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
• Article Data: 17

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

N-Benzylglycine is used as a replacement for aromatic amino acid residues in polypeptide analogues. This is done in order to determine the agonist or antagonist pharmacological properties of the analogue with respect to that specific amino acid. N-Benzylglycine is also used as a starting material to synthesize diazoketones.

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

• 7689-50-1 N-benzyl glycine hydrochloride 
• 100-46-9 benzylamine 
• 100-52-7 benzaldehyde 
• 405292-37-7 N-(cyano-phenyl-methyl)-glycine ethyl ester 
• 3287-99-8 benzylamine hydrochloride 
• 598-21-0 2-Bromoacetyl bromide 
• 56-40-6 glycine 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 103084-31-7 N-benzylideneglycine 
• 56599-00-9 diethyl N-benzyl-2-aminomalonate 
• 40682-54-0 ethyl N-benzylideneglycinate 
• 20158-69-4 2-(N-benzyl-4-methylphenylsulfonamido)acetic acid 
• 64-19-7 acetic acid 

Downstream Products

• 1140528-72-8 4-benzyl-3,4-dihydro-1H-thieno[2,3-e][1,4]diazepine-2,5-dione 

Relevant articles and documents

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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.

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.

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.