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Sigma-Aldrich

Dimethyl 5-hydroxyisophthalate

98%

Sinónimos:

Dimethyl 5-hydroxybenzene-1,3-dicarboxylate

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About This Item

Fórmula lineal:
HOC6H3-1,3-(CO2CH3)2
Número de CAS:
13036-02-7
Peso molecular:
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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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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