1,8-Diazido-3,6-dioxaoctane - CAS 59559-06-7

Azido-PEG2-azide is a polyethylene glycol (PEG)-based PROTAC linker. Azido-PEG2-azide can be used in the synthesis of a series of PROTACs.

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Molecular Formula
C6H12N6O2
Molecular Weight
200.20

1,8-Diazido-3,6-dioxaoctane

    • Specification
      • Purity
        NMR 1H, GC-MS (95%)
        Solubility
        In DMSO: 100 mg/mL (499.50 mM; Need ultrasonic)
        Appearance
        Clear Colorless Liquid
        Application
        Multifunctional alkylating agent.
        Storage
        Pure form, -20°C, 3 years; 4°C, 2 years; In solvent, -80°C, 6 months; -20°C, 1 month
        Shipping
        Room temperature in continental US; may vary elsewhere.
        IUPAC Name
        1-azido-2-[2-(2-azidoethoxy)ethoxy]ethane
        Synonyms
        Azide-PEG3-Azide;1,2-Bis(2-azidoethoxy)ethane; 1-Azido-2-[2-(2-azidoethoxy)ethoxy]ethane;
    • Properties
      • InChI Key
        OHZGAFKSAANFAS-UHFFFAOYSA-N
        InChI
        InChI=1S/C6H12N6O2/c7-11-9-1-3-13-5-6-14-4-2-10-12-8/h1-6H2
        Canonical SMILES
        C(COCCOCCN=[N+]=[N-])N=[N+]=[N-]
    • Reference Reading
      • 1. 2,3-[(3,6-Dioxaoctane-1,8-diyl)bis(sul-fanediylmethylene)]-6,7-bis(methylsulfanyl)-1,4,5,8-tetra-thia-fulvalene
        Rui-Bin Hou, Bao Li, Tie Chen, Bing-Zhu Yin, Li-Xin Wu Acta Crystallogr Sect E Struct Rep Online. 2009 Oct 17;65(Pt 11):o2783.doi: 10.1107/S1600536809041804.
        In the title mol-ecule, C(16)H(22)S(8)O(2), two S atoms, two O atoms and ten C atoms form a 14-membered ring with a boat conformation. In the crystal, C-H⋯O hydrogen bonds link the mol-ecules into dimers which are further connected into a chain along the a axis by C-H⋯S hydrogen bonds.
        2. Carboxymethyl-substituted bifunctional chelators: preparation of aryl isothiocyanate derivatives of 3-(carboxymethyl)-3-azapentanedioic acid, 3,12-bis(carboxymethyl)-6,9-dioxa-3,12-diazatetradecanedioic++ + acid, and 1,4,7,10-tetraazacyclododecane-N,N',N",N'''-tetraacetic acid for use as protein labels
        S J Kline, D A Betebenner, D K Johnson Bioconjug Chem. 1991 Jan-Feb;2(1):26-31.doi: 10.1021/bc00007a005.
        3-(Carboxymethyl)-3-azapentanedioic acid (NTA), 3,12-bis(carboxymethyl)-6,9-dioxa-3,12-diazatetradecanedioic acid (EGTA), and 1,4,7,10-tetraazacyclododecane-N,N',N",N'''-tetraacetic acid (DOTA) structures having a 4-nitrophenyl substituent attached via an alkyl spacer to the methylene carbon atom of one carboxymethyl arm of the chelator were obtained by alkylation of 4-nitrophenylalanine with bromoacetic acid (NTA), by reductive alkylation of 1,8-diamino-3,6-dioxaoctane with (4-nitrophenyl)-pyruvic acid followed by alkylation with bromoacetic acid (EGTA), and by alkylation of the trimethyl ester of 1,4,7,10-tetraazacyclododecane-N,N',N"-triacetic acid with the methyl ester of alpha-bromo-4-(4-nitrophenyl)pentanoic acid and subsequent saponification (DOTA). The nitrophenyl-substituted chelators were converted to the corresponding amines by hydrogenation then reacted with thiophosgene to give the protein-reactive aryl isothiocyanate derivatives.
        3. 2,9,16,19,22,25-Hexaoxatetra-cyclo-[24.4.0.2.0]dotriaconta-1(26),4,6,10(15),11,13,27,29,31-nona-ene
        Jai Young Lee, Ji-Eun Lee, Wonbo Sim, Ki-Min Park Acta Crystallogr Sect E Struct Rep Online. 2009 Sep 9;65(Pt 10):o2369-70.doi: 10.1107/S1600536809035399.
        The title 22-crown-6 unit, C(26)H(28)O(6), comprising of three benzo groups and triethyl-ene glycol, was prepared by the reaction of α,α'-dibromo-p-xylene with 1,8-bis-(2-hydroxy-phen-oxy)-3,6-dioxaoctane in the presence of Cs(2)CO(3) with tetra-hydro-furan (THF) and recrystallized from dichloro-methane-hexane (1:20 v/v) at room temperature. In the mol-ecular structure, two O atoms of the central ethyl-ene glycol in the triethyl-ene glycol unit exhibit exo conformations due to intra-molecular C-H⋯O inter-actions. A number of C-H⋯O and C-H⋯π inter-molecular inter-actions contribute to the stabilization of the crystal packing.
    • Preparing Stock Solutions
      • ConcentrationVolumeMass1 mg5 mg10 mg
        1 mM4.9950 mL24.9750 mL49.9501 mL
        5 mM0.9990 mL4.9950 mL9.9900 mL
        10 mM0.4995 mL2.4975 mL4.9950 mL
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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