1h,1h-Perfluoro-3,6,9-trioxadecan-1-ol

Name: 1h,1h-Perfluoro-3,6,9-trioxadecan-1-ol
SKU: ACM147492577
Rating: 5 (1 reviews)

CAS

147492-57-7

Catalog Number

ACM147492577

Category

Main Products

Molecular Weight

398.07

Molecular Formula

C7H3F13O4

COA MSDS SDS Spec Sheet

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Specification

Synonyms

Fluorinated triethylene glycol monomethyl ether

Appearance

Celar liquid

1H,1H-Perfluoro-3,6,9-Trioxadecan-1-Ol for the Preparation of Cell-Penetrating Peptide Surfactant

Hingorani, Dina V., et al. Magnetic resonance in medicine, 2020, 83(3), 974-987.

In vitro cell labeling using perfluorocarbon (PFC) nanoemulsions, combined with 19F-MRI detection, is a non-invasive method for in vivo cell product detection. This work constructed PFC nanoemulsion imaging probes with a cell-penetrating peptide (CPP), the TAT (transactivating transcription sequence) of human immunodeficiency virus. Cell labeling and imaging sensitivity could be greatly improved with this peptide-PFC nanoemulsion fabrication method. Among them, 1h,1h-Perfluoro-3,6,9-trioxadecan-1-ol was used as raw material to synthesize CPP surfactant.
Synthesis of CPP surfactants
· To synthesize the CPP surfactant, 1 mmol of either 1H,1H-perfluoro-1-heptanol (0.350 g) or 1H,1H-perfluoro-3,6,9-trioxadecan-1-ol (0.398 g) was placed in a 25 mL round-bottom flask along with 232 mg (1.1 mmol) of 6-maleimidohexanoic acid. Anhydrous dichloromethane (5 mL) was introduced, and the mixture was continuously stirred under a nitrogen gas atmosphere.
· After the reactants had fully dissolved, 572.4 mg (1.1 mmol) of benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (PyBOP) was added in a single portion. Following a 2-minute wait for the coupling reagent to dissolve, 350 µL (2 mmol) of diisopropylethylamine (DIEA) was introduced to initiate the reaction. The flask was then left stirring slowly under nitrogen at room temperature for 16 hours.
· The resulting product was purified, subjected to gradient elution, concentrated, and dried, yielding a clear oil with molecular weights of 591.28 g/mol (1) and 543.28 g/mol (2), providing yields of 325 mg and 380.1 mg, respectively.

Tosyl and Triflate Derivatives of 1H, 1H-Perfluoro-3,6,9-Trioxadecan-1-Ol

Ajlouni, Amin Fathi Amin. Diss. University of Leicester, 2016.

1H,1H-Perfluoro-3,6,9-trioxadecan-1-ol can be used to prepare triarylphosphine ligands with a perfluoroethoxy tail. Two preparation methods are reported in this work.
· Method A
1H,1H-perfluoro-3,6,9-trioxadecan-1-ol was initially reacted with pyridine and an excess of p-toluenesulfonyl chloride in an ether solution. The resulting tosylate product had a low yield of 23%, attributed to inefficient deprotonation and difficulties in removing the pyridine base.
· Method B
A different reaction approach was utilized to achieve a more effective leaving group. The product containing triflate was synthesized by reacting 1H,1H-perfluoro-3,6,9-trioxadecan-1-ol with triethylamine and triflate anhydride. This method demonstrated that triethylamine efficiently deprotonated the hydroxyl group, improving upon the previous reaction with pyridine. Following the work-up, the product was isolated as a yellow oil with an excellent yield of 90%, requiring no further purification.

What is the molecular formula of 1h,1h-Perfluoro-3,6,9-trioxadecan-1-ol?

The molecular formula is CF3O(CF2CF2O)2CF2CH2OHC7H3F13O4.

What are the synonyms for 1h,1h-Perfluoro-3,6,9-trioxadecan-1-ol?

The synonyms are 147492-57-7, Fluorinated triethylene glycol monomethyl ether, and 2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy]ethoxy]ethanol.

What is the molecular weight of 1h,1h-Perfluoro-3,6,9-trioxadecan-1-ol?

The molecular weight is 398.07 g/mol.

What is the IUPAC name of 1h,1h-Perfluoro-3,6,9-trioxadecan-1-ol?

The IUPAC name is 2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy]ethoxy]ethanol.

What is the InChI of 1h,1h-Perfluoro-3,6,9-trioxadecan-1-ol?

The InChI is InChI=1S/C7H3F13O4/c8-2(9,1-21)22-3(10,11)4(12,13)23-5(14,15)6(16,17)24-7(18,19)20/h21H,1H2.

What is the InChIKey of 1h,1h-Perfluoro-3,6,9-trioxadecan-1-ol?

The InChIKey is PGUFRYZQAPBGDW-UHFFFAOYSA-N.

What is the canonical SMILES of 1h,1h-Perfluoro-3,6,9-trioxadecan-1-ol?

The canonical SMILES is C(C(OC(C(OC(C(OC(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)O.

What is the CAS number of 1h,1h-Perfluoro-3,6,9-trioxadecan-1-ol?

The CAS number is 147492-57-7.

What is the European Community (EC) number of 1h,1h-Perfluoro-3,6,9-trioxadecan-1-ol?

The European Community (EC) number is 671-184-3.

What is the molecular weight, XLogP3-AA, hydrogen bond donor count, hydrogen bond acceptor count, rotatable bond count, and topological polar surface area of 1h,1h-Perfluoro-3,6,9-trioxadecan-1-ol?

The molecular weight is 398.07 g/mol.
The XLogP3-AA is 4.2.
The hydrogen bond donor count is 1.
The hydrogen bond acceptor count is 17.
The rotatable bond count is 8.
The topological polar surface area is 47.9Å².

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