49663-94-7

Basic information

• Product Name: BENZYL-DBU-CHLORIDE
• Synonyms: Pyrimido[1,2-.alpha.]azepinium,2,3,4,6,7,8,9,10-octahydro-1-(phenylmethyl)-,chloride;1-BENZYL-1,8-DIAZA-BICYCLO[5.4.0]UNDEC-7-ENIUM CHLORIDE;BENZYL-DBU-CHLORIDE;1-benzyl-2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepinium chloride;1-benzyl-2,3,4,6,7,8,9,10-octahydropyriMido[1,2-a]azepin-1-iuM chloride;8-Benzyl-1,8-diazabicyclo[5.4.0]undec-7-enium chloride;N-8-Benzyl-1,8-diazabicyclo[5.4.0]undec-7-ene ammonium chloride;1-benzyl-2,3,4,6,7,8,9,10-octahydro-1H-pyrimido[1,2-a]azepin-5-ium chloride
• CAS NO: 49663-94-7
• Molecular Formula: C16H23ClN2
• Molecular Weight: 278.82
• EINECS: 256-419-6
• Mol File: 49663-94-7.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: BENZYL-DBU-CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL-DBU-CHLORIDE(49663-94-7)
• EPA Substance Registry System: BENZYL-DBU-CHLORIDE(49663-94-7)

Safety Data

• Hazardous Substances Data: 49663-94-7(Hazardous Substances Data)

Usage

Description

BENZYL-DBU-CHLORIDE, a derivative of chlorobenzyl and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene), is a potent chemical base with three reactive functional groups a benzyl group, a DBU moiety, and a chloride ion. It is widely recognized for its role in organic synthesis as a base catalyst, facilitating the deprotonation of acidic protons and the formation of carbon-carbon or carbon-nitrogen bonds. Furthermore, its effectiveness as an initiator in controlled/"living" radical polymerization of various monomers highlights its versatility in both small molecule and polymer chemistry.

Uses

Used in Organic Synthesis:
BENZYL-DBU-CHLORIDE is used as a base catalyst for its ability to deprotonate acidic protons and promote the formation of carbon-carbon or carbon-nitrogen bonds. This makes it a valuable reagent in the synthesis of complex organic molecules and pharmaceutical compounds.
Used in Polymer Chemistry:
In the Polymer Chemistry industry, BENZYL-DBU-CHLORIDE is used as an effective initiator in the controlled/"living" radical polymerization of a variety of monomers. Its role in this process allows for the creation of polymers with well-defined structures and properties, which are essential for numerous applications, including materials science and advanced coatings.
Used in Pharmaceutical Industry:
BENZYL-DBU-CHLORIDE is utilized in the Pharmaceutical Industry as a catalyst in the synthesis of various drug molecules. Its ability to facilitate the formation of crucial chemical bonds makes it an indispensable tool in the development of new medications and the improvement of existing ones.
Used in Materials Science:
In the Materials Science field, BENZYL-DBU-CHLORIDE is employed in the synthesis of advanced materials with specific properties. Its role in controlled polymerization contributes to the development of materials with tailored characteristics for use in high-performance applications, such as electronics, sensors, and energy storage devices.

InChI:InChI=1/C16H23N2.ClH/c1-3-8-15(9-4-1)14-18-13-7-12-17-11-6-2-5-10-16(17)18;/h1,3-4,8-9H,2,5-7,10-14H2;1H/q+1;/p-1

Upstream product

• 100-44-7 benzyl chloride 
• 6674-22-2 1,8-diazabicyclo[5.4.0]undec-7-ene 

Downstream Products

• 1613470-16-8 C₁₆H₂₃N₂⁽¹⁺⁾*C₆H₅O₃S^(1-) 

Relevant articles and documents

Experimental and theoretical probing of the physicochemical properties of ionic liquids composed of [Bn-DBU]+ cation and various anions

The experimental approaches coupled with computational methods are powerful tools to understand the physicochemical properties of ionic liquids. The 1,8-diazobicyclo[5.4.0]undec-7-ene-8-benzylium ([Bn-DBU]+) cation is a N-substituted DBU cation that was joined with various anions for production of [Bn-DBU][Y1-8], (Y1-8 = CH3CO2 ?, PhSO2 ?, PhSO3 ?, HCO3 ?, HSO4 ?, CF3CO2 ?, BF4 ?, and SCN?) ionic liquids (ILs). In this study, at first, several aprotic ionic liquids composed of [Bn-DBU]+ cation and various anions were synthesized and characterized experimentally by the combined of 1HNMR and FTIR spectroscopies, and thermogravimetric analysis (TGA). Then, density functional theory (DFT) at M06–2X/6–311++G(d,p) level of theory was used for calculation of the molecular electrostatic potential (MESP), interaction energies, structural parameters, vibrational frequencies, topological properties, charge transfer (CT) values and non-covalent interaction index.

Experimental and DFT mechanistic insights into one-pot synthesis of 1: H -pyrazolo[1,2- b] phthalazine-5,10-diones under catalysis of DBU-based ionic liquids

Benzylation of DBU followed by anion exchange of the resulting salt with trifluoroacetate gave nearly quantitatively the ionic liquid [Bn-DBU][TFA]. It is shown here to be an efficient catalyst for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones via the three-component reaction of phthalhydrazide, aromatic aldehydes, and active α-methylene nitriles. DFT calculations at the B3LYP/SVP level and the experimental results are in agreement with a three-step mechanism for this reaction. Based on the DFT calculations, the catalytic effect largely arises from the intrinsic ionic properties of the ionic liquid rather than its action as a simple base. These calculations also predict the existence of two close-in-energy activated complexes whose rate determining roles and energies depend on their interaction with the anionic component of the ionic liquid, as [Bn-DBU][TFA] has shown a higher catalytic activity than [Bn-DBU][OAc]. This mechanistic approach opens up new and promising insights into the rational design of ionic liquid catalysts for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones. The synthetic method presented here has several prominent advantages.

PHOTOBASE GENERATOR

Provided are a photobase generator having higher sensitivity to light than do conventional photobase generators, and a photosensitive resin composition containing the photobase generator. The present invention is a photobase generator characterized in containing a salt represented by general formula (1). (In formula (1), R 1 -R 4 are mutually independent groups represented by general formula (2), C1-18 alkyl groups, or Ar, with at least one being a group represented by general formula (2); in formula (2), (D) is a divalent group bonded on at least one side to elemental boron, and Ar 1 is the same as the aforementioned Ar; and Q + is a monovalent onium cation.) €?€?€?€?€?€?€?€?-(D)-Ar 1 €?€?€?€?€?(2)