DL-Allylglycine

Base Information

• Chemical Name: DL-Allylglycine
• CAS No.: 7685-44-1
• Deprecated CAS: 1069-48-3
• Molecular Formula: C₅H₉NO₂
• Molecular Weight: 115.132
• Hs Code.: 29224999
• European Community (EC) Number: 231-689-8
• NSC Number: 70870,20898
• DSSTox Substance ID: DTXSID701313217
• Nikkaji Number: J797.363B
• Wikipedia: Allylglycine
• Wikidata: Q4733443
• ChEMBL ID: CHEMBL4096969
• Mol file: 7685-44-1.mol

Synonyms:2-Amino-4-Pentenoic Acid;Allylglycine

Chemical Property of DL-Allylglycine

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0.0226mmHg at 25°C
• Melting Point: 258-260 °C(lit.)
• Refractive Index: 1.484
• Boiling Point: 231 °C at 760 mmHg
• PKA: 2.22±0.10(Predicted)
• Flash Point: 93.5 °C
• PSA: 63.32000
• Density: 1.098 g/cm³
• LogP: 0.67470
• Storage Temp.: 2-8°C
• Water Solubility.: Soluble in water
• XLogP3: -2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 115.063328530
• Heavy Atom Count: 8
• Complexity: 101

Purity/Quality:

98%,99%, ^*data from raw suppliers

DL-Allylglycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-36/37-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCC(C(=O)O)N

Technology Process of DL-Allylglycine

There total 33 articles about DL-Allylglycine 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: 100.0%

2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (72824-04-5) + 2,2-dihydroxyacetic acid (563-96-2) → rac-allylglycine (1069-48-3,7685-44-1)

Guidance literature:

2,2-dihydroxyacetic acid; With ammonium hydroxide; In ethanol; at 20 ℃; for 0.5h;

2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In ethanol; at 20 ℃; for 3h;

DOI:10.1021/ja049689o

Reference yield: 96.0%

C21H15N3O3(2-)*Ni(2+) + allyl bromide (106-95-6) → rac-allylglycine (1069-48-3,7685-44-1)

Guidance literature:

With potassium hydroxide; C-2; In dichloromethane; at 20 ℃;

DOI:10.1007/BF00959641

Reference yield: 90.0%

2-amino-2-hydroxyacetic acid (4746-62-7) + 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (72824-04-5) → rac-allylglycine (1069-48-3,7685-44-1)

Guidance literature:

With triethylamine; In methanol; at 20 ℃; for 18h;

DOI:10.1139/v05-096

upstream raw materials:

allyl-amino-malonic acid diethyl ester

Ethyl 2-Acetamido-2-cyano-4-pentenoate

diethyl (allyl)(formamido)malonate

ethyl 2-acetamido-2-(ethoxycarbonyl)-4-pentenoate

Downstream raw materials:

(2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid

L-allylglycine

(R)-2-(benzyloxycarbonylamino)pent-4-enoic acid

2-tert-Butoxycarbonylamino-pent-4-enoic acid; compound with dicyclohexyl-amine

Refernces

• 1、 McCormick, Jeffrey,Grunfeld, Alexander M.,Ertas, Yavuz N.,Biswas, Akash N.,Marsh, Kristofer L.,Wagner, Shawn,Gl?ggler, Stefan,Bouchard, Louis-S.. "Aqueous Ligand-Stabilized Palladium Nanoparticle Catalysts for Parahydrogen-Induced 13C Hyperpolarization". . p. 7190 - 7194. Retrieved 2017/07/22.
• 2、 Maurs, Michele,Acher, Francine,Azerad, Robert. "Microbial enantioselective removal of the N-benzyloxycarbonyl amino protecting group". . p. 22 - 26. Retrieved 2012/10/29.