(S)-2-(2,3-Bis(dicyclohexylamino)cyclopropenimine)-3-phenylpropan-1-ol hydrochloride
ALDRICH/900811 - ≥95%
Synonym: (βS)-β-[[2,3-bis(dicyclohexylamino)-2-cyclopropen-1-ylidene]amino]-benzenepropanol hydrochloride (1:1); Dicyclohexyl cyclopropenimine; Lambert cyclopropenimine catalyst
CAS Number: 1366421-67-1
Empirical Formula (Hill Notation): C36H55N3O · HCl
Molecular Weight: 582.30
MDL Number: MFCD22417240
Linear Formula: C36H55N3O · HCl
Product Type: Chemical
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: 900811-1G.
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: 900811-500MG.
12 Principles of Green Chemistry: Principle 9—Catalytic reagents (as selective as possible) are superior to stoichiometric reagents.
| assay | ≥95% |
| form | powder or solid |
| functional group | amine |
| hydroxyl | |
| imine | |
| phenyl | |
| greener alternative category |  , Aligned |
| greener alternative product characteristics | Catalysis Learn more about the Principles of Green Chemistry . |
| InChI key | RTCSAEOYHXMTHG-UHFFFAOYSA |
| Quality Level | 100 |
| reaction suitability | reagent type: catalyst reaction type: Asymmetric synthesis |
| SMILES string | Cl.N(C6CCCCC6)(C5CCCCC5)C |
| sustainability | Greener Alternative Product |
| Application: | Chiral cyclopropenimines are a highly effective new class of enantioselective Brønsted base catalysts - the so-called “superbases” for enantioselective organocatalysis. Due to the prevalence of chemical reactions involving proton transfer as a key mechanistic event, Brønsted bases have become indispensable tools for the practice of organic synthetic chemistry, capable of catalyzing proton transfer reactions enantioselectively for the production of optically enriched products. Catalyst is stored as co-salt for stability. Conversion of the HCl salt to free catalyst requires a simple wash with aqueous base. This is one of a suite of Brønsted catalysts reported by Tristan Lambert and coworkers available through Sigma-Aldrich. |
| General description: | We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here  for more information. |
| Other Notes: | Enantioselective Bronsted Base Catalysis with Chiral Cyclopropenimines Cyclopropenimine-Catalyze Transition State Analysis of Enantioselective Bronsted Base Catalysis by Chiral Cyclopropenimines Structure-activity relationship studies of cyclopropenimines as enantioselective Bronsted base catalysts Asymmetric Bronsted Base-Catalyzed and -Directed [3+2] Cycloaddition of 2-Acyl Cycloheptatrienes with Azomethine Ylides |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 3 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| Purity | ≥95% |
| UNSPSC | 12161600 |