Sodium bis(trimethylsilyl)amide
N-sodiohexamethyldisilazane
CAS: 1070-89-9
Molecular Formula: C6H18NNaSi2
Sodium bis(trimethylsilyl)amide - Names and Identifiers
Sodium bis(trimethylsilyl)amide - Physico-chemical Properties
| Molecular Formula | C6H18NNaSi2 |
| Molar Mass | 183.37 |
| Density | 0.904g/mLat 25°C |
| Melting Point | 171-175 °C (lit.) |
| Boling Point | 67°C |
| Flash Point | 43°F |
| Water Solubility | reacts |
| Solubility | Soluble in hexane, toluene, ether,terahydrofuran, benzene and toluene. |
| Appearance | Liquid |
| Specific Gravity | 0.9 |
| Color | Clear orange to brown |
| Exposure Limit | ACGIH: TWA 50 ppm; STEL 100 ppm (Skin)OSHA: TWA 200 ppm(590 mg/m3)NIOSH: IDLH 2000 ppm; TWA 200 ppm(590 mg/m3); STEL 250 ppm(735 mg/m3) |
| BRN | 3629917 |
| Storage Condition | 2-8°C |
| Sensitive | 8: reacts rapidly with moisture, water, protic solvents |
Sodium bis(trimethylsilyl)amide - Risk and Safety
| Risk Codes | R14 - Reacts violently with water R34 - Causes burns R19 - May form explosive peroxides R11 - Highly Flammable R67 - Vapors may cause drowsiness and dizziness R65 - Harmful: May cause lung damage if swallowed R63 - Possible risk of harm to the unborn child R48/20 - R14/15 - R40 - Limited evidence of a carcinogenic effect R37 - Irritating to the respiratory system |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S62 - If swallowed, do not induce vomitting; seek medical advice immediately and show this container or label. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S33 - Take precautionary measures against static discharges. S16 - Keep away from sources of ignition. S43 - In case of fire use ... (there follows the type of fire-fighting equipment to be used.) S8 - Keep container dry. |
| UN IDs | UN 3263 8/PG 2 |
| WGK Germany | 3 |
| FLUKA BRAND F CODES | 10-21 |
| TSCA | Yes |
| HS Code | 29319090 |
| Hazard Class | 4.3 |
| Packing Group | III |
Sodium bis(trimethylsilyl)amide - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Introduction | Sodium di (trimethylsilyl) amide is usually called NaHMDS (sodium hexamethyldisilane diazonium), which is a strong base and is often used for deprotonation in reactions or as a catalyst in alkaline reactions. The advantage of this compound is that it can be a solid reagent and is soluble in a wide range of aprotic solvents, such as tetrahydrofuran, ether, benzene or toluene. It has very strong basicity but poor nucleophilicity. This is due to the fact that there are two large and lipophilic trimethylsilyl (TMS) groups in the molecule that affect its participation in nucleophilic substitution reactions. |
| Application | Bis (trimethylsilyl) sodium amide is a non-nucleophilic strong base that can be used to prepare pharmaceutical intermediates. NaHMDS is widely used to neutralize C- H acids. For example, some typical examples: deprotonation of ketones and esters to obtain their enol derivatives. By dehydrohalogenating CH2X2(X = Br, I), halogenated carbene similar to CHBr and CHI forms are obtained. These carbene compounds can be added to olefins to obtain cyclopropane compounds containing substituents. Georg Wittig reagent was prepared by deprotonation of quaternary ammonium salt. Deprotonation of cyanohydrins. NaHMDS can also be used as a neutralizing base for N-H acids. |
| Use | Sodium di (trimethylsilyl) amide (NaHMDS) is a representative of synonymous compounds, as well as lithium di (trimethylsilyl) amide (LiHMDS) and potassium di (trimethylsilyl) amide (KHMDS). They are widely used in organic synthesis of large sterically hindered alkali reagents, di (trimethylsilyl) amino in tetrahydrofuran pKa = 29.5. Compared with lithium diisopropylamide (LDA), it has weak alkalinity, but it is very convenient to operate and use. It has good solubility in most organic solvents, and the temperature range used is very wide, and its reaction ability can be adjusted from -78°C to the reflux temperature of toluene. Its chemical reactivity is very similar to LDA, and it is often used to generate carbanions and enol ions. Non-nucleophilic strong base |
Last Update：2024-04-10 22:29:15
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