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  • 101-06-4 Structure
  • Basic information

    1. Product Name: N,N-Dibenzyl-2-aminoethanol
    2. 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
    3. CAS NO:101-06-4
    4. Molecular Formula: C16H19NO
    5. Molecular Weight: 241.33
    6. EINECS: 202-911-0
    7. Product Categories: N/A
    8. Mol File: 101-06-4.mol
    9. Article Data: 39
  • Chemical Properties

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

    1. Hazard Codes: N/A
    2. Statements: 36/37/38
    3. Safety Statements: 26-36/37/39
    4. WGK Germany:
    5. RTECS: KJ8125000
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 101-06-4(Hazardous Substances Data)

101-06-4 Usage

Description

N,N-Dibenzylethanolamine, also known as DBAE, is a chemical compound with a unique molecular structure that features a central aminoethanol moiety to which two benzyl groups (phenyl rings) are attached to the amino nitrogen atom. This structure endows it with the ability to serve as a chiral auxiliary or a ligand in various chemical reactions, imparting chirality and enhancing the selectivity of the reactions.

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.

Check Digit Verification of cas no

The CAS Registry Mumber 101-06-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 1 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 101-06:
(5*1)+(4*0)+(3*1)+(2*0)+(1*6)=14
14 % 10 = 4
So 101-06-4 is a valid CAS Registry Number.
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

101-06-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name N,N-Dibenzylethanolamine

1.2 Other means of identification

Product number -
Other names 2-(dibenzylamino)ethanol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:101-06-4 SDS

101-06-4Relevant articles and documents

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

Li, Bin,Lin, Qiao,Zhang, Shiling

, p. 492 - 501 (2020)

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.

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

Hall, Christopher J. J.,Goundry, William R. F.,Donohoe, Timothy J.

supporting information, p. 6981 - 6985 (2021/03/01)

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.

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

Kaicharla, Trinadh,Ngoc, Trung Tran,Teichert, Johannes F.,Tzaras, Dimitrios-Ioannis,Zimmermann, Birte M.

supporting information, p. 16865 - 16873 (2021/10/20)

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.

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