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Merck
CN

672068

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
329760454
EC Number:
217-123-2
Beilstein/REAXYS Number:
1741622
MDL number:
MFCD00043866
Assay:
≥90% (T)

Key Documents

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InChI

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

InChI key

ZTWTYVWXUKTLCP-UHFFFAOYSA-N

SMILES string

OP(O)(=O)C=C

assay

≥90% (T)

impurities

≤7.0% water

mp

36 °C (Lit. dry VPA) (lit.)

density

1.37 g/mL at 20 °C (lit.)

Quality Level

100

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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

WGK 1

flash_point_f

467.6 °F

flash_point_c

242 °C

ppe

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

Regulatory Information

监管及禁止进口产品
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Certificates of Analysis (COA)

Lot/Batch Number
SDBB0276
STBB3728V
STBC6081V
STBB3728
S65968

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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)
J Kim et al.
Journal of dental research, 89(5), 482-487 (2010-03-05)
Continuous etching of aggressive all-in-one adhesives occurs in wet dentin tubules after polymerization of the adhesives. This study challenged the hypothesis that unpolymerized acidic monomers from an aggressive all-in-one self-etching adhesive continue to etch beyond dentin hybrid layers. Dentin surfaces
Ozlem Dogan et al.
Langmuir : the ACS journal of surfaces and colloids, 22(23), 9671-9675 (2006-11-01)
In the present work, copolymers of vinylphosphonic acid and 4-vinilyimidazole (poly(4-VIm-co-VPA)) were found to be substrates favoring the precipitation of nanohydroxyapatite (HAP) crystals from stable supersaturated solutions at pH 7.4 and 37 degrees C. Deposition kinetics were studied by the
J W Nicholson et al.
Journal of oral rehabilitation, 30(2), 160-164 (2003-01-22)
A glass-ionomer cement containing an acrylic acid/vinyl phosphonic acid copolymer, has been investigated for its interaction with water and with aqueous lactic acid and the results compared with those from conventional glass-ionomers based on polyacrylic acid. Cylindrical specimens (12 mm
Stephan Salzinger et al.
Macromolecular rapid communications, 33(16), 1327-1345 (2012-07-11)
Recent studies have shown that poly(vinylphosphonate)s are readily accessible by rare earth metal-mediated group transfer polymerization (GTP). This article highlights the progress in this new field and advantages of GTP in comparison to classical anionic and radical polymerization approaches. Late
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