1,4-Butanediphosphonic acid

 CAS No.: 4671-77-6  Cat No.: BP-500975  Purity: 98 % 4.5  

1,4-Butanediphosphonic acid is a phosphonate-terminated aliphatic linker component containing a compact carbon spacer and strongly polar phosphonic acid groups. Its bisphosphonic acid structure provides a distinct polar and ionizable linker environment compared with common PEG, amide, or alkyl spacers. In PROTAC linker research, this product is suitable for exploratory designs involving phosphonate-rich motifs, polar spacer effects, coordination-oriented conjugates, or specialized control compounds. It may help researchers investigate how strongly acidic linker elements influence molecular behavior, binding context, and physicochemical properties in targeted degradation-related chemical design.

1,4-Butanediphosphonic acid

Structure of 4671-77-6

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PROTAC Linker
Molecular Formula
C4H12O6P2
Molecular Weight
218.08

* For research and manufacturing use only. Not for human or clinical use.

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Purity
98 %
Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
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Room temperature in continental US; may vary elsewhere.
IUPACName
4-phosphonobutylphosphonic acid
Synonyms
1,4-BUTANEDIPHOSPHONIC ACID; 1,4-BUTANEBISPHOSPHONIC ACID; 1,4-BUTYLENEBISPHOSPHONIC ACID; 1,4-Butylenebisphosphonic acid, 98 %; 1,4-Butanediphosphonic acid,98%
InChI Key
JKTORXLUQLQJCM-UHFFFAOYSA-N
InChI
InChI=1S/C4H12O6P2/c5-11(6,7)3-1-2-4-12(8,9)10/h1-4H2,(H2,5,6,7)(H2,8,9,10)
SMILES
C(CCP(=O)(O)O)CP(=O)(O)O
1. A Simple Nanoscale Interface Directs Alignment of a Confluent Cell Layer on Oxide and Polymer Surfaces
Patrick E Donnelly, Casey M Jones, Stephen B Bandini, Shivani Singh, Jeffrey Schwartz, Jean E Schwarzbauer J Mater Chem B. 2013 Aug 7;1(29):3553-3561.doi: 10.1039/C3TB20565G.
Templating of cell spreading and proliferation is described that yields confluent layers of cells aligned across an entire two-dimensional surface. The template is a reactive, two-component interface that is synthesized in three steps in nanometer thick, micron-scaled patterns on silicon and on several biomaterial polymers. In this method, a volatile zirconium alkoxide complex is first deposited at reduced pressure onto a surface pattern that is prepared by photolithography; the substrate is then heated to thermolyze the organic ligands to form surface-bound zirconium oxide patterns. The thickness of this oxide layer ranges from 10 to 70 nanometers, which is controlled by alkoxide complex deposition time. The oxide layer is treated with 1,4-butanediphosphonic acid to give a monolayer pattern whose composition and spatial conformity to the photolithographic mask are determined spectroscopically. NIH 3T3 fibroblasts and human bone marrow-derived mesenchymal stem cells attach and spread in alignment with the pattern without constraint by physical means or by arrays of cytophilic and cytophobic molecules. Cell alignment with the pattern is maintained as cells grow to form a confluent monolayer across the entire substrate surface.
2. Perforation Does Not Compromise Patterned Two-Dimensional Substrates for Cell Attachment and Aligned Spreading
Stephen B Bandini, Joshua A Spechler, Patrick E Donnelly, Kelly Lim, Craig B Arnold, Jean E Schwarzbauer, Jeffrey Schwartz ACS Biomater Sci Eng. 2017 Dec 11;3(12):3123-3127.doi: 10.1021/acsbiomaterials.7b00339.Epub 2017 Oct 4.
Polymeric sheets were perforated by laser ablation and were uncompromised by a debris field when first treated with a thin layer of photoresist. Polymer sheets perforated with holes comprising 5, 10, and 20% of the nominal surface area were then patterned in stripes by photolithography, which was followed by synthesis in exposed regions of a cell-attractive zirconium oxide-1,4-butanediphosphonic acid interface. Microscopic and scanning electron microscopy analyses following removal of unexposed photoresist show well-aligned stripes for all levels of these perforations. NIH 3T3 fibroblasts plated on each of these perforated surfaces attached to the interface and spread in alignment with pattern fidelity in every case that is as high as that measured on a nonperforated, patterned substrate.

1,4-Butanediphosphonic acid, provides a rigid, highly polar bisphosphonate motif that can support stable conjugation strategies in targeted protein degradation workflows. Its strong anionic character and capacity for coordination make it useful for designing linker architectures that maintain effective spatial relationships between ligands. The subsequent points describe its structural features and practical considerations for PROTAC construction in detail below.

Structure: 1,4-Butanediphosphonic acid contains a four-carbon chain bearing two phosphonic acid groups at terminal positions. The molecule features P–C and P–O bonding within phosphonate functionalities, with multiple acidic, hydrogen-bonding sites that strongly influence solubility and ionization behavior.

Reactivity: For PROTAC assembly, bisphosphonic acids are typically employed via phosphonate activation or conversion to reactive derivatives compatible with ligand coupling. Common approaches include forming phosphonate esters or using coupling chemistries that enable amide or ester bond formation while preserving phosphonate integrity. Suitable conditions generally rely on anhydrous, controlled pH environments and compatible bases, with polar solvents often required to solubilize the acidic linker.

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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