Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

122696

Sigma-Aldrich

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

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

Quality Level

200

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.)

SMILES string

CC1(C)OCC(CO)O1

InChI

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

InChI key

RNVYQYLELCKWAN-UHFFFAOYSA-N

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

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H319,H361d

Hazard Classifications

Eye Irrit. 2 - Repr. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

194.0 °F - closed cup

Flash Point(C)

90 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 2

1 of 2

2,2-Dimethyl-1,3-dioxolane 98%

Sigma-Aldrich

D155624

2,2-Dimethyl-1,3-dioxolane

2-Phenyl-1,3-dioxan-5-ol mixture of cis and trans, ≥97.0% (HPLC)

Sigma-Aldrich

13468

2-Phenyl-1,3-dioxan-5-ol

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
Enzymatic synthesis of 2,3-O-isopropylidene-sn-glycerol, a chiral building block for platelet-activating factor.
H Suemune et al.
Chemical & pharmaceutical bulletin, 34(8), 3440-3444 (1986-08-01)
P Kanda et al.
Journal of lipid research, 21(2), 257-258 (1980-02-01)
A new procedure for the preparation of 2,3-O-isopropylidene-sn-glycerol is described. L-arabinose is converted to its 4,5-monoisopropylidene diethyl mercaptal derivative. This compound is then subjected to periodate oxidation and borohydride reduction. Following neutralization, the aceton-glycerol is extracted from the aqueous solution
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service