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106615

Sigma-Aldrich

2,2-Bis(hydroxymethyl)propionic acid

98%

Synonym(s):

Bis-MPA, DMPA®, Dimethylolpropionic acid

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About This Item

Linear Formula:
(HOCH2)2C(CH3)COOH
CAS Number:
4767-03-7
Molecular Weight:
134.13
Beilstein:
1756385
EC Number:
225-306-3
MDL number:
MFCD00004199
UNSPSC Code:
12352100
PubChem Substance ID:
24846739
NACRES:
NA.22

vapor density

<1 (vs air)

Assay

98%

form

solid

mp

189-191 °C (lit.)

solubility

H2O: soluble
acetone: slightly soluble
benzene: insoluble
methanol: soluble

functional group

carboxylic acid

SMILES string

CC(CO)(CO)C(O)=O

InChI

1S/C5H10O4/c1-5(2-6,3-7)4(8)9/h6-7H,2-3H2,1H3,(H,8,9)

InChI key

PTBDIHRZYDMNKB-UHFFFAOYSA-N

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Application

2,2-Bis(hydroxymethyl)propionic acid based fourth generation tridendron dendrimer having 48 hydroxyl groups was synthesized.
2,2-Bis(hydroxymethyl)propionic acid is commonly used as an AB2 monomer for the synthesis of hyperbranched (hb) polymers and dendrimers.
2,2-Bis(hydroxymethyl)propionic acid was used in the synthesis and characterization studies of polyurethane dispersion modified with polymethylsiloxane (Si-PUD) and its nanocomposites incorporated with clays.2,2-Bis(hydroxymethyl)propionic acid based dendrimers have potent applications as delivery systems for potent anticancer drugs such as cisplatin and doxorubicin, as well as agents for both boron neutron capture therapy and photodynamic therapy.
Simple derivatives of this acid have been used to construct dendritic architectures via the "click" azide-acetylene cycloaddition.

Legal Information

DMPA is a registered trademark of GEO Specialty Chemicals, Inc.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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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Kazuki Fukushima et al.
Biomaterials science, 7(6), 2288-2296 (2019-04-25)
Cationic aliphatic polycarbonates bearing primary ammonium side chains have been developed with relatively high molecular weights and controlled macromolecular architectures. These polycarbonates exhibit reasonable antimicrobial activity against Gram-negative and Gram-positive bacteria. The prepared homopolymers could be effective against Gram-negative bacteria
First divergent strategy using two AB2 unprotected monomers for the rapid synthesis of dendrimers.
Brauge L, et al.
Journal of the American Chemical Society, 123(27), 6698-6699 (2001)
Double-stage convergent approach for the synthesis of functionalized dendritic aliphatic polyesters based on 2, 2-bis (hydroxymethyl) propionic acid.
Ihre H and Hult A.
Macromolecules, 31(13), 4061-4068 (1998)
Elizabeth R Gillies et al.
Drug discovery today, 10(1), 35-43 (2005-01-29)
The unique properties of dendrimers, such as their high degree of branching, multivalency, globular architecture and well-defined molecular weight, make them promising new scaffolds for drug delivery. In the past decade, research has increased on the design and synthesis of
Synthesis and Characterization of Siloxane-Modified Polyurethane Dispersion/Clay Nanocomposites.
Noh HH, et al.
Advanced Materials Research, 415, 1196-1199 (2012)
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