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Hexamethylphosphorsaeuretriamid
HMPA · N,N,N,N,N,N-Hexamethylphosphoric triamide · HEXAMETHYLPHOSPHORIC TRIAMIDE · HEMPA · HEXAMETHYLPHOSPHORIC ACID TRIAMIDE · HMPTA · HPT · hexamethyl
Identifikatoren & physikalische Daten
| CAS No. | 630-31-9 |
|---|---|
| Summenformel | C6H18N3OP |
| Durchschnittliche Molmasse | 179,2 g/mol |
| Monoisotopische Masse | 179,11874883 g/mol |
| SMILES | CN(C)P(=O)(N(C)C)N(C)C |
| InChIKey | GNOIPBMMFNIUFM-UHFFFAOYSA-N |
| PubChem CID | 12679 |
| ChEMBL | CHEMBL3187047 |
| ChEBI | CHEBI:24565 |
| EC No. | 211-653-8 |
| DTXSID | DTXSID6020694 |
| Lokaler Name | Hexamethylphosphorsaeuretriamid |
Chemische & physikalische Eigenschaften
| XLogP | 0,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 26,8 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 139 |
| Stoffklassen | Hazardous Air Pollutants (HAPs)Other Classes -> Phosphorus CompoundsCarcinogens |
| SpringerMaterials Properties | Chemical shift |
| LogP (Verteilungskoeffizient) | 0.09 |
| Geruch | AROMATIC ODORSPICY ODORAromatic or mild, amine-like odor. |
| Dichte | 1.024 at 77 °F (NTP, 1992) - Denser than waterwill sink1.03 @ 20 °CRelative density (water = 1): 1.031.03 @ 20°C1.03 g/mL at 25 °C (lit.) |
| Color/Form | COLORLESS, MOBILE LIQUIDClear, colorless liquid [Note: A solid below 43 degrees F]. |
| Löslichkeit | greater than or equal to 100 mg/mL at 64 °F (NTP, 1992)MISCIBLE WITH WATER & WITH MOST ORG LIQIMMISCIBLE WITH HIGH-BOILING SATURATED HYDROCARBONSSolubility in water: very goodChloroform (Soluble), Methanol (Slightly) |
| Flammpunkt | 222 °F (NTP, 1992)NIOSH REL = lowest feasible conc. 222 °F105 °C220 °F |
| Siedepunkt | 451 °F at 760 mmHg (NTP, 1992)233 °C @ 760 MM HG232 °C232.5 °C @760 [mm Hg]230-232 °C/740 mmHg (lit.) |
| Decomposition | When heated to decomposition it emits very toxic fume of /phosphine, phosphorus oxides and nitrogen oxides/. |
| Schmelzpunkt | 41 to 45 °F (NTP, 1992)FP: 5-7 °C7.2 °C43 °F7 °C (lit.) |
| Dampfdichte | 6.18 (NTP, 1992) - Heavier than airwill sink (Relative to Air)6.18 (Air= 1)Relative vapor density (air = 1): 6.186.18 (vs air) |
| Dampfdruck | 0.07 mm Hg ( 25 °C) |
| Brechungsindex | n20/D 1.459(lit.) |
| Lagerbedingungen | Inert atmosphere,Room Temperature |
| Aggregatzustand | liquid |
| pKa (Säurekonstante) | 4.69±0.70(Predicted) |
| Farbe | Colorless to light yellow liquid |
| Geruch | Spicy odor (no threshold data) |
| Spezifische Wärmekapazität | Cp(liquid): 1.79 J/(g·K), at 25℃ |
| Merck | 14,4725 |
| BRN | 1099903 |
| Henry-Konstante | 4.9×102 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Dielektrizitätskonstante | 30.0(20℃) |
| Stabilität | Stable. Incompatible with strong acids, strong oxidizing agents. |
| InChI | 1S/C6H18N3OP/c1-7(2)11(10,8(3)4)9(5)6/h1-6H3 |
| InChIKey | GNOIPBMMFNIUFM-UHFFFAOYSA-N |
| SMILES | CN(C)P(=O)(N(C)C)N(C)C |
| CAS Datenbank | 680-31-9(CAS DataBase Reference) |
| NIST chemische Informationen | N,N,N',N',N",N'-Hexamethylphosphorotriamide(680-31-9) |
| EPA chemische Informationen | Hexamethylphosphoramide (680-31-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH340: May cause genetic defects [Danger Germ cell mutagenicity]P203, P280, P318, P405, and P501 (click each P-code to see the statement)H340 (100%): May cause genetic defects [Danger Germ cell mutagenicity] |
|---|---|
| Regulatorische Informationen | Chemical: Phosphoric triamide, hexamethyl-Hazard Traits - CarcinogenicityGenotoxicityNephrotoxicity and Other Toxicity to the Urinary SystemReproductive ToxicityRespiratory ToxicityS - indicates a substance that is identified in a final Significant New Use Rule.Hexamethylphosphoramide: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| Weitere Sicherheitsinformationen | IMAP assessments - CMR chemicals not registered under REACH: Human health tier II assessment |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | This chemical is combustible. (NTP, 1992)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. |
| Gesundheitsgefahren | Excerpt from NIOSH Pocket Guide for Hexamethyl phosphoramide: |
| Gefahrenübersicht | Hexamethylphosphoramide is no longer used in large quantities in the United States. No information is available on the acute (short-term), chronic (long-term), reproductive, developmental, or carcinogenic effects of hexamethylphosphoramide in humans. Acute animal studies have reported effects on the kidneys and lungs from oral exposure to hexamethylphosphoramide, while chronic oral studies in animals have reported an increased incidence of lung disease. An increased incidence of nasal tumors from inhalation exposure to hexamethylphosphoramide was reported in rats. EPA has not classified hexamethylphosphoramide for carcinogenicityhowever, the International Agency for Research on Cancer (IARC) has classified it as a Group 2B, possible human carcinogen. |
Anwendungen & Verwendung
Verwenden
Hexamethylphosphoramide is a dipolar co-solvent and an effective additive used in reactions like reduction of halides, deoxygenation of sulfones, halide olefin couplings and cleavage of carbon-sulfur bond.