2-((TRIMETHYLSILYL)ETHYNYL)ANILINE - CAS 103529-16-4

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Category
Main Product
Product Name
2-((TRIMETHYLSILYL)ETHYNYL)ANILINE
Catalog Number
103529-16-4
Synonyms
2-((Trimethylsilyl)ethynyl)aniline; 2-[(Trimethylsilyl)ethynyl]aniline; 103529-16-4; 2-(2-trimethylsilylethynyl)aniline; AC1N90GE; 510963_ALDRICH
CAS Number
103529-16-4
Molecular Weight
189.33
Molecular Formula
C11H15NSi
Quantity
Data not available, please inquire.
COA
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MSDS
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Canonical SMILES
C[Si](C)(C)C#CC1=CC=CC=C1N
InChI
InChI=1S/C11H15NSi/c1-13(2,3)9-8-10-6-4-5-7-11(10)12/h4-7H,12H2,1-3H3
InChIKey
ISXSBRZDPKQYSC-UHFFFAOYSA-N
Structure
CAS 103529-16-4 2-((TRIMETHYLSILYL)ETHYNYL)ANILINE
Specification
Purity
95%
Boiling Point
120ºC0.1 mm Hg(lit.)
Density
0.94 g/mL at 25ºC(lit.)
Related Products
Reference Reading
1.Novel planar and star-shaped molecules: synthesis, electrochemical and photophysical properties.
Niu Q1, Lu Y, Sun H, Li X. Spectrochim Acta A Mol Biomol Spectrosc. 2013 Apr 15;107:377-85. doi: 10.1016/j.saa.2013.01.047. Epub 2013 Feb 1.
Three novel planar and star-shaped molecules containing thiophene-functionalized group and acetylenic spacers, 4-((5″-iodo-[2,2':5',2″-terthiophen]-5-yl)ethynyl)aniline (I3TEA), 4,4'-([2,2':5',2″-terthiophene]-5,5″-diylbis(ethyne-2,1-diyl))dianiline (3TDDA), 1,3,5-tris((5-((trimethylsilyl)ethynyl)thiophen-2-yl)ethynyl)benzene (TETEB) were synthesized through Sonogashira coupling reaction. Their photophysical and electrochemical properties were explored by UV-vis, photoluminescence (PL) emission and DFT calculation. Three compounds possess unusual phenomena of PL, with the concentration of gradually decreased, the intensity of PL firstly increased and then decreased, this may be due to the aggregate-enhanced emission (AEE) effect and aggregation-caused quenching (ACQ) effect. Their spectroscopic data demonstrate that D-π-A-π-D structured organic dye 3TDDA based on NH2 as donor units and 3T as acceptor units with acetylenic spacers π-conjugated chain between them exhibits good luminescent properties.
2.Four related diethyl [(arylamino)(4-ethynylphenyl)methyl]phosphonates.
Ouahrouch A1, Krim J, Taourirte M, Lazrek HB, Engels JW, Bats JW. Acta Crystallogr C. 2013 Oct;69(Pt 10):1157-63. doi: 10.1107/S0108270113022981. Epub 2013 Sep 6.
Crystal structures are reported for four related diethyl [(arylamino)(4-ethynylphenyl)lmethyl]phosphonate derivatives, namely diethyl [(4-bromoanilino)(4-ethynylphenyl)methyl]phosphonate, C19H21BrNO3P, (I), diethyl ((4-chloro-2-methylanilino){4-[2-(trimethylsilyl)ethynyl]phenyl}methyl)phosphonate, C23H31ClNO3PSi, (II), diethyl ((4-fluoroanilino){4-[2-(trimethylsilyl)ethynyl]phenyl}methyl)phosphonate, C22H29FNO3PSi, (III), and diethyl [(4-ethynylphenyl)(naphthalen-2-ylamino)methyl]phosphonate, C23H24NO3P, (IV). The conformation of the anilinobenzyl group is very similar in all four compounds. The P-C bond has an approximately staggered conformation, with the aniline and ethynylphenyl groups in gauche positions with respect to the P=O double bond. The two six-membered rings are almost perpendicular. The sums of the valence angles about the N atoms vary from 344 (2) to 351 (2)°. In the crystal structures, molecules of (I), (III) and (IV) are arranged as centrosymmetric or pseudocentrosymmetric dimers connected by two N-H···O=P hydrogen bonds.
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