Tert-butyl 5-iodopentanoate

Base Information

• Chemical Name: Tert-butyl 5-iodopentanoate
• CAS No.: 56198-37-9
• Molecular Formula: C9H17IO2
• Molecular Weight: 284.137
• DSSTox Substance ID: DTXSID50564046
• Nikkaji Number: J370.822E
• Wikidata: Q82448625
• Mol file: 56198-37-9.mol

Synonyms:TERT-BUTYL 5-IODOPENTANOATE;56198-37-9;tert-Butyl5-Iodovalerate;tert-Butyl 5-iodovalerate;5-Iodo-pentanoic acid tert-butyl ester;starbld0038796;t-butyl 5-iodopentanoate;SCHEMBL21811526;DTXSID50564046;F71794

Chemical Property of Tert-butyl 5-iodopentanoate

Chemical Property:

• Boiling Point: 249.5±23.0 °C(Predicted)
• PSA: 26.30000
• Density: 1.424±0.06 g/cm3(Predicted)
• LogP: 2.93340
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 284.02733
• Heavy Atom Count: 12
• Complexity: 138

Purity/Quality:

97% ^*data from raw suppliers

tert-Butyl5-Iodovalerate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)CCCCI
• Uses: tert-Butyl 5-Iodovalerate is used as a reactant in the labeling of site-specific cell surface proteins with biophysical probes using biotin ligase.

Technology Process of Tert-butyl 5-iodopentanoate

There total 3 articles about Tert-butyl 5-iodopentanoate 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: 67.0%

5-iodopentanoic acid (19448-36-3) + isobutene (115-11-7,15220-85-6) → 5-iodovaleric acid tert-butyl ester (56198-37-9)

Guidance literature:

With sulfuric acid; In diethyl ether; at 20 ℃; for 20h;

DOI:10.1021/ja063735y

Reference yield:

3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9,26354-94-9) → 5-iodovaleric acid tert-butyl ester (56198-37-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / TMSCl; NaI / acetonitrile

2: 67 percent / sulfuric acid / diethyl ether / 20 h / 20 °C

With chloro-trimethyl-silane; sulfuric acid; sodium iodide; In diethyl ether; acetonitrile;

DOI:10.1021/ja063735y

Reference yield:

5-bromopentanoic acid (2067-33-6) + isobutene (115-11-7,15220-85-6) → 5-iodovaleric acid tert-butyl ester (56198-37-9)

Guidance literature:

Multistep reaction; (i) NaI, (ii) /BRN= 773645/, H₂SO₄;

DOI:10.1021/ja00473a038

upstream raw materials:

5-bromopentanoic acid

isobutene

5-iodopentanoic acid

3,4,5,6-tetrahydro-2H-pyran-2-one

Downstream raw materials:

5-(1,3-dibenzyl-6c-methyl-2,5c-dioxo-(3ar,6ac)-octahydro-5λ⁴-thieno[3,4-d]imidazol-4t-yl)-pentanoic acid tert-butyl ester

5-(1,3-dibenzyl-6t-methyl-2,5c-dioxo-(3ar,6ac)-octahydro-5λ⁴-thieno[3,4-d]imidazol-4t-yl)-pentanoic acid tert-butyl ester

5-(1-phenyl-1H-tetrazol-5-ylsulfanyl)valeric acid tert-butyl ester

6-[(S)-2-[2-[(1R,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-hydroxy-cyclohex-(E)-ylidene]-hexanoic acid