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1-(TRIMETHYLSILYL)PYRROLIDINE, also known as N-trimethylsilyl pyrrolidine, is an organic compound with the chemical formula (CH3)3Si-N-(CH2)3-NH. It is a colorless liquid with a characteristic amine-like odor. 1-(TRIMETHYLSILYL)PYRROLIDINE is known for its reactivity and is commonly used in various chemical reactions due to its silyl group, which can be easily removed under mild conditions.

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  • 15097-49-1 Structure
  • Basic information

    1. Product Name: 1-(TRIMETHYLSILYL)PYRROLIDINE
    2. Synonyms: N-(TRIMETHYLSILYL)PYRROLIDINE;TRIMETHYLSILYLPYRROLIDINE;1-(TRIMETHYLSILYL)PYRROLIDINE;1-(trimethylsilyl)-pyrrolidin;Pyrrolidine,1-(trimethylsilyl)-;1-(TRIMETHYLSILYL)PYRROLIDINE 97+%;1-trimethylsilylpyrrolidine,95%;Trimethyl(pyrrolizino)silane
    3. CAS NO:15097-49-1
    4. Molecular Formula: C7H17NSi
    5. Molecular Weight: 143.3
    6. EINECS: 239-149-3
    7. Product Categories: Building Blocks;Heterocyclic Building Blocks;Pyrrolidines
    8. Mol File: 15097-49-1.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 139-140 °C(lit.)
    3. Flash Point: 40 °F
    4. Appearance: /
    5. Density: 0.821 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 7.98mmHg at 25°C
    7. Refractive Index: n20/D 1.433(lit.)
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. BRN: 1304636
    11. CAS DataBase Reference: 1-(TRIMETHYLSILYL)PYRROLIDINE(CAS DataBase Reference)
    12. NIST Chemistry Reference: 1-(TRIMETHYLSILYL)PYRROLIDINE(15097-49-1)
    13. EPA Substance Registry System: 1-(TRIMETHYLSILYL)PYRROLIDINE(15097-49-1)
  • Safety Data

    1. Hazard Codes: F,C
    2. Statements: 11-34
    3. Safety Statements: 16-26-36/37/39-45
    4. RIDADR: UN 2924 3/PG 2
    5. WGK Germany: 3
    6. RTECS:
    7. F: 10-21
    8. HazardClass: 3.1
    9. PackingGroup: II
    10. Hazardous Substances Data: 15097-49-1(Hazardous Substances Data)

15097-49-1 Usage

Uses

1. Used in Chemical Synthesis:
1-(TRIMETHYLSILYL)PYRROLIDINE is used as a reagent for the ring-opening reaction of L-serine β-lactone to yield corresponding 5-amino-L-alanine derivatives. The application reason is that the compound's silyl group can be easily removed, allowing for the formation of the desired product with minimal side reactions.
2. Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-(TRIMETHYLSILYL)PYRROLIDINE is used as a precursor for the preparation of iminium triflate salts. The application reason is that these iminium triflate salts are valuable intermediates in the synthesis of various biologically active compounds, such as pharmaceuticals and agrochemicals.
3. Used in Organic Chemistry Research:
1-(TRIMETHYLSILYL)PYRROLIDINE is also used as a protecting group in organic chemistry research. The application reason is that the silyl group can be selectively removed under mild conditions, allowing for the controlled deprotection of amines and other functional groups in complex organic molecules.
4. Used in Material Science:
In material science, 1-(TRIMETHYLSILYL)PYRROLIDINE can be used as a component in the synthesis of novel materials, such as polymers and dendrimers, due to its unique reactivity and the ease of removal of the silyl group.

Check Digit Verification of cas no

The CAS Registry Mumber 15097-49-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,5,0,9 and 7 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 15097-49:
(7*1)+(6*5)+(5*0)+(4*9)+(3*7)+(2*4)+(1*9)=111
111 % 10 = 1
So 15097-49-1 is a valid CAS Registry Number.
InChI:InChI=1/C7H17NSi/c1-9(2,3)8-6-4-5-7-8/h4-7H2,1-3H3

15097-49-1 Well-known Company Product Price

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  • Aldrich

  • (277371)  1-(Trimethylsilyl)pyrrolidine  97%

  • 15097-49-1

  • 277371-25G

  • 1,585.35CNY

  • Detail

15097-49-1SDS

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 trimethyl(pyrrolidin-1-yl)silane

1.2 Other means of identification

Product number -
Other names N-Trimethylsilylpyrrolidine

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:15097-49-1 SDS

15097-49-1Relevant articles and documents

Palladium and nickel complexes of (P,N)-ligands based on quinolines: Catalytic activity for polymerization and oligomerization

Sirbu, Doina,Consiglio, Giambattista,Gischig, Sebastian

, p. 1143 - 1150 (2006)

Four (P,N)-ligands (1-4) with different steric and electronic properties were synthesized. They were used to prepare the monocationic palladium complexes [Pd(P,N)(CH3)(NCCH3)](PF6) (9-12). The structures of the newly prepared ligand 3 and the neutral palladium complex [Pd(P,N)(CH3)Cl] (10) were analysed by X-ray. The catalytic activity of the palladium complexes toward the copolymerization of styrene and ethylene with CO was low or non-existent. The nickel complexes [Ni(P,N)(1-naphthyl)Cl] (13-16), modified with the ligands 1-4, were prepared and their catalytic activity toward ethylene oligomerization was studied. They showed high activity at ambient temperature and low ethylene pressure (1-12 bar) in the presence of MAO.

Preparation, Characterization, and Reactivity of Aliphatic Amino Iodane(III) Reagents

Zhang, Yue,Lu, Jing,Lan, Tianlei,Cheng, Shaoling,Liu, Wei,Chen, Chao

supporting information, p. 436 - 442 (2020/12/21)

The preparation of a new class of aliphatic amino iodane(III) reagents has been realized with the N-TMS?amine and acetoxybenziodazole participated in the formation of N?I bond. The amino-containing iodane(III) reagent 2 d was characterized by single-crystal X-ray diffraction, which revealed the expected hypervalent iodane distorted T-shaped geometry. A practical copper-catalyzed, directed electrophilic amination of aryl amines employing amino-iodane(III) as amination agents was disclosed that proceeded smoothly without external additives.

An Alumino-Mannich Reaction of Organoaluminum Reagents, Silylated Amines, and Aldehydes

Tarasewicz, Anika,Ensan, Deeba,Batey, Robert A.

supporting information, p. 6071 - 6074 (2018/04/27)

A multi-component coupling using organoaluminum reagents, silylated amines, and aldehydes results in the formation of tertiary amines. Both alkenyl- and alkylaluminum reagents undergo reaction with iminium ion substrates for which the corresponding Petasis borono-Mannich reactions are unsuccessful.

Nucleophilic bromodifluoromethylation of iminium ions

Tsymbal, Artem V.,Kosobokov, Mikhail D.,Levin, Vitalij V.,Struchkova, Marina I.,Dilman, Alexander D.

, p. 7831 - 7835 (2015/03/18)

A method for bromodifluoromethylation of iminium ions using Me3SiCF2Br is described. The reaction involves room temperature activation of the silicon reagent by HMPA to generate difluorocarbene, which upon interacting with excess of bromide ion provides bromodifluoromethyl carbanionic species. The iminium electrophiles are generated in situ from aldehydes, secondary amines, proton sponge, and silyl triflate. The reaction can be extended for introduction of chlorodifluoromethyl and iododifluoromethyl groups.

Deoxofluorination reactions using N,N-disubstituted aminodifluorosulfinium tetrafluoroborate salts

Mahé, Olivier,L'Heureux, Alexandre,Couturier, Michel,Bennett, Christopher,Clayton, Simon,Tovell, David,Beaulieu, Francis,Paquin, Jean-Fran?ois

, p. 57 - 60 (2013/11/06)

The synthesis of N,N-disubstituted aminodifluorosulfinium tetrafluoroborate salts is reported, and their behavior as deoxofluorinating agent was evaluated. The deoxofluorination reactions were performed using a primary alcohol, a secondary alcohol and a ketone. Results show that subtle modification of the structure of the reagents can noticeably affect the reactivity and the selectivity in deoxofluorination reactions.

DISUBSTITUTED-AMINODIFLUOROSULFINIUM SALTS, PROCESS FOR PREPARING SAME AND METHOD OF USE AS DEOXOFLUORINATION REAGENTS

-

Page/Page column 28, (2010/12/31)

The invention relates to disubstituted-aminodifluorosulfinium salts represented by the formula (I). Processes for preparing same and methods of use as deoxofluorinating reagent is also provided.

Three-component coupling using arynes and aminosilanes for ortho-selective double functionalization of aromatic skeletons

Morishita, Takami,Fukushima, Hiroyuki,Yoshida, Hiroto,Ohshita, Joji,Kunai, Atsutaka

, p. 5452 - 5457 (2008/12/20)

(Chemical Equation Presented) Arynes were found to couple with aminosilanes and carbonyl compounds in the presence of benzoic acid to provide 2-aminobenzhydrols. Sulfonylimines could also be applied to the reaction, enabling amino and aminomethyl moieties to be incorporated into contiguous positions of aromatic skeletons. Only a small amount of the three-component coupling product was obtained in the absence of benzoic acid, which confirms its vital role in the present reaction.

A Simple and Highly Diastereoselective One-Pot Synthesis of Mannich-Bases

Arend, Michael,Risch, Nikolaus

, p. 974 - 976 (2007/10/03)

A convenient one-pot procedure for the synthesis of β-amino ketones 5 from economical shelf reagents is described. Iminium salts 3 are generated in virtually quantitative yields from secondary amines 1 and aldehydes 2 mediated by NaI/Me3SiCl/NEt3. Subsequently, the salts 3 are used for the in situ aminoalkylation of enamines 4. The method provides the Mannich bases 5 in high yields and excellent diastereoselectivities (>96 % ds). It can also be applied for the aminoalkylation of other nucleophiles such as imines or electron-rich aromatic compounds.

Synthesis of deoxydinucleoside phosphorodithioates

Brill, Wolfgang K.-D.,Nielsen, John,Caruthers, Marvin H.

, p. 3972 - 3980 (2007/10/02)

The synthesis of a new class of DNA analogues called phosphorodithioate DNA is described. This analogue, which has a deoxynucleoside-OPS2O-deoxynucleoside internucleotide linkage, is isosteric and isopolar with the normal phosphodiester, inert toward nucleases, and potentially useful for a large number of biochemical and biological applications. Two methods are described for synthesizing this derivative. One route begins by condensing a deoxynucleoside phosphorodiamidite with a second appropriately protected deoxynucleoside to yield a deoxydinucleoside phosphoramidite. Sulfhydrolysis with H2S generates the H-phosphonothioate, which upon oxidation with sulfur yields the deoxydinucleoside phosphorodithioate. Alternatively, sequential treatment of the deoxydinucleoside phosphoramidite with a mercaptan and sulfur yields the deoxydinucleoside phosphorodithioate triester. These deoxydinucleotides in protected form can then be used to introduce the dithioate internucleotide linkage into DNA. The second route for generating dithioate DNA uses deoxynucleoside phosphorothioamidites. Two derivatives, the deoxynucleoside 3′-N,N-dimetnyl- or 3′-(N,N-tetramethylenephosphorothioamidite), were found to be especially attractive synthons as they could be prepared in stable form via a one-flask synthesis procedure and used to form the deoxydinucleoside thiophosphite rapidly (1-2 min with tetrazole as activator) in high yield. Subsequent oxidation with sulfur generates the completely protected phosphorodithioate linkage.

A NEW SYNTHESIS OF AMIDES FROM ACYL FLUORIDES AND N-SILYLAMINES

Rajeswari, Sundaramoorthi,Jones, Robert J.,Cava, Michael P.

, p. 5099 - 5102 (2007/10/02)

Amide bonds are formed readily under mild conditions by the reaction of N-silylamines with the hydrolytically stable acyl fluorides.

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