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Sigma-Aldrich

Vinylphosphonic acid

97%

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Synonym(s):
p -Ethenylphosphonic acid
Linear Formula:
CH2=CHP(O)(OH)2
CAS Number:
Molecular Weight:
108.03
Beilstein:
1741622
EC Number:
MDL number:
UNSPSC Code:
12162002
PubChem Substance ID:
NACRES:
NA.23

Quality Level

Assay

97%

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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General description

Vinylphosphonic acid (VPA) is an organophosphorus compound that is used in the surface treatment of metal substrates. It can be used in the preparation of poly(VPA) by radical polymerization in the presence of initiator systems and chain transfer agents. PVPA tends to have an electrolytic nature, which is useful for a variety of energy based applications.

Application

VPA based homopolymers and copolymers find usage in corrosion treatment, fuel cells, dental cement, drug delivery, and bio-mimicry.

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Met. Corr. 1 - Skin Corr. 1B

WGK

WGK 1

Flash Point(F)

235.4 °F

Flash Point(C)

113 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Anhydrous proton conducting polymer electrolytes based on poly (vinylphosphonic acid)-heterocycle composite material
Yamada M and Honma I
Polymer, 46(9), 2986-2992 (2005)
Polyphosphonate cements: a new class of dental materials
Ellis J and Wilson AD
Journal of Materials Science Letters, 9(9), 1058-1060 (1990)
Improving the adhesion between epoxy coatings and aluminium substrates
Van den Brand J, et al.
Progress in Organic Coatings, 51(4), 339-350 (2004)
Synthesis and characterization of functionalized poly (ε-caprolactone)
Wurth JJ and Shastri VP
Journal of Polymer Science Part A: Polymer Chemistry, 51(16), 3375-3382 (2013)
Patrick L Garcia et al.
Nucleic acids research, 32(12), 3771-3778 (2004-07-17)
Bloom (BLM) and Werner (WRN) syndrome proteins are members of the RecQ family of SF2 DNA helicases. In this paper, we show that restricting the rotational DNA backbone flexibility, by introducing vinylphosphonate internucleotide linkages in the translocating DNA strand, inhibits

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