1-Azido-2-hydroxy-3-tosyloxypropane

Base Information

• Chemical Name: 1-Azido-2-hydroxy-3-tosyloxypropane
• CAS No.: 168431-73-0
• Molecular Formula: C₁₀H₁₃N₃O₄S
• Molecular Weight: 271.297
• DSSTox Substance ID: DTXSID50558445
• Nikkaji Number: J1.318.454B
• Mol file: 168431-73-0.mol

Synonyms:1-Azido-2-hydroxy-3-tosyloxypropane;168431-73-0;1,2-Propanediol, 3-azido-, 1-(4-methylbenzenesulfonate);(3-azido-2-hydroxypropyl) 4-methylbenzenesulfonate;3-azido-2-hydroxypropyl 4-methylbenzenesulfonate;1-AZIDO-3-[(4-METHYLBENZENESULFONYL)OXY]PROPAN-2-OL;SCHEMBL13934944;DTXSID50558445;GSOZMIFQWCNBHZ-UHFFFAOYSA-N;MFCD02179400;AKOS037643855;AS-38395;A13064;3-Azido-2-hydroxypropyl 4-methylbenzene-1-sulfonate;toluene-4-sulfonic acid 3-azido-2-hydroxy-propyl ester

Chemical Property of 1-Azido-2-hydroxy-3-tosyloxypropane

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 271.06267708
• Heavy Atom Count: 18
• Complexity: 392

Purity/Quality:

97% ^*data from raw suppliers

1-Azido-2-hydroxy-3-tosyloxypropane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OCC(CN=[N+]=[N-])O

Technology Process of 1-Azido-2-hydroxy-3-tosyloxypropane

There total 3 articles about 1-Azido-2-hydroxy-3-tosyloxypropane 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: 66.0%

3-azidopropane-1,2-diol (73018-98-1) + p-toluenesulfonyl chloride (98-59-9) → 1-azido-3-(p-toluenesulfonyloxy)propan-2-ol (168431-73-0)

Guidance literature:

In pyridine; acetonitrile; 1.)0 deg C, 3 days 2.)H₂O, r.t., 1 h;

Reference yield: 48.0%

4-(azidomethyl)-2,2?dimethyl-1,3-dioxolane (25261-56-7) + p-toluenesulfonyl chloride (98-59-9) → 1-azido-3-(p-toluenesulfonyloxy)propan-2-ol (168431-73-0)

Guidance literature:

4-(azidomethyl)-2,2?dimethyl-1,3-dioxolane; With hydrogenchloride; In methanol; diethyl ether; water; ethyl acetate; at 0 - 20 ℃;

p-toluenesulfonyl chloride; With triethylamine; In dichloromethane; at 20 ℃; for 3h;

Reference yield:

glycidyl p-toluenesulfonate (118712-54-2,6746-81-2) → 1-azido-3-(p-toluenesulfonyloxy)propan-2-ol (168431-73-0) + Toluene-4-sulfonic acid 2-azido-3-hydroxy-propyl ester

Guidance literature:

With hydrogenchloride; trimethylsilylazide; lithium isopropoxide; ytterbium(III) triflate; Yield given. Multistep reaction. Yields of byproduct given; 1) THF, r.t., 12 h, 2) THF;

DOI:10.1039/c39950001021

upstream raw materials:

3-azidopropane-1,2-diol

p-toluenesulfonyl chloride

glycidyl p-toluenesulfonate

4-(azidomethyl)-2,2?dimethyl-1,3-dioxolane

Downstream raw materials:

α-(azidomethyl)-4-[2-(1-methoxy)phenyl]-1-piperazineethanol

1-azido-3-(tosyloxy)propan-2-yl acetate

α-(azidomethyl)-4-[2-(1-methylethoxy)phenyl]-1-piperazineethanol

α-(azidomethyl)-4-[2-(1-ethoxy)phenyl]-1-piperazineethanol