16331-79-6

Usage

Physical State

Colorless to slightly yellow liquid

Primary Use

Catalyst in the production of polyurethane foams and elastomers

Function

Acts as a base catalyst, promoting the urethane reaction in polyurethane systems

Reaction Rate

High

Resulting Product Properties

Excellent mechanical properties and heat resistance

Safety Precautions

Handle and use with caution, as it is a hazardous substance that can cause skin and eye irritation upon contact

Upstream product

• 6852-58-0 N-benzylidene tert-butylamine 
• 6852-58-0 (E)-N-benzylidene-2-methylpropan-2-amine 
• 100-52-7 benzaldehyde 

Relevant academic research and scientific papers

Zn-mediated catalytic photoreduction of aldimines. One-pot synthesis and separation of meso and d,l C2 symmetrical diamines

A new one-pot method for the synthesis and selective separation of 1,2-diamines is reported. The methodology, which involves the photoreduction of imines using catalytic amounts of zinc as a photosensitizer, allows the direct preparation and separation of meso and d,l compounds on a multigram scale.

Photoreductive coupling of aldimines. Synthesis of C2 symmetrical diamines

The photoreductive coupling of pyridine-, arene- and alkynecarboxaldimines is a very convenient procedure for the preparation of vicinal diamines in good to excellent yields. The usual trend gave an excess of meso diamine, which enhances the usefulness of

A Metal-Free Approach to 1,2-Diamines via Visible Light-Driven Reductive Coupling of Imines with Perylene as a Photoredox Catalyst

A simple, metal-free, and versatile approach to 1,2-diamines has been developed based on reductive coupling reactions of various imines, where perylene, an aromatic hydrocarbon, was used as a photoredox catalyst under visible light irradiation using a white light-emitting diode. The use of 1 mol % perylene enabled almost complete conversion of the imines, leading to the formation of their corresponding 1,2-diamines, which were isolated in good yields. The ratios between dl and meso diamines ranged from 31:69 to 82:18 depending on the substituents of the imines.

Synthesis of enantiomerically pure C2-symmetric acyclic and cyclic 1,2-diamines via pinacol coupling of imines

The inter- and intramolecular coupling of imines promoted by samarium diiodide and Lewis acids or by Zn/MsOH was extensively studied. The intramolecular reaction of chiral, enantiomerically pure bis-imines was also considered, and allowed the efficient, s

Iminopinacol coupling with lithium: Electron-transfer mediators

The addition of tert-butyl borate or ethyl formate to N-alkylbenzalimines directs the reaction pathway from the Birch reduction to the pinacol-type coupling with lithium in THF; an analogous reaction with a dimethylimmonium salt requires a trace titanium catalyst as the electron-transfer mediator.

Reductive coupling of aromatic aldehydes and imines by the low valent titanium species generated in the reaction of TiCl4 with Et3N

Aromatic aldehydes and imines are converted to the corresponding diols and diamines using the low valent titanium species generated by the reaction of TiCl4 with triethylamine.

Samarium diiodide/nickel diiodide an efficient system for homo and heterocoupling reactions of imines

Samarium diiodide in the presence of a catalytic amount of nickel diiodide mediates a very fast dimerization of imines into vicinal diamines and the mixed coupling of imines and ketones to give β-amino alcohols.

Diastereoselective synthesis of 1,2-diphenyl-1,2-diaminoethanes by Yb(OTf)3 accelerated reductive coupling of imines

New reaction protocols have been established to perform the reductive coupling of N-benzyl benzaldimines to 1,2-diphenyl-1,2-diaminoethanes in mild, stereoselective, and catalytic conditions by the use of SmI2 and Yb(OTf)3.

Samarium Diiodide-Promoted Reductive Coupling of Imines

Aromatic aldimines are reductively coupled to 1,2-diamines by treatment with samarium diiodide.Cross-coupling of aromatic ketimines with ketones to 2-aminoalcohols is also promoted by the same reagent.

Titanium Induced Coupling of Imines to Symmetrical Vicinal (R*,R*)-Diamines

Symmetrical vicinal (R*,R*) -d,l-diamines were prepared from the corresponding imines and low valent titanium species generated by the action of titanium tetrachloride on amalgamated magnesium.