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Merck
CN

122696

DL-1,2-Isopropylideneglycerol

≥97.0%

Synonym(s):

(±)-2,2-Dimethyl-1,3-dioxolane-4-methanol, (±)-2,2-Dimethyl-4-hydroxymethyl-1,3-dioxolane, 1,2-Isopropylidene-rac-glycerol, Solketal

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About This Item

Empirical Formula (Hill Notation):
C6H12O3
CAS Number:
100-79-8
Molecular Weight:
132.16
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24847503
EC Number:
202-888-7
Beilstein/REAXYS Number:
104465
MDL number:
MFCD00063238
Assay:
≥97.0%
Form:
liquid

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InChI key

RNVYQYLELCKWAN-UHFFFAOYSA-N

InChI

1S/C6H12O3/c1-6(2)8-4-5(3-7)9-6/h5,7H,3-4H2,1-2H3

SMILES string

CC1(C)OCC(CO)O1

assay

≥97.0%

form

liquid

refractive index

n20/D 1.434 (lit.)

bp

188-189 °C (lit.)

solubility

H2O: miscible, alcohol: miscible, diethyl ether: miscible, oil: miscible, petroleum ether: miscible

density

1.063 g/mL at 25 °C (lit.)

functional group

ether, hydroxyl, ketal

Quality Level

200

Related Categories

General description

DL-1,2-Isopropylideneglycerol undergoes effective isopropylidenation and deprotection reaction catalyzed by phosphotungstic acid.

Application

DL-1,2-Isopropylideneglycerol was used as the starting reagent for synthesis of tulipaline derivatives.

Legal Information

Hazard Classifications

Eye Irrit. 2 - Repr. 2

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

Storage Class

10 - Combustible liquids

wgk

WGK 1

flash_point_f

194.0 °F - closed cup

flash_point_c

90 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB1155
STBL1455
STBK9988
STBK4828
STBK2790

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Useful methods for the synthesis of isopropylidenes and their chemoselective cleavage.
Vanlaldinpuia K and Bez G.
Tetrahedron Letters, 52(29), 3759-3764 (2011)
Alvise Perosa et al.
Molecules (Basel, Switzerland), 21(2), 170-170 (2016-02-04)
The caprylic, lauric, palmitic and stearic esters of solketal and glycerol formal were synthesized with high selectivity and in good yields by a solvent-free acid catalyzed procedure. No acetal hydrolysis was observed, notwithstanding the acidic reaction conditions.
Thomas Mendgen et al.
Bioorganic & medicinal chemistry letters, 20(19), 5757-5762 (2010-08-24)
The enzyme MurA performs an essential step in peptidoglycan biosynthesis and is therefore a target for the discovery of novel antibacterial compounds. We report here the inhibition of MurA by natural products from tulips (tulipalines and tuliposides), and the structure-activity
Renjie Liu et al.
Bioconjugate chemistry, 28(7), 1955-1964 (2017-06-22)
Electrospun biodegradable membranes have attracted great attention for a range of tissue engineering applications. Among them, poly(ε-caprolactone) (PCL) is one of the most widely used polymers, owing to its well-controlled biocompatibility and biodegradability. However, PCL also has a number of
Changning Guo et al.
Chirality, 18(10), 775-782 (2006-08-15)
Near-infrared (near-IR) Fourier transform vibrational circular dichroism (FT-VCD) spectroscopy has been used to monitor the epimerization of (S)-(+)-2,2-dimethyl-1,3-dioxolane-4-methanol (S-DDM). The near-IR-VCD spectra display clear isolated VCD bands at the range of 4700-5050 cm(-1) resulting from the OH stretch-bend combination bands
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