. The hydrochloric acid is titrated with sodium hydroxide from which the percent of free formaldehyde is determined. Autotitrator 726 Titroprocessor from Metrohm Ltd. is used for titration. The instrument is calibrated with pH standard solutions at 4, 7, and 10 before titration. 0.1 N NaOH is used as titrant and deionized water as solvent. A blank is analyzed in the same manner as the sample.Percent Water by Karl Fischer. Water content in the sample is determined by potentiometric detection using volumetric Karl Fischer (KF) titration. Hydranal-Composite 5 is used as titrant and methanol as solvent.Experimental procedures used in Examples 1-8 are described below.Nitroalcohol Adjustment (NEPD with varying levels of free formaldehyde). For these studies, commercial NEPD concentrate is analyzed for weight percent (wt/wt) NEPD, 2-NB, and free formaldehyde. In order to understand the effect of excess formaldehyde on the composition of the NEPD product, the following study is conducted. To 10 g samples of NEPD solution is added 0.27, 0.54, 0.81, and 1.08 g of 37% aqueous formaldehyde. The samples are placed in a 40 C. water bath for 2 hours and analyzed. Analytical results are shown in Table 1. TABLE 1 weight percent 37% aqueous free formaldehyde added NEPD 2-NB formaldehyde none 66.06 4.26 0.05 0.27 g 67.46 1.38 0.28 0.54 g 66.80 0.51 1.24 0.81 g 66.32 0.29 2.11 1.08 g 64.05 0.23 2.88 With this information, the NEPD concentrate is adjusted to a desired formaldehyde level by charging a certain amount of 37% aqueous formaldehyde, mixing, and heating to 40 C. for 2 hours.Hydrogenation (reduction of NEPD to AEPD). The reactor used for these experiments is a two liter Parr 316 stainless steel autoclave equipped with a Parr model 4842 controller. The system is furnished with internal cooling coils and an external heating mantle for temperature control. The reactor is fitted with a magnetically driven agitator shaft with 3 pitched blade turbine impellers.The autoclave is charged with 240 g methanol, RANEY 3111 (a molybdenum promoted RANEY type nickel catalyst) at 5% loading based on the nitroalcohol feed, and 1-propylamine at 0-28 mole % based on nitroalcohol feed and free formaldehyde level. The autoclave is sealed, pressure purged 3 times with nitrogen (N2), 3 times with hydrogen (H2), and then pressured to and regulated at approximately 700 psig H2. Agitation is begun and set at 600 rpm. Heating is applied until the autoclave temperature reaches 35 C. The cooling water solenoid is set to control the reaction temperature at 55 C.The nitroalcohol feed is pumped to the reactor using an Eldex Duros model CC-100-S high pressure positive displacement pump. The supply side of the pump is connected to a graduated cylinder and the delivery side is fitted with a relief device. Depending on the amount of free formaldehyde in the NEPD solution (0.05-5.0%), 900-1000 g NEPD solution is pumped to the autoclave. The autoclave contents are sampled for GC analysis at 25, 50, and 75% of the NEPD feed. Following completion of the feed, the contents are held for 10 minutes at constant temperature under hydrogen pressure. The autoclave is then cooled to 25 C., vented, and purged with N2. The reaction product (final sample) is filtered through a glass microfiber filter to remove catalyst, transferred to glass bottles, and analyzed by GC.Concentration. A Buechi rotary evaporator, model 011, is used in the laboratory to remove methanol, propylamines, and enough water to produce 2-amino-2-ethyl-1,3-propanediol (AEPD) at 85 concentration. The pressure in the... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In methanol; at 0 - 20℃; for 16.6667h; | (19-1) Synthesis of [1,1-bis(hydroxymethyl)propyl]carbamic acid t-butyl ester (compound 19-1) To a solution of <strong>[115-70-8]2-amino-2-ethyl-1,3-propanediol</strong> (22.0 g) in methanol (500 ml) and N,N-diisopropylethylamine (64.3 ml) was added di-t-butyl dicarbonate (60.5 g) under ice-cooling, and the mixture was stirred for 40 min under ice-cooling and further at room temperature for 16 hr. 1M aqueous sodium hydroxide solution (184 ml) was added to the reaction mixture under ice-cooling and the mixture was stirred for 40 min. Methanol was removed under reduced pressure. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the object product (41.0 g) as a colorless oil. 1H-NMR(CDCl3)delta(ppm): 0.90(3H, t, J=7.5Hz), 1.45(9H, s), 1.59(2H, q, J=7.5Hz), 3.45(2H, brs), 3.60(2H, dd, J=6.9, 11.6Hz), 3.84(2H, dd, J=4.8, 11.6Hz), 4.89(1H, brs). | |
With N-ethyl-N,N-diisopropylamine; In methanol; at 20℃; for 16.6667h;Ice-cooling; | (30-1) Synthesis of [1,1-bis(hydroxymethyl)propyl]carbamic acid t-butyl ester (compound 30-1) [Show Image] To a solution of <strong>[115-70-8]2-amino-2-ethyl-1,3-propanediol</strong> (22.0 g) and N,N-diisopropylethylamine (64.3 ml) in methanol (500 ml) was added di-t-butyl-dicarbonate (60.5 g) under ice-cooling, and the mixture was stirred under ice-cooling for 40 min and further at room temperature for 16 hr. To the reaction mixture was added 1M aqueous sodium hydroxide solution (184 ml) under ice-cooling, and the mixture was stirred for 40 min, and methanol was removed under reduced pressure. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the object product (41.0 g) as a colorless oil. 1H-NMR(CDCl3) delta (ppm): 0.90(3H, t, J=7.5Hz), 1.45(9H, s), 1.59(2H, q, J=7.5Hz), 3.45(2H, brs), 3.60(2H, dd, J=6.9, 11.6Hz), 3.84(2H, dd, J=4.8, 11.6Hz), 4.89(1H, brs). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In chloroform; | F. Preparation of 5-hydroxymethyl-5-ethyl-3,3-dimethyl-2-morpholone: In a manner analogous to that described in Example 1A hereinbefore, the reaction of 2-amino- 2-ethyl-1,3-propanediol with chloroform in excess, and with acetone in large excess, with the addition of aqueous NaOH solution, yields a sodium salt which is cyclized with conc HCl to yield the compound identified as having the structure given immediately hereinabove. | |
With sodium hydroxide; In chloroform; | F. Preparation of 5-hydroxymethyl-5-ethyl-3,3-dimethyl-2-morpholone: In a manner analogous to that described in Example 1A hereinbefore, the reaction of <strong>[115-70-8]2-amino-2-ethyl-1,3-propanediol</strong> with chloroform in excess, and with acetone in large excess, with the addition of aqueous NaOH solution, yields a sodium salt which is cyclized with conc HCl to yield the compound identified as having the structure given immediately hereinabove. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1-methyl-2-pyrrolidonone; at 120℃; for 4h; | Compound (1G) (250 mg, 0.85 mmol) and <strong>[115-70-8]2-amino-2-ethyl-1,3-propanediol</strong> (298 mg, 2.5 mmol) in NMP (0.25 mL) were stirred at 120 C. for 4 h. After cooling to room temperature, the reaction mixture was poured into water and extracted with EtOAc (2*25 mL). The combined organic layers were dried over sodium sulfate and evaporated in vacuo. The crude product was purified by chromatography (silica gel, CH2Cl2: MeOH, 95:5) to afford 150 mg of the above-titled compound (Example 1). Mp=110-112.9 C. MW (M+H)+=376. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium hydroxide; triethylamine; In chloroform; water; toluene; | Example A14 3-Methyl-3-ethyl-5-hydroxymethyl-5-ethyl-2-morpholinone STR81 To a solution of 50.0 g (0.42 mol) of <strong>[115-70-8]2-amino-2-ethyl-1,3-propanediol</strong> in 75.3 g (0.63 moles) of chloroform and 302 g (4.2 moles) of 2-butanone, cooled to (0-5) C., 84 g (2.1 moles) of ground sodium hydroxide are added. After the addition, the mixture is maintained under stirring at room temperature overnight. To the mixture water is added in order to dissolve the salts. The water layer is separated and 70.0 ml (0.84 moles) of HCl 37% (% w/w) were added. The suspension is heated to reflux for 2 hours, concentrated in vacuum (90 C./10 mbar). The residue is taken up with 300 ml of toluene and the mixture heated to reflux being the residual water distilled off by azeotropation. The organic solution is then added with 46 g (0.46 moles) of triethylamine and heated to reflux for 2 hours. After cooling to room temperature, the mixture is filtered and the organic solution is concentrated in vacuum (60 C./10 mbar). NMR Analysis (300 MHz, CDCl3) confirms the structure: delta=0.83 (m, 6H); 1.5 (m, 6H); 3.28 (d, 2H); 4.25 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With nitrogen; urea; | EXAMPLE 12 (6918-43) Preparation of 4-ethyl-4-hydroxymethyl-2-oxazolidinone. A two-liter three-necked flask equipped with a thermometer, condenser, stirrer, and nitrogen inlet was charged with 2-amino-2-ethyl- 1,3-propandiol(786g, 6.3 mole) and urea(380 g, 6.3 mole). The reaction mixture was heated to 125 C. for seven hours and then 170 C. until no more gas releasing was observed. About 929 g of product was obtained. The product was confirmed by NMR spectrum to be 4-ethyl-4-hydroxymethyl-2-oxazolidinone. The reaction may be depicted as follows: STR17 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium methylate; In acetone; | (a) (+-)-Ethyl-4-(hydroxymethyl)-2-oxazolidinone Sodium methoxide (2.2 g, Aldrich) was added to a solution of <strong>[115-70-8]2-amino-2-ethyl-1,3-propanediol</strong> (100.0 g, Aldrich) and diethyl carbonate (169.0 g, Aldrich) This solution was refluxed in a Dean Stark apparatus until no more EtOH was collected. The reaction mixture was cooled, added acetone (200 ml) and allowed to stand overnite at room temperature. The resulting suspension was filtered to give 81.0 g of the desired product as a beige solid. 1 H NMR consistent with the proposed structure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33.19 g (90%) | EXAMPLE 14 Preparation of 4-hydroxymethyl-4-ethyl-2-undecyl-2-oxazoline 26 g (130 mmoles) of dodecanoic acid and 31 g (260 mmoles) of <strong>[115-70-8]2-amino-2-ethyl-1,3-propanediol</strong> were condensed together by heating at 185-190 C. for 30 hours. Work up and distillation of the residue at 160-162 C./1 mm Hg gave 33.19 g (90%) of the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
sodium methylate; In chloroform; benzene; | EXAMPLE 1 2-[(p-chloro-phenoxy)-isopropyl]-4-ethyl-4-hydroxymethyl-2-oxazoline 19.57 g. (0.1 moles) of 2-(p-chloro-phenoxy)-2-methylpropionitrile are reacted under stirring for 7 hours with 17.88 g. (0.15 moles) of 2-amino-2-ethyl-1,3-propane-diol in the presence of 0.41 g. (0.0075 moles) of sodium-methylate catalyst at a temperature between 140-150C. The reaction starts within a few minutes with an intensive development of ammonia gas at this temperature. The end of the reaction is indicated by the cessation of the gas development. After cooling to room temperature the grey-brown coloured oil is dissolved in 200 ml. of chloroform. The chloroform solution is washed with water to neutral reaction, the organic phase is dried on anhydrous magnesium sulphate and the chloroform is distilled off. The remaining oil (26.7 g.) is admixed with 100 ml. of petrolether and the precipitated crystals are filtered out and dried. The raw product obtained (22 g.) is dissolved in 30 ml. of benzene and after the addition of 80 ml. of petrolether the mixture is cooled to -10C and the precipitated white crystals are filtered. 19.35 g. of the product are obtained. M.p.: 94-95C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
sodium methylate; In chloroform; Petroleum ether; | EXAMPLE I 2-[(p-chlorophenoxy)-isopropyl]-4-ethyl-4-hydroxy-methyl-2-oxazoline 19.57 g (0.1 moles) of 2-(p-chlorophenoxy)-2-methyl-propionitrile are reacted under stirring for 7 hours with 17.88 g (0.15 moles) of 2-amino-2-ethyl-1,3-propane-diol in the presence of 0.41 g (0.0075 moles) of sodium-methylate catalyst at a temperature between 140-150 C. The reaction starts within a few minutes by an intensive development of ammonia gas at this temperature. The end of the reaction is indicated by the cessation of the gas development. After cooling to room temperature the grey-brown colored oil is dissolved in 200 ml of chloroform. The chloroform solution is washed with water to neutral reaction, the organic phase is dried on anhydrous magnesium sulphate and the chloroform is distilled off. The remaining oil (26.7 g) is admixed with 100 ml of petroleum ether and the precipitated crystals are filtered out and dried. The raw product 2-[(p-chlorophenoxy)-isopropyl]-4-ethyl-4-hydroxy-methyl-2-oxazoline obtained (22 g) is dissolved in 30 ml of benzene and after the addition of 80 ml of petroleum ether the mixture is cooled to -10 C. and precipitated white crystals are filtered. 19.35 g of the product are obtained. M.p.: 94-95 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In tetrahydrofuran; at 20℃; for 24h; | General procedure: To anhyd K2CO3 (1.15 g, 8.30 mmol) suspended in a dry THF (75 mL) solution containing cyanuric chloride (1.53 g, 8.30 mmol), solid 2-amino-2-methylpropanol (0.740 g, 8.30 mmol) was added, at room temperature, with vigorous stirring. The stirred suspension was kept at room temperature for an additional 24 h. when TLC monitoring (toluene/i-PrOH 2:1) indicated formation of the intermediate 3d as a single major spot. Water (7.50 mL) and anhyd K2CO3 (2.30 g, 16.60 mmol) were added and the reaction mixture was cooled at -10 C (-15 C). At this temperature, solid 1,4-dioxa-8-azaspiro[4.5]decane hydrochloride 2 (1.49 g, 8.30 mmol) was added portionwise (five equal portions as 0.298 g/portion each 90 min). The reaction mixture was kept at -10 C (-15 C) for an additional 36 h then allowed to reach room temperature very slowly. After filtering minerals, water (50 mL) and chloroform (100 mL) were added to the organic solution. The aqueous layer was extracted with chloroform (2×35 mL) and the combined organic layer was washed with water (3×35 mL) to neutrality. After drying over anhyd Na2SO4, the organic solution was evaporated under reduced pressure to dryness to provide 2.88 g crude product, which was crystallised from boiling ethanol (6 mL) to yield, after standing for 24 h at -18 C, the pure title compound 4d (2.42 g, 85% yield with respect to cyanuric chloride). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.7% | In methanol;Reflux; | General procedure: The ligands and complexes were synthesized following the procedureshown in Scheme 1. The methanol solution of (R)-(+)-2-amino-3-phenyl-1-propanol (0.151g,1 mmol) was added to o-vanillin (0.152g, 1 mmol) in 10 mL methanol. The mixed solution wasrefluxed under stirring for 3-4 h. The resulting yellow solution was filtered and dried in vacuum.Then the yellow product of H2L1 was obtained, which was washed with ether for threetimes and dried at room temperature. Yield: 86.3% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; | Example 902-(N-1,1-dihydroxymethylpropyl)aminoethyl-5-chloro-2-naphthylketone 8332 Vinyl-5-chloro-2-naphthylketone (28.4 mg) and <strong>[115-70-8]2-amino-2-ethyl-1,3-propanediol</strong> (11.4 mg) were reacted in dichloromethane (0.3 mL).NMR (CDCl3) 0.9 (m, 3H), 1.6 (m, 2H), 3.05 (m, 2H), 3.2 (m, 2H), 3.4 (m, 2H), 3.6 (m, 2H), 7.4-8.3 (6H)TG 64.5 (3 mumol) 44.5 (10 mumol) 11.7 (30 mumol)SOCE 0 (10 mumol) 10 (30 mumol) 30 (100 mumol)IICR 10 (10 mumol) 20 (30 mumol) 100 (100 mumol) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | In methanol; for 4h;Reflux; | The Schiff base ligand was prepared by the reflux condensation of 15 mL methanolic solution of 2-hydroxy-1-naphthaldehyde (1.72 g, 10 mmol) with 15 mL methanolic solution of <strong>[115-70-8]2-amino-2-ethyl-1,3-propanediol</strong> (1.19 g, 10 mmol) for 4 h with vigorous stirring and subsequently cooled to r.t. The volume of the resultant yellow solution was reduced in vacuo using a rotary evaporator to ca. 5 cm3. A yellow precipitate was deposited adding the anhydrous diethyl ether. The precipitates were then recrystallized from methanol. Yield: 78%. M.p.: 138-41 C. IR (KBr pellet: cm- 1): 3444s, 2923s, 1644s, 1542m, 1384m, 1252w. 1H NMR data (400 MHz, CDCl3) delta/ppm 8.907(s, 1H, -CH=N), 7.694-7.695(d, 1H, AR-H), 7.322-7.370(t, 1H, AR-H), 7.245-7.291(m, 2H, AR-H), 7.073-7.110(t, 1H, AR-H), 6.657-6.602(d, 1H, AR-H), 4.677(br, 2H, -OH), 3.934-4.00(t, 4H, -CH2OH), 1.62-1.783(m, 2H, -CH2CH3), 0.935-0.975(t, 3H, -CH3); 13C NMR (CDCl3): delta/ppm 178.627(1C, AR-OH), 156.189(1C, -CH=N), 138.103, 134.174, 129.189, 127.911, 128.841, 125.204, 122.426, 117.715, 106.416(9C, -C10H6), 63.332-66.425(2C, -CH2OH), 53.365(1C, tert-C), 25.823(1C, -CH2CH3), 7.335(-CH2CH3). UV-vis (CH3OH): lambdamax, nm 231, 248, 305, 398. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1,4-dioxane; at 150℃; for 2h; | Example 1412-(N-methyl-1,1-dihydroxymethylpropyl)aminoethyl-1-naphthylketone 8410 1-acetyl naphthalene (170 mg), <strong>[115-70-8]2-amino-2-ethyl-1,3-propanediol</strong> (161 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150 C. for 2 hours.NMR (CDCl3) 0.9 (m, 3H), 2.5 (m, 2H), 3.6 (m, 2H), 3.7 (m, 2H), 4.4 (m, 4H), 7.4-8.0 (7H)TG 81.5 (3 mumol) 80.2 (10 mumol) 61.6 (30 mumol)SOCE 0 (10 mumol) 0 (30 mumol) 0 (100 mumol)IICR 20 (10 mumol) 20 (30 mumol) 20 (100 mumol) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | In chlorobenzene; for 72h;Inert atmosphere; Reflux; | 2,2'-Dipyridyl-6-carboximidic acid methyl ester (108 mg, 0.51 mmol, 1 equiv) was added to a solution of 2-amino-2-ethylpropane-1,3-diol (61 mg, 0.51 mmol, 1 equiv) in chlorobenzene (5 mL) at rt. The reaction mixture was refluxed for three days, and then concentrated. The crude material was purifiedby column chromatography (petroleum ether/EtOAc: 50/50) to afford the diol-amide 11 as a pale yellow oil (63 mg, 0.19 mmol, 39%yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With potassium carbonate; In dimethyl sulfoxide; at 100℃; for 0.75h;Inert atmosphere; Microwave irradiation; | Ethyl quinoline-8-carboxylate (200 mg,1 mmol, 1 equiv), 2-amino-2-ethylpropane-1,3-diol (131 mg,1.1 mmol, 1.1 equiv), and K2CO3 (151 mg, 1.1 mmol, 1.1 equiv) were dissolved in DMSO (3 mL) in a sealed microwave vial containing a stir bar. The mixture was heated under MW to 100 C for 45 min.The suspension was filtered and the solvent was evaporated under reduced pressure (water bath 90 C). The crude material was purified by column chromatography (DCM/MeOH: 90/10) to afford the diol-amide 13 as an orange oil (200 mg, 0.73 mmol, 73% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
216 mg | With triethylamine; In tetrahydrofuran;Inert atmosphere; | Methyl chloroformate (116 mL, 1.5 mmol,1 equiv) was slowly added to a solution of 6-phenyl-pyridine-2-carboxylic acid (300 mg, 1.5 mmol, 1 equiv) and Et3N (230 mL,1.7 mmol, 1.13 equiv) in THF (30 mL) at 0 C and the resulting mixture was stirred in an ice bath for 30 min. Then, the white precipitate of triethyl ammonium chloride was removed by filtration.A clear solution of the mixed anhydride was thus obtained and was added to a solution of 2-amino-2-ethylpropane-1,3-diol(178 mg, 1.5 mmol, 1 equiv) and Et3N (230 mL, 1.7 mmol,1.13 equiv) in THF. The reaction mixture was stirred overnight, and then concentrated. The crude material was purified by column chromatography (petroleum ether/EtOAc: 50/50) to afford the diolamide 9 as a white solid (216 mg, 0.72 mmol, 48% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | General procedure: The mixture of 5,6-dimethyl-1-formyl-9-methoxy-6H-pyrido[4,3-b]carbazole (4) (0.91 g, 3mmol), toluene-4-sulfonic acid (0.86 g, 5 mmol),appropriate amine (5 mmol): (2-amino-1,3-propanediol or 2-amino-2-methyl-1-propanol or 2-aminoethanol or 2-amino-2-methyl-1,3-propanediolor <strong>[115-70-8]2-amino-2-ethyl-1,3-propanediol</strong>) and toluene(300 mL) was refluxed for 4 h. After this time, thesolvent was evaporated to 1/3 volume. Sodiumborohydride (0.91 g) was added to the residue andthe mixture was stirred for 24 h. Next, the solventwas evaporated, the solid was dissolved in water(100 mL), and hydrochloric acid was added to pH =4. After 0.5 h, conc. aq. ammonia (or sodium hydrogencarbonate) was added to the mixture to pH = 9. The residue was extracted with chloroform and theextract was dried with magnesium sulfate. Afterevaporation of solvent, the solid residue was purifiedby chromatography on a silica gel column withchloroform : methanol, in an appropriate proportion. |
Tags: 115-70-8 synthesis path| 115-70-8 SDS| 115-70-8 COA| 115-70-8 purity| 115-70-8 application| 115-70-8 NMR| 115-70-8 COA| 115-70-8 structure
[ 17016-89-6 ]
(S)-2-Amino-3-methylbutan-1-ol hydrochloride
Similarity: 0.78
[ 115-69-5 ]
2-Amino-2-methyl-1,3-propanediol
Similarity: 0.76
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Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
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 |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
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 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
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 |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
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. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
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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