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672068

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

Quality Level

100

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

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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)
Elise Claveau et al.
The Journal of organic chemistry, 72(13), 4832-4836 (2007-05-18)
In the course of our investigations on the synthesis of new nitrogen heterocyclic derivatives, we were interested in the synthesis and study of new 1,4-oxazine rings. To this aim, the desired bisvinylphosphate was prepared from N-Boc morpholine-3,5-dione and was then
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
Zara A Doddridge et al.
Biochemistry, 42(11), 3239-3246 (2003-03-19)
We have previously reported the synthesis of vinylphosphonate-linked thymidine dimers and their incorporation into synthetic oligonucleotides to create vinylphosphonate internucleotide linkages in the DNA. Such linkages have a profound effect on DNA backbone rotational flexibility, and we have shown that
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
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