N,O-ビス(トリメチルシリル)ヒドロキシルアミン

化学名:N,O-ビス(トリメチルシリル)ヒドロキシルアミン

英語名:N,O-Bis(trimethylsilyl)hydroxylamine

CBNumberCB0779294

MFC6H19NOSi2

MW177.39

别名

N,O-ビス(トリメチルシリル)ヒドロキシルアミン

α,α,α-トリメチル-N-[(トリメチルシリル)オキシ]シランアミン

O,N-ビス(トリメチルシリル)ヒドロキシルアミン

N,O-ビス(トリメチルシリル)ヒドロキシルアミン物理性質

沸点	78-80 °C100 mm Hg(lit.)
比重(密度)	0.83 g/mL at 25 °C(lit.)
屈折率	n20/D 1.411(lit.)
闪点	84 °F
貯蔵温度	2-8°C
溶解性	sol THF、エーテル、ペンタン、CH2Cl2。
酸解離定数(Pka)	5.94±0.70(Predicted)
外見	clear liquid
色	Colorless to Almost colorless
比重	0.83
Hydrolytic Sensitivity	7: reacts slowly with moisture/water
BRN	1920452
InChI	1S/C6H19NOSi2/c1-9(2,3)7-8-10(4,5)6/h7H,1-6H3
InChIKey	ZAEUMMRLGAMWKE-UHFFFAOYSA-N
SMILES	C[Si](C)(C)NO[Si](C)(C)C
CAS データベース	22737-37-7(CAS DataBase Reference)

安全性情報

危険有害性情報のコード(GHS)

外観
無色～ほとんど無色透明液体
化学的特性
Clear colorless liquid
物理的性質
bp 137–139°C, 78–80°C/100 mmHg; d 0.830 g cm3; flash point 28°C.
使用
N,O-Bis(trimethylsilyl)hydroxylamine is a protected, lipophilic form of hydroxylamine. It reacts with a variety of electrophiles predominantly by attack on the nitrogen nucleophilic center. Reaction with acid chlorides (1 equiv) in the presence of triethylamine gives N,O-bis(trimethylsilyl)- hydroxamic acids by N-acylation.A related reagent, tris(trimethylsilyl) hydroxylamine, gives the same product in high yields, also by N-acylation.Hydrolysis gives the free hydroxamic acids, whereas thermal fragmentation affords isocyanates (eq 1).
製造方法
N,O-Bis(trimethylsilyl)hydroxylamine can be prepared in 69% yield by treating dry hydroxylamine with equiv chlorotrimethylsilane and equiv triethylamine.A safer preparation, which avoids the use of the explosive solid, hydroxylamine, uses the reaction of hydroxylamine hydrochloride with excess hexamethyldisilazane (71–75% yield).Alternatively, neutralization of hydroxylamine hydrochloride with ethylenediamine followed by addition of chlorotrimethylsilane can be used.
一般的な説明
N,O-Bis(trimethylsilyl)hydroxylamine on reaction with 9-chloro-9-borafluorene yields 10-trimethylsilyloxy-9-aza-10-boraphenanthrene. It reacts with free phenolic steroids during the analysis of conjugated estrogen tablets and injectable formulations by GLC.

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