Trimethylsilyldiazomethane

Structural formula
General
Surname	Trimethylsilyldiazomethane
other names	(Diazomethyl) trimethylsilane
Molecular formula	(CH 3 ) 3 SiCHN 2
Brief description	yellowish-green liquid
External identifiers / databases
CAS number 18107-18-1 EC number 605-915-4 ECHA InfoCard 100.131.243 PubChem 167693 Wikidata Q1990988
properties
Molar mass	114.22 g mol −1
Physical state	liquid
boiling point	96 ° C
solubility	almost insoluble in water soluble in most organic solvents
Refractive index	1.4362 (25 ° C)
safety instructions
GHS hazard labeling no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Trimethylsilyldiazomethane is an organic chemical compound from the group of azo compounds .

Extraction and presentation

Trimethylsilyldiazomethane can be obtained from trimethylsilylmethylmagnesium chloride by a Grignard reaction with diphenyl azidophosphate.

${\displaystyle \mathrm {Me_{3}SiCH_{2}MgCl+(PhO)_{2}P)O)N_{3}+H_{2}O\longrightarrow Me_{3}SiCHN_{2}+(PhO)_{2}P(O)NH_{2}} }$

properties

Trimethylsilyldiazomethane is a yellowish green liquid that is insoluble in water but soluble in most organic solvents . It is stable in pure form or in hydrocarbon solution, but rapidly decomposes on contact with carbon tetrachloride or when exposed to light. It is not saponified by neutral water or 20% potassium hydroxide solution. It can undergo a number of reactions, such as with carboxylic acids, cyclohexene, or activated olefins.

use

Trimethylsilyldiazomethane is used as a substitute for diazomethane for the derivatization of phenols in the presence of diisopropylamine . It is also used in organic syntheses to esterify various naturally occurring carboxylic acids . It also converts sterically hindered alcohols into the corresponding methyl ethers . For example, it is used in the production of macrolactam analogues of natural macrolides and aigialomycin analogues.

safety instructions

Trimethylsilyldiazomethane is marketed as a ready-to-use solution in hexane or diethyl ether . In contrast to diazomethane, it has no tendency to explode, but it is also carcinogenic and a strong breath poison.

Individual evidence

1. ↑ ^{a b c d e f g h} Entry on trimethylsilyldiazomethane in the Hazardous Substances Data Bank , accessed on June 20, 2014.
2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
3. ↑ Takayuki Shioiri, Toyohiko Aoyama and Shigehiro Mori: Trimethylsilyldiazomethane In: Organic Syntheses . 68, 1990, p. 1, doi : 10.15227 / orgsyn.068.0001 ; Coll. Vol. 8, 1993, p. 612 ( PDF ).
4. ^ US Department of Health and Human Services: NTP Chemical Information Review Document for Trimethylsilyldiazomethane .
5. ↑ Data sheet (Trimethylsilyl) diazomethane solution, 2.0 M in hexanes from Sigma-Aldrich , accessed on June 16, 2014 ( PDF ).
6. ↑ Hazardous substances in internships ( Memento from January 22, 2015 in the Internet Archive ).