2208-05-1

Basic information

• Product Name: 2-(Dimethylamino)ethyl benzoate
• Synonyms: Quantacure DMB;BENZOIC ACID 2-DIMETHYLAMINOETHYL ESTER;2-(DIMETHYLAMINO)ETHYL BENZOATE;SPEEDCURE DMB;2-DIMETHYLAMINOETHYLBENZOATE (DMB);DMB;2-(Dimethylamino)eth
• CAS NO: 2208-05-1
• Molecular Formula: C₁₁H₁₅NO₂
• Molecular Weight: 193.24
• EINECS: 218-630-1
• Product Categories: Amine Photochemical Coinitiators;Polymer Science;Polymerization Initiators
• Mol File: 2208-05-1.mol

Chemical Properties

• Boiling Point: 155-159 °C20 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Slightly yellow liquid
• Density: 1.014 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00683mmHg at 25°C
• Refractive Index: n20/D 1.5077(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 8.42±0.28(Predicted)
• CAS DataBase Reference: 2-(Dimethylamino)ethyl benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Dimethylamino)ethyl benzoate(2208-05-1)
• EPA Substance Registry System: 2-(Dimethylamino)ethyl benzoate(2208-05-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 2208-05-1(Hazardous Substances Data)

Usage

Uses

Used in Photoinitiating Systems:
2-(Dimethylamino)ethyl benzoate is used as an alternative initiator for bimolecular photoinitiating systems in the field of polymer chemistry. Its application reason is its ability to effectively initiate the curing process of photopolymers, which is crucial in the production of various materials such as coatings, inks, and adhesives.
Used in Coatings Industry:
In the coatings industry, 2-(Dimethylamino)ethyl benzoate is used as a photoinitiator for UV-curable coatings. Its application reason is its high reactivity and efficiency in initiating the polymerization process, leading to faster curing times and improved performance of the final product.
Used in Inks and Adhesives:
2-(Dimethylamino)ethyl benzoate is also used as a photoinitiator in the production of UV-curable inks and adhesives. Its application reason is its ability to provide rapid curing and strong adhesion properties, making it suitable for various applications such as printing, packaging, and product assembly.
Used in Dental Applications:
In the dental industry, 2-(Dimethylamino)ethyl benzoate is used as a component in dental restorative materials, such as composite resins and adhesives. Its application reason is its role in initiating the polymerization process, which is essential for the hardening and setting of dental materials, ensuring a strong and durable restoration.
Used in Electronic Applications:
2-(Dimethylamino)ethyl benzoate is utilized in the electronics industry as a photoinitiator for the production of printed circuit boards (PCBs) and other electronic components. Its application reason is its ability to facilitate the rapid curing of conductive inks and adhesives, which is crucial for the manufacturing process and the performance of electronic devices.

InChI:InChI=1/C11H15NO2/c1-12(2)8-9-14-11(13)10-6-4-3-5-7-10/h3-7H,8-9H2,1-2H3

Upstream product

• 108-01-0 2-(N,N-dimethylamino)ethanol 
• 98-88-4 benzoyl chloride 
• 93-97-0 benzoic acid anhydride 
• 939-55-9 2-chloroethyl benzoate 
• 124-40-3 dimethyl amine 
• 582-25-2 Potassium benzoate 
• 107-99-3 2-(dimethylamino)ethyl chloride 
• 85909-02-0 N-benzyl-N-(tert-butoxycarbonyl)-benzamide 
• 4584-46-7 (2-chloroethyl)dimethylamine hydrochloride 
• 65-85-0 benzoic acid 
• 617-86-7 triethylsilane 
• 26926-35-2 Benzoesaeure-methansulfonsaeure-anhydrid 
• 13079-28-2 benzoic toluene-p-sulphonic anhydride 
• 4971-80-6 ethyl N-benzoylcarbamate 

Downstream Products

• 91247-64-2 1-benzoyloxy-2-(dimethyl-oxy-amino)-ethane 
• 17518-43-3 benzoylcholine iodide 
• 2964-09-2 benzoylcholine chloride 
• 93-58-3 benzoic acid methyl ester 
• 103935-67-7 (2-(benzoyloxy)ethyl)dimethylamine-borane 

Relevant articles and documents

Cesium Carbonate Catalyzed Esterification of N-Benzyl- N-Boc-amides under Ambient Conditions

We report a general activated amide to ester transformation catalyzed by Cs2CO3. Using this approach, esterification proceeds under relatively mild conditions and without the need for a transition metal catalyst. This method exhibits broad substrate scope and represents a practical alternative to existing esterification strategies. The synthetic utility of this protocol is demonstrated via the facile synthesis of crown ether derivatives and the late-stage modification of a representative natural product and several sugars in reasonable yields.

Identification, synthesis, and strategy for minimization of potential impurities in the preclinical anti-HBV drug Y101

The identification of actual, potential, and theoretical impurities of N-[N-benzoyl-O-(2-dimethylaminoethyl)-l-tyrosyl]-l-phenylalaninol (Y101), a preclinical anti-HBV drug, is described in this article. The impurities were monitored by HPLC, and their structures were established on the basis of NMR, IR, and MS. Most of the impurities were synthesized, and their assigned constitutions were confirmed by HPLC co-injection with an ordinary column (Phenomenex Gemini, 250 mm × 4.6 mm, 5 μm) or a chiral column (DAICEL Chiralcel OD-H). According to the synthetic route, the origins of all of these related impurities were analyzed, and some practical strategies were applied for minimizing these impurities to the level accepted by the International Conference on Harmonization (ICH), and therefore, these strategies can be well applied to the quality control in Y101 clinical sample manufacture.

Platinum oxide catalyzed silylation of aryl halides with triethylsilane: An efficient synthetic route to functionalized aryltriethylsilanes

The first platinum-catalyzed selective silylation of aryl halides including aryl iodides and bromides having an electron-withdrawing group is described. The reaction takes place rapidly in NMP with triethylsilane as a silicon source and sodium acetate to provide functionalized aryltriethylsilanes in moderate to good yields. Heteroaromatic halides also were found to be readily silylated with triethylsilane. The procedure is chemoselective and tolerates a wide variety of functional groups.

Room temperature ionic liquids - New choline derivatives

New room temperature ionic liquids - choline derivatives were prepared by Menschutkin reaction with alkyl chloromethyl ethers and anion changed to bis(trifluoromethylsulfonyl)amide ion. The newly obtained butoxymethyl(2-hydroxyethyl)dimethylammonium bis(trifluoromethanesulfonyl)amide was successfully tested as a solvent for O-acylation in two-phase reaction system. The ionic liquid-catalyst system was recycled and reused.

Design, synthesis, and biological evaluation of substituted benzoate analogues of the selective nicotinic acetylcholine receptor antagonist, methyllycaconitine

The norditerpenoid alkaloid methyllycaconitine (MLA) acts as a competitive antagonist on the nicotinic acetylcholine receptor (nAChR) with a high preference for the neuronal α-bungarotoxin (αBgt)-sensitive nAChR over the muscle nAChR in mammals. MLA is thus a useful pharmacological tool. Furthermore, its efficient binding to insect nAChR indicates a high insecticidal potency. Within the complex hexacyclic structure of MLA, we envisaged a potential simple pharmacophore. This led to the design and synthesis of acyclic and monocyclic analogues of MLA. The biological activity of these derivatives at both neuronal nicotinic and muscarinic AChR was evaluated. Some of these structurally simple compounds, despite displaying a modest affinity for the nAChR, showed good specificity. We were able to show the importance of the 2-(methylsuccinimido)benzoate ester moiety and the E-ring of MLA. None of the analogues tested displayed any affinity for [3H]nicotine binding sites in brain membranes, indicating that α7-selectivity is already inherent in these simple structures. If higher affinities are to be obtained, however, there is a clear need for more structural information in the design of second generation simple analogues of MLA.

Ester-containing quaternary ammonium salts as adhesion improving toner charge agents

Toner particles comprising a polyester binder and a charge control agent are provided wherein such agent is a quaternary ammonium salt having one or more ester-containing moieties. Such an ester-containing salt causes toner particles to display lower fusing temperature, improved paper adhesion indexes, and improved polyester binder compatibility compared to nonesterified salts.

Ester-containing quaternary ammonium salts as adhesion improving toner charge agents

Toner particles comprising a polyester binder and a charge control agent are provided wherein such agent is a quaternary ammonium salt having one or more ester-containing moieties. Such an ester-containing salt causes toner particles to display lower fusing temperature, improved paper adhesion indexes, and improved polyester binder compatibility compared to nonesterified salts.

Phase-Transfer Catalyzed Synthesis of Amides and Esters of Carboxylic Acids

A convenient one-pot procedure is reported for the preparation of carboxamides and carboxylic acid esters from carboxylic acids and amines or alcohols, respectively.The carboxylic acids are activated by sulfonyl chlorides under solid-liquid phase-transfer conditions using solid potassium carbonate as base and a lipophilic quaternary ammonium salt as catalyst.

Dimethylamino derivatives and their use

(Dimethylaminoalkyl)carboxylic and -carbamic acid esters and (dimethylaminoalkyl) ethers and ureas are compounds which are especially suitable for use as amine curing agents for polyepoxide compounds. They impart longer curing times to the curable mixtures and thus good processing properties, especially when the mixtures are used as adhesives. In addition, the mechanical properties are often improved. Further, these compounds afford advantages when used as curing agents on account of their low volatility.