bis(trimethylsilyl)amine

• ChemBase ID: 88033
• Molecular Formular: C6H19NSi2
• Molecular Mass: 161.39276
• Monoisotopic Mass: 161.10560268
• SMILES: [Si](C)(N[Si](C)(C)C)(C)C
• Canonical SMILES: C[Si](N[Si](C)(C)C)(C)C
• InChI: InChI=1S/C6H19NSi2/c1-8(2,3)7-9(4,5)6/h7H,1-6H3
• InChIKey: FFUAGWLWBBFQJT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(trimethylsilyl)amine
• IUPAC Traditional name: hexamethyldisilizane
• Synonyms: Dow Corning® product Z-6079; Hexamethyldisilazane, Electronic grade; Bis(trimethylsilyl)amine; HMDS; Hexamethyldisilazane 99%; 1,1,1,3,3,3-HEXAMETHYLDISILAZANE; Hexamethyldisilazane; 1,1,1,3,3,3-Hexamethyldisilazane; Bis(trimethylsilyl)amine; Hexamethyldisilazane; Silazane HMN; 1,1,1,3,3,3-六甲基二硅氮烷; Dow Corning® 产品 Z-6079; 六甲基二硅胺烷, 电子级; 六甲基二硅杂氮烷; 六甲基二硅杂氮烷,电子级; 六甲基二硅氮烷; 六甲基二硅氮烷

Database IDs

• CAS Number: 999-97-3
• EC Number: 213-668-5
• MDL Number: MFCD00008259
• Beilstein Number: 635752
• Merck Index: 144689
• PubChem SID: 162075073; 24865053; 24888838; 24874541; 24863226; 24867576
• PubChem CID: 13838
• Chemspider ID: 13238
• MeSH Name: Hexamethylsilazane
• Wikipedia Title: Bis(trimethylsilyl)amine

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): -0.8950769
• LogD (pH = 7.4): -0.8299159
• Log P: 2.7111
• Molar Refractivity: 48.5955 cm^3
• Polarizability: 19.175602 Å^3
• Polar Surface Area: 12.03 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: slow hydrolysis in water
• Apperance: colorless liquid; Liquid
• Melting Point: < -78 °C; -78°C; -78°C; -80°C
• Boiling Point: 125 °C at 1013 hPa; 125 °C(lit.); 125-127°C; 126°C; 126°C
• Flash Point: 11 °C; 51.8 °F; 8°C; 8°C(46°F); ca. 15 °C (closed cup and Directive 84/449/EEC, A.9)
• Auto Ignition Point: 325 °C at 1013 hPa
• Density: 0.77; 0.77 g cm^-3; 0.774; 0.774 g/mL at 25 °C(lit.); ca. .774 g/cm^3 at 20 °C
• Refractive Index: 1.4080; n20/D 1.407(lit.); n20/D 1.408
• Vapor Pressure: ca. 20 hPa at 20 °C

Safety Information

• Storage Condition: 2-8°C, Store Under Nitrogen
• Storage Warning: Highly Flammable/Corrosive/Toxic/Moisture Sensitive/Store under Argon; Moisture Sensitive
• RTECS: JM9230000
• European Hazard Symbols: Corrosive (C); Flammable (F); X; Harmful (Xn)
• UN Number: 2924; 2924, 3286; 3286; UN2924
• German water hazard class: 2
• Hazard Class: 3; 8
• Packing Group: 2; II
• Australian Hazchem: 3WE
• Risk Statements: 11-20/21/22-34; 11-20/21/22-34-52/53; R:9-11-22-27
• Safety Statements: 16-26-33-36/37/39-45-60; 16-26-36/37/39-45; 16-26-36/37/39-45-61; 9-16-26-36/37/39-45; S:16-17-36/37/39-51
• EU Classification: FC
• EU Hazard Identification Number: 8A
• Emergency Response Guidebook(ERG) Number: 132
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS06
• GHS Signal Word: Danger
• NFPA704:
  

  3

  1

  1
• GHS Hazard statements: H225-H302 + H332-H311-H314-H412; H225-H311-H331-H302-H314-H318
• GHS Precautionary statements: P210-P273-P280-P305 + P351 + P338-P310; P210-P303+P361+P353-P305+P351+P338-P361-P405-P501A
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3286 3/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (GC); ≥98.0% (GC); ≥99%; ≥99.0% (GC); 98+%; 99.9%; 99+%
• Grade: for GC derivatization; produced by Wacker; purum; reagent grade; ReagentPlus®; semiconductor grade PURANAL™ (Honeywell 17713)
• Derivatization reagent for: Silylations
• Linear Formula: (CH3)3SiNHSi(CH3)3

DETAILS

MP Biomedicals - 02195219

Used to prepare N-trimethylsilyl-amino acids for peptide synthesis.
1 ml = approx. 0.77 g

Sigma Aldrich - H4875

Application
用于制备三甲基甲硅烷基衍生物的试剂。

Sigma Aldrich - 40215

Legal Information
PURANAL is a trademark of Honeywell Specialty Chemicals Seelze GmbH

Sigma Aldrich - 379212

Packaging
25, 100 mL in Sure/Seal™
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 86944

Other Notes
prices for bulk quantities on request

Sigma Aldrich - 52619

Other Notes
Important silylating agent1,2

Sigma Aldrich - 440191

Packaging
1 L in Sure/Seal™
100 mL in Sure/Seal™
Legal Information
Repackaged by Aldrich Chemical Company, Inc. Manufactured by Dow Corning Corporation, U.S.A.
Dow Corning is a registered trademark of The Dow Chemical Company or an affiliated company of Dow

REFERENCES

• Convenient, mild silylating reagent which generates gaseous ammonia as the only by-product (see Appendix 4). Non-acidic substrates normally require a catalyst.
• For conversion of carbonyl groups to silyl enol ethers, see Iodotrimethylsilane, A12902.
• Silylation of alcohols, including carbohydrates, is catalyzed by TMS chloride: J. Org. Chem., 23, 50 (1958); J. Am. Chem. Soc., 85, 2497 (1963); Chem. Ind. (London), 794 (1984). Silylation of phenols occurs readily, see also: Liebigs Ann. Chem., 20 (1973).
• HMDS in the presence of TMS chloride permits the selective O-silylation of amino alcohols: Synthesis, 990 (1988). Alcohols and phenols can be silylated in the presence of amines and thiols with ZnCl₂ as catalyst: Synth. Commun., 23, 1633 (1993).
• A range of catalysts for silylation with HMDS, including saccharin and sodium saccharin, has been recommended: J. Org. Chem., 47, 3966 (1982), for silylation of alcohols, phenols, thiols, carboxylic acids, amides, thioamides, hydroxamic acids, hydrazides, NH-groups of heterocycles, hydrazines, 1,3-diketones, etc. The use of TBAF (0.02 eq.) or iodine (0.01 eq.) also provide mild procedures for O-silylation: Tetrahedron Lett., 35, 8409 (1994); J. Org. Chem., 65, 7228 (2000).
• Can also function as a protected form of ammonia, e.g. to convert acid chlorides to primary amides: Synthesis, 517 (1985), and substituted maleic anhydrides to maleimides: Tetrahedron Lett., 31, 5201 (1990).
• In combination with DMSO, thiols are oxidized to disulfides under nearly neutral conditions: Synlett, 346 (2002).
• The Na, Li and K derivatives are useful strong bases; see Sodium bis(trimethylsilyl)amide, L13352, Lithium bis(trimethylsilyl)amide, L15012, and Potassium bis(trimethylsilyl)amide, L15022.