17136-36-6

Basic information

• Product Name: N-Benzylglycine
• Synonyms: N-BENZYL GLYCINE HCL;TIMTEC-BB SBB003529;2-(BENZYLAMINO)ACETIC ACID HYDROCHLORIDE;LABOTEST-BB LT00452429;BZL-GLYCINE-HCL;BZL-GLY-OH HCL;BENZYL-L-GLYCINE HYDROCHLORIDE;BENZYL GLYCINE HYDROCHLORIDE
• CAS NO: 17136-36-6
• Molecular Formula: C₉H₁₁NO₂
• Molecular Weight: 165.19
• EINECS: 241-194-9
• Product Categories: Food and Feed Additive;Amino Acids and Derivatives
• Mol File: 17136-36-6.mol

Chemical Properties

• Melting Point: 232 °C (dec.)(lit.)
• Boiling Point: 308.9 °C at 760 mmHg
• Flash Point: 140.6 °C
• Appearance: /
• Density: 1.161 g/cm³
• Vapor Pressure: 0.000285mmHg at 25°C
• Refractive Index: 1.554
• Storage Temp.: 2-8°C(protect from light)
• PKA: 2.29±0.10(Predicted)
• BRN: 2209788
• CAS DataBase Reference: N-Benzylglycine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Benzylglycine(17136-36-6)
• EPA Substance Registry System: N-Benzylglycine(17136-36-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 17136-36-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
N-Benzylglycine is used as a replacement for aromatic amino acid residues in polypeptide analogues. This substitution allows researchers to study the agonist or antagonist pharmacological properties of the analogue with respect to that specific amino acid. By understanding the effects of these modifications, scientists can gain insights into the structure-activity relationships of polypeptides and potentially develop new therapeutic agents.
Used in Chemical Synthesis:
N-Benzylglycine is also used as a starting material to synthesize diazoketones. Diazoketones are a class of compounds with diverse applications, including as photoinitiators, dyes, and intermediates in the synthesis of various organic compounds. The use of N-Benzylglycine as a starting material for diazoketone synthesis highlights its versatility and importance in the field of organic chemistry.

InChI:InChI=1/C9H11NO2/c11-9(12)7-10-6-8-4-2-1-3-5-8/h1-5,10H,6-7H2,(H,11,12)

Upstream product

• 495-69-2 Hippuric Acid 
• 40682-54-0 ethyl N-benzylideneglycinate 
• 17360-47-3 N,N-dibenzylglycine 
• 42492-87-5 N,N'-dibenzylpiperazine-2,5-dione 
• 63086-36-2 2-(benzylamino)acetonitrile hydrochloride 
• 17136-38-8 (ethoxycarbonylmethyl-benzyl-amino)-malonic acid diethyl ester 
• 100-52-7 benzaldehyde 
• 56-40-6 glycine 
• 685-87-0 Diethyl 2-bromomalonate 
• 100-46-9 benzylamine 
• 6436-90-4 ethyl 2-(benzylamino)acetate 
• 3987-53-9 N-benzyliminodiacetic acid 
• 875656-66-9 N-benzylidene glycine 
• 7662-76-2 tert-butyl 2-(benzylamino)acetate 

Downstream Products

• 35404-63-8 N-benzyl-N-carbamimidoyl glycine 
• 53386-64-4 methyl 2-(benzylamino)acetate 
• 17012-21-4 1-benzylpyrrolidine-3-carboxylic acid methyl ester 
• 87813-03-4 (3SR,4SR)methyl 1-benzyl-4-phenylpyrrolidine-3-carboxylate 
• 201405-92-7 [benzoyl(benzyl)amino]acetic acid 
• 87813-06-7 dimethyl 1-benzylpyrrolidine-3,4-dicarboxylate 
• 5747-92-2 1-benzyl-3-carboethoxypyrrolidine 
• 87813-05-6 dimethyl (3R,4R)-1-benzylpyrrolidine-3,4-dicarboxylate 
• 76315-01-0 N-benzyl-N-(tert-butoxycarbonyl)glycine 

Relevant articles and documents

Nonstabilized Azomethine Ylides Generated by Decarboxylative Condensation of α-Amino Acids. Structural Variation, Reactivity, and Stereoselectivity

A variety of aldehydes, containing enolizable aldehydes other than acetaldehyde can be used in the generation method of nonstabilized azomethine ylides by decarboxylative condesation of α-amino acids.Reactivity of the nonstabilized ylides was examined in intermolecular and intramolecular cycloadditions with olefins; stereoselectivity of the intramolecular cycloaddition using nonstabilized ylides was compared with that of ester-stabilized ylides.

Antimicrobial activity of peptidomimetics against multidrug-resistant Escherichia coli: A comparative study of different backbones

Novel remedies in the battle against multidrug-resistant bacterial strains are urgently needed, and one obvious approach involves antimicrobial peptides and mimics hereof. The impact of α- and β-peptoid as well as β3-amino acid modifications on the activity profile against β-lactamase-producing Escherichia coli was assessed by testing an array comprising different types of cationic peptidomimetics obtained by a general monomer-based solid-phase synthesis protocol. Most of the peptidomimetics possessed high to moderate activity toward multidrug-resistant E. coli as opposed to the corresponding inactive peptides. Nevertheless, differences in hemolytic activities indicate that a careful choice of backbone design constitutes a significant parameter in the search for effective cationic antimicrobial peptidomimetics targeting specific bacteria.

Mechanism of α-Amino Acids decomposition in the gas phase. Experimental and theoretical study of the elimination kinetics of N-Benzyl Glycine Ethyl Ester

The gas-phase elimination kinetics of N-benzylglycine ethyl ester was examined in a static system, seasoned with allyl bromide, and in the presence of the free chain radical suppressor toluene. The working temperature and pressure range were 386.4-426.7 °C and 16.7-40.0 torr, respectively. The reaction showed to be homogeneous, unimolecular, and obeys a first-order rate law. The elimination products are benzylglycine and ethylene. However, the intermediate benzylglycine is unstable under the reaction conditions decomposing into benzyl methylamine and CO2 gas. The variation of the rate coefficients with temperature is expressed by the following Arrhenius equation: log k1 (s-1) = (11.83 ± 0.52) - (190.3 ± 6.9) kJ mol -1 (2.303RT)-1. The theoretical calculation of the kinetic parameters and mechanism of elimination of this ester were performed at B3LYP/6-31G*, B3LYP/6-31+G**, MPW1PW91/6-31G*, and MPW1PW91/6-31+G** levels of theory. The calculation results suggest a molecular mechanism of a concerted nonsynchronous six-membered cyclic transition state process. The analysis of bond order and natural bond orbital charges implies that the bond polarization of C(=O)O-C, in the sense of C(=O)Oδ-...Cδ+, is rate determining. The experimental and theoretical parameters have been found to be in reasonable agreement.

Soluble Polymer-Supported Synthesis of α-Amino Acid Derivatives

A practical and efficient synthesis of N-substituted α-amino acid derivatives on soluble polymer support is described.

Design of selective peptidomimetic agonists for the human orphan receptor BRS-3

New tool substances may help to unravel the physiological role of the human orphan receptor BRS-3 and its possible use as a drug target for the treatment of obesity and cancer. In continuation of our work on BRS-3, the solid- and solution-phase synthesis of a library of low molecular weight peptidomimetic agonists based on the recently developed short peptide agonist 4 is described. Functional potencies of the compounds were determined measuring calcium mobilization in a fluorometric imaging plate reader (FLIPR) assay. Focusing on the N-terminus, the D-Phe-Gln moiety of 4 was modified in a combinatorial SAR-oriented medicinal chemistry approach. With the incorporation of N-arylated glycine and alanine building blocks azaglycine, piperazine, or piperidine and the synthesis of semicarbazides and semicarbazones, a number of highly potent and selective compounds with a reduced number of peptide bonds were obtained, which also should have enhanced metabolic stability.

Analogues of arginine vasopressin (AVP) modified in the N-terminal part of the molecule with N-benzylglycine

The synthesis and some pharmacological properties of five new analogues of arginine vasopressin (AVP) substituted with N-benzylglycine are described. All new peptides were tested for pressor and uterotonic activity. The results obtained imply that the structural change studied is in general incompatible with interaction of the analogues with V1A and OT receptors, however, in combination with suitable additional changes, may be of value in the design of new antagonists of these receptors.

Fast ester cleavage of sterically hindered α- and β-aminoesters under non-aqueous conditions. Application to the kinetic resolution of aziridine esters

Various protected α- and β-aminoesters undergo fast ester cleavage by treatment with t-BuOK in THF. The accelerating effect of a neighboring chelating group was used for the efficient kinetic resolution of non-racemic aziridine esters. (C) 2000 elsevier Science Ltd.

N-Benzyl-N-(tert-butyloxycarbonyl)-glycine, an N-substituted glycine (peptoid) monomer

The title compound, C14H19NO4, an amino acid mimic, was crystallized from ethyl acetate solution in a centrosymmetric space group. The distance between the side chain and the backbone was shorter than usually found in amino acids. The positional shift from α-carbon to nitrogen produced no significant steric hindrance between the side chain and the tert-butyl group.

Synthesis and reactions of 9,10-diazatetracyclo-[6.3.0.0.4,110.5.9]undecanes

The tandem 1,3-dipolar cycloaddition between sydnones and 1,5-cyclooctadiene provides 9,10-diazatetracyclo[6.3.0.0.4,110.5,9]undecanes (the Weintraub reaction) in modest to good yields.

Preparation of N-Boc N-alkyl glycines for peptoid synthesis

A series of N-tert-butoxycarbonylated N-allyl, N-propargyl, N-benzyl or branched N-alkyl glycines, useful building blocks for the synthesis of N-alkyl glycine oligomers, have been prepared by N-alkylation of N-Boc glycine or by a two-step method: reductive alkylation and tert-butoxycarbonylation.