
Bromoacetamido-PEG3-azide | CAS 940005-81-2
| Catalog Number | R14-0178 |
| Category | Azides |
| Molecular Formula | C10H19BrN4O4 |
| Molecular Weight | 339.19 |
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Product Introduction
Bromoacetamido-PEG3-azide is a crosslinking reagent with 3 PEG units. The azide group enables Click Chemistry. Bromoacetamido is a very reactive group for nucleophilic substitution. The hydrophilic PEG spacer increases solubility in aqueous media.
Chemical Information
Product Specification
Application
Computed Properties
Patents
Chemical Information
| Synonyms | BrCH2CONH-PEG3-N3; Bromoacetamido-PEG3-N3; Bromo-Amido-PEG3-Azide; Acetamide, N-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethyl]-2-bromo- |
| Purity | >95% |
| IUPAC Name | N-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethyl]-2-bromoacetamide |
| SMILES | C(COCCOCCOCCN=[N+]=[N-])NC(=O)CBr |
| InChI | InChI=1S/C10H19BrN4O4/c11-9-10(16)13-1-3-17-5-7-19-8-6-18-4-2-14-15-12/h1-9H2,(H,13,16) |
| InChIKey | BIPRHBHFKQEZTR-UHFFFAOYSA-N |
| Appearance | Pale Yellow or Colorless Oily Liquid |
Product Specification
| Storage | Store at 2-8°C |
Application
Bromoacetamido-PEG3-azide is a PEG-linked azide click handle bearing a bromoacetamide electrophile for chemoselective conjugation to nucleophilic thiols and amines. As a click chemistry reagent, it is designed to participate in azide-based bioorthogonal labeling workflows, enabling modular attachment of biomolecules, surfaces, and materials to complementary alkyne partners. The short PEG3 spacer and the reactive bromoacetamide motif make it particularly useful when a balance of reactivity and reduced steric hindrance is needed for downstream imaging, diagnostics development, and material functionalization.
1. Thiol-Targeted Bioconjugation
Bromoacetamido-PEG3-azide is widely used to install an azide functionality onto thiol-containing biomolecules such as peptides, proteins, and antibody fragments via the bromoacetamide group. Researchers and reagent developers use this strategy to generate azide-bearing conjugates that can subsequently be coupled to alkyne-functional probes, linkers, or solid supports through copper-free or copper-assisted azide–alkyne click chemistry. The PEG3 spacer helps maintain conjugate solubility and accessibility of the azide for efficient labeling in complex biological buffers, supporting workflows in chemical biology and molecular imaging reagent preparation.
2. Surface And Material Functionalization
Bromoacetamido-PEG3-azide is commonly applied to functionalize biomaterial surfaces and engineered materials by reacting its bromoacetamide electrophile with surface-exposed nucleophiles, followed by azide-based click attachment of fluorescent tags, affinity ligands, or imaging moieties. This approach is used in research settings where researchers need stable, modular surface chemistries that tolerate multistep assembly and allow rapid exchange of downstream alkyne components. The PEG3 segment contributes to improved interface hydration and reduces nonspecific interactions, which is valuable for creating reproducible probe-bearing coatings and diagnostic reagent surfaces.
3. Molecular Imaging Probe Assembly
Bromoacetamido-PEG3-azide supports the construction of modular imaging probes by providing a convenient azide handle for coupling to alkyne-bearing fluorophores, enrichment tags, or imaging-compatible reporters. In molecular imaging and chemical biology laboratories, the reagent is used to generate probe conjugates with controlled linker length and improved probe accessibility, which can be important when labeling targets in heterogeneous assay formats. The combination of a conjugation-ready bromoacetamide group and a click-reactive azide enables streamlined probe build-outs for microscopy, flow-based readouts, and platform development.
4. Diagnostic Reagent And Assay Labeling
Bromoacetamido-PEG3-azide is used in the development of labeled assay reagents where azide-functional conjugates are required for consistent coupling to detection chemistries. Assay developers often incorporate this reagent to introduce azide groups onto capture molecules, secondary reagents, or labeling components, enabling subsequent attachment of reporter constructs through azide–alkyne click chemistry. The PEG3 linker is frequently selected to improve reagent handling and maintain labeling accessibility, supporting scalable assay chemistry workflows and multiplexed reagent panel construction.
Computed Properties
| XLogP3 | 0.8 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 13 |
| Exact Mass | 338.05897 g/mol |
| Monoisotopic Mass | 338.05897 g/mol |
| Topological Polar Surface Area | 71.2Ų |
| Heavy Atom Count | 19 |
| Formal Charge | 0 |
| Complexity | 274 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| WO-2022264114-A2 | Ros sensitive diazaborines for the construction of stimuli-responsive bioconjugates | 2021-06-18 |
| WO-2020201350-A1 | Means and methods for single molecule peptide sequencing | 2019-04-03 |
| EP-3948297-A1 | Means and methods for single molecule peptide sequencing | 2019-04-03 |
| US-2022214354-A1 | Means and methods for single molecule peptide sequencing | 2019-04-03 |
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