371785
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:
Molecular Weight:
210.18
Beilstein:
2650120
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Assay
98%
form
powder
mp
162-164 °C (lit.)
functional group
ester
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
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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
Amphiphilic diblock dendrimers: synthesis and incorporation in Langmuir and Langmuir-Blodgett films.
J F Nierengarten et al.
Journal of the American Chemical Society, 123(40), 9743-9748 (2001-10-05)
A new dendron with peripheral long alkyl chains and containing five C(60) units in the branching shell has been prepared and attached to a Fréchet-type dendron functionalized with ethylene glycol chains. The peripheral substitution of the resulting globular dendrimer with
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
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)
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
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