880-68-2

Basic information

• Product Name: 1,4-BENZENEBISPHOSPHONIC ACID
• Synonyms: 1,4-BENZENEBISPHOSPHONIC ACID;1,4-Benzenebisphosphonic acid, min. 95 %;Phenylene-1,4-diphosphonic acid;1,4-Phenylenediphosphonic Acid;(4-Phosphonophenyl)phosphonic acid
• CAS NO: 880-68-2
• Molecular Formula: C₆H₈O₆P₂
• Molecular Weight: 238.07
• Mol File: 880-68-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: 275 °C
• Boiling Point: 580.4±60.0 °C(Predicted)
• Appearance: /
• Density: 1.80±0.1 g/cm3(Predicted)
• PKA: 1.28±0.10(Predicted)
• CAS DataBase Reference: 1,4-BENZENEBISPHOSPHONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-BENZENEBISPHOSPHONIC ACID(880-68-2)
• EPA Substance Registry System: 1,4-BENZENEBISPHOSPHONIC ACID(880-68-2)

Safety Data

• RIDADR: UN 3261 8/PG III
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 880-68-2(Hazardous Substances Data)

Usage

General Description

1,4-BENZENEBISPHOSPHONIC ACID is a chemical compound with the formula C6H8O6P2. It is a colorless, crystalline solid that is used in a variety of industrial and scientific applications. 1,4-BENZENEBISPHOSPHONIC ACID is commonly utilized as a chelating agent, binding to metal ions and helping to control the formation and growth of metal-based deposits in water treatment and industrial processes. It also has potential applications as a corrosion inhibitor and flame retardant. Additionally, its ability to form stable complexes with metal ions makes it valuable in analytical chemistry for the determination of trace metals. Overall, 1,4-BENZENEBISPHOSPHONIC ACID is a versatile compound with important uses in multiple industries.

Synthetic route

C18H40O6P2Si4 → 1,4-phenylenebis(phosphonic acid) (880-68-2)

Conditions	Yield
With methanol for 24h; Ambient temperature;	100%

tetraethyl 1,4-phenylbis(phosphonate) (21267-14-1) → 1,4-phenylenebis(phosphonic acid) (880-68-2)

Conditions	Yield
With trimethylsilyl bromide In dichloromethane at 20℃; for 4h; Inert atmosphere;	91%
Stage #1: tetraethyl 1,4-phenylbis(phosphonate) With trimethylsilyl bromide In acetonitrile at 20℃; for 3h; Stage #2: With water In diethyl ether at 20℃; for 0.5h; Further stages.;
With hydrogenchloride; water at 110℃;	Ca. 2 g

diethyl ether (60-29-7) + carbon dioxide (124-38-9) + tetraethyl 1,4-phenylbis(phosphonate) (21267-14-1) → 1,4-phenylenebis(phosphonic acid) (880-68-2)

Conditions	Yield
With hydrogen bromide In ethanol; acetic acid	89%
With hydrogen bromide In ethanol; acetic acid	89%

1.4-dibromobenzene (106-37-6) → 1,4-phenylenebis(phosphonic acid) (880-68-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / NiCl2 / 0.5 h / 150 °C 2: 100 percent / MeOH / 24 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: nickel dichloride 2: trimethylsilyl bromide / dichloromethane / 4 h / 20 °C / Inert atmosphere View Scheme

copper(ll) sulfate pentahydrate + 1,4-phenylenebis(phosphonic acid) (880-68-2) → copper 1,4-phenylenebis(phosphonate) monohydrate

Conditions	Yield
In water refluxing ligand with 4 equiv. of Cu-salt (60°C, 24 h, pptn.); filtration, washing, drying (room temp.);	89%

heptane-1,7-diamine (646-19-5) + 1,4-phenylenebis(phosphonic acid) (880-68-2) + vanadia → [1,2-heptylenediammonium]2[V3O4(1,4-phenyldiphosphonic acid(-4H))2]

Conditions	Yield
With HF In water High Pressure; V2O5 (0.87 mmol), 1,4-phenyldiphosphonic acid (0.41 mmol), amine (1.79 mmol), H2O (554.94 mmol), and HF (23.2 mmol), initail pH 1, sealed, heated at 150°C for 5 d h, final pH 1; filtered off, elem. anal.;	85%

chromium(III) nitrate nonahydrate + 1,4-phenylenebis(phosphonic acid) (880-68-2) + acetone (67-64-1) → 2CrH12O6(3+)*2C6H5O6P2(3-)*2C3H6O

Conditions	Yield
Stage #1: chromium(III) nitrate nonahydrate; 1,4-phenylenebis(phosphonic acid) In water Stage #2: acetone In water	85%

zirconium oxide chloride octahydrate + phosphoric acid (86119-84-8, 7664-38-2) + 1,4-phenylenebis(phosphonic acid) (880-68-2) + hydrogen fluoride (7664-39-3) → Zr(4+)*0.26H(1+)*0.91C6H4P2O6(4-)*0.2HPO4(2-)*0.22F(1-)*H2O= Zr(C6H4P2O6)0.78(C6H6P2O6)0.13(HPO4)0.2F0.22*H2O

Conditions	Yield
In ethanol dissolving of (H3PO2)2C6H4 (2.10 mmol) and 85% H3PO4 (12.59 mmol) in abs. C2H5OH in vial, dissolving of ZrOCl2*8H2O (9.25 mmol) and 48 % HF (180mmol) in abs. C2H5OH in small bottle, shaking, addn. to vial, sealing, heating at 75°C for 6 days; pptn., washing with water, drying at 50°C, elem. anal.;	82%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + 1,4-phenylenebis(phosphonic acid) (880-68-2) + hydrogen fluoride (7664-39-3) + water (7732-18-5) + vanadia → [1,4-diazobicyclo[2.2.2]octane(+2H)][V2F3O2(1,4-phenyldiphosphonic acid(-3H))]*H2O

Conditions	Yield
In water High Pressure; V2O5 (0.86 mmol), 1,4-phenyldiphosphonic acid (0.43 mmol), amine (1.80 mmol), H2O (554.94 mmol), and HF (40.60 mmol), initail pH 1, sealed, heated at 180°C for 6 d h, final pH 1; filtered off, elem. anal.;	80%

zirconium oxide chloride octahydrate + 1,4-phenylenebis(phosphonic acid) (880-68-2) → Zr(4+)*0.52H(1+)*1.13O3PC6H4PO3(4-)*0.2H2O=Zr(O3PC6H4PO3)0.87(O3PC6H4PO3H2)026*0.2H2O

Conditions	Yield
With HF In water dissolving of (H3PO2)2C6H4 (4.20 mmol) in 20 ml of distd. H2O in a plastic beaker, in a separate bottle dissolving of ZrOCl2*8H2O (2.87 mmol) in20 ml of distd. H2O, addn. of 48 % HF (47.7 mmol), heating at 60.degree .C for 7 days in an oil bath; collection of solid, washing with water, drying at 50°C, elem. anal.;	79%

titanium(IV) isopropylate (546-68-9) + 1,4-phenylenebis(phosphonic acid) (880-68-2) → C6H4O6P2(4-)*Ti(4+)*H2O

Conditions	Yield
In water; isopropyl alcohol at 180℃; for 20h;	75%

1,4-phenylenebis(phosphonic acid) (880-68-2) + 2,3,5,6-tetrakis(2-pyridyl)pyrazine (25005-97-4) + water (7732-18-5) + copper(II) acetate monohydrate (6046-93-1) + molybdenum(VI) oxide → [(Cu2(tetra-2-pyridylpyrazine)(H2O)3)Mo5O15(HPO4)2]*2H2O

Conditions	Yield
With H2SO4 In water a mixt. of MoO3 (1.320 mmol), Cu-contg. compd. (0.511 mmol), ligand (0.263 mmol), 1,4-diphosphonobenzene (0.659 mmol), H2O (556 mmol) and concd.H2SO4 was stirred briefly brfore heating to 150°C for 48.5 h; in itial pH 1.5; final pH 1.0;	72%

1,4-phenylenebis(phosphonic acid) (880-68-2) + cesium chloride + hydrogen fluoride (7664-39-3) + uranyl(VI) acetate dihydrate → 3.62Cs(1+)*0.38H(1+)*4UO2(2+)*3C6H4(PO2OH)2(2-)*C6H4(PO3)2(4-)*2F(1-)=Cs3.62H0.38[(UO2)4(C6H4(PO2OH)2)3(C6H4(PO3)2)F2]

Conditions	Yield
In water High Pressure; loaded into autoclave, sealed, heated to 200°C in box furnace for3 d, cooled (5°C/h) to 25°C; washed with boiling water, rinsed with methanol, dried in air at room temp.;	70.5%

1,4-phenylenebis(phosphonic acid) (880-68-2) + water (7732-18-5) + zinc(II) chloride (7646-85-7) → zinc 1,4-phenylenebis(phosphonate) hydrate

Conditions	Yield
In water 2 equiv. ZnCl2, 60°C, 7 d (pptn.); collection (filtration), washing, drying (room temp.); elem. anal.;	70.3%

ammonium vanadate(V) + 1,4-phenylenebis(phosphonic acid) (880-68-2) → [VO(1,4-phenylenediphosphonic acid(2-))] (1104076-86-9)

Conditions	Yield
With HF In water High Pressure; soln. NH3VO3, arylphosphonic acid, H2O and HF (2.16:1.00:772:20.13) in poly(tetrafluoroethylene)-lined stainless steel container was heated to 200°C for 48 h (initial and final pH 1.0 and 1.5); elem. anal.;	70%

1,4-phenylenebis(phosphonic acid) (880-68-2) + vanadia + ethylenediamine (107-15-3) → [1,2-ethylenediammonium][V2O2(1,4-phenyldiphosphonic acid(-3H))2]

Conditions	Yield
With HF In water High Pressure; V2O5 (0.85 mmol), 1,4-phenyldiphosphonic acid (0.42 mmol), amine (1.79 mmol), H2O (544.94 mmol), and HF (11.6 mmol), initial pH 3, sealed, heated at 200°C for 72 h, final pH 3; filtered off, elem. anal.;	70%

piperazine (110-85-0) + 1,4-phenylenebis(phosphonic acid) (880-68-2) + vanadia → [piperazinium][V2O2(1,4-phenyldiphosphonic acid(-3H))2]

Conditions	Yield
With HF In water High Pressure; V2O5 (0.89 mmol), 1,4-phenyldiphosphonic acid (0.40 mmol), amine (1.79 mmol), H2O (554.94 mmol), and HF (29.0 mmol), initail pH 2, sealed, heated at 200°C for 72 h, final pH 1; filtered off, elem. anal.;	70%

thallium(I) carbonate + 1,4-phenylenebis(phosphonic acid) (880-68-2) + molybdic acid → Tl2(Mo2O5)(O3P(C6H4)PO3)

Conditions	Yield
In water at 200℃;	67%

1,4-phenylenebis(phosphonic acid) (880-68-2) + molybdic acid + caesium carbonate (534-17-8) → Cs2(Mo2O5)(O3P(C6H4)PO3)

Conditions	Yield
In water at 200℃;	66%

nickel(II) sulfate hexahydrate + 1,4-phenylenebis(phosphonic acid) (880-68-2) → 2Ni(2+)*C6H4(PO3)2(4-)*2H2O=Ni2(C6H4(PO3)2)(H2O)2

Conditions	Yield
With NaOH In water High Pressure; mixt. NiSO4*6H2O and 1,4-phenylenebisphosphonic acid in water was adjusted to pH 3-4 with 1 M NaOH and kept in Teflon-lined autoclave at 140°C for 54 h; react. mixt. was cooled slowly to room temp.; elem. anal.;	65%

1,4-phenylenebis(phosphonic acid) (880-68-2) + vanadia + 1,4-diaminobutane (110-60-1) → [1,4-butylenediammonium][V2O4(1,4-phenyldiphosphonic acid(-4H))]

Conditions	Yield
With HF In water High Pressure; V2O5 (0.88 mmol), 1,4-phenyldiphosphonic acid (0.42 mmol), amine (1.79 mmol), H2O (277.47 mmol), and HF (5.8 mmol), initail pH 1, sealed, heatedat 100°C for 7 d, final pH 1; filtered off, elem. anal.;	65%

1,4-phenylenebis(phosphonic acid) (880-68-2) + molybdic acid + potassium carbonate (584-08-7) → K2(Mo2O5)(O3P(C6H4)PO3)

Conditions	Yield
In water at 200℃;	63%

[tris(1,2-diaminoethane)cobalt(III)] chloride + 1,4-phenylenebis(phosphonic acid) (880-68-2) + water (7732-18-5) → 2Co(2+)*C6H4(PO3)2(4-)*2H2O=Co2(C6H4(PO3)2)(H2O)2

Conditions	Yield
With NaOH In water High Pressure; mixt. Co(en)3Cl3 and 1,4-phenylenebisphosphonic acid in water was adjusted to pH 3-4 with 1 M NaOH and kept in Teflon-lined autoclave at 140°C for 54 h; react. mixt. was cooled slowly to room temp.; elem. anal.;	62%

zirconium oxide chloride octahydrate + phosphoric acid (86119-84-8, 7664-38-2) + 1,4-phenylenebis(phosphonic acid) (880-68-2) + hydrogen fluoride (7664-39-3) → Zr(4+)*0.6H(1+)*0.9C6H4P2O6(4-)*0.3HPO4(2-)*0.4F(1-)*1.25H2O=Zr(C6H4P2O6)0.6(C6H6P2O6)0.3(HPO4)0.3F0.4*1.25H2O

Conditions	Yield
In dimethyl sulfoxide dissolving of (H3PO2)2C6H4 (2.10 mmol) and 85% H3PO4 (12.58 mmol) in DMSO in vial, dissolving of ZrOCl2*8H2O (2.10 mmol) and 48 % HF (190 mmol) in DMSO in polyethylene bottle, addn. to vial, sealing, heating at 75°C for 6 days; pptn., washing with water, drying at 50°C, elem. anal.;	52%

rubidium carbonate + 1,4-phenylenebis(phosphonic acid) (880-68-2) + molybdic acid → Rb2(Mo2O5)(O3P(C6H4)PO3)

Conditions	Yield
In water at 200℃;	51%

2,2'-biimidazoline (934-03-2) + 1,4-phenylenebis(phosphonic acid) (880-68-2) → C6H10N4*C6H8O6P2*4H2O

Conditions	Yield
With water In ethanol at 25℃;	47%

1,4-phenylenebis(phosphonic acid) (880-68-2) + ammonium carbonate (506-87-6) + molybdic acid → (NH4)2(Mo2O5)(O3P(C6H4)PO3)

Conditions	Yield
In water at 200℃;	42%

sodium metavanadate + 1,4-phenylenebis(phosphonic acid) (880-68-2) + water (7732-18-5) → Na8[2H2O.cntnd.2(H2V10O18(1,4-benzenebisphosphonate)4)]*34H2O

Conditions	Yield
With NaN3; N2H4*H2O; HCl In water; N,N-dimethyl-formamide mixt. of NaVO3, NaN3, acid, H2O, DMF and Et3N was stirred at 70°Cuntil clear soln. formed; concd. aq. HCl, N2H4*H2O, concd. aq. HCl were added at 70°C to pH 7.5; reacted for 1 d;	41%

2,2'-biimidazoline (934-03-2) + 1,4-phenylenebis(phosphonic acid) (880-68-2) → C6H10N4*C6H8O6P2

Conditions	Yield
In dimethyl sulfoxide at 25℃;	6%

styrene (292638-84-7) + 1,4-phenylenebis(phosphonic acid) (880-68-2) → 1,4-distyrylbenzene (1608-41-9)

Conditions	Yield
With trimethylamine-N-oxide; tetrabutyl ammonium fluoride; palladium diacetate In tetrahydrofuran; 1,4-dioxane at 100℃; for 24h; Heck-type reaction;	42 % Spectr.

Upstream product

• 15104-47-9 tetramethyl 1,4-phenylenebis(phosphonate) 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 106-39-8 bromochlorobenzene 
• 60-29-7 diethyl ether 
• 124-38-9 carbon dioxide 
• 21267-14-1 tetraethyl 1,4-phenylbis(phosphonate) 
• 106-37-6 1.4-dibromobenzene 

Downstream Products

• 173196-50-4 (E,E')-di-tert-butyl benzene-1,4-dipropenoate 

Relevant articles and documents

C-P bond formation of cyclophanyl-, and aryl halides: Via a UV-induced photo Arbuzov reaction: A versatile portal to phosphonate-grafted scaffolds

A new versatile method for the C-P bond formation of (hetero)aryl halides with trimethyl phosphite via a UV-induced photo-Arbuzov reaction, accessing diverse phosphonate-grafted arenes, heteroarenes and co-facially stacked cyclophanes under mild reaction

Efficient energy and electron transfer between donor and acceptor chromophores in aluminophosphate hybrid materials

The first organic-inorganic hybrid materials (OIHMs) having one or a combination of two chromophores in different ratios are obtained from the aryl phosphonic acid and aluminum lactate via sol gel process. The structures of these OIHMs are analyzed by the 27Al and 31P NMR. The fluorescence resonance energy transfer (FRET) as well as photoinduced electron transfer (PET) between donor and acceptor chromophores in these hybrid materials have been investigated and the efficiencies can be up to 97 and 93%, respectively.

Mesoporous crystalline solid compound of a diphosphonate/phosphite of a tetravalent metal, with a narrow distribution of mesopores

The present invention discloses a compound comprising a diphosphonate/phosphite of a tetravalent metal: (where M, R, x and y have the meaning given in the description), in the form of a crystalline solid with an alpha-type lamellar structure with a distance between layers of 7.4 to 20? (depending on the dimensions of radical R), a BET surface area of 250 to 400m2 /g, and porosity within the mesopore range, with at least 50% of the pores measuring 20 to 30?. The compound, depending on the radical R used, may or may not have microporosity in the region between layers. Such a diphosphonate/phosphite of a tetravalent metal is obtained by reaction between diphosphonic acid, phosphorous acid and an oxyhalide of a tetravalent metal, in a solvent comprising dimethyl-sulphoxide/water containing hydrofluoric acid.