| Identification | More | [Name]
Sodium bis(trimethylsilyl)amide | [CAS]
1070-89-9 | [Synonyms]
1,1,1,3,3,3-HEXAMETHYLDISILAZANE SODIUM SALT
HEXAMETHYLDISILAZANE SODIUM SALT
HMN NA SALT
NAHMDS
N-SODIOHEXAMETHYLDISILAZANE
N-SODIUMHEXAMETHYLDISILAZANE
SODIUM BIS(TRIMETHYLSILYL)AMIDE
SODIUM HEXAMETHYLDISILAZANE
SODIUM HEXAMETHYLDISILAZIDE
1,1,1-trimethyl-n-(trimethylsilyl)-silanaminsodiumsalt
sodium-bis-(trimethylsilyl)-amide(solutioninthf)
sodiumhexamethyldisilazane,nahmds,in
sodiumhexamethyldisilazane,nahmds,intetrahydrofuran
SODIUM BIS(TRIMETHYLSILYL)AMIDE SOL., ~2 M IN THF
SODIUM BIS(TRIMETHYLSILYL)AMIDE, ~1 M IN THF
SODIUM BIS(TRIMETHYLSILYL)AMIDE SOL., ~0 .6 M IN TOLUENE
SODIUM BIS(TRIMETHYLSILYL)AMIDE, 1.0M SO LUTION IN TETRAHYDROFURAN
SODIUM BIS(TRIMETHYLSILYL)AMIDE, 0.6M SO LUTION IN TOLUENE
Sodium bis(trimethylsilyl)amide, 2M solution in THF, pure
Sodium bis(trimethylsilyl)amide, pure, 95+% | [EINECS(EC#)]
213-983-8 | [Molecular Formula]
C6H18NNaSi2 | [MDL Number]
MFCD00009835 | [Molecular Weight]
183.37 | [MOL File]
1070-89-9.mol |
| Chemical Properties | Back Directory | [Appearance]
Slightly yellow to light beige crystalline powder | [Melting point ]
171-175 °C (lit.) | [Boiling point ]
67°C | [density ]
0.904 g/mL at 25 °C
| [Fp ]
43 °F
| [storage temp. ]
2-8°C
| [solubility ]
Soluble in hexane, toluene, ether,terahydrofuran, benzene and toluene. | [form ]
Liquid | [color ]
Clear orange to brown | [Specific Gravity]
0.9 | [Water Solubility ]
reacts | [Hydrolytic Sensitivity]
8: reacts rapidly with moisture, water, protic solvents | [Sensitive ]
Moisture Sensitive | [Detection Methods]
TITR,T | [BRN ]
3629917 | [Exposure limits]
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) | [CAS DataBase Reference]
1070-89-9(CAS DataBase Reference) | [Storage Precautions]
Moisture sensitive;Store under nitrogen | [EPA Substance Registry System]
1070-89-9(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
C,F | [Risk Statements ]
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:Harmful: danger of serious damage to health by prolonged exposure through inhalation .
R14/15:Reacts violently with water, liberating extremely flammable gases . | [Safety Statements ]
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 label where possible) .
S62:If swallowed, do not induce vomiting: 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-No smoking .
S43:In case of fire, use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add-Never use water) .
S8:Keep container dry . | [RIDADR ]
UN 3263 8/PG 2
| [WGK Germany ]
3
| [F ]
10-21 | [TSCA ]
Yes | [HazardClass ]
4.3 | [PackingGroup ]
III | [HS Code ]
29319090 |
| Hazard Information | Back Directory | [Chemical Properties]
Slightly yellow to light beige crystalline powder | [Physical properties]
mp 171–175 °C; bp 170 °C/2 mmHg. | [Uses]
It is a strong base; deprotonates ketones and esters to generate enolate derivative. | [Uses]
Significantly accelerated the polymerization of pheneylacetylene in conjunction with rhodium (I) catalysis
| [Uses]
Sodium bis(trimethylsilyl)amide is a synthetically useful reagent in that it combines both high basicity and nucleophilicity, each of which may be exploited for useful organic transformations such as selective formation of enolates, preparation of Wittig reagents, formation of acyl anion equivalents, and the generation of carbenoid species. As a nucleophile, it has been used as a nitrogen source for the preparation of primary amines.It is useful as a sterically hindered base and as a nucleophile. | [General Description]
Sodium bis(trimethylsilyl)amide solution (NaHMDS) is widely used as a strong base in organic synthesis for deprotonation reactions and base-catalyzed reactions. It is also involved in the generation of enolates, Wittig reagents and carbenes. | [Purification Methods]
It can be sublimed at 170o/2mm (bath temperature 220-250o) onto a cold finger, and can be recrystallised from *C6H6 (its solubility is: 10g in 100mL at 60o). It is slightly soluble in Et2O and is decomposed by H2O. [Wannagat & Niederprüm Chem Ber 94 1540 1961.]It is available commercially under N2 in Sure/Seal bottles in tetrahydrofuran (various concentrations) and at ~0.6M in toluene. [Beilstein 4 IV 4014.] |
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