6-Heptyn-1-ol, 4-methylbenzenesulfonate

Base Information

• Chemical Name: 6-Heptyn-1-ol, 4-methylbenzenesulfonate
• CAS No.: 87462-63-3
• Molecular Formula: C14H18O3S
• Molecular Weight: 266.361
• Mol file: 87462-63-3.mol

Synonyms:6-Heptyn-1-ol,4-methylbenzenesulfonate;6-heptyn-1-yl p-toluenesulfonate;6-heptynyl p-toluenesulfonate;5-heptynyl tosylate;6-heptynyl 4-methylbenzenesulfonate;6-heptynyl tosylate;

Chemical Property of 6-Heptyn-1-ol, 4-methylbenzenesulfonate

Chemical Property:

• PSA: 82.98000
• LogP: 3.49480

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Hept-6-yn-1-yl 4-methylbenzenesulfonate is a PEG linker containing a tosyl group and a propargyl group. The hydrophilic PEG spacer increases solubility in aqueous media. The tosyl group is a very good leaving group for nucleophilic substitution reactions. The propargyl group can react with azide-bearing compounds or biomolecules via copper catalyzed azide-alkyne Click Chemistry to yield a stable triazole linkage.

Technology Process of 6-Heptyn-1-ol, 4-methylbenzenesulfonate

There total 6 articles about 6-Heptyn-1-ol, 4-methylbenzenesulfonate 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: 91.0%

1-hydroxy-6-heptyne (63478-76-2) + p-toluenesulfonyl chloride (98-59-9) → hept-6-yn-1-yl 4-methylbenzenesulfonate (87462-63-3)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1021/acs.jmedchem.9b00871

Reference yield: 21.0%

1,5-bis(p-toluenesulfonyloxy)pentane (24293-28-5) + sodium acetylide (1066-26-8) → hept-6-yn-1-yl 4-methylbenzenesulfonate (87462-63-3)

Guidance literature:

In N,N-dimethyl-formamide; toluene; at 20 ℃;

DOI:10.1016/j.bmcl.2014.12.023

Reference yield:

3-heptyn-1-ol (14916-79-1) → hept-6-yn-1-yl 4-methylbenzenesulfonate (87462-63-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / 1,3-diaminopropane, sodamide / 2 h / 80 °C

2: 87 percent / pyridine

With pyridine; sodium amide; Trimethylenediamine;

DOI:10.1021/jm00367a011

upstream raw materials:

1-hydroxy-6-heptyne

p-toluenesulfonyl chloride

3-heptyn-1-ol

hep-2-yn-1-ol

Downstream raw materials:

pentylidenecyclohexane

(cyclohexylidenemethyl)benzene

1-Phenylcycloheptene

5-(o-carboran-1-yl)pentyl 4-methylbenzenesulfonate