Structure via PubChem · Public domain (PubChem)
hexamethyldisilazane
Sign in to saveAlso known as Trimethyl-N-(trimethylsilyl)silanamine, (TMS)2NH, Hexamethylsilazane, ((CH3)3Si)2NH, Bis(trimethylsilyl)amine, 1,1,1,3,3,3-Hexamethyldisilazane, HMDS
Bis(trimethylsilyl)amine (also known as hexamethyldisilazane and HMDS) is an organosilicon compound with the molecular formula [(CH3)3Si]2NH. The molecule is a derivative of ammonia with trimethylsilyl groups in place of two hydrogen atoms. An electron diffraction study shows that silicon-nitrogen bond length (173.5 pm) and Si-N-Si bond angle (125.5°) to be similar to disilazane (in which methyl groups are replaced by hydrogen atoms) suggesting that steric factors are not a factor in regulating angles in this case. This colorless liquid is a reagent and a precursor to bases that are popular in
Chemical data
- Formula
- C6H19NSi2
- Molecular weight
- 161.39 g/mol
- IUPAC name
- [dimethyl-(trimethylsilylamino)silyl]methane
- SMILES
- C[Si](C)(C)N[Si](C)(C)C
- InChIKey
- FFUAGWLWBBFQJT-UHFFFAOYSA-N
- Polar surface area
- 12 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
438 papers- Hexamethyldisilazane-Mediated Amidination of Sulfonamides and Amines with Formamides.The Journal of organic chemistry · 2022
- 1,1,1,3,3,3-Hexamethyldisilazane (2018).Toxicology and industrial health · 2019
- Hexamethyldisilazane Lithium (LiHMDS)-Promoted Hydroboration of Alkynes and Alkenes with Pinacolborane.The Journal of organic chemistry · 2022
- Hexamethyldisilazane-triggered room temperature synthesis of hydrophobic perovskite nanocrystals with enhanced stability for light-emitting diodes.Journal of colloid and interface science · 2019
- Hydrophobization of Cold Plasma Activated Glass Surfaces by Hexamethyldisilazane Treatment.Molecules (Basel, Switzerland) · 2024
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Has part
- hydrogen
- Mass
- 161.106
Show 4 more facts
- chemical formula
- C₆H₁₉NSi₂
- canonical SMILES
- C[Si](C)(C)N[Si](C)(C)C
- Commons category
- Bis(trimethylsilyl)amine
- melting point
- -78
Sources (2)
via Wikidata · CC0
~4 min read
Encyclopedic overview
5 sectionsContents
- Synthesis and derivatives
- Use as reagent
- Other uses
- See also
- References
Bis(trimethylsilyl)amine (also known as hexamethyldisilazane and HMDS) is an organosilicon compound with the molecular formula [(CH3)3Si]2NH. The molecule is a derivative of ammonia with trimethylsilyl groups in place of two hydrogen atoms. An electron diffraction study shows that silicon-nitrogen bond length (173.5 pm) and Si-N-Si bond angle (125.5°) to be similar to disilazane (in which methyl groups are replaced by hydrogen atoms) suggesting that steric factors are not a factor in regulating angles in this case. This colorless liquid is a reagent and a precursor to bases that are popular in organic synthesis and organometallic chemistry. Additionally, HMDS is also increasingly used as molecular precursor in chemical vapor deposition techniques to deposit silicon carbonitride thin films or coatings.
==Synthesis and derivatives== Bis(trimethylsilyl)amine is synthesized by treatment of trimethylsilyl chloride with ammonia: 2 (CH3)3SiCl + 3 NH3 → [(CH3)3Si]2NH + 2 NH4Cl Ammonium nitrate together with triethylamine can be used instead. This method is also useful for 15N isotopic enrichment of HMDS. 700 px
Excerpted from Wikipedia’s “hexamethyldisilazane” article, available under the CC BY-SA 4.0 licence.