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2004-14-0 Usage

Purification Methods

Wash it with Et2O and pet ether. It sublimes at 180o/1mm as fine transparent needles. [Tatlock & Rochnow J Org Chem 17 1555 1952, Beilstein 4 IV 3992.] Suspected CARCINOGEN.

Check Digit Verification of cas no

The CAS Registry Mumber 2004-14-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,0,0 and 4 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 2004-14:
30 % 10 = 0
So 2004-14-0 is a valid CAS Registry Number.

2004-14-0 Well-known Company Product Price

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  • Aldrich

  • (345474)  Lithiumtrimethylsilanolate  97%

  • 2004-14-0

  • 345474-10G

  • 1,232.01CNY

  • Detail



According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017


1.1 GHS Product identifier

Product name lithium,trimethyl(oxido)silane

1.2 Other means of identification

Product number -
Other names Trimethylsilanol lithium deriv

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2004-14-0 SDS

2004-14-0Relevant articles and documents

Metal-induced reductive cleavage reactions: An experimental and theoretical (MNDO) study on the stereochemical puzzle of birch and vinylogous birch processes

Saa, Jose M.,Ballester, Pablo,Deya, Pere M.,Capo, Magdalena,Garcias, Xavier

, p. 1035 - 1046 (1996)

The stereochemical puzzle posed by the lithium-promoted Birch and vinylogous Birch reductive cleavage of unsaturated benzyl ethers (BICLE; takes place with retention of configuration of the sensitive 2Δ double bond) and the corresponding cinnamyl analogs (VIBICLE; gives rise to ca. 2.5:1 E:Z mixtures) has been approached by experimental and theoretical means. NMR experiments indicate that the π-type organolithium compounds resulting from these reactions do not form observable mixed aggregates with the lithium silyloxide species generated alongside in the reaction and do not undergo observable isomerization at the temperature of operation. A simplified model for contact, solvent-separated, and isolated ion pairs has allowed us to evaluate these complex reactions in great detail from a theoretical viewpoint, using the MNDO semiempirical method. Relevant features that come out from these comprehensive studies, for which we have employed lithium naphthalenide (LiNaph) or lithium benzenide (LiBenz) as promoters, are as follows: (1) the lowest energy routes for cleavage are those involving contact ion pairs (CIPs) in which the lithium counterion plays a key role by acting as a handle (Lewis acid) to which the leaving group -OR adheres prior to detachment; (2) the different haptomeric structures which reside (local minima) in the potential hypersurface of either the so-called radical anion or the dianion routes show that haptomeric activation is key to understanding cleavage of the C-O bond which, eventually, takes place as a syn β elimination of LiOR; and (3) reductive cleavage of unsaturated benzyl ethers (BICLE) involves transient cation/anion radicals which undergo cleavage and subsequent reduction to the final organolithium with retention of configuration, in accordance with experiment, whereas that of vinylogous cinnamyl ethers (VIBICLE) involve transient dianion/dication species resulting from long-lived cation/anion radicals. In good qualitative agreement with experiment, MNDO finds two diastereomeric routes (ΔΔG* = 0.2 kcal/mol) for cleavage of (appropriately substituted) cinnamyl ethers, but only one for cleavage of the unsaturated benzyl analogs.

Reactivity of the triple ion and separated ion pair of tris(trimethylsilyl) methyllithium with aldehydes: A RINMR study

Jones, Amanda C.,Sanders, Aaron W.,Sikorski, William H.,Jansen, Kristin L.,Reich, Hans J.

, p. 6060 - 6061 (2008/12/20)

Low-temperature rapid-injection NMR (RINMR) experiments were performed on tris(trimethylsilyl)methyllithium. In THF/Me2O solutions, the separated ion (1S) reacted faster than can be measured at -130 °C with MeI and substituted benzaldehydes (k ≥ 2 s-1), whereas the contact ion (1C) dissociated to 1S before reacting. Unexpectedly, the triple ion reacted faster with electron-rich benzaldehydes relative to electron-deficient ones. The addition of HMPA had no effect on the rate of reaction of the triple ion with p-diethylaminobenzaldehyde, and the immediate product of the reaction was the HMPA-solvated separated ion 1S, with the Peterson product forming only slowly. Thus, the aldehyde is catalyzing the dissociation of the triple ion. HMPA greatly decelerated the reaction of 1S (-10), providing an estimate of the Lewis acid activating effect of a THF-solvated lithium cation in an organolithium addition to an aldehyde. Copyright


Baryshnikov, Yu. N.,Kurskii, Yu. A.,Kaloshina, N. N.,Vesnovskaya, G. I.

, p. 2037 - 2040 (2007/10/02)


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