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4648-54-8

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4648-54-8 Usage

Chemical Properties

clear colorless to slightly yellow liquid

Physical properties

bp 95–96°C; n20 D 1.416; d 0.868 g cm?3; fp23°C; IR νmax 2100 cm?1; 1H NMR (CDCl3) δ = 0.22.

Uses

Different sources of media describe the Uses of 4648-54-8 differently. You can refer to the following data:
1. Many applications of TMSA in organic synthesis have been reported but only representative examples are described herein.Substitution Reactions.Benzyl,allyl,and substituted alkyl halides are converted to the corresponding azides in 60–100% yields via reactions with TMSA under neutral conditions in a nonaqueous solvent (eq 1).By using tin(IV) chloride as a catalyst, secondary and tertiary cyclic and polycyclic halides are similarly transformed into the corresponding azides in 50–92% yields (eq 1).
2. Trimethylsilyl azide is used as an azidonation reagent for amines, amides, aldehydes and ketones. It is involved in the preparation of alfa- and beta-siloxy azides from carbonyl compounds and epoxides. It is also used in the preparation of heterocyclic compounds and also acts as an effective substitute for hydrazoic acid. Further, it is used in the Oseltamivir total synthesis.
3. Versatile azidonation reagent for amines, amides, aldehydes, and ketones.

Preparation

several methods for the synthesis of this azide have been reported.The procedure involving aluminum chloride is not recommended, since an explosive product is formed.Azidotrimethylsilane is now commercially available, and a representative synthetic procedure is as follows. A mixture of sodium azide and chlorotrimethylsilane is refluxed in di-n-butyl ether for 2 days and the azide is safely distilled directly from the reaction vessel. Purer compound (99% content) is obtained by redistillation of the product. Several improved conditions have been reported for the preparation of this azide.In these procedures, trimethylsilyl chloride is reacted with sodium azide either neat or in a high boiling point solvent, such as a mixture of silicone oil and polyethylene glycol. Distillation of the crude product usually provides trimethylsilyl azide (TMSA) in high purity (97.9%) and yield (97%).

Purification Methods

Distil the azide through a Vigreux column (p 11) in a N2 atmosphere maintaining the oil bath temperature thermostat at 135-140o . Check the purity by 1H NMR [CHCl3, : single peak at 13cps from Me4Si]. Likely impurities are siloxane hydrolysis products. The azide is thermally stable even at 200o when it decomposes slowly without explosive violence. All the same, it is advisable to carry out the distillation behind a thick safety screen in a fumehood because unforseen EXPLOSIVE azides may be formed on long standing. [Birkofer & Wagner Org Synth Coll Vol VI 1030 1988.]

Check Digit Verification of cas no

The CAS Registry Mumber 4648-54-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,6,4 and 8 respectively; the second part has 2 digits, 5 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 4648-54:
(6*4)+(5*6)+(4*4)+(3*8)+(2*5)+(1*4)=108
108 % 10 = 8
So 4648-54-8 is a valid CAS Registry Number.
InChI:InChI=1/C3H9Si.N3/c1-4(2)3;1-3-2/h1-3H3;/q+1;-1

4648-54-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Detail
  • TCI America

  • (T0801)  Trimethylsilyl Azide  >95.0%(GC)

  • 4648-54-8

  • 5g

  • 280.00CNY

  • Detail
  • TCI America

  • (T0801)  Trimethylsilyl Azide  >95.0%(GC)

  • 4648-54-8

  • 25g

  • 695.00CNY

  • Detail
  • TCI America

  • (T0801)  Trimethylsilyl Azide  >95.0%(GC)

  • 4648-54-8

  • 100g

  • 1,390.00CNY

  • Detail
  • Alfa Aesar

  • (L00173)  Trimethylsilyl azide, 94%   

  • 4648-54-8

  • 5g

  • 300.0CNY

  • Detail
  • Alfa Aesar

  • (L00173)  Trimethylsilyl azide, 94%   

  • 4648-54-8

  • 25g

  • 939.0CNY

  • Detail
  • Alfa Aesar

  • (L00173)  Trimethylsilyl azide, 94%   

  • 4648-54-8

  • 100g

  • 2945.0CNY

  • Detail
  • Aldrich

  • (155071)  Azidotrimethylsilane  95%

  • 4648-54-8

  • 155071-10G

  • 898.56CNY

  • Detail
  • Aldrich

  • (155071)  Azidotrimethylsilane  95%

  • 4648-54-8

  • 155071-50G

  • 2,590.38CNY

  • Detail

4648-54-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Azidotrimethylsilane

1.2 Other means of identification

Product number -
Other names Trimethylsilyl azide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:4648-54-8 SDS

4648-54-8Relevant articles and documents

Wiberg et al.

, p. 223,224 (1968)

Trimethylsilyl Pseudohalide Adducts of GaCl3 and B(C6F5)3

Bl?sing, Kevin,Bresien, Jonas,Maurer, Steffen,Schulz, Axel,Villinger, Alexander

supporting information, p. 1913 - 1920 (2021/05/10)

Me3Si?X (X=CN, N3, OCN, and SCN) was treated with the Lewis acids GaCl3 and B(C6F5)3 in toluene yielding the desired adducts Me3Si?X→GaCl3 and Me3Si?X→B(C6F5)3. All synthesized adducts were isolated and completely characterized including single crystal structure elucidations. The different structures, thermodynamics of formation and charge transfer effects are discussed on the basis of experimental and theoretical data.

Synthesis, DNA-binding abilities and anticancer activities of triazole-pyrrolo[2,1-c][1,4]benzodiazepines hybrid scaffolds

Chen, Chung-Yu,Lee, Pei-Hua,Lin, Yong-Yong,Yu, Wen-Ting,Hu, Wan-Ping,Hsu, Chia-Chen,Lin, Ying-Ting,Chang, Long-Sen,Hsiao, Cheng-Tien,Wang, Jeh-Jeng,Chung, Mei-Ing

, p. 6854 - 6859 (2014/01/06)

We synthesized a new series of PBD-hybrid derivatives having tethered triazoles and investigated for their cytotoxicity. The studies indicated that cis-olefin compounds induce higher cytotoxicity with increase in the G1 cell cycle phase compared with the trans-compounds. Quantitative RT-PCR assay indicated that compounds (16a-d) induced G1 phase arrest through down-regulation of cyclin D1 and up-regulation of p21, p27, and p53 mRNA expressions. Compounds 16a-d induced A375 early apoptosis as detected by flow cytometry after double-staining with annexin V and propidium iodide. Moreover, the Western blot analysis showed that A375 treated by compounds (16a-d) resulted in decreased levels of Bcl-2 and Bcl-xL, increased levels of Bax and Bad, and caspase/PARP degradation to identify apoptotic cells.

Process for preparation of penam derivatives

-

Page/Page column 8, (2008/06/13)

The invention relates to novel processes for preparing penam derivatives, such as Tazobactam and derivatives thereof. The processes according to the invention encompass procedures for the protection and deprotection of the carboxylic group as well as for the oxidation of the sulphur moiety of penam derivatives. Additionally, the present invention relates to new intermediates for the production of penam derivatives, allowing the desired penam-derivatives to be formulated with high purity and in good yields.

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