13468
2-Phenyl-1,3-dioxan-5-ol
mixture of cis and trans, ≥97.0% (HPLC)
Synonym(s):
1,3-O-Benzylideneglycerol
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About This Item
Empirical Formula (Hill Notation):
C10H12O3
CAS Number:
Molecular Weight:
180.20
Beilstein:
84059
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Assay
≥97.0% (HPLC)
form
powder
storage temp.
2-8°C
SMILES string
OC1COC(OC1)c2ccccc2
InChI
1S/C10H12O3/c11-9-6-12-10(13-7-9)8-4-2-1-3-5-8/h1-5,9-11H,6-7H2
InChI key
BWKDAAFSXYPQOS-UHFFFAOYSA-N
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General description
cis-2-phenyl-1,3-dioxan-5-ol reacts with triphenylphosphine-carbon tetrabromide to yield cis-4-bromomethyl-2-phenyl-1,3-dioxolan, its trans-diastereoisomer and trans-5-bromo-2-phenyl-1,3-dioxan.
Application
2-Phenyl-1,3-dioxan-5-ol can be used as a starting material in the synthesis of 5-benzyloxy1,3-dioxan-2-one (a carbonate of glycerol monomer). It undergoes ring-opening polymerization with ε-caprolactone in presence of tin(II) 2-ethylhexanoate (Sn(oct)2).
2-Phenyl-1,3-dioxan-5-ol was used as starting reagent in the synthesis of carbonate of glycerol monomer, 5-benzyloxy-1,3-dioxan-2-one which forms copolymers with ε-caprolactone.
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
Certificates of Analysis (COA)
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Poly (carbonate ester) s based on units of 6-hydroxyhexanoic acid and glycerol.
Wolinsky JB, et al.
Macromolecules, 40(20), 7065-7068 (2007)
Nucleophilic substitution in glycerol derivatives. Part VI. Halogenodeoxygenation of 2-phenyl-1, 3-dioxan-5-ol to give 1, 3-dioxans and 1, 3-dioxolans.
Aneja R and Davies AP.
Journal of the Chemical Society. Perkin Transactions 1, 141-145 (1974)
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