2842-44-6 Usage
Description
N-(2-HYDROXYETHYL)-N-METHYL-4-TOLUIDINE is an amine organic compound characterized by its molecular structure that features a hydroxyethyl and a methyl group attached to a toluidine backbone. N-(2-HYDROXYETHYL)-N-METHYL-4-TOLUIDINE is known for its versatile chemical properties, making it a valuable intermediate in various organic synthesis processes.
Uses
Used in Organic Synthesis:
N-(2-HYDROXYETHYL)-N-METHYL-4-TOLUIDINE is used as an intermediate in organic synthesis for its ability to participate in a range of chemical reactions, facilitating the creation of diverse chemical products and compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-(2-HYDROXYETHYL)-N-METHYL-4-TOLUIDINE is used as a building block for the development of new drugs. Its unique structure allows it to be a key component in the synthesis of various medicinal compounds, potentially leading to the discovery of novel therapeutic agents.
Used in Chemical Research:
N-(2-HYDROXYETHYL)-N-METHYL-4-TOLUIDINE is also utilized in chemical research as a model compound for studying the properties and reactivity of amine organic compounds. This helps researchers understand the underlying principles of chemical reactions and develop new synthetic methods or improve existing ones.
Used in Dye and Pigment Industry:
In the dye and pigment industry, N-(2-HYDROXYETHYL)-N-METHYL-4-TOLUIDINE may be used as an intermediate to produce various types of dyes and pigments. Its chemical structure can be modified to create colorants with specific properties, such as lightfastness, stability, and solubility, which are essential for various applications in the textile, plastics, and printing industries.
Used in Material Science:
N-(2-HYDROXYETHYL)-N-METHYL-4-TOLUIDINE can be employed in the development of new materials with specific properties, such as conductivity, magnetism, or optical characteristics. Its role as an intermediate in organic synthesis allows for the creation of novel polymers, composites, or other advanced materials with potential applications in electronics, energy storage, and other high-tech industries.
Synthesis
Add reactant (0.2 mmol, 1.0 equiv), THF (2.0 mL) and CH2Br2?(0.6 mmol, 3.0 equiv) to a flame-dried 10 mL Schlenk tube in a glove box. Seal and take out of the glove box. Cool the reaction mixture to -78°C. Add nBuLi (0.56 mmol, 2.8 equiv) dropwise under N2?atmosphere within 3minutes. Stir the reaction at -78°C for 30 minutes and add ZnCl2?(0.1 mL, 0.5equiv, 1.0 M in Et2O). Allow the mixture to warm to room temperature and stir for 1 hour. Cool the mixture to 0°C. Add a premixture of H2O2?(30% in H2O, 0.5 mL) and NaOH (2.0 M, 1.0 mL). Stir the mixture at room temperature for another 1 hour and dilute with water (20 mL). Extract with DCM (30 mL x 2) and dry over Na2SO4. Filter and concentrate under vacuum. Purify the crude product by silica gel flash column chromatography to obtain product.?1H NMR (CDCl3, 500 MHz) δ 7.08 (d, J = 8.4 Hz, 2H), 6.78 (d, J = 8.4 Hz,2H), 3.80 (t, J = 5.6 Hz, 2H), 3.43 (t, J = 5.4 Hz, 2H), 2.93 (s, 3H), 2.28 (s, 3H), 2.01 (brs, 1H).?13C NMR (CDCl3, 125 MHz) δ 148.3, 129.8, 127.1, 114.0, 60.1, 56.2, 39.1, 20.4.
Fig The synthetic method of N-(2-hydroxyethyl)-N-methyl-4-toluidine
Check Digit Verification of cas no
The CAS Registry Mumber 2842-44-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,8,4 and 2 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 2842-44:
(6*2)+(5*8)+(4*4)+(3*2)+(2*4)+(1*4)=86
86 % 10 = 6
So 2842-44-6 is a valid CAS Registry Number.
InChI:InChI=1/C10H15NO/c1-9-3-5-10(6-4-9)11(2)7-8-12/h3-6,12H,7-8H2,1-2H3
2842-44-6Relevant articles and documents
Aza-Matteson Reactions via Controlled Mono-and Double-Methylene Insertions into Nitrogen-Boron Bonds
Xie, Qiqiang,Dong, Guangbin
supporting information, p. 14422 - 14427 (2021/09/29)
Boron-homologation reactions represent an efficient and programmable approach to prepare alkylboronates, which are valuable and versatile synthetic intermediates. The typical boron-homologation reaction, also known as the Matteson reaction, involves formal carbenoid insertions into C-B bonds. Here we report the development of aza-Matteson reactions via carbenoid insertions into the N-B bonds of aminoboranes. By changing the leaving groups of the carbenoids and altering Lewis acid activators, selective mono- and double-methylene insertions can be realized to access various α- and β-boron-substituted tertiary amines, respectively, from common secondary amines. The derivatization of complex amine-containing bioactive molecules, diverse functionalization of the boronate products, and sequential insertions of different carbenoids have also been achieved.
Direct hydroxyethylation of amines by carbohydrates: Via ruthenium catalysis
Jia, Le,Makha, Mohamed,Du, Chen-Xia,Quan, Zheng-Jun,Wang, Xi-Cun,Li, Yuehui
supporting information, p. 3127 - 3132 (2019/06/18)
An efficient and halogen-free catalytic methodology for the synthesis of β-amino alcohols from aromatic amines and biomass-derived carbohydrates is demonstrated for the first time. The activation of C5/C6 sugars by a ruthenium catalyst selectively generates the C2 alkylating reagent glycolaldehyde. The transformation involves metal-catalyzed hydrogen borrowing for the reduction of the imine intermediate. A series of arylamines bearing various substituents were successfully transformed into the desired products in good to excellent yields.
Strategy for imidazotetrazine prodrugs with anticancer activity independent of MGMT and MMR
Garelnabi, Elrashied A. E.,Pletsas, Dimitrios,Li, Li,Kiakos, Konstantinos,Karodia, Nazira,Hartley, John A.,Phillips, Roger M.,Wheelhouse, Richard T.
supporting information, p. 965 - 968 (2013/02/23)
The imidazotetrazine ring is an acid-stable precursor and prodrug of highly reactive alkyl diazonium ions. We have shown that this reactivity can be managed productively in an aqueous system for the generation of aziridinium ions with 96% efficiency. The