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1911-01-9

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1911-01-9 Usage

General Description

2-(1,3-dimethylimidazolidin-2-ylidene)-1,3-dimethyl-imidazolidine is a chemical compound with the formula C9H18N2. It is a cyclic organic compound that contains two imidazolidine rings and a ylidene group. 2-(1,3-dimethylimidazolidin-2-ylidene)-1,3-dimethyl-imidazolidine is commonly used as a N-heterocyclic carbene (NHC) ligand in organometallic chemistry, where it can coordinate with various transition metals, such as palladium and platinum, to form stable complexes. These complexes are utilized in a variety of catalytic reactions, including cross-coupling reactions and olefin metathesis. The chemical properties of 2-(1,3-dimethylimidazolidin-2-ylidene)-1,3-dimethyl-imidazolidine make it a valuable tool in synthetic organic chemistry for the construction of complex molecules.

Check Digit Verification of cas no

The CAS Registry Mumber 1911-01-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,9,1 and 1 respectively; the second part has 2 digits, 0 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 1911-01:
(6*1)+(5*9)+(4*1)+(3*1)+(2*0)+(1*1)=59
59 % 10 = 9
So 1911-01-9 is a valid CAS Registry Number.
InChI:InChI=1/C10H20N4/c1-11-5-6-12(2)9(11)10-13(3)7-8-14(10)4/h5-8H2,1-4H3

1911-01-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-(1,3-dimethylimidazolidin-2-ylidene)-1,3-dimethylimidazolidine

1.2 Other means of identification

Product number -
Other names 1,1',3,3'-Tetramethyl-2,2'-biimidazolidinylidene

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:1911-01-9 SDS

1911-01-9Relevant articles and documents

Aromaticity and sterics control whether a cationic olefin radical is resistant to disproportionation

Messelberger, Julian,Grünwald, Annette,Goodner, Stephen J.,Zeilinger, Florian,Pinter, Piermaria,Miehlich, Matthias E.,Heinemann, Frank W.,Hansmann, Max M.,Munz, Dominik

, p. 4138 - 4149 (2020)

We elucidate why some electron rich-olefins such as tetrathiafulvalene (TTF) or paraquat (1,1'-dimethyl-4,4'-bipyridinylidene) form persistent radical cations, whereas others such as the dimer ofN,N'-dimethyl benzimidazolin-2-ylidene (benzNHC) do not. Specifically, three heterodimers derived from cyclic (alkyl) (amino) carbenes (CAAC) withN,N'-dimethyl imidazolin-2-ylidene (NHC),N,N'-dimethyl imidazolidin-2-ylidene (saNHC) andN-methyl benzothiazolin-2-ylidene (btNHC) are reported. Whereas the olefin radical cations with the NHC and btNHC are isolable, the NHC compound with a saturated backbone (saNHC) disproportionates instead to the biscation and olefin. Furthermore, the electrochemical properties of the electron-rich olefins derived from the dimerization of the saNHC and btNHC were assessed. Based on the experiments, we propose a general computational method to model the electrochemical potentials and disproportionation equilibrium. This method, which achieves an accuracy of 0.07 V (0.06 V with calibration) in reference to the experimental values, allows for the first time to rationalize and predict the (in)stability of olefin radical cations towards disproportionation. The combined results reveal that the stability of heterodimeric olefin radical cations towards disproportionation is mostly due to aromaticity. In contrast, homodimeric radical cations are in principle isolable, if lacking steric bulk in the 2,2' positions of the heterocyclic monomers. Rigid tethers increase accordingly the stability of homodimeric radical cations, whereas the electronic effects of substituents seem much less important for the disproportionation equilibrium.

Steric stabilization of nucleophilic carbenes

Denk,Thadani,Hatano,Lough

, p. 2607 - 2609 (1997)

Two tert-butyl groups at the nitrogen atoms of the cyclic carbene 2, which is accessible from 1 by reduction with potassium, provide sufficient stability to enable it to be stored indefinitely under exclusion of air and moisture. In contrast, sterically less shielded carbenes of type 2 (R = Me, Et, iPr) dimerize slowly at room temperature to olefins 3.

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