Diglycolic anhydride CAS#: 4480-83-5; 凯望编码 (ChemWhat Code): 59948
Identification
| 英文名 | Diglycolic anhydride |
| IUPAC Name | 1,4-dioxane-2,6-dione |
| 分子结构 |  |
| CAS编号 | 4480-83-5 |
| EINECS Number | 224-761-5 |
| MDL Number | MFCD00006677 |
| Beilstein Registry Number | 112527 |
| 别名 | 1,4-dioxane-2,6-dione, diglycolic acid anhydride, diethylene glycol anhydride, [1,4] dioxane-2,6-dione, [1,4]-dioxane-2,6-dione, anhydrous diglycol acid, oxydiacetic anhydride; CAS NO.: 4480-83-5;CAS Number:Diglycolic anhydride CAS#: 4480-83-5 |
| 分子式 | C4H4O4 |
| 分子量 | 116.072 |
| InChI | InChI=1S/C4H4O4/c5-3-1-7-2-4(6)8-3/h1-2H2COPY |
| InChI Key | PIYNUZCGMLCXKJ-UHFFFAOYSA-N |
| Canonical SMILES | C1C(=O)OC(=O)CO1 |
| Patent Information | ||
| Patent ID | Title | Publication Date |
| US2013/209358 | RADIOTRACER COMPOSITIONS | 2013 |
| US2015/139902 | PURIFICATION OF [18F] – FLUCICLATIDE | 2015 |
| EP1431287 | Optically pure paroxetine precursos | 2004 |
| EP1223167 | Substituted isoxazoles for the treatment of inflammation | 2002 |
Physical Data
| Appearance | A slightly brown or off-white crystalline powder |
| Solubility | Soluble in chloroform |
| Flash Point | 240-241°C |
| Sensitivity | Moisture Sensitive |
| Melting Point, °C | Solvent (Melting Point) |
| 95 – 96.2 | |
| 92 – 94 | |
| 93 – 95 | |
| 96 – 97 | |
| 94 – 95 | |
| 97 | CHCl3 |
| Boiling Point, °C | Pressure (Boiling Point), Torr |
| 130 | 20 |
| 240 – 241 | 760 |
| 120 | 12 |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Temperature (NMR Spectroscopy), °C | Frequency (NMR Spectroscopy), MHz |
| Chemical shifts | 1H | chloroform-d1 | 400 | |
| Chemical shifts, Spectrum | 1H | chloroform-d1 | 400 | |
| Chemical shifts, Spectrum | 1H | dimethylsulfoxide-d6 | 20.5 | 600 |
| Chemical shifts, Spectrum | 13C | dimethylsulfoxide-d6 | 21.2 | 151 |
| Chemical shifts | 17O | acetonitrile | 75 | |
| Linewidth of NMR absorption |
| Description (Mass Spectrometry) |
| high resolution mass spectrometry (HRMS), electrospray ionisation (ESI), time-of-flight mass spectra (TOFMS), spectrum |
Route of Synthesis (ROS)
| Conditions | Yield |
| With oxalyl dichloride; N,N-dimethyl-formamide In toluene for 3h; Inert atmosphere; Reflux; Experimental Procedure General procedure for the preparation of cyclic anhydrides 1a-v General procedure: Dicarboxylic acid 2 (1 mmol) and oxalyl chloride (1.2 mmol) were combined in dry toluene (5 mL) and a drop of freshly distilled DMF was added. The reaction vessel was purged with argon and the reaction was heated under stirring for 3 h. The stirring was stopped and the toluene solution was decanted off the oily residue and filtered. Evaporation of the volatiles provided the analytically pure target product which, if necessary, was transformed intro crystalline form by trituration with diethyl ether. In some cases (see ESI) additional crystallization or trituration with 1:2 v/v hexane-toluene mixture was used. | 93% |
| With phosphoric acid; acetic anhydride at 145℃; for 2h; Temperature; Experimental Procedure 2.3 (3): 50.01 g of diglycolic acid was dissolved in 140 mL of acetic anhydride,Heated to 145 ° C,Add 5 drops of phosphoric acid as initiator,And the mixture was refluxed for 2 hours.After the reaction was stopped,Most acetic anhydride was removed by rotary evaporation at 80 ,Approximately 100 mL of liquid was obtained,300 mL of toluene was added,Stirring,And allowed to stand for 10 hours.Vacuum filtration,To give 38.89g colorless to white diglycol anhydride crystalsThe yield was 90%. | 90% |
| With niobium(V) oxide hydrate In o-xylene at 160℃; for 72h; Inert atmosphere; Molecular sieve; | 86% |
Safety and Hazards
| Pictogram(s) |  |
| Signal | Warning |
| GHS Hazard Statements | H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H335 (97.78%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation] Information may vary between notifications depending on impurities, additives, and other factors. |
| Precautionary Statement Codes | P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) |
Other Data
| Transportation | NONH for all modes of transport |
| Under the room temperature and away from light | |
| HS Code | 291890 |
| Storage | Under the room temperature and away from light |
| Market Price | USD 1450/kg |
| Druglikeness | |
| Lipinski rules component | |
| 分子量 | 116.073 |
| logP | -0.945 |
| HBA | 4 |
| HBD | 0 |
| Matching Lipinski Rules | 4 |
| Veber rules component | |
| Polar Surface Area (PSA) | 52.6 |
| Rotatable Bond (RotB) | 0 |
| Matching Veber Rules | 2 |
| Bioactivity |
| In vitro: Efficacy |
| Quantitative Results |
| pX | Parameter | Value (quant) | Unit |
| 4.28 | inhibition rate | 100.5 | % |
| 3.54 | inhibition rate | 77.3 – 77.8 | % |
| 2.47 | inhibition rate | 47.1 | % |
| 1 | inhibition rate | -0.25 | % |
| 1 | inhibition rate | 0.26 – 0.57 | % |
| 1 | inhibition rate | 0.89 – 1.67 | % |
| intrinsic fluorescence percentage | 52.8 | % | |
| intrinsic fluorescence percentage | 45.7 | % | |
| intrinsic fluorescence percentage | 13.7 | % | |
| intrinsic fluorescence percentage | 3.5 | % | |
| intrinsic fluorescence percentage | 5.2 | % |
| Use Pattern |
| Monomer/condensant |
| Polymers/polymer applications |
| functionalizing agent for gastric acid resistant gelatin capsule |
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认证生产商 | |
| Caming Pharmaceutical Ltd | http://www.caming.com/ |
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