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Home > Encyclopedia > 1,14-Dibromo-3,6,9,12-tetraoxatetradecane

1,14-Dibromo-3,6,9,12-tetraoxatetradecane

1,14-Dibromo-3,6,9,12-tetraoxatetradecane structure

1,14-Dibromo-3,6,9,12-tetraoxatetradecane 

structure
  • CAS No:

    57602-02-5

  • Formula:

    C10H20Br2O4

  • Chemical Name:

    1,14-Dibromo-3,6,9,12-tetraoxatetradecane

  • Synonyms:

    3,6,9,12-Tetraoxatetradecane,1,14-dibromo-;1,14-Dibromo-3,6,9,12-tetraoxatetradecane;1,2-Bis[2-(2-bromoethoxy)ethoxy]ethane

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

Bromo-PEG4-bromide is a PEG-based PROTAC linker can be used in the synthesis of PROTACs[1].

1,14-Dibromo-3,6,9,12-tetraoxatetradecane Basic Attributes

364.07

364.07

DTXSID50454837

2909199090

Characteristics

36.9

1.2

1.5±0.1 g/cm3

169-173 °C @ Press: 1.8 Torr

152.9±23.6 °C

1.489

Refrigerator

1,14-Dibromo-3,6,9,12-tetraoxatetradecane Use and Manufacturing

Methods of Manufacturing

General procedure: To a solution of the diol (1.0 eq) in pyridine, methanesulfonyl chloride (3.0 eq) was added dropwise at 0C. The reaction mixture was stirred at room temperature for 3 h. The reaction was washed with HCl (1 M) and NaHCO 3 (aq), extracted with CH 2Cl 2 and dried with Na 2SO 4. The solvent was removed in vacuo and the residue was dissolved in acetone. Lithium bromide (4 eq) was added. The reaction mixture was stirred and heated up to reflux overnight. The reaction was concentrated in vacuo and the crude product was purified by chromatography to obtain the product.Pentaethyleneglycol disulfonate (3.94 g, 10 mmol) and 13.3 g tetrabutyl ammonium bromide are dissolved in acetonitrile 50 mL, and stirred and react 16 hours under nitrogen gas protection. Solvent is evaporated out, acetic ether and water are added for extraction, extract is dried by using anhydrous sodium sulfate, concentrates and goes through column separation to obtain 2.73 g product, with a yield rate 75%. 1H-NMR (CDCl3): 3.49 (t, 4H), 3.69 (s, 12H), 3.84 (t, 4H).

Uses

A cross-linking reagent.

Computed Properties

Molecular Weight:364.07
XLogP3:1.2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:13
Exact Mass:363.97078
Monoisotopic Mass:361.97283
Topological Polar Surface Area:36.9
Heavy Atom Count:16
Complexity:113
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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