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Structure of 5397-31-9
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 5397-31-9 |
Formula : | C11H25NO |
M.W : | 187.32 |
SMILES Code : | NCCCOCC(CC)CCCC |
MDL No. : | MFCD00025619 |
InChI Key : | DVFGEIYOLIFSRX-UHFFFAOYSA-N |
Pubchem ID : | 21499 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H227-H302-H311-H314-H412 |
Precautionary Statements: | P210-P273-P280-P305+P351+P338-P310 |
Class: | 8(6.1) |
UN#: | 2922 |
Packing Group: | Ⅲ |
* 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 |
---|---|---|
93.2% | In water; at 120℃; for 4h; | While 93.5 g (0.50 moles) of <strong>[5397-31-9]3-(2-ethylhexyloxy)propylamine</strong> were agitated under cooling with water, 18.7 g (0.10 moles) of a compound (A) were added gradually. Thereafter, agitation was conducted for further 4 hours at 120C. After the obtained reaction liquid was cooled to the room temperature, 300 ml of ethyl acetate and 300 ml of water were added, then the liquid layers were separated and an ethyl acetate layer was washed twice with 200 ml of a saturated aqueous solution of sodium chloride. Subsequently ethyl acetate was distilled off under a reduced pressure and an obtained viscous liquid was purified with silica gel column chromatography to obtain 45.5 g of a compound (B) as colorless viscous liquid (yield 93.2%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonia; In tert-Amyl alcohol; water; toluene; at 60℃;pH 8.0 - 9; | 52 grams of 3 amino BENZOTRIFLUORIDE is mixed with 50 grams of 2 methyl 2 butanol and 200 mis of water are added, followed by 38 grams of sulfuric acid 96%. The mixture is iced to 5C and diazotized by the addition of 55 grams of a 40% solution of sodium nitrite. When the solution has become clear excess nitrous acid is reduced with SULFAMIC acid. This diazo is then added to a solution of 38 grams of 2 amino para cresol which has been dissolved in a mixture of 100 grams of 2 methyl 2 butanol and 100 grams of an aqueous solution containing 0.3 equivalents of naphthalene SULFONIC acids to which 1 gram each of acrylic acid and butyl methacrylate have been added as free radical suppressors. Coupling proceeds quickly at 5-10C and is brought to completion by the addition of sufficient sodium acetate solution to raise the pH to 2.5. When the azo coupling is complete 150 grams of toluene and 55 grams of hydrochloric acid 32% is added to the reaction. 60 grams of a 40% solution of sodium nitrite is now added to diazotize the amino azo compound. When this reaction is complete 0.3 molar equivalents of a composition made by condensing 0.3 equivalents of 3 amino phenol and 0.6 equivalents of 2 ethyl hexyl glycidyl ether dissolved as an 80% solution in toluene is added to the system. Coupling proceeds readily with the formation of a magenta red bisazo dye. The coupling is now adjusted to pH 9 by the addition of aqueous ammonia and heated to 60C. 0.3 molar equivalents of nickel chloride are now added to the system together with sufficient ammonia to stop the pH falling below 8.0. Formation of the metal complex is essentially instant as determined by TLC. 60 grams of 2 ethyl hexoxy propylamine is now added to the system and after a few minutes stirring agitation is stopped and the dye layer allowed to separate as an upper phase. The dye is then dried under vacuum to 110C and brought to a total weight of 700 grams with n-propanol. The product is a violet black with very good light fastness and solvent compatibility. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide; for 6.75h;Heating / reflux; | 26.82 g of a naphthalene-1,4,5,8-tetracarboxylic dianhydride and 250 ml of dehydrated DMF were introduced into a reactor. The reactor was heated to reflux. 19.5 g of <strong>[5397-31-9]3-(2-ethylhexyloxy)propylamine</strong> dissolved in 50 ml of dehydrated DMF was added dropwise into the reactor over 45 minutes while stirring. After the dropwise addition was completed, the resultant was further heated to reflux for 6 hours. After cooling, the resulting mixture was concentrated under a reduced pressure. The residue was diluted with toluene and the insoluble portion was filtered off. The filtrate was purified by silica gel column chromatography to obtain the desired product of a light yellow naphthalene monoimide derivative (12-1). Yield: 28.6 g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The reaction mixture contains toluene duisocyanate as a mixture of the 2,4 isomer and the 2,6 isomer in a 95/5 proportion (m=0.72 g and n=4.1 mmol) and a mixture of amines consisting of 0 mol % of tert-butylamine (m=0.31 g and n=4.2 mmol) and 50 mol % of <strong>[5397-31-9]3-(2-ethylhexyloxy)propylamine</strong> (m=0.79 g and n=4.2 mmol). The composition of the white powder obtained contains the mixture of products below: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Product distribution / selectivity; | The reaction mixture contains toluene diisocyanate as a mixture of the 2,4 isomer and the 2,6 isomer in a 95/5 proportion (m=15 g and n=86 mmol) and a mixture of amines consisting of 80 mol % of 2-ethylhexylamine (m=1.8 g and n=139 mmol) and 20 mol % of <strong>[5397-31-9]3-(2-ethylhexyloxy)propylamine</strong> (m=6.5 g and n=35 mmol). The composition of the white powder obtained is determined by HPLC coupled to mass spectrometry, and contains the mixture of products below in the expected proportions:; The reaction mixture contains toluene duisocyanate as a mixture of the 2,4 isomer and the 2,6 isomer in a 95/5 proportion (m=0.52 g and n=3 mmol) and a mixture of amines consisting of 50 mol % of 2-ethyihexylamine (m=0.39 g and n=3 mmol) and 50 mol % of <strong>[5397-31-9]3-(2-ethylhexyloxy)propylamine</strong> (m=0.56 g and n=3 mmol). The composition of the white powder obtained contains the same mixture of products as that obtained from Example 3, but in different proportions (confirmation by HPLC coupled to mass spectrometry). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 60℃; for 10h; | 2 g of para-fluoronitrobenzene was added to a solution of 20 ml of N-methylpyrrolidinone, 3.19 g of 2-ethylhexyl 3-aminopropyl ether and 2.35 g of K2CO3. The reaction medium was heated at 60 C. for 10 hours and, after it was cooled to room temperature, poured into a water+ice mixture. The resulting medium was extracted with ethyl acetate, and the organic phase was then concentrated by evaporating under vacuum. 2.73 g of N-[2-(3-ethylheptyloxy)ethyl]-4-nitro-1-aminobenzene (9) were obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
c) 19.9 parts of the trisazo dyestuffs of part b) above are suspended in 100 parts of water, 10.0 parts of [DIPROPYLENE] glycol monomethyl ether and 4. [8] parts of sodium acetate. After warming at [96C] for over one hour, 5.9 parts of copper sulphate are added in small portions for over one hour, followed by 20.0 parts of 25% ammonia. The mixture is heated to reflux for 12 hours whereupon a voluminous suspension of the copper complex results. The temperature is allowed to fall to [45C] over 2 hours (while stirring well) and the suspension is slowly reacted with a solution of 13.3 parts of [3-[(2-ETHYLHEXYL) OXY]-1-] propanamine in 70 parts of water and [8.] 3 parts of 30% HCI. The resulting precipitate is stirred a further hour at room temperature, filtered and the residue is washed salt free and dried. A compound of formula wherein R is methoxy, is obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | In methanol; at 70℃; for 3h; | Example 13A reaction vessel was charged with 180 parts by weight of <strong>[5397-31-9]3-(2-ethylhexyloxy)propylamine</strong>, 180 parts by weight of DL-4,4-dimethyl pyroglutamine acid, and 100 parts by weight of methanol, and the mixture was stirred at 70 C. for 3 hours. The resulting reaction mixture was stripped at 90 C. under reduced pressure to remove the methanol, and 335 parts by weight of white solid was obtained at a yield of 93%. Results of the 13C-NMR shown in Table 13, below, and absorption at 1685 cm-1 (from amide bond) in the measurement of IR spectrum confirmed that the resulting product was an amino acid compound represented by the following formula: TABLE 13 13C-NMR (CDCl3) 11.2~74.3ppm (CH, -CH2-, -CH3) 180.9ppm (-NH-CO-) 35.0ppm (-CO-C) 22.4ppm (C-CH3) 41.8ppm (-C-CH2-) 56.4ppm [-CH(NH2)(COOH)] 179.2ppm (-COOH) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 1 Red Complex from Reactive Red 120, 3-(2-Ethylhexyloxyl)Propylamine and Aliquat 336 (0102) 14.7 gram of Reactive Red 120 (50% dye content), 2.81 gram of 3-(2-ethylhexyloxy)-propyl amine, 0.84 gram of sodium bicarbonate and 30 mL of water were charged into a reactor equipped with agitator, temperature control and condenser. The mixture was heated to 80 C. for several hours until the starting material Reactive Red 120 was gone as monitored by TLC. Then 12.1 gram of Aliquat 336 was added slowly and stirred at 80 C. for one hour. The reaction mixture was cooled to room temperature and dark red solid was precipitated. The solid was filtered and washed with water to remove salts. 24.1 gram of red solid with color value of 12.8 was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; at 10 - 85℃; for 6h; | 18.4 parts of 2-chloro-4,6-diamino-1,3,5-triazine and 21 parts of 3- (2-ethylhexyloxy) propylamine were added to 100 parts of water and reacted at 10 DEG C for 1 hour.The obtained reaction product was reacted at 85C for 5 hours. The residue obtained by leaching the obtained reaction product was washed with water and then allowed to stand overnight in a thermostatic chamber at 100 for drying to obtain a compound represented by the following general formula (2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.25g | at 20℃; for 1h; | 1.87 g (10mmo1) of 3-(2-ethylhexyloxy) propylamine and the salicylic acid 1.38g (10mmol) were measured, respectively, and it taught the reaction container. Contents were stirred and mixed at the room temperature for 1 hour, and 3.25 g of 3-(2-ethylhexyloxy) propyl ammonium salicylate (the chemical formula 9, an orange liquid) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 0 - 20℃; for 2.5h; | General procedure: The BOC protected diversity building blocks were prepared from tert-butyl 2-bromoacetate towhich was added the different primary amine. To a stirred solution of the primary amine and 1equiv. of DIEA in 3 mL acetonitrile, 1 equiv. of tert-butyl 2-bromoacetate was added slowly in 0oC.After stirring in 0oC for 30 min, the reaction mixture was warmed to rt and stirred for 2 hr. Aftercompletion of the reaction, the solvent was concentrated in vacuum. The residue was purified bycolumn chromatography on silica gel (DCM: MeOH =95:5) to afford the amine linker as lightyellow oil. 64 different aromatic and aliphatic primary amines were used for diversity buildingblocks synthesis and the yields are between 40 %-60 %. |