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1066-54-2 - (Trimethylsilyl)acetylene, 98% - Ethynyltrimethylsilane - TMS acetylene - A12856 - Alfa Aesar

A12856 (Trimethylsilyl)acetylene, 98%

CAS 번호
1066-54-2
동의어
Ethynyltrimethylsilane
TMS acetylene

사이즈 가격 ($) 수량 재고 여부
5g 36.70
25g 157.00
100g 408.00
장바구니에 추가 대량 견적에 추가 항목 보기

(Trimethylsilyl)acetylene, 98%

MDL
MFCD00008569
EINECS
213-919-9

화학적 특성

화학식
C5H10Si
화학 식량
98.22
비등점
52-53°
인화점
<-34°(-29°F)
밀도
0.710
굴절률
1.3900
용해도
Miscible with organic solvents.

용도

(Trimethylsilyl)acetylene is used in the preparation of trimethylsilanyl-propiolic acid ethyl ester by reacting with carbonochloridic acid ethyl ester as well as in the synthesis of iodoalkenes by radical addition of perfluoroalkyl iodides. It is used as a nucleophile in Friedel-Crafts type acylations and alkylations reactions, as a ligand in organometallic chemistry and an useful reagent in cycloaddition reactions. It acts as a precursor to lithium trimethylsilylacetylide It finds application in the synthesis of (±)-estrone.

참고

Store in a cool place. Incompatible with strong oxidizing agents.

참조 문헌

Pd catalyzed coupling with aryl bromides or iodides gives aryl TMS alkynes, from which the TMS group is readily cleaved by K2CO3 in MeOH: Synthesis, 627 (1980); J. Org. Chem., 46, 2280 (1981). Coupling with 1-bromo-2-nitrobenzene or ethyl 2-bromocarbanilate gives indole precursors. Other terminal alkynes lead to 2-substituted indoles: Heterocycles, 24, 31 (1986):

Cross-coupling with aryl halides can also be catalyzed by Pd-C in the presence of Ph3P, CuI and Et3N: Synth. Commun., 20, 2059 (1990); for an example, see 2-Bromonaphthalene, A15300. Pd catalyzed coupling with quinolinol and isoquinolinol triflates has also been reported: Tetrahedron, 51, 3737 (1995). For coupling with vinyl halides catalyzed by Tetrakis(triphenyl­phosphine)­palladium(0)­, 10548 in the presence of CuI as an example of a route to enynes, see: Tetrahedron Lett., 30, 6997 (1989); Org. Synth. Coll., 9, 117 (1998). CuCl-TMEDA catalyzed oxidative (Hay) coupling gives bis(TMS)-1,3-butadiyne: Org. Synth. Coll., 8, 63 (1993).

For the synthesis of iodoalkenes by radical addition of perfluoroalkyl iodides, see: J. Org. Chem., 47, 2251 (1982).

Das, S.; Samanta, S.; Ray, S.; Biswas, P. 3, 6-Di (pyridin-2-yl)-1, 2, 4, 5-tetrazine capped Pd (0) nanoparticles: a catalyst for copper-free Sonogashira coupling of aryl halides in aqueous medium. J. Chromatogr. A 2015, 1379, 56-64.

GHS 해저드 및 주의 설명서

해저드 설명서 (EU): H225

Highly flammable liquid and vapour.

주의 설명서: P210-P280a-P240-P241-P303+P361+P353-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves and eye/face protection. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. Dispose of contents/container in accordance with local/regional/national/international regulations.

기타 참조

바일슈타인
906752
위험 등급
3
포장 그룹
II
통합 관세 코드
2931.90
TSCA(독성물질규제법)"
Yes

권장

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    1-Bromo-2-iodobenzene, 98+%, stab. with copper
  • 10491

    trans-Dichlorobis(triphenylphosphine)palladium(II), Pd 14.0% min
  • 43153

    Copper(I) iodide, Puratronic®, 99.998% (metals basis)

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