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Merck
모든 사진(1)

주요 문서

73328

Sigma-Aldrich

Trimethylsilyl cyanide

technical, ≥95% (GC)

동의어(들):

Cyanotrimethylsilane, TMSCN

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About This Item

Linear Formula:
(CH3)3SiCN
CAS Number:
Molecular Weight:
99.21
Beilstein:
1737612
EC Number:
MDL number:
UNSPSC 코드:
12352100
PubChem Substance ID:
NACRES:
NA.22

grade

technical

Quality Level

분석

≥95% (GC)

양식

liquid

refractive index

n20/D 1.392 (lit.)

bp

114-117 °C (lit.)

mp

8-11 °C (lit.)

density

0.793 g/mL at 20 °C (lit.)

SMILES string

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

InChI

1S/C4H9NSi/c1-6(2,3)4-5/h1-3H3

InChI key

LEIMLDGFXIOXMT-UHFFFAOYSA-N

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관련 카테고리

애플리케이션

Trimethylsilyl cyanide (TMSCN) can be used as a reagent in the:
  • Cyanosilylation of carbonyl compounds using various catalysts.
  • Synthesis of α-aminonitriles by one-pot, three-component Strecker reaction of ketones with various amines using Brønsted acid catalyst.
  • Cyanation of aryl halides using palladium-complex as a catalyst.

픽토그램

FlameSkull and crossbonesEnvironment

신호어

Danger

유해 및 위험 성명서

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Flam. Liq. 2

보충제 위험성

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point (°F)

33.8 °F - closed cup

Flash Point (°C)

1 °C - closed cup

개인 보호 장비

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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시험 성적서(COA)

Lot/Batch Number

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문서 라이브러리 방문

A convenient and efficient procedure for the palladium-catalyzed cyanation of aryl halides using trimethylsilylcyanide
Sundermeier M, et al.
Journal of Organometallic Chemistry, 684(1-2), 50-55 (2003)
Asymmetric addition of trimethylsilyl cyanide to ketones catalyzed by Al (salen)/triphenylphosphine oxide
Kim SS and Kwak Ju M
Tetrahedron, 62(1), 49-53 (2006)
Indium tribromide: a highly effective catalyst for the addition of trimethylsilyl cyanide to ?-hetero-substituted ketones
Bandini M, et al.
Tetrahedron Letters, 42(16), 3041-3043 (2001)
Siddhartha R Shenoy et al.
Journal of the American Chemical Society, 128(26), 8671-8677 (2006-06-29)
The limitations of stereoelectronic models in assessing the stereoselective nucleophilic substitution reactions of cyclic oxocarbenium ions at high reaction rates are discussed. Evidence is provided suggesting that the diastereoselectivity of nucleophilic substitution reactions is attenuated at the limits of diffusion
Guang-Wu Zhang et al.
Organic & biomolecular chemistry, 8(6), 1399-1405 (2010-03-06)
A general method for the one-pot, three-component Strecker reaction of ketones was developed using Brønsted acids as organocatalysts. A series of alpha-aminonitriles were obtained in good to excellent yields (79-99%). A preliminary extension to a catalytic enantioselective three-component Strecker reaction

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