Crotonylglycine

Base Information

• Chemical Name: Crotonylglycine
• CAS No.: 71428-89-2
• Molecular Formula: C6H9NO3
• Molecular Weight: 143.142
• NSC Number: 117391
• Nikkaji Number: J2.809.707G
• Wikidata: Q106029312
• Metabolomics Workbench ID: 78565
• Mol file: 71428-89-2.mol

Synonyms:Crotonylglycine;71428-89-2;2-[[(E)-but-2-enoyl]amino]acetic acid;CROTONYL GLYCINE;2-butenoylglycine;2-[(2E)-but-2-enamido]acetic acid;N-Crotonoylglycine;NSC117391;SCHEMBL232855;SCHEMBL232856;CHEBI:165848;AKOS000171758;NSC-117391

Chemical Property of Crotonylglycine

Chemical Property:

• Vapor Pressure: 1.89E-07mmHg at 25°C
• Refractive Index: 1.488
• Boiling Point: 398.1 °C at 760 mmHg
• Flash Point: 194.6 °C
• PSA: 66.40000
• Density: 1.175 g/cm³
• LogP: 0.15420
• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 143.058243149
• Heavy Atom Count: 10
• Complexity: 162

Purity/Quality:

99% ^*data from raw suppliers

2-[(2E)-BUT-2-ENAMIDO]ACETIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CC(=O)NCC(=O)O
• Isomeric SMILES: C/C=C/C(=O)NCC(=O)O

Technology Process of Crotonylglycine

There total 5 articles about Crotonylglycine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 77.0%

crotonyl chloride (10487-71-5) + glycine (56-40-6,18875-39-3,25718-94-9) → N-crotonylglycine (71428-89-2)

Guidance literature:

With sodium hydroxide;

Reference yield: 75.0%

trans-chrotonyl chloride (625-35-4,3488-22-0,10487-71-5) + glycine (56-40-6,18875-39-3,25718-94-9) → N-crotonylglycine (71428-89-2)

Guidance literature:

With potassium hydroxide; In water; for 0.25h; pH=12; cooling;

DOI:10.1021/ol0200403

Reference yield:

(E)-but-2-enoic acid (107-93-7) + glycine (56-40-6,18875-39-3,25718-94-9) → N-crotonylglycine (71428-89-2)

Guidance literature:

Multistep reaction; (i) SOCl₂, Et₂O, (ii) /BRN= 635782/, aq. NaOH;

DOI:10.1002/bms.1200061007

upstream raw materials:

crotonyl chloride

glycine

(E)-but-2-enoic acid

trans-chrotonyl chloride

Downstream raw materials:

4-ethoxymethylene-2-propenyl-4H-oxazol-5-one

(S)-2-[2-((E)-But-2-enoylamino)-acetylamino]-4-methyl-pentanoic acid 4-nitro-phenyl ester

(Z)-4-(4-hydroxybenzylidene)-1,2-dimethyl-1H-imidazol-5(4H)-one

3,5-dihydro-5-(4-hydroxybenzylidene)-3-methyl-2-propen-1-yl-4H-imidazol-4-one

Refernces

• 1、 He, Xiang,Bell, Alasdair F,Tonge, Peter J. "Synthesis and spectroscopic studies of model red fluorescent protein chromophores.". . p. 1523 - 1526. Retrieved 2007/10/03.
• 2、 Gregersen,Keiding,Kolvraa. "N-Acylglycines: Gas chromatographic mass spectrometric identification and determination in urine by selected ion monitoring". . p. 439 - 443. Retrieved 2007/10/05.