Phosphoric Acid, Tris(2,3-Dibromopropyl) Ester

Catalog NumberACM126727-1

CAS Number126-72-7

CategoryPhosphate Ester Flame Retardant

Synonyms	Anfram 3PB; Apex 462-5; Bromkal P 67-6HP; ES 685; Firemaster LV-T 23P; Firemaster T 23P; Flamex T 23P; Flammex AP; Flammex T 23P; Fyrol HB 32; T 23P; Tris; Tris (Flame retardant); Tris(2,3-dibromopropyl) phosphate; TDBPP; Zetofex ZN; Phosphoric acid tri(2,3-dibromopropyl) ester; (2,3-Dibromopropyl) phosphate; Firemaster t23p-lv; NCI-C03270; Phosphoric acid, tris(2,3-dibromopropyl) ester; Tdbp; Tris(dibromopropyl) phosphate; Tris-Bp; Tris-2,3-dibrompropyl ester kyseliny fosforecne; USAF do-41; 2,3-Dibromo-1-propanol phosphate; Flammex lv-T 23P; Rcra waste number U235; Tris(2,3-dibromopropyl) phosphoric acid ester; Tris-(2,3-dibrompropyl)fosfat; Zetifex zn; 1-Propanol, 2,3-dibromo-, phosphate; FR-2406; TDCPP; Flacavon R; 1-Propanol, 2,3-dibromo-, 1,1',1''-phosphate; 3PBR; FireMaster T 23; NSC 3240; Phoscon PE 60; Phoscon UF-S;1-Propanol, 2,3-dibromo-, phosphate; 1-Propanol, 2,3-dibromo-, phosphate (3:1); 1-Propanol,2,3-dibromo-,phosphate(3:1); 2,3-dibromo-1-propanolphosphate(3:1); 2,3-dibromo-1-propanophosphate(3:1); 3pbr; Anfram 3PB; anfram3pb;TRIS(2,3-DIBROMOPROPYL)PHOSPHATE;Tris (2,3-dibromopropyl) phosphate;2,3-Dibromo-1-propanol phosphate; 2,3-Dibromo-1-propanol, phosphate (31); Phosphoric acid, tris (2,3-dibromopropyl) ester; 1-Propanol, 2,3-dibromo-, phosphate; Tris-BP Tris (dibromopropyl) phosphate; Tris (2,3-dibromopropyl) phosphoric acid ester
Molecular Weight	697.61
Molecular Formula	C9H15Br6O4P
InChI	1S/C9H15Br6O4P/c10-1-7(13)4-17-20(16,18-5-8(14)2-11)19-6-9(15)3-12/h7-9H,1-6H2
InChI Key	PQYJRMFWJJONBO-UHFFFAOYSA-N
Melting Point	5.5 ° C
Solubility	8 mg/L
Application	Flame Retardant
Atmospheric OH Rate Constant	2.77E-11 cm³/molecule-sec
Henry's Law Constants	2.18E-05 atm-m3/mole
Notes	Phosphoric Acid, Tris(2,3-Dibromopropyl) Ester uses and applications include: Flame retardant for plastics, synthetic fibers, formerly in childrens sleepwear
Vapor Pressure	1.90E-04 mm Hg

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Case Study

Molecular Interaction and Cytotoxicity Assessment of Tris(2,3-dibromopropyl) Phosphate

Zhang, Zihang, et al. International Journal of Biological Macromolecules 270 (2024): 132383.

This toxicological study investigated the molecular interaction of the halogenated flame retardant Tris(2,3-dibromopropyl) phosphate (TDBP) with human serum albumin (HSA) to elucidate a potential mechanism related to its cellular toxicity. The study compared TDBP with a structural analog, tris(1,3-dichloro-2-propyl) phosphate (TDCP).
Methodology: The binding interactions between TDBP/TDCP and HSA were analyzed using biophysical techniques and molecular simulations. Cytotoxicity was assessed in parallel to correlate binding affinity with biological effect.
Key Findings:
· Contrasting Effects on HSA: Despite structural similarity, TDBP and TDCP differentially modulated HSA enzyme activity; TDBP acted as an activator, while TDCP was an inhibitor.
· Binding Mechanism: Both compounds bound to the same site on HSA, interacting with key residues like Arg222 and causing protein unfolding. However, the primary binding forces differed: TDBP binding was driven by hydrogen bonding and van der Waals forces, whereas TDCP interacted mainly via hydrophobic forces.
· Structural Basis for Difference: Molecular simulations revealed that TDBP formed more hydrogen bonds during binding and possessed a larger charge distribution area than TDCP, accounting for its distinct interaction profile.
· Cytotoxicity Correlation: A critical finding was an inverse relationship between HSA-binding affinity and cytotoxicity. TDBP's stronger, more polar binding to HSA correlated with its observed cellular toxicity profile.

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