Azide-PEG8-Alcohol

Base Information

• Chemical Name: Azide-PEG8-Alcohol
• CAS No.: 352439-36-2
• Molecular Formula: C16H33N3O8
• Molecular Weight: 395.453
• Hs Code.: 2929909090
• European Community (EC) Number: 635-360-3
• DSSTox Substance ID: DTXSID80449877
• Wikidata: Q72444581
• Mol file: 352439-36-2.mol

Synonyms:Azide-PEG8-Alcohol;352439-36-2;O-(2-Azidoethyl)heptaethylene glycol;N3-PEG8-OH;N3-Peg(8)-oh;azido-PEG8-OH;23-azido-3,6,9,12,15,18,21-heptaoxatricosan-1-ol;Azido-PEG8-alcohol;2-[2-[2-[2-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol;O-(2-Azidoethyl)heptaethyleneglycol;MFCD08274607;3,6,9,12,15,18,21-heptaoxatricosan-1-ol,23-azide;PEG8-azide;Azido-PEG8-Hydroxy;Azido-PEG (n=7);SCHEMBL13540881;DTXSID80449877;BUMODEBRFGPXRM-UHFFFAOYSA-N;AKOS030213426;GS-9423;BP-21075;SY269981;HY-140799;CS-0114456;alpha-Hydroxy-omega-azido octa(ethylene glycol);C70394;A934196

Chemical Property of Azide-PEG8-Alcohol

Chemical Property:

• PSA: 134.59000
• LogP: -0.14204
• Storage Temp.: 2-8°C
• Solubility.: Soluble in Water, DMSO, DCM, DMF
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 23
• Exact Mass: 395.22676502
• Heavy Atom Count: 27
• Complexity: 333

Purity/Quality:

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

23-Azido-3,6,9,12,15,18,21-Heptaoxatricosan-1-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 8940056
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(COCCOCCOCCOCCOCCOCCOCCO)N=[N+]=[N-]
• Description: Azide-PEG8-alcohol is a click chemistry reagent with an azide(N3) and a terminal hydroxyl group. The azide group is reactive with alkyne, BCN, DBCO via Click Chemistry to yield a stable triazole linkage. The hydroxyl (OH) group enables further derivatization or replacement with other functional groups.
• Uses: O-(2-Azidoethyl)heptaethylene glycol is used to synthesize oligo and poly(ethylene glycol) derivatives that are used as structural units of dendrimers, hydrogels, surface modifiers, self-assembling systems and molecular crosslinkers. This precursor is compatible for acetylene-azide click reactions.Some of the reported applications include:Synthesis of strain-stiffening hydrogels through self-assembly of oligomers fibres derived from Azido-PEG (n=7).Synthesis of biodegradable tetra-PEG hydrogels for drug delivery system.Synthesis of heterobifunctional oligo(ethylene glycol) linkers for bioconjugation and targeted drug delivery.Preparation of synthetic amphiphiles for programmed pH-dependent dispersions of carbon nanotubes (CNTs).Selective glycoprotein detection through allosteric click-imprinting by using a self-assembled monolayer developed from the above oligomer.Preparation of bioactivated quantum dot micelles containing fluorescent nanocrystals.

Technology Process of Azide-PEG8-Alcohol

There total 17 articles about Azide-PEG8-Alcohol 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: 99.0%

2-(2-{2-[2-(2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}ethoxy)ethoxy]ethoxy}ethoxy)ethyl 4-methylbenzenesulfonate (886469-23-4) → α-(2-azidoethyl)-ω-hydroxyhexa(oxyethylene) (352439-36-2)

Guidance literature:

With sodium azide; In ethanol; at 90 ℃; for 18h; Concentration; Temperature;

Reference yield: 93.0%

1,3,6,9,12-pentaoxa-2-thiacyclotetradecane 2,2-dioxide + 2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethanol (86770-67-4) → α-(2-azidoethyl)-ω-hydroxyhexa(oxyethylene) (352439-36-2)

Guidance literature:

1,3,6,9,12-pentaoxa-2-thiacyclotetradecane 2,2-dioxide; 2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethanol; With sodium hydride; In tetrahydrofuran; at 20 ℃;

With sulfuric acid; water; In tetrahydrofuran; at 20 ℃;

DOI:10.1039/c8cc09151j

Reference yield: 81.0%

α-allyl-ω-(2-azidoethoxy)hexa(oxyethylene) (938190-67-1) → α-(2-azidoethyl)-ω-hydroxyhexa(oxyethylene) (352439-36-2)

Guidance literature:

α-allyl-ω-(2-azidoethoxy)hexa(oxyethylene); With ozone; In dichloromethane; at -78 ℃; for 0.25h;

With sodium tetrahydroborate; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1055/s-0032-1318433

upstream raw materials:

Tetraethylene glycol

2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethanol

11-azide-1-{(methylsulfonyl)oxy}-3,6,9-trioxaundecane

2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}ethyl methanesulfonate

Downstream raw materials:

23-azido-3,6,9,12,15,18,21-heptaoxatricosyl 4-methylbenzenesulfonate

C₂₃H₃₆N₄O₁₂

α-amino,ω-azido,α,ω-dideoxy-octaethyleneglycol

59-azido-3,6,9,12,15,18,21,24,27,30,33,36,39,42,45,48,51,54,57-nonadecaoxanonapentacontan-1-ol

Refernces

• 1、 Béquignat, Jean-Baptiste,Boucheix, Claude,Canitrot, Damien,Chezal, Jean-Michel,Degoul, Fran?oise,Miot-Noirault, Elisabeth,Moreau, Emmanuel,Navarro-Teulon, Isabelle,Quintana, Mercedes,Rondon, Aurélie,Taiariol, Ludivine,Ty, Nancy. "Optimization of IEDDA bioorthogonal system: Efficient process to improve trans-cyclooctene/tetrazine interaction". . . Retrieved 2020/07/21.
• 2、 -. "PROTAC compound for targeted degradation of IDO1, and preparation method and application thereof". Paragraph 0024-0026; 0044-0045. . Retrieved 2020/06/17.