CAS 999-97-3|1,1,1,3,3,3-Hexamethyldisilazane|Hexamethyldisilazane|Bis(trimethylsilyl)amine|hexamethyldisilizane|bis(trimethylsilyl)amine|六甲基二硅氮烷|HMDS|Hexamethyldisilazane|1,1,1,3,3,3-六甲基二...

General Information

Structure

Molecular Formula

C₆H₁₉NSi₂

Molecular Mass

161.39276

Exact Mass

161.10560268

Charge

InChI

InChI=1S/C6H19NSi2/c1-8(2,3)7-9(4,5)6/h7H,1-6H3

InChIKey

FFUAGWLWBBFQJT-UHFFFAOYSA-N

Canonic Smiles

C[Si](N[Si](C)(C)C)(C)C

Isomeric Smiles

[Si](C)(N[Si](C)(C)C)(C)C

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

-0.8950769

LogD (pH = 7.4)

-0.8299159

Log P

2.7111

Molar Refractivity

48.5955

Polarizability

19.175602

Polar Surface Area

12.03

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

1,1,1,3,3,3-HexamethyldisilazaneHexamethyldisilazaneBis(trimethylsilyl)amineHMDSHexamethyldisilazane六甲基二硅氮烷1,1,1,3,3,3-六甲基二硅氮烷Bis(trimethylsilyl)amineHexamethyldisilazane 99%Hexamethyldisilazane, Electronic grade六甲基二硅杂氮烷,电子级1,1,1,3,3,3-HEXAMETHYLDISILAZANEDow Corning® product Z-6079Silazane HMN六甲基二硅氮烷Dow Corning® 产品 Z-6079六甲基二硅杂氮烷六甲基二硅胺烷, 电子级

IUPAC Traditional name

hexamethyldisilizane

IUPAC name

bis(trimethylsilyl)amine

Names and Identifiers

Registration numbers

CAS Number

MDL Number

Merck Index

EC Number

Beilstein Number

PubChem SID

1620750732488883824874541248675762486505324863226

PubChem CID

13838

Chemspider ID

13238

Wikipedia Title

Bis(trimethylsilyl)amine

MeSH Name

Hexamethylsilazane

Registration numbers

Properties

Product Information

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

MP Biomedicals

02195219

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

Wikipedia

Bis(trimethylsilyl)amine

Sigma Aldrich

H4875

Application
用于制备三甲基甲硅烷基衍生物的试剂。

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

379212

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

40215

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

52619

Other Notes
Important silylating agent1,2

86944

Other Notes
prices for bulk quantities on request

Molecule Details

References

PubChem Literature

From Data Sources

• In combination with DMSO, thiols are oxidized to disulfides under nearly neutral conditions: Synlett, 346 (2002).

• Convenient, mild silylating reagent which generates gaseous ammonia as the only by-product (see Appendix 4). Non-acidic substrates normally require a catalyst.

• 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).

• 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).

• 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).

• 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).

• For conversion of carbonyl groups to silyl enol ethers, see Iodotrimethylsilane, A12902.

• 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.

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC Traditional name

hexamethyldisilizane

IUPAC name

bis(trimethylsilyl)amine

Registration numbers

CAS Number

MDL Number

Merck Index

EC Number

Beilstein Number

PubChem SID

1620750732488883824874541248675762486505324863226

PubChem CID

13838

Chemspider ID

13238

Wikipedia Title

Bis(trimethylsilyl)amine

MeSH Name

Hexamethylsilazane

Molecule Details

MP Biomedicals

02195219

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

Wikipedia

Bis(trimethylsilyl)amine

Sigma Aldrich

H4875

Application
用于制备三甲基甲硅烷基衍生物的试剂。

440191

379212

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

40215

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

52619

Other Notes
Important silylating agent1,2

86944

Other Notes
prices for bulk quantities on request

References

PubChem Literature

From Data Sources

• In combination with DMSO, thiols are oxidized to disulfides under nearly neutral conditions: Synlett, 346 (2002).

• 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.

Bioactivity

PubChem BioAssay

Properties

Product Information

Molecule

ID:88033