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Sigma-Aldrich

Vinylphosphonic acid

≥90% (T)

Synonym(s):

Ethenephosphonic acid, Ethylenephosphonic acid, P-Ethenylphosphonic acid

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About This Item

Linear Formula:
CH2=CHP(O)(OH)2
CAS Number:
1746-03-8
Molecular Weight:
108.03
Beilstein/REAXYS Number:
1741622
EC Number:
217-123-2
MDL number:
MFCD00043866
UNSPSC Code:
12352100
PubChem Substance ID:
329760454
NACRES:
NA.22

assay

≥90% (T)

impurities

≤7.0% water

mp

36 °C (Lit. dry VPA) (lit.)

density

1.37 g/mL at 20 °C (lit.)

SMILES string

OP(O)(=O)C=C

InChI

1S/C2H5O3P/c1-2-6(3,4)5/h2H,1H2,(H2,3,4,5)

InChI key

ZTWTYVWXUKTLCP-UHFFFAOYSA-N

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Application

Vinylphosphonic acid (VPA) can be used as a monomer unit for the synthesis of poly(vinylphosphonic acid) via free radical polymerization. It is also used to develop copolymers of VPA with acrylonitrile, N-isopropylacrylamide, styrene, vinylpyrrolidone, and acrylic and methacrylic acid. These copolymers find potential application in hydrogels, drug delivery, biomimetic mineralization, and polymer electrolyte membranes in fuel cells.
It can also be used as an organic building block to prepare (E)-styryl phosphonic acid derivatives by reacting with various aryl halides via Pd-catalyzed Heck coupling reaction.

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H290,H314

Hazard Classifications

Met. Corr. 1 - Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 1

flash_point_f

467.6 °F

flash_point_c

242 °C

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Noh-Seok Kwak et al.
Journal of hazardous materials, 203-204, 213-220 (2012-01-03)
Poly(vinylphosphonic acid-co-methacrylic acid) microbeads were synthesized by suspension polymerization, and their indium adsorption properties were investigated. The obtained microbeads were characterized by Fourier transform infrared (FT-IR) spectroscopy and scanning electron microscopy (SEM). The microbeads were wrinkled spheres, irrespective of the
Synthesis, microstructure, and acidity of poly (vinylphosphonic acid)
Bingol B, et al.
Macromolecular Rapid Communications, 27(20), 1719-1724 (2006)
Richard D Bertram et al.
Biochemistry, 41(24), 7725-7731 (2002-06-12)
During the past 5 years a great deal of structural and biochemical information has given us a detailed insight into the molecular mechanism of action of the PcrA DNA helicase and challenged previous notions about the molecular mechanism of action
Young Kyung Kim et al.
Biomaterials, 31(25), 6618-6627 (2010-07-14)
The complex morphologies of mineralised collagen fibrils are regulated through interactions between the collagen matrix and non-collagenous extracellular proteins. In the present study, polyvinylphosphonic acid, a biomimetic analogue of matrix phosphoproteins, was synthesised and confirmed with FTIR and NMR. Biomimetic
Single-step synthesis of styryl phosphonic acids via palladium-catalyzed Heck coupling of vinyl phosphonic acid with aryl halides
McNichols BW, et al.
Chemical Communications (Cambridge, England), 53(92), 12454-12456 (2017)
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