六甲基環三矽氮烷

六甲基環三矽氮烷
	IUPAC名; 2,2,4,4,6,6-hexamethyl-1,3,5,2,4,6-triazatrisilinane
英文名	hexamethylcyclotrisilazane
別名	二甲基矽氮烷三聚體; 三聚二甲基矽氮烷; HMCTS; HCMTSZ
識別
CAS號	1009-93-4
PubChem	66094
ChemSpider	59483
SMILES	C[Si]1(N[Si](N[Si](N1)(C)C)(C)C)C;
性質
化學式	C6H21N3Si3
摩爾質量	219.51 g·mol−1
密度	d20 0.9196 g/mL
熔點	−10 °C
沸點	188 °C
折光度n; D	n20/D 1.445
危險性
	GHS危險性符號;
GHS提示詞	Danger
H-術語	H226, H302, H314, H315, H318, H319, H335
P-術語	P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P301+312, P301+330+331
	致死量或濃度：
LD50（中位劑量）	500 mg/kg（大鼠）
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

六甲基環三矽氮烷，簡稱HMCTS^[3]或HMCTSZN，^[4]是一種有機化合物，化學式 C
6H
21N
3Si
3 或[–Si(CH
3)
2–NH–]
3。這個分子裏面有由三個矽原子和三個氮原子交替排列而成的六元環，每個矽原子都連接兩個甲基，氮原子則連接氫原子。它也可以看作是假想化合物環三矽氮烷 [–SiH
2–NH–]
3的衍生物，或是假想化合物二甲基矽氮烷 (CH
3)
2SiNH的三聚體。^[2]^[5]

六甲基環三矽氮烷在室溫下是無色清澈液體。^[2]

由於其在半導體工業中的應用，六甲基環三矽氮烷作為氮化矽^[6]^[7]^[4]和碳氮化矽^[8]沉積的前體已被廣泛研究，並作為光刻膠中的添加劑。也有人建議將其作為二氧化矽的添加劑，用於色譜法。^[9]

結構

六甲基環三矽氮烷的環幾乎是一個平面。這個分子內的鍵長為 Si-N = 1.728 Å、Si-C = 1.871 Å、C-H = 1.124 Å。它的鍵角則為 N-Si-N ≈ 108°、Si-N-Si ≈ 127°、 C-Si-C ≈ 109°、H-C-H ≈ 112°。^[10]^[11]

製備

六甲基環三矽氮烷是在1948年由 Brewer 和 Haber 通過二甲基二氯矽烷 Si(CH
3)
2Cl
2和液氨 NH
3反應，然後用苯萃取沉澱首次合成的。反應會產生多種產物，主要是三聚體和四聚體八甲基環四矽氮烷。三聚體可以通過分餾與其他產物分離。^[1]

通過在合適的催化劑存在下與氫氣反應轉化四聚體，可以提高產率。^[12]^[13]

參見

三聚硫代丙酮

參考資料

^ ^1.0 ^1.1 ^1.2 ^1.3 ^1.4 Stuart D. Brewer and Charles P. Haber (1948): "Alkylsilazanes and Some Related Compounds". Journal of the American Chemical Society, volume 70, issue 11, pages 3888-3891. doi:10.1021/ja01191a106
^ ^2.0 ^2.1 ^2.2 ^2.3 ^2.4 NCBI, U.S. National Institutes of Health (2020): "2,2,4,4,6,6-Hexamethylcyclotrisilazane". Compound data sheet, PubChem online database. Accessed on 2020-01-04.
^ FAR Chemical (2020): "Product 654201: Hexamethylcyclotrisilazane （頁面存檔備份，存於互聯網檔案館）". Catalog page. Accessed on 2020-01-04.
^ ^4.0 ^4.1 T. A. Brooks and D. W. Hess (1988): "Deposition chemistry and structure of plasma‐deposited silicon nitride films from 1,1,3,3,5,5‐hexamethylcyclotrisilazane". Journal of Applied Physics, volume 64, page 841. doi:10.1063/1.341935
^ Beilstein 4 III 1887.
^ Dennis W. Hess and Todd A. Brooks (1987): "Plasma enhanced chemical vapor deposition of thin films of silicon nitride from cyclic organosilicon nitrogen （頁面存檔備份，存於互聯網檔案館）". United States Patent 4863755A.
^ T. A. Brooks and D. W. Hess (1987): "Plasma-enhanced chemical vapor deposition of silicon nitride from 1,1,3,3,5,5-hexamethylcyclotrisilazane and ammonia". Thin Solid Films, volume 153, issues 1–3, pages 521-529. doi:10.1016/0040-6090(87)90211-2
^ N. I. Fainer, A. N. Golubenko, Yu. M. Rumyantsev, and E. A. Maximovskii (2009): "Use of hexamethylcyclotrisilazane for preparation of transparent films of complex compositions". Glass Physics and Chemistry, volume 35, issue 3, pages 274–283. doi:10.1134/S1087659609030067
^ J. Nawrocki (1985): "Modification of silica with mixtures of hexamethylcyclotrisilazane and hexamethyldisilazane". Chromatographia´ volume 20, pages 308–312. doi:10.1007/BF02310388
^ Béla Rozsondai, István Hargittai, Aleksei V. Golubinskii, Lev V.Vilkov, and Vladimir S.Mastryukov (1975): "Electron diffraction study on the molecular structure of hexamethylcyclotrisilazane, [(CH
3)
2SiNH]
3". Journal of Molecular Structure, volume 28, issue 2, pages 339-348. doi:10.1016/0022-2860(75)80104-9
^ D. M. Adams and W. S. Fernando (1973): "The vibrational spectra of hexamethylcyclotrisiloxane and hexamethylcyclotrisilazane". Journal of the Chemical Society, Dalton Transactions, issue 4, pages 410-413.doi:10.1039/DT9730000410
^ Hiromi Ohsaki, Yoshihumi Takeda, Toshinobu Ishihara, and Akira Hayashida (1991) "Method for preparing hexamethyl cyclotrisilazane （頁面存檔備份，存於互聯網檔案館）". United States Patent 5075474A
^ Barry C. Arkles and Burrell N. Hamon (1985): "Method of preparing hexamethylcyclotrisilazane （頁面存檔備份，存於互聯網檔案館）" United States Patent 4577039A.

[brew1948-1] 1.0 ^1.1 ^1.2 ^1.3 ^1.4 Stuart D. Brewer and Charles P. Haber (1948): "Alkylsilazanes and Some Related Compounds". Journal of the American Chemical Society, volume 70, issue 11, pages 3888-3891. doi:10.1021/ja01191a106

[pubchem-2] 2.0 ^2.1 ^2.2 ^2.3 ^2.4 NCBI, U.S. National Institutes of Health (2020): "2,2,4,4,6,6-Hexamethylcyclotrisilazane". Compound data sheet, PubChem online database. Accessed on 2020-01-04.

[farc2020-3] FAR Chemical (2020): "Product 654201: Hexamethylcyclotrisilazane （頁面存檔備份，存於互聯網檔案館）". Catalog page. Accessed on 2020-01-04.

[broo1988-4] 4.0 ^4.1 T. A. Brooks and D. W. Hess (1988): "Deposition chemistry and structure of plasma‐deposited silicon nitride films from 1,1,3,3,5,5‐hexamethylcyclotrisilazane". Journal of Applied Physics, volume 64, page 841. doi:10.1063/1.341935

[beil1887-5] Beilstein 4 III 1887.

[hess1987-6] Dennis W. Hess and Todd A. Brooks (1987): "Plasma enhanced chemical vapor deposition of thin films of silicon nitride from cyclic organosilicon nitrogen （頁面存檔備份，存於互聯網檔案館）". United States Patent 4863755A.

[broo1987-7] T. A. Brooks and D. W. Hess (1987): "Plasma-enhanced chemical vapor deposition of silicon nitride from 1,1,3,3,5,5-hexamethylcyclotrisilazane and ammonia". Thin Solid Films, volume 153, issues 1–3, pages 521-529. doi:10.1016/0040-6090(87)90211-2

[fain2009-8] N. I. Fainer, A. N. Golubenko, Yu. M. Rumyantsev, and E. A. Maximovskii (2009): "Use of hexamethylcyclotrisilazane for preparation of transparent films of complex compositions". Glass Physics and Chemistry, volume 35, issue 3, pages 274–283. doi:10.1134/S1087659609030067

[nawr1985-9] J. Nawrocki (1985): "Modification of silica with mixtures of hexamethylcyclotrisilazane and hexamethyldisilazane". Chromatographia´ volume 20, pages 308–312. doi:10.1007/BF02310388

[rosz1975-10] Béla Rozsondai, István Hargittai, Aleksei V. Golubinskii, Lev V.Vilkov, and Vladimir S.Mastryukov (1975): "Electron diffraction study on the molecular structure of hexamethylcyclotrisilazane, [(CH
3)
2SiNH]
3". Journal of Molecular Structure, volume 28, issue 2, pages 339-348. doi:10.1016/0022-2860(75)80104-9

[adam1973-11] D. M. Adams and W. S. Fernando (1973): "The vibrational spectra of hexamethylcyclotrisiloxane and hexamethylcyclotrisilazane". Journal of the Chemical Society, Dalton Transactions, issue 4, pages 410-413.doi:10.1039/DT9730000410

[ohsa1991-12] Hiromi Ohsaki, Yoshihumi Takeda, Toshinobu Ishihara, and Akira Hayashida (1991) "Method for preparing hexamethyl cyclotrisilazane （頁面存檔備份，存於互聯網檔案館）". United States Patent 5075474A

[arkl1985-13] Barry C. Arkles and Burrell N. Hamon (1985): "Method of preparing hexamethylcyclotrisilazane （頁面存檔備份，存於互聯網檔案館）" United States Patent 4577039A.

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