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371785

Sigma-Aldrich

Dimethyl 5-hydroxyisophthalate

98%

Synonyme(s) :

Dimethyl 5-hydroxybenzene-1,3-dicarboxylate

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About This Item

Formule linéaire :
HOC6H3-1,3-(CO2CH3)2
Numéro CAS:
13036-02-7
Poids moléculaire :
210.18
Numéro Beilstein :
2650120
Numéro CE :
235-899-0
Numéro MDL:
MFCD00134367
Code UNSPSC :
12352100
ID de substance PubChem :
24863128
Nomenclature NACRES :
NA.22

Niveau de qualité

100

Pureté

98%

Forme

powder

Pf

162-164 °C (lit.)

Chaîne SMILES 

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

Clé InChI

DOSDTCPDBPRFHQ-UHFFFAOYSA-N

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Description générale

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

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (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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