CAS 4648-54-8|azidotrimethylsilane|Azidotrimethylsilane|trimethylsilyl azide|Trimethylsilyl azide|azidotrimethylsilane|三甲基硅叠氮|叠氮三甲基硅烷|Azidotrimethylsilane|Trimethylsilyl azide|叠氮化三甲...

General Information

Structure

Molecular Formula

C₃H₉N₃Si

Molecular Mass

115.20916

Exact Mass

115.05657384

Charge

InChI

InChI=1S/C3H9N3Si/c1-7(2,3)6-5-4/h1-3H3

InChIKey

SEDZOYHHAIAQIW-UHFFFAOYSA-N

Canonic Smiles

C[Si](N=[N+]=[N-])(C)C

Isomeric Smiles

[Si](N=[N+]=[N-])(C)(C)C

Calculated Properties

JChem

Acid pKa

5.0596914

H Acceptors

H Donor

LogD (pH = 5.5)

2.0404

LogD (pH = 7.4)

2.0404

Log P

2.1005

Molar Refractivity

28.2116

Polarizability

11.4796295

Polar Surface Area

29.43

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC name

azidotrimethylsilane

Synonyms

AzidotrimethylsilaneTrimethylsilyl azideazidotrimethylsilane三甲基硅叠氮叠氮三甲基硅烷AzidotrimethylsilaneTrimethylsilyl azide叠氮化三甲基硅烷Trimethylsilyl azide叠氮三甲基硅烷三甲基叠氮化硅

IUPAC Traditional name

trimethylsilyl azide

Names and Identifiers

Registration numbers

CAS Number

4648-54-8

PubChem SID

1620757562488971324849336

MDL Number

PubChem CID

EC Number

Beilstein Number

Wikipedia Title

Chemspider ID

Registration numbers

Properties

Safety Information

Highly Flammable/Toxic/Moisture Sensitive/Keep Cold/Store under Argon

Moisture Sensitive

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Wikipedia

Trimethylsilyl_azide

Sigma Aldrich

155071

Packaging
10, 50 g in glass bottle
Application
Versatile azidonation reagent for amines,1 amides,2 aldehydes,3 and ketones.3

92753

Other Notes
Stable, reactive source of azide, reviews1,2,3

Molecule Details

References

PubChem Literature

From Data Sources

• A mild, convenient synthesis of alkyl azides involves S_N2 reaction with the corresponding alkyl halide, phosphate or tosylate, promoted by TBAF: Synthesis, 376 (1995).

• Mitsunobu reaction, in the presence of DIAD, with 1,2- and 1,3-diols leads to regioselective, stereospecific azidation to give predominantly the 2- or 3-azido alcohol with inversion of configuration: J. Org. Chem., 64, 6049 (1999).

• In combination with triflic acid, is useful for the direct amination of aromatics. Aminodiazonium triflate is suggested as the active intermediate. Thus, benzene gives aniline in 95% yield and toluene gives a mixture of o- and p-toluidine: J. Org. Chem., 54, 1203 (1989). See also: Tetrahedron Lett., 32, 4321 (1991).

• For reviews, see: Chem. Soc. Rev., 7, 15 (1978); Synthesis, 861 (1980); Chem. Rev., 88, 351 (1988).

• In combination withSnCl₄,?-D-ribofuranosyl acetates are converted to azides: Carbohydr. Res., 232, 359 (1992). Similarly, reaction with tert-halides in the presence of tin(IV) chloride gives tert-azides, which can be converted to iminophosphoranes by Staudinger reduction with Triethyl phosphite, L00339. Hydrolysis completes a one-pot sequence for the conversion of a tert-halide to the corresponding amine: Synthesis, 487 (1987).

• Non-explosive hydrazoic acid equivalent in many cycloaddition reactions: e.g. with alkynes to give 1,2,3-triazoles: Chem. Ber., 99, 2512 (1966), nitriles, catalyzed by Di-n-butyltin oxide, L14491, to give tetrazoles: J. Org. Chem., 58, 4139 (1993).

• Curtius reaction with acid halides gives isocyanates in one operation: Synth. Commun., 2, 227 (1972): Synthesis, 551 (1972); J. Org. Chem., 38, 2982 (1973). Similarly, pyridine-2,3-dicarboxylic anhydride is converted to 3-azaisatoic anhydride: Synthesis, 972 (1982):

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC name

azidotrimethylsilane

Synonyms

IUPAC Traditional name

trimethylsilyl azide

Registration numbers

CAS Number

4648-54-8

PubChem SID

1620757562488971324849336

MDL Number

PubChem CID

EC Number

Beilstein Number

Wikipedia Title

Chemspider ID

Molecule Details

155071

Packaging
10, 50 g in glass bottle
Application
Versatile azidonation reagent for amines,1 amides,2 aldehydes,3 and ketones.3

92753

Other Notes
Stable, reactive source of azide, reviews1,2,3

References

PubChem Literature

From Data Sources

• A mild, convenient synthesis of alkyl azides involves S_N2 reaction with the corresponding alkyl halide, phosphate or tosylate, promoted by TBAF: Synthesis, 376 (1995).

• For reviews, see: Chem. Soc. Rev., 7, 15 (1978); Synthesis, 861 (1980); Chem. Rev., 88, 351 (1988).

Bioactivity

PubChem BioAssay

Properties

Safety Information

Highly Flammable/Toxic/Moisture Sensitive/Keep Cold/Store under Argon

Moisture Sensitive

Molecule

ID:88858