101-06-4

Basic information

• Product Name: N,N-Dibenzyl-2-aminoethanol
• Synonyms: DBZELA;N,N-DIBENZYLETHANOLAMINE;N,N-DIBENZYL-2-AMINOETHANOL;N-(2-HYDROXYETHYL)DIBENZYLAMINE;2-(bis(phenylmethyl)amino)-ethano;2-(bis(phenylmethyl)amino)ethanol;2-(dibenzylamino)-ethano;2-(dibenzylamino)ethanol
• CAS NO: 101-06-4
• Molecular Formula: C₁₆H₁₉NO
• Molecular Weight: 241.33
• EINECS: 202-911-0
• Mol File: 101-06-4.mol

Chemical Properties

• Melting Point: 38°C
• Boiling Point: 206 °C / 15mmHg
• Flash Point: 38 °C
• Appearance: colorless or light yellow liquid
• Density: 1,06 g/cm3
• Vapor Pressure: 5.55E-06mmHg at 25°C
• Refractive Index: 1.593
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.73±0.10(Predicted)
• CAS DataBase Reference: N,N-Dibenzyl-2-aminoethanol(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Dibenzyl-2-aminoethanol(101-06-4)
• EPA Substance Registry System: N,N-Dibenzyl-2-aminoethanol(101-06-4)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RTECS: KJ8125000
• Hazardous Substances Data: 101-06-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
N,N-Dibenzylethanolamine is used as a chiral auxiliary in organic synthesis for its ability to induce chirality in reactions, leading to the formation of enantiomerically pure products. This is particularly important in the synthesis of pharmaceuticals and agrochemicals, where the desired biological activity is often associated with a specific enantiomer.
Used in Chemical Reactions:
In chemical reactions, N,N-Dibenzylethanolamine is used as a ligand to improve the selectivity and efficiency of certain transformations. Its presence can facilitate the formation of specific products by stabilizing transition states or intermediates, thereby guiding the reaction pathway.
Used in Pharmaceutical Industry:
N,N-Dibenzylethanolamine is used as a building block or intermediate in the synthesis of various pharmaceutical compounds. Its chiral nature allows for the creation of enantiomerically pure drug candidates, which is crucial for ensuring the desired therapeutic effects and minimizing potential side effects associated with the less active enantiomer.
Used in Catalyst Design:
N,N-Dibenzylethanolamine can be incorporated into the design of chiral catalysts, which are essential for enantioselective catalysis. These catalysts can accelerate chemical reactions while simultaneously controlling the stereochemistry of the products, enabling the production of enantiomerically pure compounds with high yields and selectivity.

InChI:InChI=1/C16H19NO/c18-12-11-17(13-15-7-3-1-4-8-15)14-16-9-5-2-6-10-16/h1-10,18H,11-14H2

Upstream product

• 75-21-8 oxirane 
• 103-49-1 dibenzylamine 
• 100-44-7 benzyl chloride 
• 141-43-5 ethanolamine 
• 51-50-3 N,N-dibenzyl-2-chloroethanamine 
• 19520-88-8 O-acetyl-N,N-dibenzylethanolamine 
• 540-51-2 2-bromoethanol 
• 100-39-0 benzyl bromide 
• 141483-49-0 N,N-dibenzyl-glycine benzyl ester 
• 67965-28-0 (1-chloroprop-2-enyl)trimethyl silane 
• 94397-41-8 (1-chloro-2-methylprop-2-enyl)trimethyl silane 
• 100-52-7 benzaldehyde 
• 96-49-1 [1,3]-dioxolan-2-one 
• 124-38-9 carbon dioxide 

Downstream Products

• 109867-24-5 nicotinic acid-(2-dibenzylamino-ethyl ester); dihydrochloride 
• 103276-85-3 1-dibenzylamino-2-(toluene-4-sulfonyloxy)-ethane; toluene-4-sulfonate 
• 51-50-3 N,N-dibenzyl-2-chloroethanamine 
• 2133-09-7 sulfuric acid mono-(2-dibenzylamino-ethyl ester) 
• 537-11-1 SKF 1037C 
• 38540-29-3 (3R,5S,8S,9S,10S,13S,14S,17S)-10,13-Dimethyl-3-nitrooxy-11-oxo-hexadecahydro-cyclopenta[a]phenanthrene-17-carboxylic acid 2-dibenzylamino-ethyl ester 
• 109651-07-2 1-(N,N-dibenzylamino)-2-iodoethane 
• 71784-32-2 2-(dibenzylamino)ethyl acetoacetate 
• 137089-44-2 N,N-dibenzyl-O-carbamoylmethylethanolamine 
• 153498-50-1 2-(N,N-dibenzylamino)ethyl (E)-3-benzoylacrylate 
• 97476-53-4 2-(Dibenzylamino)ethyl benzoylacetate 
• 123420-23-5 2-(2-Dibenzylaminoethoxy)-1-<(2-methyl-1,3-dioxolan-2-yl)methyl>ethyltriphenylphosphonium iodide 
• 76534-70-8 2-(2-dibenzylaminoethoxy)-1,1-diethoxyethane 

Relevant articles and documents

KOt-Bu-promoted selective ring-opening N-alkylation of 2-oxazolines to access 2-aminoethyl acetates and N-substituted thiazolidinones

An efficient and simple KOt-Bu-promoted selective ring-opening N-alkylation of 2-methyl-2-oxazoline or 2-(methylthio)-4,5-dihydrothiazole with benzyl halides under basic conditions is described for the first time. The method provides a convenient and practical pathway for the synthesis of versatile 2-aminoethyl acetates and N-substituted thiazolidinones with good functional group tolerance and selectivity. KOt-Bu not only plays an important role to promote this ring-opening N-alkylation, but also acts as an oxygen donor.

Copper(I) chloride-catalyzed three-component coupling reaction of primary amines with electrophiles and α-halogen-substituted allylsilanes to form unsymmetrical tertiary amines

Tertiary amines with three different substituents, in one of which a vinylsilane functionality was included, were straightforwardly formed by the copper(I) chloride-catalyzed tandem reaction of primary amines, α-halogen-substituted allylsilanes, and electrophiles such as electron-deficient olefins, alkyl halides, alkyl tosylates, or epoxides. In the case using electron-deficient olefins as the electrophile, the addition of chloroacetone to the reaction system afforded the three-component coupling reaction more effectively. The addition of trimethyl borate as a co-catalyst improved the yields of the three-component coupling products in the reaction using alkyl halides, alkyl tosylates, or epoxides as the electrophiles, although the reaction times were lengthened.

Hydrogen-Borrowing Alkylation of 1,2-Amino Alcohols in the Synthesis of Enantioenriched γ-Aminobutyric Acids

For the first time we have been able to employ enantiopure 1,2-amino alcohols derived from abundant amino acids in C?C bond-forming hydrogen-borrowing alkylation reactions. These reactions are facilitated by the use of the aryl ketone Ph*COMe. Racemisation of the amine stereocentre during alkylation can be prevented by the use of sub-stoichiometric base and protection of the nitrogen with a sterically hindered triphenylmethane (trityl) or benzyl group. The Ph* and trityl groups are readily cleaved in one pot to give γ-aminobutyric acid (GABA) products as their HCl salts without further purification. Both steps may be performed in sequence without isolation of the hydrogen-borrowing intermediate, removing the need for column chromatography.

GAS TREATING SOLUTIONS CONTAINING IMIDAZOLE-AMINE COMPOUNDS AND METHODS OF MAKING THE SAME

Systems comprising a composition where an imidazole is tethered to an amine and a solvent are described herein. Methods of their preparation and use are also described herein. The methods of using the systems include the reduction of volatile compounds from gas streams and a liquid stream.

A Bifunctional Copper Catalyst Enables Ester Reduction with H2: Expanding the Reactivity Space of Nucleophilic Copper Hydrides

Employing a bifunctional catalyst based on a copper(I)/NHC complex and a guanidine organocatalyst, catalytic ester reductions to alcohols with H2 as terminal reducing agent are facilitated. The approach taken here enables the simultaneous activation of esters through hydrogen bonding and formation of nucleophilic copper(I) hydrides from H2, resulting in a catalytic hydride transfer to esters. The reduction step is further facilitated by a proton shuttle mediated by the guanidinium subunit. This bifunctional approach to ester reductions for the first time shifts the reactivity of generally considered "soft"copper(I) hydrides to previously unreactive "hard"ester electrophiles and paves the way for a replacement of stoichiometric reducing agents by a catalyst and H2.

Manganese-catalysed transfer hydrogenation of esters

Manganese catalysed ester reduction using ethanol as a hydrogen transfer agent in place of dihydrogen is reported. High yields can be achieved for a range of substrates using 1 mol% of a Mn(i) catalyst, with an alkoxide promoter. The catalyst is derived from a tridentate P,N,N ligand.

Preparation method of amino polyethylene glycol propionic acid

The invention relates to the field of organic synthesis, in particular to a preparation method of amino polyethylene glycol propionic acid. The preparation method comprises the steps that catalytic hydrogenation is carried out on dibenzyl amino polyethylene glycol tert-butyl propionate shown in formula I-2 to obtain amino polyethylene glycol tert-butyl propionate shown in formula I-3; (2) the amino polyethylene glycol tert-butyl propionate shown in formula I-3 is hydrolyzed under the acidic condition to obtain amino polyethylene glycol propionic acid shown in formula I. The preparation methodof the amino polyethylene glycol propionic acid has the advantages that the defects in the prior art that the yield is low, the dangerousness is high, and the enlargement of production is difficult are overcome, the reaction conditions are mild, the operation is simple, an intermediate does not to be purified, the next reaction can be directly carried out, the whole yield reaches up to 87-92%, thepurity of end products reaches up to 97-99.5%, and a safe and efficient synthetic route is provided for the preparation of amino polyethylene glycol propionic acid.

Cs2CO3-Promoted Direct N-Alkylation: Highly Chemoselective Synthesis of N-Alkylated Benzylamines and Anilines

Herein is described an efficient and chemoselective method for the synthesis of diversely substituted secondary amines in yields up to 98 %. Direct mono-N-alkylation of primary benzylamines and anilines with a wide range of alkyl halides is promoted by a cesium base in the absence of any additive or catalyst. The basicity and solubility of cesium carbonate in anhydrous N,N-dimethylformamide not only enables mono-N-alkylation of primary amines but also suppresses undesired dialkylation of the desired amines.

AZACARBAZOLE BTK INHIBITORS

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