2,2′-dithiobis[N-methylbenzamide] CAS#: 2527-58-4; 凯望编码 (ChemWhat Code): 16952
Identification
| 英文名 | 2,2′-dithiobis[N-methylbenzamide] |
| IUPAC Name | N-methyl-2-[[2-(methylcarbamoyl)phenyl]disulfanyl]benzamide |
| 分子结构 | ![Structure of 2,2'-dithiobis[N-methylbenzamide] CAS# 2527-58-4](http://www.chemwhat.com/wp-content/uploads/2017/11/Structure-of-22-dithiobisN-methylbenzamide-CAS-2527-58-4-.png) |
| CAS编号 | 2527-58-4 |
| EINECS Number | 219-768-5 |
| MDL Number | MFCD00025633 |
| 别名 | 2,2′-dithiobis(N-methylbenzamide), 2,2′-disulfanediylbis(N,N’-dimethylbenzamide), 2,2′-dithiosalicylic acid dichloride, bis[2-(N-methylcarbamoyl)phenyl] disulfide, 2,2’-dithiobis(N-methylbenzamide), dithio-2,2’-bis-benzmethylamide, N,N’-dimethyl-2,2′-dithiodibenzamide;CAS Number: 2527-58-4 |
| 分子式 | C16H16N2O2S2 |
| 分子量 | 332.45 |
| InChI | InChI=1S/C16H16N2O2S2/c1-17-15(19)11-7-3-5-9-13(11)21-22-14-10-6-4-8-12(14)16(20)18-2/h3-10H,1-2H3,(H,17,19)(H,18,20) |
| InChI Key | JEVCLNJEBFWVPD-UHFFFAOYSA-N |
| Canonical SMILES | CNC(=O)c1ccccc1SSc2ccccc2C(=O)NC |
| Patent Information | ||
| Patent ID | Title | Publication Date |
| CN111269159 | Preparation method of chemical intermediate 2,2 ‘ – dithiodiphenylamine compound (by machine translation) | 2020 |
| CN110483438 | Pipeline type continuous 3- production method of isothiazolone compound (by machine translation) | 2019 |
| US4705805 | Antithrombotic agent | 1987 |
Physical Data
| Appearance | White to gray wet solids |
| Melting Point, °C | Solvent (Melting Point) |
| 208 – 216 | |
| 218 – 220 | |
| 220 – 221 | acetic acid |
| 221 | dioxane |
| 221 | acetic acid |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Frequency (NMR Spectroscopy), MHz | Original Text (NMR Spectroscopy) | Comment (NMR Spectroscopy) |
| Chemical shifts | 1H | chloroform-d1 | 400 | 1H NMR (400 MHz, CDCl3) δ 7.75 (2H, br d, J = 7.6 Hz), 7.47 (2H, dd, J = 7.6, 1.2 Hz), 7.36 (2H, td, J = 7.6, 1.2 Hz),7.24 (2H, td, J = 7.6, 1.2 Hz), 6.13 (2H, br m), 2.97 (6H, d, J = 4.8 Hz) | |
| Chemical shifts | 1H | dimethylsulfoxide-d6 | 300.133 | ambient temperature | |
| Chemical shifts | 1H | CDCl3 | 300.133 | ambient temperature | |
| Chemical shifts | 13C | dimethylsulfoxide-d6 | 75.4693 | ambient temperature |
| Description (IR Spectroscopy) | Solvent (IR Spectroscopy) |
| Bands | KBr |
| Spectrum | KBr |
Route of Synthesis (ROS)
![Route of Synthesis (ROS) of 2,2'-dithiobis[N-methylbenzamide] CAS 2527-58-4](http://www.chemwhat.com/wp-content/uploads/2017/11/Route-of-Synthesis-ROS-of-22-dithiobisN-methylbenzamide-CAS-2527-58-4.png)
| Conditions | Yield |
| With sodium tetrahydroborate In tetrahydrofuran; ethanol at 20℃; for 4h; | 90% |
| Stage #1: 2,2′-dithiobis(N-methylbenzamide) With sodium tetrahydroborate In ethanol at 0℃; for 9h; Stage #2: With hydrogenchloride In ethanol; water for 0.25h; pH=1.73; Experimental Procedure 2,2′-dithio-N-methylbenzamide (967.2 g) is suspended in ethanol (9.0 L) and cooled to O0C. Sodium borohydride (253 g) is added in portions over 4 hours, and the mixture is agitated for 5 hours at O0C. 3 M hydrochloric acid (3.15 L) is then added to the mixture in over 15 minutes which adjusted the pH to 1.73. The mixture is concentrated under reduced pressure and 450C to remove the ethanol. The concentrate is diluted with ethyl acetate (8 L) and water (4 L) and agitated for 20 minutes. The layers are allowed to separate (30 minutes), and the aqueous layer is removed. Solids and an emulsion remain in the organic layer. Water (1 L) is added to the organic layer and the mixture is agitated for 20 minutes. The aqueous layer is removed and a solution of saturated aqueous sodium chloride (3 L) is added to the organic layer. The mixture is agitated and the layers are separated. The organic layer is dried over sodium sulfate, filtered, and evaporated to a volume of ~4L before solids began to form. Heptanes (2 L) are added to the concentrate and the mixture is evaporated to provide 701.3 g of 2-mercapto-N-methylbenzamide (72% yield with a purity of 95% by HPLC). HPLC of this material showed only 1% of the disulfide present. Avoid exposure to air as this material readily forms the disulfide. | 72% |
| With sodium tetrahydroborate; ethanol at 0 – 20℃; for 16h; Experimental Procedure 60 Production of 2-mercapto-N-methylbenzamide Sodium borohydride (3.05 g, 80.7 mmol) was added to a solution of 2,2’-dithiobis(N-methylbenzamide) (11.7g, 35.1 mmol) in ethanol (110 mL) at 0°C and stirred at room temperature for 16 hours. The solution was diluted withwater, adjusted to pH = 1 with 2N hydrochloric acid, and then the solvent was distilled away under a reduced pressure.Water was added to the residue, and extraction was carried out with ethyl acetate. The organic layer was dried withanhydrous magnesium sulfate, the solvent was distilled away under a reduced pressure to obtain the title compound(7.72 g, 66%) as a pale yellow solid.1H NMR (400 MHz, CDCl3) δ 7.42 (1H, dd, J = 7.8, 1.5 Hz), 7.32 (1H, dd, J = 7.8, 1.3 Hz), 7.25 (1H, td, J = 7.8, 1.5 Hz),7.13 (1H, td, J = 7.8, 1.3 Hz), 6.12 (1H, br m), 4.77 (1H, s), 2.99 (3H, d, J = 4.8 Hz) | 66% |
Safety and Hazards
| Pictogram(s) |   |
| Signal | Warning |
| GHS Hazard Statements | H317 (99.17%): May cause an allergic skin reaction [Warning Sensitization, Skin] H400 (95.04%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard] H410 (89.59%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard] Information may vary between notifications depending on impurities, additives, and other factors. |
| Precautionary Statement Codes | P261, P272, P273, P280, P302+P352, P321, P333+P313, P363, P391, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) |
Other Data
| Transportation | No data available |
| Under the room temperature and away from light | |
| HS Code | No data available |
| Storage | Under the room temperature and away from light |
| Shelf Life | 1 year |
| Market Price | USD |
| Druglikeness | |
| Lipinski rules component | |
| 分子量 | 332.447 |
| logP | 3.282 |
| HBA | 4 |
| HBD | 2 |
| Matching Lipinski Rules | 4 |
| Veber rules component | |
| Polar Surface Area (PSA) | 108.8 |
| Rotatable Bond (RotB) | 7 |
| Matching Veber Rules | 2 |
| Bioactivity |
| In vitro: Efficacy |
| Quantitative Results |
| pX | Parameter | Value (quant) | Unit |
| 6.55 | IC50 | 282 | nM |
| 5.22 | MIC | 2 | ppm |
| 5.04 | MIC | 3 | ppm |
| 4.96 | TC50 | 11 | µM |
| 4.22 | MIC | 20 | ppm |
| 3.92 | MIC | 40 | ppm |
| 2.74 | MIC | 600 | μg/ml |
| 1 | MIC | 1000 | µg/mL |
| 1 | EC50 | 11 | μm |
| Quantitative Results | ||
| 1 of 1 | Target | Nucleocapsid Protein P7 [Human immunodeficiency virus 1]:Wild |
| Biological material | Human immunodeficiency virus 1 | |
| Assay Description | Ability of the compound to extrude zinc from nucleocapsid protein NCp7 using fluorescence-based assay; Active |
| Toxicity/Safety Pharmacology |
| Quantitative Results |
| pX | Parameter | Value (quant) | Unit |
| 5.63 | MIC | 0.78 | mg/L |
| 5.33 | MIC | 1.56 | mg/L |
| Use Pattern |
| 2,2′-dithiobis[N-methylbenzamide] CAS#: 2527-58-4 Detergents/disinfections |
| 2,2′-dithiobis[N-methylbenzamide] CAS#: 2527-58-4 biocidal compositions comprising an isothiazolone biocidal active compound with guanidine adjuvant formula I |
| 2,2′-dithiobis[N-methylbenzamide] CAS#: 2527-58-4 preventing deterioration and decay caused by microbial contamination |
| protecting a locus subject or susceptible to infestation with and/or destruction or deterioration by microorganisms |
| inhibiting the growth of or controlling the growth of microorganisms in combination with N-(3-aminopropyl)-N-dodecylpropane-1,3-diamine |
| synergistic antimicrobial composition in combination with N-(3-aminopropyl)-N-dodecylpropane-1,3-diamine |
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