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

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

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.

Synthesis and characterization of dicationic and monocationic fluorine-containing DBU based ionic liquids: Experimental and quantum chemical approaches

In this study, the new dication ionic liquids (DILs) based on para-xylyl linked bis-1,8-diazobicyclo [5.4.0] undec-7-ene ([p-C6H4(CH2DBU)2]2+) dication and their corresponding monocation ionic liquids (MILs) containing the bis(trifluoromethanesulfonyl) imide [NTf2]? and trifluoromethanesulfonate [OTF]? anions are synthesized. The method is based on the functionalization reaction of DBU salts using a simple procedure under microwave irradiation, followed by anion exchange. The obtained ILs are characterized by 1H-NMR, 13C-NMR, and FT-IR spectroscopy. The thermal decomposition of [p-C6H4(CH2DBU)2][NTf2]2, [p-C6H4(CH2DBU)2][OTF]2, [C6H5?CH2DBU][NTf2] and [C6H5?CH2DBU][OTF] ILs are measured using thermogravimetric (TGA) analyses and differential scanning calorimetry (DSC) in the temperature range from 25 to 800 °C. The thermal behavior confirmed that the DILs and MILs including [NTf2]? are more stable than the DILs and MILs including [OTF]? that is in good agreement with the greater dispersion energy calculated for [NTf2]? based ILs. The [p-C6H4(CH2DBU)2][NTf2]2 DIL shows good thermal stability up to 435°C which makes them suitable for thermal application. Finally, the cation-anion interactions were investigated in both DILs and MILs using DFT-M06-2X functional in conjunction with the 6-311++G(d,p) basis set. The results indicate that hydrogen bonding is stronger in the IL containing [OTF]? anion. The calculations in the solution phase with COSMO-RS method show that the ILs including [OTF]? anion have greater solvation energy and for the DILs are larger than those of MILs.

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

There is provided a photobase generator and a photosensitive resin composition containing the photobase generator. The photobase generator includes an ammonium salt represented by general formula (1). In formula (1), R1 to R4 independently represent an alkyl group having 1 to 18 carbon atoms or Ar, wherein at least one of R1 to R4 represents Ar; Ar represents an aryl group having 6 to 14 carbon atoms (excluding carbon atoms contained in a substituent as mentioned below), wherein some of hydrogen atoms in the aryl group may be independently substituted by an alkyl group having 1 to 18 carbon atoms or the like; Y+ represents an ammonio group represented by general formula (2) or (3); and E represents a hydrogen atom or a group represented by general formula (5).

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)

Very efficient conversion of glucose to 5-hydroxymethylfurfural in DBU-based ionic liquids with benzenesulfonate anion

Efficient conversion of glucose to 5-hydroxymethylfurfural (HMF), an important platform molecular for fuels and chemicals, is a promising topic in green chemistry. In this work, several new DBU-based (DBU = 1,8-diazabicyclo[5. 4.0]undec-7-ene) ionic liquids (ILs) with benzene sulfonate (BS) anion were synthesized and used as the solvents for the dehydration of glucose to HMF. It was found that all the ILs were excellent solvents for the dehydration of glucose to form HMF using CrCl3 as the catalyst. The effects of various factors, such as kind of catalysts, catalyst amount, reaction time and reaction temperature, on the yields of HMF were studied systematically in the Et-DBUBS/CrCl3 catalytic system. The yield of HMF from glucose could reach 83.4% under the optimized reaction conditions, and the reasons for the high yield were investigated on the basis of control experiments. The Et-DBUBS/CrCl3 system could be reused at least five times without considerable reduction in the efficiency. Further study indicated that the catalytic system was also very efficient for transformation of fructose, inulin, and cellobiose to HMF. This journal is the Partner Organisations 2014.

Ionic liquids on the basis of 2,3,4,6,7,8,9,10-octahydropyrimido-[1,2-a] azepine (1,8-diazabicyclo[5.4.0]undec-7-ene)

New ionic liquids containing alkyl and polyfluoroalkyl substituents and various anions were synthesized from 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a] azepinium ion (1,8-diazabicyclo[5.4.0]undec-7-en-8-ium). Their NMR spectra and miscibility with water and organic solvents were studied. Pleiades Publishing, Inc., 2006.