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510963

Sigma-Aldrich

2-[(Trimethylsilyl)ethynyl]aniline

97%

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About This Item

Linear Formula:
(CH3)3SiC≡CC6H4NH2
CAS Number:
Molecular Weight:
189.33
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

refractive index

n20/D 1.564 (lit.)

bp

120 °C/0.1 mmHg (lit.)

density

0.94 g/mL at 25 °C (lit.)

SMILES string

C[Si](C)(C)C#Cc1ccccc1N

InChI

1S/C11H15NSi/c1-13(2,3)9-8-10-6-4-5-7-11(10)12/h4-7H,12H2,1-3H3

InChI key

ISXSBRZDPKQYSC-UHFFFAOYSA-N

General description

2-[(Trimethylsilyl)ethynyl]aniline is a 2-ethynylaniline derivative that can be prepared by the palladium-catalyzed reaction between 2-bromonitrobenzene and trimethylsilylacetylene.[1]

Application

2-[(Trimethylsilyl)ethynyl]aniline (2-(2-Trimethylsilylethynyl)aniline) may be used in the synthesis of:
  • N-(2-trimethylsilylethynylphenyl)methanesulfonamide[1]
  • 8-(2-((trimethylsilyl)ethynyl)phenylamino)-7H-naphtho[1,8-bc]acridin-7-one[2]
  • 2-phenyl-4-alkoxy quinolines[3]

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Synthesis and Characterization of 8-(2-((Trimethylsilyl) ethynyl) phenylamino)-7H-naphtho [1,8-bc] acridin-7-one.
Li L, et al.
Synthetic Communications, 38(24), 4415-4425 (2008)
Condensed heteroaromatic ring systems. XIII. One-step synthesis of 2-substituted 1-methylsulfonylindoles from N-(2-halophenyl) methanesulfonamides.
Sakamoto T, et al.
Chemical & Pharmaceutical Bulletin, 36, 1305-1308 (1988)
Marella A, et al.
Saudi Pharmaceutical Journal : SPJ : The Official Publication of the Saudi Pharmaceutical Society, 21(1), 1-2 (2013)

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