* Storage: Sealed in dry,Room Temperature
CAS No. : | 56-95-1 | MDL No. : | MFCD00012532 |
Formula : | C26H38Cl2N10O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WDRFFJWBUDTUCA-UHFFFAOYSA-N |
M.W : | 625.55 | Pubchem ID : | 9562059 |
Synonyms : |
Hibitane diacetate
| Chemical Name : | 1,1'-Hexamethylenebis[5-(p-chlorophenyl)biguanide] diacetate |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 potassium hydroxide; In water; at 50℃;pH 11.0;Product distribution / selectivity; | Chlorhexidine (C22H30N10Cl2), obtained commercially, was reacted with sodium hydroxide to form chlorhexidine dihydrate (C22H30N10Cl2.1.3H2O). Approximately 100 g of a starting material <strong>[56-95-1]chlorhexidine diacetate</strong> was dissolved in 1300 mL of warm deionized water at approximately 50 C. 6 M potassium hydroxide (KOH) was added drop-wise with stirring. A precipitate formed immediately and continued to form upon addition of base until the solution reached a pH of 11. The precipitate was filtered and washed six times with warm, 50 C., deionized water, and then dried in an oven at 60 C. to produce approximately 78 g of chlorhexidine dihydrate. These compounds were analyzed using energy dispersive x-ray spectroscopy (EDX), Fourier transform infrared spectroscopy (FTIR), thermogravimetric analysis (TGA), and proton nuclear magnetic resonance (1H NMR),EDXChlorhexidine and chlorhexidine dihydrate were analyzed using EDX, a technique well known to those of skill in the art. Table 1 provides both the theoretical and actual elemental composition of chlorhexidine and chlorhexidine dihydrate obtained from the EDX analysis.; FTIRFTIR was used to compare the characteristic peaks of different functional groups in chlorhexidine dihydrate and chlorhexidine. Chlorhexidine had peaks at 3513, 3473, 3410, 3371 cm-1, characteristic of N-H stretching, and peaks at 1635 and 1595 cm-1, characteristic of aromatic and aliphatic guanidine absorptions (ArNHC(N-H)NHAr) and ((CH3)2NC(N-H)C(CH3)2). The chlorhexidine dihydrate spectrum of FIG. 3 had peaks at 3458 and 3406 cm-1, characteristic of N-H stretching. The decreased frequencies likely were attributable to hydrogen bonding. The chlorhexidine dihydrate spectrum also had a broad band between 3300-2850 cm-1 that was characteristic of an intermolecular OH hydrogen-bonded bridge (typically appearing between 3405 and 2936 cm-1). Chlorhexidine dihydrate also had the aromatic guanadine peak at 1605 cm-1. The decreased frequency, again, likely was attributable to hydrogen bonding.TGATGA was used to determine the moisture content of chlorhexidine base (FIG. 4) and chlorhexidine dehydrate (FIG. 5). As shown by the derivative weight loss curve of FIG. 5, there was a loss of a small molecule (presumably water) at 100 C. and a mass decrease of 4.700% at 120.07 C. for chlorhexidine dihydrate. The mass loss likely corresponded to the 3.98% water present in the chlorhexidine dihydrate.1H NMRProton nuclear magnetic resonance (1H NMR) spectroscopy was used to analyze the structure of chlorhexidine dihydrate. The 1H NMR spectrum of chlorhexidine (FIG. 6) had peaks at 8.5, 7.25, 7.0, 3.3, 3.15, 1.9, 1.6, 1.4, and 1.25 ppm. The 1H NMR spectrum of chlorhexidine dihydrate (FIG. 7) had peaks at 8.5, 7.2, 6.9, 3.3, 3.15, 1.85, 1.6, 1.35, and 1.25 ppm, similar to that of chlorhexidine. The intensities, however, were different. Specifically, the peak at 8.5 ppm was significantly less intense in the chlorhexidine dihydrate spectrum. The peaks at 8.5, 1.85, and 1.35 ppm showed no spin-spin coupling and were therefore in rapid equilibrium in the deuterated methanol solvent (tautomerization). The water appeared to preferentially stabilize some of the tautomers of chlorhexidine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In water; at 50℃;pH 11.0; | Commercially obtained chlorhexidine (C22H30N10Cl2), obtained commercially, was reacted with sodium hydroxide to form chlorhexidine hydrate. Approximately 100 g of a starting material <strong>[56-95-1]chlorhexidine diacetate</strong> was dissolved in 1300 ml of warm deionized water at approximately 50 C. 6 M potassium hydroxide (KOH) was added drop-wise with stirring. A precipitate formed immediately and continued to form upon addition of base until the solution reached a pH of 11. The precipitate was filtered and washed six times with warm, 50 C., deionized water, and then dried in an oven at 60 C. to produce approximately 78 g of chlorhexidine hydrate.The chlorhexidine hydrate has a theoretical formulation of C22H30N10Cl2.nH2O. In multiple production runs, the chlorhexidine hydrate product was determined to have an actual degree of hydration (n) of about 1.4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | In water; butan-1-ol; at 20℃; for 48.0h; | General procedure: The synthesis and physical characterization of four beta-lactam-based chlorhexidine GUMBOS, namely chlorhexidine di-ampicillin, chlorhexidine carbenicillin, chlorhexidine di-cephalothin and chlorhexidinedi-oxacillin, were performed using methods previously reported by Cole et al. (2013) [24], but with slight modification. Briefly, stoichiometric amounts of <strong>[56-95-1]chlorhexidine diacetate</strong> and beta-lactam antibiotic, with the latter in slight excess, was stirred for 48 h at room temperature in a butanol:water (1:1) mixture to ensure the complete formation of the beta-lactam-based chlorhexidine GUMBOS. After removing butanol from the GUMBOS products, they were purified by washing several times with cold deionized water and dried overnight with a high vacuum. The structures of chlorhexidine di-ampicillin, chlorhexidine carbenicillin, chlorhexidine di-oxacillin and chlorhexidine di-cephalothin (Figure 1) were mainly confirmed by NMR, mass spectrometry and elemental analysis, among other spectroscopic data. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In water; butan-1-ol; at 20℃; for 48.0h; | General procedure: The synthesis and physical characterization of four beta-lactam-based chlorhexidine GUMBOS, namely chlorhexidine di-ampicillin, chlorhexidine carbenicillin, chlorhexidine di-cephalothin and chlorhexidinedi-oxacillin, were performed using methods previously reported by Cole et al. (2013) [24], but with slight modification. Briefly, stoichiometric amounts of <strong>[56-95-1]chlorhexidine diacetate</strong> and beta-lactam antibiotic, with the latter in slight excess, was stirred for 48 h at room temperature in a butanol:water (1:1) mixture to ensure the complete formation of the beta-lactam-based chlorhexidine GUMBOS. After removing butanol from the GUMBOS products, they were purified by washing several times with cold deionized water and dried overnight with a high vacuum. The structures of chlorhexidine di-ampicillin, chlorhexidine carbenicillin, chlorhexidine di-oxacillin and chlorhexidine di-cephalothin (Figure 1) were mainly confirmed by NMR, mass spectrometry and elemental analysis, among other spectroscopic data. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In water; butan-1-ol; at 20℃; for 48.0h; | General procedure: The synthesis and physical characterization of four beta-lactam-based chlorhexidine GUMBOS, namely chlorhexidine di-ampicillin, chlorhexidine carbenicillin, chlorhexidine di-cephalothin and chlorhexidinedi-oxacillin, were performed using methods previously reported by Cole et al. (2013) [24], but with slight modification. Briefly, stoichiometric amounts of <strong>[56-95-1]chlorhexidine diacetate</strong> and beta-lactam antibiotic, with the latter in slight excess, was stirred for 48 h at room temperature in a butanol:water (1:1) mixture to ensure the complete formation of the beta-lactam-based chlorhexidine GUMBOS. After removing butanol from the GUMBOS products, they were purified by washing several times with cold deionized water and dried overnight with a high vacuum. The structures of chlorhexidine di-ampicillin, chlorhexidine carbenicillin, chlorhexidine di-oxacillin and chlorhexidine di-cephalothin (Figure 1) were mainly confirmed by NMR, mass spectrometry and elemental analysis, among other spectroscopic data. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | In water; butan-1-ol; at 20℃; for 48.0h; | General procedure: The synthesis and physical characterization of four beta-lactam-based chlorhexidine GUMBOS, namely chlorhexidine di-ampicillin, chlorhexidine carbenicillin, chlorhexidine di-cephalothin and chlorhexidinedi-oxacillin, were performed using methods previously reported by Cole et al. (2013) [24], but with slight modification. Briefly, stoichiometric amounts of <strong>[56-95-1]chlorhexidine diacetate</strong> and beta-lactam antibiotic, with the latter in slight excess, was stirred for 48 h at room temperature in a butanol:water (1:1) mixture to ensure the complete formation of the beta-lactam-based chlorhexidine GUMBOS. After removing butanol from the GUMBOS products, they were purified by washing several times with cold deionized water and dried overnight with a high vacuum. The structures of chlorhexidine di-ampicillin, chlorhexidine carbenicillin, chlorhexidine di-oxacillin and chlorhexidine di-cephalothin (Figure 1) were mainly confirmed by NMR, mass spectrometry and elemental analysis, among other spectroscopic data. Chlorhexidine di-ampicillin. Off-White Solid, yield 98%, Water solubility: 126 mug/mL. Solubilityproduct constant (Ksp): 4.63 × 10-12 M3. 1H-NMR (400 Hz, DMSO-d6) delta 8.58-8.36 (m, 2 H) 7.21-7.50(m, 18 H), 5.08 (d, J = 2.74 Hz, 2 H), 4.96 (s, 4 H), 3.69 (d, J = 3.13 Hz, 2 H), 3.26 (s, 2 H), 3.07 (dt,J = 7.04, 6.65 Hz, 4 H), 1.85 (s, 4 H), 1.57 (s, 6 H), 1.49 (s, 4 H), 1.46 (quin, 4 H), 1.44 (s, 4 H), 1.27(quin, 4 H), 1.17 (s, 6 H), 1.15 (s, 2 H). 13C-NMR (101 MHz, DMSO) delta 180.88, 72.88, 172.36, 166.94,166.76, 139.07, 128.24, 127.01-128.43, 121.90, 76.07, 68.38, 60.80, 60.01, 58.64, 27.38, 26.76, 25.97.Anal. calcd. for C54H68Cl2N16O8S2: C, 53.86; H, 5.69; Cl, 5.89; N, 18.61; O, 10.63; S, 5.33. Found: C,53.22; H, 5.81; Cl, 5.56; N, 18.37; S, 5.16. HRMS (ESI) m/z calcd. for C54H68Cl2N16O8S2, [M+H+],1203.4424; found, 1203.4136. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; for 2.0h;Heating; | General procedure: The nickel(II) complexes, chlorhexidinenickel(II) chloride dihydrate (complex 1), chlorhexidinenickel(II) bromide dihydrate (complex 2) and chlorhexidinenickel(II) acetate ethanolate(complex 3), were prepared by the following general method. <strong>[56-95-1]Chlorhexidine diacetate</strong>monohydrate, 0.6435 g (1 mmol), was dissolved in 30 mL ethanol, under slight heating. Therequired solid metal salt, i.e., NiCl2·6H2O (0.2377 g, 1.0 mmol for complex 1), NiBr2·(0.2185g, 1.0 mmol for complex 2) and Ni(CH3COO)2·4H2O (0.2486 g, 1.0 mmol for complex 3),was added slowly under stirring, keeping the temperature below 40 C. The color of thesolutions became orange after a few minutes. The precipitate began to form after 2 h of stirringwith heating. The mixture was left overnight and then the orange precipitate was filteredoff, washed with ethanol and dried under air. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; for 2.0h;Heating; | General procedure: The nickel(II) complexes, chlorhexidinenickel(II) chloride dihydrate (complex 1), chlorhexidinenickel(II) bromide dihydrate (complex 2) and chlorhexidinenickel(II) acetate ethanolate(complex 3), were prepared by the following general method. <strong>[56-95-1]Chlorhexidine diacetate</strong>monohydrate, 0.6435 g (1 mmol), was dissolved in 30 mL ethanol, under slight heating. Therequired solid metal salt, i.e., NiCl2·6H2O (0.2377 g, 1.0 mmol for complex 1), NiBr2·(0.2185g, 1.0 mmol for complex 2) and Ni(CH3COO)2·4H2O (0.2486 g, 1.0 mmol for complex 3),was added slowly under stirring, keeping the temperature below 40 C. The color of thesolutions became orange after a few minutes. The precipitate began to form after 2 h of stirringwith heating. The mixture was left overnight and then the orange precipitate was filteredoff, washed with ethanol and dried under air. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
for 2.0h;Heating; | General procedure: The nickel(II) complexes, chlorhexidinenickel(II) chloride dihydrate (complex 1), chlorhexidinenickel(II) bromide dihydrate (complex 2) and chlorhexidinenickel(II) acetate ethanolate(complex 3), were prepared by the following general method. <strong>[56-95-1]Chlorhexidine diacetate</strong>monohydrate, 0.6435 g (1 mmol), was dissolved in 30 mL ethanol, under slight heating. Therequired solid metal salt, i.e., NiCl2·6H2O (0.2377 g, 1.0 mmol for complex 1), NiBr2·(0.2185g, 1.0 mmol for complex 2) and Ni(CH3COO)2·4H2O (0.2486 g, 1.0 mmol for complex 3),was added slowly under stirring, keeping the temperature below 40 C. The color of thesolutions became orange after a few minutes. The precipitate began to form after 2 h of stirringwith heating. The mixture was left overnight and then the orange precipitate was filteredoff, washed with ethanol and dried under air. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; acetonitrile; at 20℃; for 2.0h; | General procedure: The palladium(II) complexes, chlorhexidinepalladium(II) tetrachloridopalladate(II) dihydrate(complex 4) and chlorhexidinepalladium(II) acetate (complex 5), were obtained by mixinga solution of PdCl2 dissolved in acetonitrile with a solution of chlorhexidine dissolved inethanol, using a 2:1 metal:ligand mole ratio for complex 4 and a 1:1 mole ratio for complex 5.Complex 4 was prepared by adding an ethanolic solution of <strong>[56-95-1]chlorhexidine diacetate</strong> monohydrate(0.6435 g, 1.0 mmol, in 30 mL ethanol) to a refluxing solution containing 0.3546 g(2.0 mmol) of PdCl2 dissolved in acetonitrile. The resulting suspension that was immediatelyformed was stirred at room temperature for 2 h and then filtered under vacuum. The orangeprecipitate was washed with ethanol and dried under air. Complex 5, orange, was obtained inthe same way as complex 4, but using a 1:1 metal:ligand mole ratio, by mixing 0.6435 g (1.0mmol) of ligand dissolved in 30 mL ethanol and 0.1773 g (1.0 mmol) of PdCl2 in acetonitrile. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; acetonitrile; at 20℃; for 2.0h; | General procedure: The palladium(II) complexes, chlorhexidinepalladium(II) tetrachloridopalladate(II) dihydrate(complex 4) and chlorhexidinepalladium(II) acetate (complex 5), were obtained by mixinga solution of PdCl2 dissolved in acetonitrile with a solution of chlorhexidine dissolved inethanol, using a 2:1 metal:ligand mole ratio for complex 4 and a 1:1 mole ratio for complex 5.Complex 4 was prepared by adding an ethanolic solution of <strong>[56-95-1]chlorhexidine diacetate</strong> monohydrate(0.6435 g, 1.0 mmol, in 30 mL ethanol) to a refluxing solution containing 0.3546 g(2.0 mmol) of PdCl2 dissolved in acetonitrile. The resulting suspension that was immediatelyformed was stirred at room temperature for 2 h and then filtered under vacuum. The orangeprecipitate was washed with ethanol and dried under air. Complex 5, orange, was obtained inthe same way as complex 4, but using a 1:1 metal:ligand mole ratio, by mixing 0.6435 g (1.0mmol) of ligand dissolved in 30 mL ethanol and 0.1773 g (1.0 mmol) of PdCl2 in acetonitrile. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; at 40 - 50℃; for 1.0h; | General procedure: The chromium(III) complex, dichloridochlorhexidinechromium(III) acetate (complex 6)was prepared by adding a solution of CrCl36H2O (0.266 g, 1.0 mmol) in ethanol to a solutionof chlorhexidine ligand in ethanol (0.6435 g, 1.0 mmol) and the reaction mixture was heatedat 40-50 C, under constant stirring, for 1 h. The light blue precipitate obtained was separatedby filtration under vacuum, washed with ethanol and dried under air. |
Tags: 56-95-1 synthesis path| 56-95-1 SDS| 56-95-1 COA| 56-95-1 purity| 56-95-1 application| 56-95-1 NMR| 56-95-1 COA| 56-95-1 structure
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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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