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331074

Sigma-Aldrich

(4R)-4-(2-Hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

96%

Synonym(s):

2-[(4R)-2,2-Dimethyl-1,3-dioxolan-4-yl]ethanol

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About This Item

Empirical Formula (Hill Notation):
C7H14O3
CAS Number:
Molecular Weight:
146.18
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

96%

form

liquid

refractive index

n20/D 1.4390 (lit.)

bp

207 °C (lit.)

density

1.045 g/mL at 25 °C (lit.)

functional group

ether
hydroxyl
ketal

SMILES string

CC1(C)OC[C@@H](CCO)O1

InChI

1S/C7H14O3/c1-7(2)9-5-6(10-7)3-4-8/h6,8H,3-5H2,1-2H3/t6-/m1/s1

InChI key

YYEZYENJAMOWHW-ZCFIWIBFSA-N

Application

(4R)-4-(2-Hydroxyethyl)-2,2-dimethyl-1,3-dioxolane can be used:
  • To introduce a chiral center selectively in the carbon chain C10 during the total synthesis of protectin D1.
  • As a starting material in the total synthesis of an anti-diabetic molecule cytopiloyne.
  • As a starting material in the preparation of 4-15N-amino-2-butane-1,2-diol, which is used to synthesize 15N-labeled oligodeoxynucleotides.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

222.8 °F - closed cup

flash_point_c

106 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


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Total synthesis of the potent anti-inflammatory lipid mediator Protectin D1.
Rodriguez AR and Spur BW.
Tetrahedron Letters, 55(43), 6011-6015 (2014)

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