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371785

Sigma-Aldrich

Dimethyl 5-hydroxyisophthalate

98%

Synonym(s):

Dimethyl 5-hydroxybenzene-1,3-dicarboxylate

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About This Item

Linear Formula:
HOC6H3-1,3-(CO2CH3)2
CAS Number:
13036-02-7
Molecular Weight:
210.18
Beilstein/REAXYS Number:
2650120
EC Number:
235-899-0
MDL number:
MFCD00134367
UNSPSC Code:
12352100
PubChem Substance ID:
24863128
NACRES:
NA.22

Quality Level

100

assay

98%

form

powder

mp

162-164 °C (lit.)

SMILES string

COC(=O)c1cc(O)cc(c1)C(=O)OC

InChI

1S/C10H10O5/c1-14-9(12)6-3-7(10(13)15-2)5-8(11)4-6/h3-5,11H,1-2H3

Inchi Key

DOSDTCPDBPRFHQ-UHFFFAOYSA-N

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General description

Dimethyl 5-hydroxyisophthalate undergoes a base-catalyzed nucleophilic oxirane ring-opening addition reaction with allyl glycidyl ether, to afford 5-substituted derivatives of isophthalic acid. Influence of third component, i.e. a series of 1,ω-alkanediols on the copolymerization reaction of dimethyl 5-hydroxyisophthalate with poly(ethylene glycol) has been studied. Lipase-catalyzed condensation polymerization of dimethyl 5-hydroxyisophthalate with polyethylene glycol is reported.

Application

Novel building block derived from dimethyl 5-hydroxyisophthalate was used to prepare sterically crowded polyether dendrons, via O-allylation/Claisen rearrangement reactions. Dimethyl 5-hydroxyisophthalate may be used in the preparation of:
  • bis(phebox) derivative of the cyclophosphazene
  • 5-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}benzene-1,3-dicarboxylic acid dimethyl ester
  • fullerene derivative bearing a triethylene glycol-type polar head group

Pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Rajesh Kumar et al.
Molecular diversity, 6(3-4), 287-295 (2004-04-08)
The use of enzymes in synthetic applications has increased dramatically in the recent years and the field of polymer science is part of this trend. Synthesis of a variety of polymers using lipase catalyzed (Candida antarctica) polymerization reactions has led
Biocatalytic ?green? Synthesis of PEG-based aromatic polyesters: Optimization of the substrate and reaction conditions.
Kumar R, et al.
Green Chemistry, 6(10), 516-520 (2004)
Jeny Karabline et al.
Organic & biomolecular chemistry, 10(24), 4788-4794 (2012-05-19)
Up to third-generation sterically crowded polyether dendrons were prepared on a solid support, using a novel building block derived from dimethyl 5-hydroxyisophthalate via O-allylation/Claisen rearrangement key steps. These dendrons underwent smooth disassembly to monomers, when subjected to acidic solution. The
Esther Frederick et al.
Langmuir : the ACS journal of surfaces and colloids, 34(36), 10739-10747 (2018-08-16)
Physisorbed self-assembled monolayers (SAMs) have been suggested as potential models for three-dimensional (3D) crystallization. This work studies the effect of altering the chain length of 5-alkoxyisophthalic acid (C nISA) on self-assembled morphology in both two-dimensional (2D) and 3D to explore
Denis Nilov et al.
Tetrahedron letters, 55(36), 5078-5081 (2014-08-26)
In the course of development of novel capping ligands with variable steric factor, which will be used as an organic coating for metal oxide nanoparticles, a base-catalyzed nucleophilic oxirane ring-opening addition reaction between dimethyl 5-hydroxyisophthalate and allyl glycidyl ether was
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