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13468

Sigma-Aldrich

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:
1708-40-3
Molecular Weight:
180.20
Beilstein/REAXYS Number:
84059
EC Number:
216-963-7
MDL number:
MFCD00047504
UNSPSC Code:
12352100
PubChem Substance ID:
57647095
NACRES:
NA.22

Quality Level

100

assay

≥97.0% (HPLC)

form

powder

functional group

ether
hydroxyl
phenyl

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK6303
BCCK7855

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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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