1,3-Bis(2,4,6-trimethylphenyl)imidazolinium chloride

CAS 173035-10-4C21H27ClN2Catalysis & Inorganic

1,3-Bis(2,4,6-trimethylphenyl)imidazolinium chloride (CAS: 173035-10-4) is an organic compound with the molecular formula C21H27ClN2 and a molecular weight of 342.91 g/mol. It serves as a crucial precursor for N-heterocyclic carbene (NHC) catalysts. These catalysts are widely employed in modern synthetic organic chemistry, particularly in cross-coupling reactions and cycloaddition processes, offering regioselective and efficient transformations.

IUPAC: 1,3-Dimesitylimidazolidinium chloride,4,5-Dihydro-1,3-bis(2,4,6-trimethylphenyl)-1H-imidazolium chloride,4,5-Dihydro-1,3-dimesityl-1H-imidazolium chloride,N,N′-(2,4,6-Trimethylphenyl)dihydroimidazolium chloride
Synonyms: 1,3-Dimesitylimidazolidinium chloride4,5-Dihydro-1,3-bis(2,4,6-trimethylphenyl)-1H-imidazolium chloride4,5-Dihydro-1,3-dimesityl-1H-imidazolium chlorideN,N′-(2,4,6-Trimethylphenyl)dihydroimidazolium chloride

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1,3-Bis(2,4,6-trimethylphenyl)imidazolinium chloride (C21H27ClN2) — chemical structure, CAS 173035-10-4; Chemistry, fine chemical supplied by Tech Serve Solutions

Carbon-Donor LigandsChemical SynthesisNHC Compounds

01 /Applications

Precursor for N-Heterocyclic Carbene Catalysts

This compound is a key precursor for generating N-heterocyclic carbene (NHC) catalysts. These catalysts are instrumental in facilitating a variety of organic transformations with high efficiency and selectivity.

Regioselective Cycloaddition Reactions

The derived NHC catalysts enable regioselective cycloaddition reactions between terminal acetylenes and azides, leading to the formation of 1,4-disubstituted triazoles. Internal acetylenes can also be effectively employed.

Alkyne Hydration and Hydrosilylation

It is utilized in catalytic systems for Markovnikov-type hydration of terminal alkynes and for the hydrosilylation of ketones, expanding its utility in functional group transformations.

Suzuki-Miyaura Cross-Coupling Reactions

Catalysts derived from this imidazolinium salt are active in Suzuki-Miyaura cross-coupling reactions, a fundamental transformation for carbon-carbon bond formation in organic synthesis.

Luminescence Studies

In addition to catalytic applications, this compound and its derivatives have been explored in luminescence experiments, indicating potential uses in materials science or photophysical studies.

02 /Properties

Molecular weight	342.91
Empirical formula	C21H27ClN2
Assay	95%
Application	N-Heterocyclic Carbene Ligands Precursor to an N-heterocyclic carbene catalysts used for: • A regioselective cycloadditon of terminal acetylenes with azides leading to 1,4-disubstitutedtriazoles. Internal acetylenes can also be used with this catalyst.1• Markovnikov-type hydration of terminal alkynes2• Hydrosilylation of ketones and cycloaddition of azides and alkynes3• Suzuki-Miyaura reactions4• Luminescence experiments5
Melting point	280-286 °C

03 /Safety & handling

GHS hazard pictogram: Harmful / irritant (GHS07) — Harmful / irritant

Warning

Hazard statements

H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust, fume, gas or vapours
P305IF IN EYES

Protective equipment	Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
Water hazard class (WGK, DE)	3
Hazard codes (EU)	Xi
Risk statements (R)	36/37/38
Safety statements (S)	26-36

Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.

04 /Identifiers & registry

CAS number

173035-10-4

MDL number

MFCD09039279

PubChem substance

24884213

05 /Quality & supply

Documentation

Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.

Supply & logistics

Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.

06 /Frequently asked questions

What is 1,3-Bis(2,4,6-trimethylphenyl)imidazolinium chloride used for?

1,3-Bis(2,4,6-trimethylphenyl)imidazolinium chloride is primarily used as a precursor for N-heterocyclic carbene (NHC) catalysts. These catalysts are employed in various organic synthesis applications, including cycloadditions, alkyne hydration, hydrosilylation, and Suzuki-Miyaura coupling reactions.

What is the CAS number and molecular formula?

The CAS number for 1,3-Bis(2,4,6-trimethylphenyl)imidazolinium chloride is 173035-10-4, and its empirical formula is C21H27ClN2.

What grade and purity does Tech Serve Solutions supply?

Tech Serve Solutions supplies this chemical with an assay of 95%. We do not represent this product as USP, BP, EP, or any other pharmacopoeial grade. It is suitable for research and chemical synthesis applications.

How should 1,3-Bis(2,4,6-trimethylphenyl)imidazolinium chloride be handled?

Due to its potential to cause skin irritation, eye irritation, and respiratory irritation (H315, H319, H335), appropriate personal protective equipment should be used. This includes eyeshields and gloves. In case of accidental eye contact, rinse cautiously with water for several minutes and seek medical advice if irritation persists. Ensure adequate ventilation during handling.

Is this chemical available for export?

Yes, Tech Serve Solutions is a global supplier and exporter of fine chemicals. Please contact us for export availability and shipping information to your region.

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