1911-01-9

Basic information

• Product Name: 2-(1,3-dimethylimidazolidin-2-ylidene)-1,3-dimethyl-imidazolidine
• Synonyms: 2-(1,3-dimethylimidazolidin-2-ylidene)-1,3-dimethyl-imidazolidine;IMidazolidine, 2-(1,3-diMethyl-2-iMidazolidinylidene)-1,3-diMethyl-
• CAS NO: 1911-01-9
• Molecular Formula: C₁₀H₂₀N₄
• Molecular Weight: 196.29
• Mol File: 1911-01-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 250.7°Cat760mmHg
• Flash Point: 95.7°C
• Appearance: /
• Density: 1.063g/cm³
• Vapor Pressure: 0.0213mmHg at 25°C
• Refractive Index: 1.545
• CAS DataBase Reference: 2-(1,3-dimethylimidazolidin-2-ylidene)-1,3-dimethyl-imidazolidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1,3-dimethylimidazolidin-2-ylidene)-1,3-dimethyl-imidazolidine(1911-01-9)
• EPA Substance Registry System: 2-(1,3-dimethylimidazolidin-2-ylidene)-1,3-dimethyl-imidazolidine(1911-01-9)

Safety Data

• Hazardous Substances Data: 1911-01-9(Hazardous Substances Data)

Usage

Properties & Specific Content of 2-(1,3-dimethylimidazolidin-2-ylidene)-1,3-dimethyl-imidazolidine

The compound consists of 9 carbon atoms, 18 hydrogen atoms, and 2 nitrogen atoms.
2. Cyclic organic compound
The structure of the compound forms a closed ring, with the two imidazolidine rings being the main structural features.

Imidazolidine rings

two
The compound contains two imidazolidine rings, which are five-membered heterocyclic rings with one nitrogen atom and four carbon atoms.
4. Ylidene group
A ylidene group is a functional group consisting of a carbon atom double-bonded to a phosphorus, sulfur, or another carbon atom with a negative charge on the carbon atom.
5. N-heterocyclic carbene (NHC) ligand
The compound acts as a ligand in organometallic chemistry, containing a nitrogen atom in a heterocyclic ring that can form a stable complex with transition metals.
6. Coordination with transition metals
The compound can coordinate with various transition metals, such as palladium and platinum, to form stable complexes.
7. Catalytic reactions
The complexes formed by the compound are utilized in a variety of catalytic reactions, including cross-coupling reactions and olefin metathesis.
8. Synthetic organic chemistry
The chemical properties of the compound make it a valuable tool in synthetic organic chemistry for the construction of complex molecules.

InChI:InChI=1/C10H20N4/c1-11-5-6-12(2)9(11)10-13(3)7-8-14(10)4/h5-8H2,1-4H3

Upstream product

• 202584-80-3 1,3-dimethylimidazolidin-2-ylidene 
• 13461-16-0 1,3-dimethylimidazolidine-2-thione 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 110-70-3 N,N`-dimethylethylenediamine 
• 96444-72-3 1,1',3,3'-tetramethyl-2,2'-biimidazolidine 

Downstream Products

• 119-52-8 4,4'-dimethoxybenzoin 
• 37091-73-9 2-chloro-1,3-dimethylimidazolinium chloride 
• 82464-49-1 hexamesityldisilane 
• 80-73-9 1,3-dimethyl-2-imidazolidinone 
• 13461-16-0 1,3-dimethylimidazolidine-2-thione 
• 3265-03-0 trimesitylgermane 
• 129016-30-4 trimesityl(methylthio)germane 
• 1626-24-0 chlorotriphenylgermane 
• 82464-48-0 (C₆H₂(CH₃)3)3GeGe(C₆H₂(CH₃)3)3 
• 90753-00-7 hexakis(2,6-dimethylphenyl)digermane 
• 90753-01-8 hexakis(2,3,4,6-tetramethylphenyl)digermane 
• 90753-02-9 hexakis(2,3,4,5,6-pentamethylphenyl)digermane 
• 90752-99-1 hexakis(3,5-di-t-butylphenyl)digermane 

Relevant articles and documents

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

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

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.