4-Iodo-1-butyne

Base Information

• Chemical Name: 4-Iodo-1-butyne
• CAS No.: 43001-25-8
• Molecular Formula: C4H5I
• Molecular Weight: 179.988
• European Community (EC) Number: 832-869-4
• DSSTox Substance ID: DTXSID80454608
• Nikkaji Number: J3.085.185D
• Wikidata: Q82276232
• Mol file: 43001-25-8.mol

Synonyms:4-Iodo-1-butyne;4-iodobut-1-yne;43001-25-8;1-Butyne, 4-iodo-;MFCD20414835;4-iodobutyne;SCHEMBL3178038;DTXSID80454608;SGLSTFIXVDSVNV-UHFFFAOYSA-N;AC1965;AKOS014114611;CS-11617;SY026540;CS-0088596;FT-0755126;EN300-211423

Chemical Property of 4-Iodo-1-butyne

Chemical Property:

• Boiling Point: 61 °C(Press: 80 Torr)
• PSA: 0.00000
• Density: 1.852±0.06 g/cm3(Predicted)
• LogP: 1.44470
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 179.94360
• Heavy Atom Count: 5
• Complexity: 47.9

Purity/Quality:

97% ^*data from raw suppliers

4-Iodobut-1-yne ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C#CCCI

Technology Process of 4-Iodo-1-butyne

There total 4 articles about 4-Iodo-1-butyne 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: 73.0%

3-Butyn-1-ol (927-74-2) → 4-iodobut-1-yne (43001-25-8)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In dichloromethane; at 0 - 25 ℃; Inert atmosphere;

DOI:10.1021/ol1029047

Reference yield: 50.0%

3-butyn-1-yl p-toluenesulfonate (23418-85-1) → 4-iodobut-1-yne (43001-25-8)

Guidance literature:

With sodium iodide; In acetone; for 12h;

Reference yield:

methanesulfonic acid but-3-ynyl ester (72486-09-0) → 4-iodobut-1-yne (43001-25-8)

Guidance literature:

With sodium iodide; In acetone; for 22h; Reflux;

DOI:10.1002/anie.201108749

upstream raw materials:

3-butyn-1-yl p-toluenesulfonate

3-Butyn-1-ol

methanesulfonic acid but-3-ynyl ester

4-bromobut-1-yne

Downstream raw materials:

methyl 3-iodo-2-cyclohexanecarboxylate

2-[1-Iodo-meth-(E)-ylidene]-cyclopentanecarboxylic acid methyl ester

methyl hept-6-ynoate

1-((E)-5-iodo-3-methylpent-2-enyl)benzene

Refernces

A convenient, stereospecific synthesis of racemic juvenile hormones and some of their analogues via vinylcuprates

10.1002/recl.19811000702

This research presents a stereospecific synthesis method for racemic juvenile hormones and some of their analogues, focusing on the creation of nine 2E,6E,10(Z)-trienyl esters and their conversion into corresponding epoxides, including natural hormones JH I-III. The study utilizes specifically substituted vinylcuprates, such as [R'R2C=CH-Cu-Y]', which react with 4-iodo-1-butyne to form the desired trienyl systems. The synthesis involves a series of reactions including the preparation of enynes, dienynes, and the final esters, using various cuprate species like R,Cu,MgX for the stereospecific conversion of 1-alkynes into vinylcuprates. The process also includes selective epoxidation using N-bromosuccinimide and potassium carbonate.