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396311

Sigma-Aldrich

Vinylphosphonic acid

97%

Synonym(s):

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:
1741622
EC Number:
217-123-2
MDL number:
MFCD00043866
UNSPSC Code:
12162002
PubChem Substance ID:
24864665
NACRES:
NA.23

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
GHS05

Signal Word

Danger

Hazard Statements

H290,H314

Hazard Classifications

Met. Corr. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Phosphorus compounds, organic
Svara J, et al.
Ullmann's Encyclopedia of Industrial Chemistry (2000)
in situ thermal gelation of water-soluble poly (N-isopropylacrylamide-co-vinylphosphonic acid)
Eom GT, et al.
Journal of Applied Polymer Science, 70(10), 1947-1953 (1998)
Rebecca E Dey et al.
Journal of biomedical materials research. Part A, 106(1), 255-264 (2017-09-12)
There is a clinical need for a synthetic bone graft substitute that can be used at sites of surgical intervention to promote bone regeneration. Poly(vinylphosphonic acid-co-acrylic acid) (PVPA-co-AA) has recently been identified as a potential candidate for use in bone
Pradeep Cheruku et al.
Journal of the American Chemical Society, 131(23), 8285-8289 (2009-05-26)
Diphenylvinylphosphine oxides and di- and trisubstituted vinylphosphonates have been employed as substrates in iridium-catalyzed asymmetric hydrogenations. Complete conversions and excellent enantioselectivities (up to and above 99% ee) were observed for a range of substrates with both aromatic and aliphatic groups
S Mai et al.
Journal of dental research, 89(4), 405-410 (2010-02-23)
Biomimetic remineralization is potentially useful for the remineralization of incompletely resin-infiltrated collagen matrices created by etch-and-rinse adhesives. In this study, we tested the hypothesis that structurally altered dentin collagen cannot be remineralized to the same hierarchical order and dimension seen
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