Skip to Content
Merck
All Photos(1)

Documents

672068

Sigma-Aldrich

Vinylphosphonic acid

≥90% (T)

Synonym(s):

Ethenephosphonic acid, Ethylenephosphonic acid, P-Ethenylphosphonic acid

Sign Into View Organizational & Contract Pricing
All Photos(1)

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:
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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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

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)

467.6 °F

Flash Point(C)

242 °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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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
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
Xuequan Lu et al.
The Journal of organic chemistry, 74(8), 3192-3195 (2009-03-20)
The first enantioselective synthesis of chiral isosteric phosphonate analogues of FTY720 is described. One of these analogues, FTY720-(E)-vinylphosphonate (S)-5, but not its R enantiomer, elicited a potent antiapoptotic effect in intestinal epithelial cells, suggesting that it exerts its action via
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service