2-Bromoethyl trifluoromethanesulphonate

Name: 2-Bromoethyl trifluoromethanesulphonate
SKU: ACM103935473
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CAS

103935-47-3

Catalog Number

ACM103935473

Category

Main Products

Molecular Weight

257.00

Molecular Formula

C3H4BrF3O3S

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Specification

Synonyms

1,1,1-TrifluoroMethanesulfonic acid 2-broMo-ethyl ester

Appearance

Liquid

2-Bromoethyl Trifluoromethanesulphonate for the Synthesis of Inositol Compounds

Chen W B, et al. Chinese Chemical Letters, 2015, 26(3), 329-333.

Inositol phosphates (IPs) can regulate many biological functions in cell signaling. Using phosphonate instead of phosphate, 12 kinds of mono-phosphonate inositol compounds were prepared through two strategies: nucleophilic substitution and Arbuzov rearrangement. Among them, the bromoethyl inositol compound can be prepared by 2-bromoethyl trifluoromethanesulphonate.
Synthesis of Bromoethyl Inositol Compounds
· Bromoethyl inositol compounds 4a-d were generated from the mono-hydroxyl inositol compounds with 2-bromoethyl trifluoromethanesulfonate using 2,6-lutidine as the base.
· Direct substitution of protected myo-inositols 2a-d with dibromoethane in alkaline conditions (e.g., NaH, n-BuLi, or DBU) does not give satisfactory results due to the low reactivity of the reactants.
· However, the more reactive 2-bromoethyl trifluoromethanesulfonate was used instead of dibromoethane to make the desired bromoethyl inositol 4a-d under lower temperature in acceptable yields.

2-Bromoethyl Trifluoromethanesulphonate Used in the Cyclopropanation Process of Oxindoles via Bromoethylsulfonium Salt

Qin H, et al.Tetrahedron, 2018, 74(47), 6809-6814.

2-Bromoethyl trifluoromethanesulphonate can be used to prepare bromoethylsulfonium salt. Furthermore, oxindole can be efficiently converted into the corresponding spirocyclopropyl oxindole using bromoethylsulfonium salt, which is easy to prepare on a large scale and has stable crystallization. In fact this cyclopropanation chemistry can be conducted without Zn(OTf)2 , which is expensive reagent and is easy to pollute the environment, and with the stable crystalline bromoethylsulfonium salt as reaction substrate.
Preparation of bromoethylsulfonium salt (9)
· A solution of 2-bromoethyl trifluoromethanesulfonate15, 18 (4.12 g, 16.0 mmol) in anhydrous toluene (12 mL) was treated with phenyl sulfide (3.66 g, 19.2 mmol) at room temperature under argon with stirring. The reaction mixture was then heated 100 °C.
· The solution was allowed to cool to RT and diethyl ether (20 mL) was added to precipitate the product 9 which was isolated by filtration as a white to grey powder (3.22 g, 45%) after washing with Et2O and used in the next step without further purification.

What is the molecular formula of 2-Bromoethyl trifluoromethanesulphonate?

The molecular formula of 2-Bromoethyl trifluoromethanesulphonate is C3H4BrF3O3S.

What is the molecular weight of 2-Bromoethyl trifluoromethanesulphonate?

The molecular weight of 2-Bromoethyl trifluoromethanesulphonate is 257.03 g/mol.

What is the IUPAC name of 2-Bromoethyl trifluoromethanesulphonate?

The IUPAC name of 2-Bromoethyl trifluoromethanesulphonate is 2-bromoethyl trifluoromethanesulfonate.

What is the InChI key of 2-Bromoethyl trifluoromethanesulphonate?

The InChI key of 2-Bromoethyl trifluoromethanesulphonate is KENPFZUYYWVXNW-UHFFFAOYSA-N.

What is the canonical SMILES of 2-Bromoethyl trifluoromethanesulphonate?

The canonical SMILES of 2-Bromoethyl trifluoromethanesulphonate is C(CBr)OS(=O)(=O)C(F)(F)F.

What is the CAS number of 2-Bromoethyl trifluoromethanesulphonate?

The CAS number of 2-Bromoethyl trifluoromethanesulphonate is 103935-47-3.

How many hydrogen bond acceptors does 2-Bromoethyl trifluoromethanesulphonate have?

2-Bromoethyl trifluoromethanesulphonate has 6 hydrogen bond acceptors.

How many rotatable bond counts does 2-Bromoethyl trifluoromethanesulphonate have?

2-Bromoethyl trifluoromethanesulphonate has 3 rotatable bond counts.

What is the topological polar surface area of 2-Bromoethyl trifluoromethanesulphonate?

The topological polar surface area of 2-Bromoethyl trifluoromethanesulphonate is 51.8Å².

Is 2-Bromoethyl trifluoromethanesulphonate a canonicalized compound?

Yes, 2-Bromoethyl trifluoromethanesulphonate is a canonicalized compound.