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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.
Domiphen bromide is a chemical antiseptic and a quaternary ammonium compound, used as a cationic surfactant.
Synonyms: Domiphen (bromide); NSC-39415
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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.
Batch number can be found on the product's label following the word 'Batch'.
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.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 538-71-6 |
Formula : | C22H40BrNO |
M.W : | 414.46 |
SMILES Code : | CCCCCCCCCCCC[N+](C)(C)CCOC1=CC=CC=C1.[Br-] |
Synonyms : |
Domiphen (bromide); NSC-39415
|
MDL No. : | MFCD00011769 |
InChI Key : | OJIYIVCMRYCWSE-UHFFFAOYSA-M |
Pubchem ID : | 10866 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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 |
---|---|---|
Among these cationic compounds the following may be mentioned by way of example: diisobutylphenoxyethoxyethyldimethylbenzylammonium chloride, dodecyltrimethylammonium bromide, dodecyldimethyl(2-phenoxyethyl)ammonium bromide, benzyldimethylstearylammonium chloride, cetylpyridinium chloride, trimethylcetylammonium bromide, chlorhexidine, alexidine, and |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With sodium hydroxide; In water; for 2h; | Example III. Syntehsis of domiphen (4-chloro-2-methylphenoxy)acetate -[DOM][MCPA].0.025 Mole of <strong>[538-71-6]domiphen bromide</strong> was dissolved in 40 cm3 of distilled water. To this0.023 mole of sodium (4-chloro-2-methyl-phenoxy)acetate in aqueous NaOH was <n="7"/>added and reaction mixture was stirred for 2 hours. The product deposited as bottom layer of liquid, which was separated and dried at 333K under reduced pressure for 24 hours. The glassy product had 232K glass temperature and was isolated at 98% yield. The structure of product was confirmed by 1H and 13 NMR spectra as follows: 1H NMR (CDCl3) delta ppm = 0.88 (t, J = 6.7 Hz, 3H), 1.25 (m, 18H), 1.68 (q, J = 6.9 Hz, 2H), 2.20 (s, 3H), 3.22 (s, 6H), 3.33 (t, J = 3.4 Hz, 2H), 3.93 (t, J = 4.0 Hz, 2H), 4.34 (t, J = 3.6 Hz, 2H), 4.38 (s, 2H), 6.72 (d, J = 8.5 Hz, IH), 6.88 (d, J = Ll Hz, 2H), 6.96 (t, J = 2.5 Hz, IH), 7.00 (d, J = 3.6 Hz, IH), 7.0 l(d, J = 3.0 Hz, IH), 7.29 (t, J = 1.5 Hz, 2H); 13C NMR delta ppm = 14.0, 16.3, 22.6, 22.7, 26.2, 29.1, 29.2, 29.3, 29.4, 29.46, 31.8, 51.7, 61.8, 62.1, 65.5, 68.5, 112.7, 114.2, 121.9, 124.1, 126.0, 128.4, 129.7, 129.9, 156,0, 156.9, 173.3.Elemental analysis for CHN for obtained ionic pair of the formula C31H48ClNO4 (M = 534.17) showed: C = 69.49%, H = 9.42%, N = 2.68%. By comparison with calculated values: C = 69.70%, H = 9.06%, N = 2.62% one can conclude that obtained products are pure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99.5% | In water; | To a reaction flask, 0.025 mol <strong>[538-71-6]domiphen bromide</strong> dissolved in 40 mL of distilled water was placed. Then, 0.0025 mol of previously prepared sodium 3,6-dichloro-2- methoxybenzoate in 20 mL of water was added under continuous stirring. Immediately after mixing the reactants, the product was precipitated as the lower organic layer. The upper phase (water) was removed and the bottom layer was washed with water until disappearance of chloride ions in the effluent. Then the product was dried under reduced pressure at 60C for 24 hours. Yield 99.5%. Nuclear magnetic resonance: 1H NMR (CDC13) delta ppm = 0.88 (t, J = 6.7 Hz, 3H), 1.25 (m, 18H), 1.75 (q, J = 6.8 Hz, 2H), 3.44 (s, 6H), 3.55 (t, J = 8.4 Hz, 2H), 3.94 (s, 3H), 4.18 (t, J = 6.5 Hz, 2H), 4.43 (t, J = 6.6 Hz, 2H), 6.88 (d, J = 7.7 Hz, 2H), 7.00 (d , J = 8.5 Hz, 1H), 7.07 (d, J = 5.2 Hz, 1H), 7.26 (t, J = 2.2 Hz, 2H), 7.29 (t, J = 3.4 Hz, 1H) 13C NMR delta ppm = 14.1, 22.6, 22.9, 26.16, 26.19, 29.2, 29.33, 29.38, 29.49; 29.50, 31.8, 51.7, 61.6, 62.0, 62.1, 65.6, 114.1, 121.8, 125.3, 125.9, 127.1, 127, 7, 129.6, 140.0, 151.5, 156.7, 167.8.Elemental analysis for C30H45O4NCI2: values in percentage calculated C 64.96, H 8.19, N 2.53; measured values: C 65.12, H 8.38, N 2.41. DSC determined glass transition temperature equal to the -18C. TGA method: Tonset 5% = 177C; Tonset = 236C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | To a suspension of 0.045 mol (+)-(R)-2-(4-chloro-2-methylphenoxy) propionic acid in 40 mL of distilled water was added 10%> aqueous solution of KOH dropwise. The mixture was heated to a temperature of 313K. A stoichiometric amount of <strong>[538-71-6]domiphen bromide</strong> was added to the resultant clear solution and the reaction mixture was stirred for 24 hours. A two-layer mixture formed as a result of reaction and the product precipitated in the form of the lower layer. Chloroform (40 mL) was added and the layers were separated. The organic phase was washed with deionized water until the bromide ions were no longer present. The chloroform was evaporated and the residue dried at 353K under vacuum. Yield 99%>, purity 99%. 1H NMR (CDCl3) 5 ppm = 0.88 (t, J= 6.7 Hz, 3H), 1.26 (m, 18H), 1.59 (d, J= 6.9 Hz, 3H), 1.69 (kw, J= 6.9 Hz, 2H), 2.21 (s, 3H), 3.27 (s, 6H), 3.39 (t, J= 4.3 Hz, 2H), 4.01 (t, J = 8.4 Hz, 2H), 4.30 (t, J= 4.0 Hz, 2H), 4.46 (kw, J= 6.7 Hz, 1H), 6.82 (d, J= 8.5 Hz, 1H), 6.84 (d, J= 1.1 Hz, 2H), 6.87 (t, J= 5.6 Hz, 1H), 7.01 (dd, J1'2 = 0.6 Hz, J2 3 = 2.2 Etazeta,IotaEta) 7.02 (d, J = 0.8 Hz, 1H), 7.31 (t, J= 1.7 Hz, 2H); 13C NMR delta ppm = 14.0, 16.3, 19.4, 22.5, 22.7, 26.1, 29.07, 29.16, 29.24, 29.31, 29.41, 29.43, 31.7, 51.4, 61.87, 61.92, 65.6, 76.5, 113.2, 114.1, 122.0, 123.6, 125.8, 128.41, 128.44, 129.7, 156.1, 156.8, 176.7. Elemental analysis: C32H5oClN04: calculated C = 70.11%, H = 9.19%, N = 2.55%, observed: C = 69.79%, H = 8.99%, N = 2.67%. Glass transition: 239K, 514K |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
> 92% | With potassium hydroxide; In water; at 59.84℃; for 12h; | The API-IL domiphen L-proline ([DOM][L-PRO]) was prepared from <strong>[538-71-6]domiphen bromide</strong>and L-proline. General procedure is according to the procedures described in the literature[9]. 0.05 mol <strong>[538-71-6]domiphen bromide</strong> was dissolved in 40 mL distilled water. After thesolution was clear, equimolar amount of L-proline and potassium hydroxide in distilledwater (50 mL) were added. The mixture was stirred at 333 K for 12 h. Dichloromethanewas added and the mixture was allowed to stand overnight at room temperature. Thecrystalline KCl was removed by filtration and dichloromethane by distillation. Additionof dichloromethane was repeated until no further precipitation of KCl could be detected.The residue was dried overnight in vacuum at 80 C. The product was obtained as awhite solid with yield over 92%. The water content of the API-IL was determined byKarl-Fischer measurement, and the value was about 350 ppm. For additional characterization,the IR and 1H-NMR spectra of [DOM][L-PRO] were recorded (Figs. S1 andS2 in supplementary material). FT-IR spectra were recorded as KBr pellets, in the4000-500 cm-1 range on a Nicolet IR-470 spectrophotometer (Perkin Elmer). 1H NMRspectra were recorded in CDCl3 solution at 298 ± 1 K using Bruker DPX at 400 MHzand the solvent peak was used as reference. Elemental analysis was performed on aThermo Flash EA 1112 elemental analyzer.The characterization values obtained were: IR(KBr, cm-1): 3416(s), 3060(m), 3009(m),1597(s), 1591(s), 1497(s), 1467(m), 1410(m), 1231(s), 1176(m), 1032(m), 754(s), 720(w),690(s); 1H NMR: (400 MHz, CDCl3) d 7.32(m, 2H), 7.03(t, J = 12 Hz, 1H), 6.89(d,J = 8 Hz, 2H), 4.49(d, J = 4 Hz, 2H), 4.29(m, 2H), 3.71(q, 5H), 3.61(m, 2H), 3.48(s, 6H),1.24(m, 23H), 0.87(t, J = 12 Hz, 3H); elemental analysis found (%): C 72.25, H 10.87, N6.20; calc. for C27H48N2O3 (448.85):C 72.29, H 10.78, N 6.24. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | To a 100 mL round bottom flask was added 8.29 g (20 mmol) of compound <strong>[538-71-6]N,N-dimethyl-N-dodecyl-N-phenoxyethylammonium bromide</strong>, 100 mL of dioxane and 1.34 g of potassium hydroxide ( 24 mmol), reacting at 25 C for 6 hours, adding 1.69 g (10 mmol) of glyphosate,The reaction was stirred at 25 C for 6 hours. Filtering,The filtrate was concentrated to dryness under reduced pressure at 50 C or less.The product was washed with a small amount of dichloromethane and the product was placed in a vacuum oven.Drying at 50 C gave a white waxy solid with a yield of 92%. |