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Trimethylsilylmethyl Azide, also known as TMSMA, is an organosilicon compound with the chemical formula (CH3)3SiN3. It is a versatile reagent in organic synthesis, known for its stability and unique reactivity. Its trimethylsilyl group provides steric bulk and electron-donating properties, while the azide group offers a source of nitrogen for various chemical transformations.

87576-94-1

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87576-94-1 Usage

Uses

Used in Organic Synthesis:
Trimethylsilylmethyl Azide is used as a reagent for the amination of organometallic compounds, enabling the formation of amines from metal-nitrogen bonds. This process is particularly useful in the synthesis of complex organic molecules and pharmaceuticals.
Used in Heterocyclic Chemistry:
In the field of heterocyclic chemistry, Trimethylsilylmethyl Azide serves as a precursor for the preparation of various heterocyclic compounds. Its ability to provide a nitrogen source makes it a valuable building block for the synthesis of nitrogen-containing rings.
Used as a Precursor for Azomethine Ylide:
Trimethylsilylmethyl Azide is used as a precursor for the generation of azomethine ylides, which are reactive intermediates in organic chemistry. These ylides can be employed in various cyclization reactions, leading to the formation of complex molecular structures.
Used in Silylmethyl-Substituted Heterocumulenes:
In the synthesis of silylmethyl-substituted heterocumulenes, Trimethylsilylmethyl Azide is utilized as a key reactant. These heterocumulenes are valuable intermediates in the formation of various nitrogen-containing compounds.
Used in [3 + 2] Cycloaddition Reactions:
Trimethylsilylmethyl Azide is also used in [3 + 2] cycloaddition reactions, a type of chemical reaction that involves the formation of a five-membered ring from a three-atom component and a two-atom component. This reaction is an important method for constructing complex molecular frameworks in organic chemistry.

Preparation

Obtained in high yield by reaction of sodium azide and (chloromethyl)trimethylsilane in DMF or HMPA at 80°C.

Check Digit Verification of cas no

The CAS Registry Mumber 87576-94-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,7,5,7 and 6 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 87576-94:
(7*8)+(6*7)+(5*5)+(4*7)+(3*6)+(2*9)+(1*4)=191
191 % 10 = 1
So 87576-94-1 is a valid CAS Registry Number.

87576-94-1 Well-known Company Product Price

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  • TCI America

  • (T1184)  Trimethylsilylmethyl Azide  >97.0%(GC)

  • 87576-94-1

  • 1g

  • 390.00CNY

  • Detail
  • TCI America

  • (T1184)  Trimethylsilylmethyl Azide  >97.0%(GC)

  • 87576-94-1

  • 5g

  • 1,200.00CNY

  • Detail

87576-94-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Trimethylsilylmethyl Azide

1.2 Other means of identification

Product number -
Other names diazonio(trimethylsilylmethyl)azanide

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:87576-94-1 SDS

87576-94-1Relevant academic research and scientific papers

NOVEL TRICYCLIC COMPOUNDS AS ANTICANCER AGENTS

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Paragraph 0980; 0981, (2016/07/27)

The present invention is directed to tricyclic compounds, pharmaceutically acceptable compositions comprising compounds of the invention and methods of using said compositions in the treatment of various disorders.

SULFONAMIDE RETINOIC ACID RECEPTOR-RELATED ORPHAN RECEPTOR MODULATORS AND USES THEREOF

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Paragraph 0257; 0258, (2016/02/16)

Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of Retinoic Acid Receptor-Related Orphan Receptor regulated diseases and disorders.

TRICYCLIC COMPOUNDS AS ANTICANCER AGENTS

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Page/Page column 375, (2015/07/15)

The present invention is directed to tricyclic compounds (I), pharmaceutically acceptable compositions comprising compounds of the invention and methods of using said compositions in the treatment of various disorders.

RETINOIC ACID RECEPTOR-RELATED ORPHAN RECEPTOR MODULATORS AND USES THEREOF

-

Paragraph 0218; 0219, (2015/09/28)

Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of Retinoic Acid Receptor-Related Orphan Receptor regulated diseases and disorders.

1,2,3-triazolium ionic liquids

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Page/Page column 26, (2014/12/12)

The present invention relates to compositions of matter that are ionic liquids, the compositions comprising substituted 1,2,3-triazolium cations combined with any anion. Compositions of the invention should be useful in the separation of gases and, perhap

Probing the structure-property relationship of regioisomeric ionic liquids with click chemistry

Nulwala, Hunaid B.,Tang, Chau N.,Kail, Brian W.,Damodaran, Krishnan,Kaur, Palwinder,Wickramanayake, Shan,Shi, Wei,Luebke, David R.

supporting information; experimental part, p. 3345 - 3349 (2012/02/01)

Understanding the structure-property relationship of ionic liquids is a key to the development of optimized materials for specific applications, such as CO2 capture, battery electrolytes, or lubricants. Using Cu(i)-catalyzed click chemistry as

α-Alkyl-α-aminosilanes. 1. Metalation and alkylation between silicon and nitrogen

Sieburth, Scott McN.,Somers, Joseph J.,O'Hare, Heather K.

, p. 5669 - 5682 (2007/10/03)

tert-Butyl carbamate derivatives of readily available aminomethyltrialkylsilanes have been studied for their ability to undergo metalation between nitrogen and silicon, followed by reaction with an electrophile. Metalation is rapid and reaction with a variety of electrophiles proceeds efficiently. When a benzyl group is attached to nitrogen, benzylic deprotonation competes with deprotonation next to silicon.

Synthesis, Antitumor Activity, and Chemical Properties of Silaplatin and Related Platinum(II) and Platinum(IV) Complexes Derived from β-Silyl Amines

Anderson, Wayne K.,Kasliwal, Ravindra,Houston, D. Michael,Wang, Yueh-sha,Narayanan, Ven L.,et al.

, p. 3789 - 3797 (2007/10/03)

Platinum(II) and platinum(IV) coordination complexes derived from β-silyl-substituted amines were prepared.The solubility of selected complexes in water and physiological saline was measured, and the effect of the β-silicon on the reactivity of the complex in aqueous solution was determined by HPLC.The stabilities of selected silyl complexes were compared to the carbon analogues.The cyclic complexes 2a ("silaplatin") and its Pt(IV) analogue, 2b, were very active against L1210 leukemia in vivo.Both the platinum(II) complex 2a and the platinum(IV) complex 2b produced a significant number of cures over the dose range 10-40 mg/kg.The platinum(II) complex 2a, silaplatin, was very active in vivo against an L1210 leukemia subline that was resistant to cisplatin; 2a was also active, when given ip against ic implanted L1210.The cyclobutanedicarboxylic acid complex 3c was synthesized; this complex was active against both cisplatin sensistive and resistant L1210 leukemia but was less potent than the analogous dichloro compound 2a.The acyclic platinum(II) and platinum(IV) complexes 1a,b were synthesized and unexpectedly found to be inactive in vivo against L1210 leukemia.More lipophilic silaplatin analogues were prepared-Pt(II) complex 2c and Pt(IV) complex 2d have one additional methylene carbon compared to 2a,b, whereas Pt(II) complex 2e and Pt(IV) complex 2f have two additional methylene carbons.Cyclization of the alkyl groups attached to the silicon gave the spiro bicyclic Pt(II) complexes 10a and 11a and the Pt(IV) complexes 10 b and 11b.

The Synthesis of Pyrroles with Insecticidal Activity

Kuhn, David G.,Kamhi, Victor M.,Furch, Joseph A.,Diehl, Robert E.,Lowen, Gregory T.,Kameswaran, Venkataraman

, p. 279 - 286 (2007/10/03)

The 2-aryl-4-bromo-5-trifluoromethylpyrrole-3-carbonitriles represent a new class of insect control agents. The high insecticidal activity observed in this series prompted us to investigate the preparation of regioisomeric arylhalotrifluoromethylpyrrole c

Platinum complexes derived from b-silyamines

-

, (2008/06/13)

This invention relates to new cis diamino platinum complexes; to compositions comprising these complexes; and to processes for their utility as fungicides, bacteriocides and as inhibitors of the growth of cancer in warm-blooded animals, wherein the comple

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