Tetrakis(hydroxymethyl)phosphonium Chloride (ca. 80% in Water)

• CAS: 124-64-1
• Catalog Number: ACM124641-2
• Category: Main Products
• Molecular Weight: 190.56g/mol
• Molecular Formula: C4H12ClO4P
• Synonyms: KSC492Q8N; tetrakis(hydroxymethyl)phosphanium chloride; Pyroset TKC; SC-80017; UNII-58WB2XCF8I; Tetrakis(hydroxymethyl)phosphonium chloride, ca. 80% solution in water; MFCD00031687; EC 204-707-7; NSC30698; Phosphonium, tetrakis(hydroxymethyl)-, chloride
• IUPAC Name: tetrakis(hydroxymethyl)phosphanium;chloride
• Canonical SMILES: C(O)[P+](CO)(CO)CO.[Cl-]
• InChI: InChI=1S/C4H12O4P.ClH/c5-1-9(2-6,3-7)4-8;/h5-8H,1-4H2;1H/q+1;/p-1
• InChI Key: AKXUUJCMWZFYMV-UHFFFAOYSA-M
• Melting Point: 154 deg C
• Density: 1.322 at 64 ° F (NTP, 1992);1.341
• Solubility: greater than or equal to 100 mg/mL at 68° F (NTP, 1992);In water, 40,000 mg/l, temp not specified.
• Color/Form: Crystalline
• Complexity: 55.5
• Corrosivity: Corrosive
• Covalently-Bonded Unit Count: 2
• Decomposition: When heated to decomposition it emits very toxic fumes of /phosphorous oxides & hydrogen chloride/.;TETRAKIS(HYDROXYMETHYL)PHOSPHONIUM CHLORIDE DEGRADES THERMALLY & UNDER CERTAIN CHEMICAL CONDITIONS TO YIELD HYDROCHLORIC ACID & FORMALDEHYDE. IN SOLN, THE LATTER 2 CMPDS ARE IN EQUILIBRIUM WITH THE KNOWN POTENT CARCINOGEN BIS(CHLOROMETHYL)ETHER. PubMed Abstract
• EC Number: 204-707-7
• Exact Mass: 190.016g/mol
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Heavy Atom Count: 10
• Monoisotopic Mass: 190.016g/mol
• NSC Number: 30698
• Physical Description: TETRAKIS(HYDROXYMETHYL)PHOSPHONIUM CHLORIDE is a clear slightly viscous,colorless to yellow liquid (20% H₂O solution). (NTP, 1992);Liquid
• Rotatable Bond Count: 4
• RTECS Number: TA2450000
• Topological Polar Surface Area: 80.9A^2
• UNII: 58WB2XCF8I
• UN Number: 2810
• Vapor Pressure: 1 mm Hg at 77 ° F ; 6.0 mm Hg at 84° F; 110.0 mm Hg at 124° F (NTP, 1992)

Case Study

Tetrakis(Hydroxymethyl)Phosphonium Chloride for Cell Encapsulation in Protein-Based Hydrogels

Cindy Chung, et al. Biomacromolecules, 2012, 13(12), 3912-3916.

Tetrakis(hydroxymethyl)phosphonium chloride (THPC) can be used as an inexpensive, amine-reactive, aqueous crosslinker for 3D cell encapsulation in protein-based hydrogels. This work demonstrates the use of THPC in modulating hydrogel properties and shows cytocompatibility for cell growth and phenotypic retention in elastin-like protein (ELP) hydrogel systems.
THPC-amine reaction mechanism and characterization
· The Mannich reaction begins with the formation of formaldehyde (HCOH), which then combines with an amine to form an immonium ion. This immonium ion then reacts with the THPC derivative to substitute the hydroxymethyl arm, leading to the coupling of the amine. Further reactions with other amines can proceed in a comparable fashion with any remaining unreacted hydroxymethyl arms.
· THPC-amine reaction was characterized by demonstrating the ability of THPC to react with primary and secondary amines of various amino acids. The Mannich-type reaction was analyzed for the presence of formaldehyde using a colorimetric formaldehyde assay based on a carbazole reaction. 100 µl of THPC at different concentrations (ranging from 0 to 0.43 M) was mixed with 3 ml of concentrated sulfuric acid in borosilicate test tubes. Subsequently, 100 µl of 0.1% carbazole in ethanol was added, and the mixture was left to incubate at room temperature for 90 minutes. The absorbance was measured at 649 nm.
· To study the reaction between THPC and lysine, glycine, proline, and cysteine, the amino acids were combined in a 10:1 molar ratio with 0.43 M THPC, mixed, and allowed to incubate at room temperature for 20 minutes. The colorimetric assay was then conducted on the samples according to the same procedure.