Ethyl (p-tosyloxy)acetate

Base Information

• Chemical Name: Ethyl (p-tosyloxy)acetate
• CAS No.: 39794-75-7
• Molecular Formula: C11H14O5S
• Molecular Weight: 258.295
• DSSTox Substance ID: DTXSID30473804
• Nikkaji Number: J2.924.449I
• Wikidata: Q82303437
• Mol file: 39794-75-7.mol

Synonyms:(toluene-4-sulfonyloxy)-acetic acid ethyl ester;(Toluol-4-sulfonyloxy)-essigsaeure-aethylester;Acetic acid,[[(4-methylphenyl)sulfonyl]oxy]-,ethyl ester;ethyl 2-(tosyloxy)acetate;2-(p-Toluenesulfonyloxy)acetic Acid Ethyl Ester;E0851;Ethyl (p-tosyloxy)acetate;Ethyl 2-(p-Toluenesulfonyloxy)acetate;

Chemical Property of Ethyl (p-tosyloxy)acetate

Chemical Property:

• Melting Point: 45.0 to 49.0 °C
• Boiling Point: 171-174 °C(Press: 2 Torr)
• PSA: 78.05000
• Density: 1.248±0.06 g/cm3(Predicted)
• LogP: 2.34420
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 258.05619472
• Heavy Atom Count: 17
• Complexity: 335

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ethyl 2-(p-Toluenesulfonyloxy)acetate >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)COS(=O)(=O)C1=CC=C(C=C1)C
• Uses: (Toluene-4-sulfonyloxy)-acetic acid ethyl ester (cas# 39794-75-7) is an intermediate in the synthesis of Tosylglycolic Acid (T664020), an intermediate of Cefmetazole (C242850).

Technology Process of Ethyl (p-tosyloxy)acetate

There total 5 articles about Ethyl (p-tosyloxy)acetate 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%

diazoacetic acid ethyl ester (623-73-4) + toluene-4-sulfonic acid (104-15-4) → ethyl α-p-toluenesulfonyloxyacetate (39794-75-7)

Guidance literature:

In hexafluoropropan-2-ol; at 20 ℃; for 0.0833333h; chemoselective reaction;

DOI:10.1021/ol102923h

Reference yield: 75.0%

ethyl 2-hydroxyacetate (623-50-7) + p-toluenesulfonyl chloride (98-59-9) → ethyl α-p-toluenesulfonyloxyacetate (39794-75-7)

Guidance literature:

With triethylamine; In diethyl ether; at 0 ℃; for 2h;

DOI:10.1016/j.steroids.2011.06.012

Reference yield: 26.0%

tetrahydrofuran (109-99-9,24979-97-3,77392-70-2) + diazoacetic acid ethyl ester (623-73-4) + toluene-4-sulfonic acid (104-15-4) → ethyl α-p-toluenesulfonyloxyacetate (39794-75-7) + ethyl 7-(p-tolylsulfonyloxy)-3-oxaheptanoate

Guidance literature:

at 0 - 3 ℃; for 4h; Irradiation;

upstream raw materials:

diazoacetic acid

toluene-4-sulfonic acid

ethyl 2-hydroxyacetate

p-toluenesulfonyl chloride

Downstream raw materials:

N-phenyl-O-tosylglycolamide

2-hydroxy-4-[[2-[[(4-methylphenyl)sulfonyl]oxy]acetyl]amino]benzoic acid

4-(2-(tosyloxy)acetamido)benzoic acid

ethyl 2-(thiophen-2-sulfanyl)acetate

Refernces

• 1、 -. "Sulfur-containing andrographolide derivative and pharmaceutical composition and synthesis method thereof and application of sulfur-containing andrographolide derivative in preparation of medicine for treating prostatic cancers". Paragraph 0028; 0029. . Retrieved 2017/03/25.
• 2、 Wang, Min,Gao, Mingzhang,Miller, Kathy D.,Zheng, Qi-Huang. "Synthesis of [11C]PBR06 and [18F]PBR06 as agents for positron emission tomographic (PET) imaging of the translocator protein (TSPO)". experimental part. p. 1331 - 1340. Retrieved 2011/11/06.