Prop-2-enyl 2-iodoacetate

Base Information

• Chemical Name: Prop-2-enyl 2-iodoacetate
• CAS No.: 90711-60-7
• Molecular Formula: C5H7IO2
• Molecular Weight: 226.014
• DSSTox Substance ID: DTXSID60466542
• Nikkaji Number: J402.372B
• Wikidata: Q82293128
• Mol file: 90711-60-7.mol

Synonyms:Prop-2-enyl 2-iodoacetate;90711-60-7;Acetic acid, iodo-, 2-propenyl ester;allyl iodoacetate;Allyl 2-iodoacetate;PROP-2-EN-1-YL 2-IODOACETATE;Prop-2-enyl2-iodoacetate;SCHEMBL1722806;DTXSID60466542;AKOS030255504;CS-0459446;EN300-7596612

Chemical Property of Prop-2-enyl 2-iodoacetate

Chemical Property:

• Boiling Point: 41.5-43.5 °C(Press: 0.35 Torr)
• PSA: 26.30000
• Density: 1.759±0.06 g/cm3(Predicted)
• LogP: 1.15060
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 225.94908
• Heavy Atom Count: 8
• Complexity: 90.4

Purity/Quality:

Prop-2-enyl2-iodoacetate 95.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCOC(=O)CI

Technology Process of Prop-2-enyl 2-iodoacetate

There total 2 articles about Prop-2-enyl 2-iodoacetate 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: 79.0%

allyl chloroacetate (2916-14-5) → prop-2-en-1-yl 2-iodoacetate (90711-60-7)

Guidance literature:

With potassium iodide; In acetone; at 20 ℃; for 3.5h;

DOI:10.1021/jm200421e

Reference yield: 67.0%

Iodoacetic acid (64-69-7) + allyl trichloroacetimidate (51479-73-3) → prop-2-en-1-yl 2-iodoacetate (90711-60-7)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; cyclohexane; Ambient temperature;

DOI:10.1055/s-1997-1162

Reference yield: 95.6%

prop-2-en-1-yl 2-iodoacetate (90711-60-7) + (3S,4R)-3-<(R)-hydroxyethyl>-4-<(triphenylmethyl)thio>-2-azetidinone (87037-99-8) → (3S,4R)-1-<<(allyloxy)carbonyl>methyl>-3-<(R)-1-hydroxyethyl>-4-<(triphenylmethyl)thio>-2-azetidinone (90762-39-3)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 50 - 55 ℃; for 2.5h;

DOI:10.1016/S0040-4020(01)90781-1

upstream raw materials:

allyl chloroacetate

Iodoacetic acid

allyl trichloroacetimidate

Downstream raw materials:

(3S,4R)-1-<<(allyloxy)carbonyl>methyl>-3-<(R)-1-hydroxyethyl>-4-<(triphenylmethyl)thio>-2-azetidinone

pent-4-enoic acid

(3S,4R)-1-<<(allyloxy)carbonyl>methyl>-3-<(R)-1-(tetrahydropyranyloxy)ethyl>-4-<(triphenylmethyl)thio>-2-azetidinone

Refernces

• 1、 Kokotos, George,Chiou, Antonia. "Convenient synthesis of benzyl and allyl esters using benzyl and allyl 2,2,2-trichloro-acetimidate". . p. 168 - 170. Retrieved 2007/10/03.