DL-Propargylglycine

Base Information

• Chemical Name: DL-Propargylglycine
• CAS No.: 50428-03-0
• Deprecated CAS: 64165-64-6,540466-67-9
• Molecular Formula: C5H7NO2
• Molecular Weight: 113.116
• Hs Code.: 2922499990
• European Community (EC) Number: 628-118-3,827-880-6
• NSC Number: 21940
• UNII: FU67PLJ48R
• DSSTox Substance ID: DTXSID301033465
• Nikkaji Number: J418.464E
• Wikidata: Q27278205
• ChEMBL ID: CHEMBL4795578
• Mol file: 50428-03-0.mol

Synonyms:L-2-amino-4-pentynoic acid;propargylglycine;propargylglycine hydrochloride;propargylglycine, (+-)-isomer;propargylglycine, (R)-isomer;propargylglycine, (S)-isomer

Chemical Property of DL-Propargylglycine

Chemical Property:

• Boiling Point: 272.1°Cat760mmHg
• PKA: 2.04±0.10(Predicted)
• Flash Point: 118.3°C
• PSA: 63.32000
• Density: 1.209g/cm³
• LogP: 0.12190
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: -2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 113.047678466
• Heavy Atom Count: 8
• Complexity: 133

Purity/Quality:

98%, ^*data from raw suppliers

Dl-propargylglycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C#CCC(C(=O)O)N
• Uses: Dl-propargylglycine is an inhibitor of hydrogen sulfide (H2S) production.

Technology Process of DL-Propargylglycine

There total 13 articles about DL-Propargylglycine 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%

(R)-2-(2,2,5,7,8-Pentamethyl-chroman-6-sulfonylamino)-5-trimethylsilanyl-pent-4-ynoic acid (207459-88-9) → (R)-2-aminopent-4-ynoic acid (23235-01-0,23235-03-2,50428-03-0,64165-64-6)

Guidance literature:

With trifluoroacetic acid; Heating;

DOI:10.1039/c39940000943

Reference yield: 88.8%

N-Acetyl-α-propargylglycine (23235-02-1,23235-04-3,23234-80-2) → (2S)-2-amino-4-pentynoic acid (23235-01-0) + (R)-2-aminopent-4-ynoic acid (23235-01-0,23235-03-2,50428-03-0,64165-64-6)

Guidance literature:

at 37 ℃; for 21h;

DOI:10.1021/jm00366a015

Reference yield: 84.0%

(R)-2-amino-4-pentynoic acid methyl ester (78342-50-4) → (R)-2-aminopent-4-ynoic acid (23235-01-0,23235-03-2,50428-03-0,64165-64-6)

Guidance literature:

With hydrogenchloride; methyloxirane; 1.) 1 h, reflux, 2.) EtOH, 15 min, reflux;

upstream raw materials:

N-Acetyl-D-α-propargylglycine

N-Acetyl-α-propargylglycine

(R)-2-amino-4-pentynoic acid methyl ester

(2R,5S)-5-isopropyl-3,6-dimethoxy-2-propargyl-2,5-dihydropyrazine

Downstream raw materials:

2-(benzoylamino)-4-pentynoic acid

2-[[(phenylmethoxy)carbonyl]amino]-4-pentynoic acid

N-Acetyl-α-propargylglycine

(R)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-pent-4-ynoic acid

Refernces

• 1、 Brea, Roberto J.,Lopez-Deber, M. Pilar,Castedo, Luis,Granja, Juan R.. "Synthesis of ω-(hetero)arylalkynylated α-amino acid by sonogashira-type reactions in aqueous media". . p. 7870 - 7873. Retrieved 2007/10/03.
• 2、 Collet, Sylvain,Bauchat, Patrick,Danion-Bougot, Renee,Danion, Daniel. "Stereoselective, nonracemic synthesis of ω-borono-α-amino acids". . p. 2121 - 2131. Retrieved 2007/10/03.