2916-68-9 Usage
Description
2-(Trimethylsilyl)ethanol, also known as TMS-EtOH, is a clear, colorless liquid with a density of 0.825 g/cm3. It is characterized by its boiling points at 50-52 °C/10 mmHg and 71-73 °C/35 mmHg. This versatile compound is widely used in various applications across different industries due to its unique properties.
Uses
Used in Organic Synthesis:
2-(Trimethylsilyl)ethanol is used as a protecting reagent for carboxyl, phosphoryl, hydroxyl, and amino groups in organic synthesis. It plays a crucial role in Phenol and Acid Protection, Alcohol Protection, Hemiacetal Protection, Amine Protection, Enol Ether Synthesis, and Carbohydrate Chemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-(Trimethylsilyl)ethanol is used as a precursor to prepare trimethyl(2-phenoxyethyl)silanes by reacting with aromatic fluoride. This application is essential for the development of new drugs and pharmaceutical compounds.
Used in Chemical Synthesis:
2-(Trimethylsilyl)ethanol is also used in the synthesis of Teoc-protected amines via alcoholysis of the corresponding isocyanates. This process is vital for the production of various chemical compounds and materials.
Preparation
Three methods of preparation have been
reported: (a) from the treatment of ethyl bromoacetate with
zinc followed by the reaction with chlorotrimethylsilane1 and
subsequent reduction of the resultant ethyl trimethylsilylacetate
with lithium aluminum hydride2,3 or borane–tetrahydrofuran(eq 1); (b) from the hydroboration/oxidation or oxymercuration/demercuration of vinyltrimethylsilane (eq 2); and (c)most conveniently, by the reaction of the Grignard reagent
formed from (chloromethyl)trimethylsilane with paraformaldehyde
(eq 3).
Purification Methods
If the NMR spectrum is not clean, then dissolve the alcohol in Et2O, wash it with aqueous NH4Cl solution, dry (Na2SO4), evaporate and distil it. The 3,4-dinitrobenzoyl derivative has m 66o (from EtOH). [NMR: Speier et al. J Am Chem Soc 79 974 1957, Z Naturforsch 14b 137 1959, Beilstein 4 IV 3951.]
Check Digit Verification of cas no
The CAS Registry Mumber 2916-68-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,9,1 and 6 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 2916-68:
(6*2)+(5*9)+(4*1)+(3*6)+(2*6)+(1*8)=99
99 % 10 = 9
So 2916-68-9 is a valid CAS Registry Number.
InChI:InChI=1/C5H14OSi/c1-7(2,3)5-4-6/h6H,4-5H2,1-3H3
2916-68-9Relevant articles and documents
-
Mironov,V.F.,Pogonkina,N.A.
, (1960)
-
Soderquist,Hassner
, p. C12 (1978)
Synthesis of COX-2 and FAAH inhibitors
-
, (2008/06/13)
Methods for preparing indoles that are useful COX-2 inhibitors and intermediates useful in such methods are described.
Synthesis of germatranyl derivatives of esters of carboxylic acids via organometallic (Si, Ge, Sn) reagents
Zaitseva, Galina S.,Livantsova, Ljudmila I.,Nasim, Mohammed,Karlov, Sergei S.,Churakov, Andrci V.,Howard, Judith A. K.,Avtomonov, Evgeni V.,Lorbcrth, Joerg
, p. 739 - 746 (2007/10/03)
Trialkylstannyl esters of tris(2-hydroxyalkyl)amines, N(CH2CHROSnAlk3)3 (9-11) (R = H, Me; Alk = Et, Bu), react with X3GeC(R1)H(R2)COOR3 (12-17) (X = Cl or Br; R1, R2 = H, Me, Ph, SiMe3, COOEt; R3 = Me, Et) to give esters of α-germatranylcarboxylic acids, N(CH2CHRO)3GeQ(R1)MR2)-COOR 3 (1-8), in high yields. The synthesis of esters 12-17 is reported. Esters of α-germatranyldiphenylacetic acid 24 and 25 can be obtained by treatment of diphenylketene with Et3SnOMe to give in situ Et3SnC(Ph2)COOMe (23), followed by reaction with GeCL, to give in situ Cl3GeC(Ph2)COOMe (22) and further reactions with 9 or 11, respectively. Reduction of germatrane 6 with LiAlH4 in diethyl ether leads to cleavage of the germanium-carbon bond with subsequent formation of (2-hydroxyethyl)trimethylsilane. The crystal structures of 3, 6, and 7 are reported. 1-Acyloxygermatranes 26 and 27 are obtained by treatment of 1-methoxygermatrane (28) with diphenyl- and dichloroacetic acid, respectively. VCH Verlagsgesellschaft mbH,.
