Benzoesureanhydrid
BENZOIC ACID ANHYDRIDE · Benzoyl benzoate · Benzoylbenzoate · Benzoyl anhydride · BENZOYL OXIDE · BENZOINE · Banzoyl benzoate · Phenyl anhydride
Identifikatoren & physikalische Daten
| CAS No. | 93-97-0 |
|---|---|
| Summenformel | C14H10O3 |
| Durchschnittliche Molmasse | 226,23 g/mol |
| Monoisotopische Masse | 226,06299418 g/mol |
| SMILES | O=C(OC(=O)c1ccccc1)c1ccccc1 |
| InChIKey | CHIHQLCVLOXUJW-UHFFFAOYSA-N |
| PubChem CID | 7167 |
| ChEMBL | CHEMBL3185530 |
| ChEBI | CHEBI:38815 |
| EC No. | 202-291-1 |
| DTXSID | DTXSID1029122 |
| Lokaler Name | Benzoesureanhydrid |
Chemische & physikalische Eigenschaften
| XLogP | 3,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 43,4 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 17 |
| Formalladung | 0 |
| Komplexität | 245 |
| Stoffklassen | Other Classes -> Acid Anhydrides, Other |
| SpringerMaterials Properties | Boiling point |
| Exact Mass | 226.062994177 Da |
| Molecular Weight | 226.23 g/mol |
| Monoisotopic Mass | 226.062994177 Da |
| Physical Description | Solid[Merck Index] White crystalline powderOdorless[Alfa Aesar MSDS] |
| Compound Is Canonicalized | Yes |
| Schmelzpunkt | 38-42 °C(lit.) |
| Siedepunkt | 360 °C |
| Dichte | 1.199 g/mL at 25 °C(lit.) |
| Brechungsindex | nD15 1.57665 |
| Flammpunkt | >230 °F |
| Lagerbedingungen | Inert atmosphere,2-8°C |
| Löslichkeit | 0.01g/l (experimental)0.01 g/L |
| Aggregatzustand | Crystals or Crystalline Powder |
| Farbe | White to almost white |
| Merck | 14,1092 |
| BRN | 516726 |
| Henry-Konstante | 7.0×100 mol/(m3Pa) at 25℃, Zhang et al. (2010) |
| InChI | 1S/C14H10O3/c15-13(11-7-3-1-4-8-11)17-14(16)12-9-5-2-6-10-12/h1-10H |
| InChIKey | CHIHQLCVLOXUJW-UHFFFAOYSA-N |
| SMILES | O=C(OC(=O)c1ccccc1)c2ccccc2 |
| CAS Datenbank | 93-97-0(CAS DataBase Reference) |
| NIST chemische Informationen | Benzoic acid, anhydride(93-97-0) |
| EPA chemische Informationen | Benzoic anhydride (93-97-0) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 42.7% (41 of 96) of reports.DangerH315 (57.3%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 96 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Benzoic acid, anhydrideStatus: Active Update: 24-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24998Benzoic acid, anhydride: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | Reacts with waterA skin and strong eye irritant[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Skin Irrit. 2 (57.3%) |
| F | 10-21 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29163900 |
| R-Sätze (R) | 37/38-41-36/37/38 |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-39-37/39 |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Gefahrenklasse | Eye Dam. 1Skin Irrit. 2STOT RE 1 Inhalation |
Anwendungen & Verwendung
Verwenden
Benzoic Anhydride is the more active analogue of benzoic acid formed via dehydration. Benzoic Anhydride is used in the synthesis of a wide range of organic compounds including some dyes. Benzoic Anhyd ride is also used as an arylation agent in the Heck reaction.
Herstellung & Synthese
synthetische
To a flask containing 14.0 gm (0.1 mole) of benzoyl chloride and equipped with a stirrer is added 40 ml of dry dioxane and it is cooled to 5°C.Then 10 ml (0.1 mole) of dry pyridine is rapidly added at 5-10°C followed by 1.0 ml (0.056 mole) of water. After stirring for 10-15 min at 0-5°C, the reaction mixture is then poured into a mixture of 75 ml of cone, hydrochloric acid, 75 gm of cracked ice, and 350 ml of water. The product is filtered, washed first for 1 min with a cold 5% solution of sodium bicarbonate and then with water. The product is dried to afford 11.0 gm (97%), m.p. 43°C (recrystallized from a mixture of ether-petroleum ether).