六甲基环三硅氮烷

六甲基环三硅氮烷
	IUPAC名; 2,2,4,4,6,6-hexamethyl-1,3,5,2,4,6-triazatrisilinane
英文名	hexamethylcyclotrisilazane
别名	二甲基硅氮烷三聚体; 三聚二甲基硅氮烷; HMCTS; HCMTSZ
识别
CAS号	1009-93-4
PubChem	66094
ChemSpider	59483
SMILES	C[Si]1(N[Si](N[Si](N1)(C)C)(C)C)C;
性质
化学式	C6H21N3Si3
摩尔质量	219.51 g·mol−1
密度	d20 0.9196 g/mL
熔点	−10 °C
沸点	188 °C
折光度n; D	n20/D 1.445
危险性
	GHS危险性符号;
GHS提示词	Danger
H-术语	H226, H302, H314, H315, H318, H319, H335
P-术语	P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P301+312, P301+330+331
	致死量或浓度：
LD50（中位剂量）	500 mg/kg（大鼠）
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

六甲基环三硅氮烷，简称HMCTS^[3]或HMCTSZN，^[4]是一种有机化合物，化学式 C
6H
21N
3Si
3 或[–Si(CH
3)
2–NH–]
3。这个分子里面有由三个硅原子和三个氮原子交替排列而成的六元环，每个硅原子都连接两个甲基，氮原子则连接氢原子。它也可以看作是假想化合物环三硅氮烷 [–SiH
2–NH–]
3的衍生物，或是假想化合物二甲基硅氮烷 (CH
3)
2SiNH的三聚体。^[2]^[5]

六甲基环三硅氮烷在室温下是无色清澈液体。^[2]

由于其在半导体工业中的应用，六甲基环三硅氮烷作为氮化硅^[6]^[7]^[4]和碳氮化硅^[8]沉积的前体已被广泛研究，并作为光刻胶中的添加剂。也有人建议将其作为二氧化硅的添加剂，用于色谱法。^[9]

结构

六甲基环三硅氮烷的环几乎是一个平面。这个分子内的键长为 Si-N = 1.728 Å、Si-C = 1.871 Å、C-H = 1.124 Å。它的键角则为 N-Si-N ≈ 108°、Si-N-Si ≈ 127°、 C-Si-C ≈ 109°、H-C-H ≈ 112°。^[10]^[11]

制备

六甲基环三硅氮烷是在1948年由 Brewer 和 Haber 通过二甲基二氯硅烷 Si(CH
3)
2Cl
2和液氨 NH
3反应，然后用苯萃取沉淀首次合成的。反应会产生多种产物，主要是三聚体和四聚体八甲基环四硅氮烷。三聚体可以通过分馏与其他产物分离。^[1]

通过在合适的催化剂存在下与氢气反应转化四聚体，可以提高产率。^[12]^[13]

参见

三聚硫代丙酮

参考资料

^ ^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 （页面存档备份，存于互联网档案馆）". 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 （页面存档备份，存于互联网档案馆）". 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 （页面存档备份，存于互联网档案馆）". United States Patent 5075474A
^ Barry C. Arkles and Burrell N. Hamon (1985): "Method of preparing hexamethylcyclotrisilazane （页面存档备份，存于互联网档案馆）" 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 （页面存档备份，存于互联网档案馆）". 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 （页面存档备份，存于互联网档案馆）". 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 （页面存档备份，存于互联网档案馆）". United States Patent 5075474A

[arkl1985-13] Barry C. Arkles and Burrell N. Hamon (1985): "Method of preparing hexamethylcyclotrisilazane （页面存档备份，存于互联网档案馆）" United States Patent 4577039A.

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