Introduction：Basic information about Potassium bis(trimethylsilyl)amide CAS 40949-94-8, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Potassium bis(trimethylsilyl)amide Basic information
| Product Name: | Potassium bis(trimethylsilyl)amide |
| Synonyms: | 1,1,1,3,3,3-HEXAMETHYLDISILAZANE POTASSIUM SALT;KHMDS;HEXAMETHYLDISILAZANE POTASSIUM SALT;HEXAMETHYLDISLAZANE POTASSIUM SALT;POTASSIUM BIS(TRIMETHYLSILYL)AMIDE;POTASSIUMHEXAMETHYLDISILAZANE;POTASSIUM HEXAMETHYLDISILAZIDE;POTASSIUM HEXAMETHYLDISLAZANE |
| CAS: | 40949-94-8 |
| MF: | C6H18KNSi2 |
| MW: | 199.48 |
| EINECS: | 424-100-2 |
| Product Categories: | 25mL Sure/Seal Reagents;Aliphatics;Chemical Synthesis;Organic Bases;Organometallic Reagents;Synthetic Reagents;Classes of Metal Compounds;K (Potassium) Compounds (excluding simple potassium salts);Silicon Compounds (for Synthesis);Synthetic Organic Chemistry;Typical Metal Compounds;Analytical Chemistry;GC Derivatizing Reagents;Si (Classes of Silicon Compounds);Silazanes;Silylation (GC Derivatizing Reagents);Si-N Compounds;Trimethylsilylation (GC Derivatizing Reagents) |
| Mol File: | 40949-94-8.mol |
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Potassium bis(trimethylsilyl)amide Chemical Properties
| Melting point | 194-195°C |
| Boiling point | 111 °C |
| density | 0.877 g/mL at 25 °C |
| vapor density | 3.2 (vs air) |
| vapor pressure | 54 mm Hg ( 25 °C) |
| refractive index | 1.4920 |
| Fp | 45 °F |
| storage temp. | Refrigerator |
| solubility | Miscible with terahydrofuran, ether, benzene and toluene. |
| form | Liquid |
| color | clear to slightly hazy yellow |
| Specific Gravity | 0.877 |
| Water Solubility | Reacts with water. |
| Sensitive | Moisture Sensitive |
| Hydrolytic Sensitivity | 8: reacts rapidly with moisture, water, protic solvents |
| BRN | 4006754 |
| InChI | 1S/C6H18NSi2.K/c1-8(2,3)7-9(4,5)6;/h1-6H3;/q-1;+1 |
| InChIKey | IUBQJLUDMLPAGT-UHFFFAOYSA-N |
| SMILES | C[Si](C)(C)N([K])[Si](C)(C)C |
| CAS DataBase Reference | 40949-94-8(CAS DataBase Reference) |
| EPA Substance Registry System | Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-, potassium salt (1:1) (40949-94-8) |
Safety Information
| Hazard Codes | C,F,Xn |
| Risk Statements | 14-34-67-65-63-48/20-11-40-36/37/38-19-37 |
| Safety Statements | 26-36/37/39-45-62-43-46-16-36/37 |
| RIDADR | UN 3263 8/PG 3 |
| WGK Germany | 3 |
| F | 1-3-10 |
| TSCA | TSCA listed |
| HazardClass | 3 |
| PackingGroup | II |
| HS Code | 29319090 |
| Storage Class | 8A - Combustible corrosive hazardous materials |
| Hazard Classifications | Eye Dam. 1
Skin Corr. 1B |
Potassium bis(trimethylsilyl)amide Usage And Synthesis
| Chemical Properties | Colorless to amber solution |
| Uses | Potassium bis(trimethylsilyl)amide is a strong base used in the alkylation carbonyl compounds.1 |
| Uses | Potassium Hexamethyldisilazide is widely used as a Sterically Hindered Base for Enolate Generation in Selective Formation of Linear Conjugated Dienolates and Alkyl (Z)-3-Alkenoates. |
| Uses | Potassium Bis(trimethylsilyl)amide (1M in THF) is used in the preparation of 5-azacytidine, an antineoplastic drug. Also applied in the preparation of β3-AR agonists used in anti-stress formulations. It is also used as a reagent in the preparation of lanthanide complexes employed in selective cyclization reactions. |
| Preparation | Potassium Hexamethyldisilazide is prepared and isolated by the procedureof Wannagat and Niederpruem. A more convenient in situgeneration from potassium hydride and hexamethyldisilane isdescribed by Brown. |
| General Description | This product, 1.0 M in 2-methyltetrahydrofuran aligns with "Safer Solvents and Auxiliaries", "Use of Renewable Feedstocks" and "Inherently Safer Chemistry for Accident Prevention". |
| Synthesis | Potassium bis(trimethylsilyl)amide is an important non-nucleophilic base widely used in organic synthesis. The main method for its preparation is are interaction of hexamethyldisilazane with potassium amide) potassium hydride, potassium metal, mad styrene, isoprene, or naphthalene as electron acceptors.
An oven-dried 100 ml round-bottom flask was charged with KH (3.22 g, 20.1 mmol, 25 wt. 96 in oil) and flushed with argon. The hydride was then washed with hexane (4x5 ml). To the flask was fitted, a reflux condenser was made, and then THF (20 ml) and bis(trimethylsi1yl)amine (3.81 ml, 18.1 mmol) were added. The resultant slurry was sonicated until the hydrogen gas evolution had ceased, and almost all the potassium hydride had been consumed (3.25 h). The slurry was allowed to settle, and the supernatant was then cannulated into a Schlenk flask. Titration4 for the amide base concentration showed it to be 0.80 M, while the concentration of the total base was 0.86 M[1-2]. |
| References | [1] I. V. Magedov. “Convenient method for the preparation of a solution of potassium bis(trimethylsilyl)amide.” Russian Chemical Bulletin 44 11 (1995): 2197–2198.
[2] J. Ahman, P. Somfai. “An Efficient Preparation of Potassium Bis (Trimethylsilyl) Amide (KHMDS).” Synthetic Communications 25 1 (1995): 2301–2303. |
Potassium bis(trimethylsilyl)amide Preparation Products And Raw materials
| Preparation Products | CYCLOHEXANE-1 4-DICARBONITRILE 98% MIXT& |
