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241806

Sigma-Aldrich

(R)-(−)-2,2-Dimethyl-1,3-dioxolane-4-methanol

98%

Synonym(s):

2,3-Isopropylidene-sn-glycerol, L-α,β-Isopropylideneglycerol, L-2,3-O-isopropylidene-sn-glycerol

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About This Item

Empirical Formula (Hill Notation):
C6H12O3
CAS Number:
14347-78-5
Molecular Weight:
132.16
Beilstein:
80117
MDL number:
MFCD00003213
UNSPSC Code:
12352005
PubChem Substance ID:
24854331
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

100

Assay

98%

form

liquid

optical activity

[α]20/D −13.7°, neat

optical purity

ee: 98% (GLC)

refractive index

n20/D 1.434 (lit.)

bp

72-73 °C/8 mmHg (lit.)

density

1.062 g/mL at 25 °C (lit.)

functional group

ether
hydroxyl
ketal

storage temp.

2-8°C

SMILES string

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

InChI

1S/C6H12O3/c1-6(2)8-4-5(3-7)9-6/h5,7H,3-4H2,1-2H3/t5-/m1/s1

InChI key

RNVYQYLELCKWAN-RXMQYKEDSA-N

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Application

(R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol may be used to prepare:
  • (R)-2,2-Dimethyl-4-benzoxymethyl-1,3-dioxolane.[1]
  • ((S)-(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate)-1,3-dioxolane.[2]
  • (S)-Glyceraldehyde acetonide.[3]
  • Tetraoxaspiroundecanes[4], diglycerides,[5] glyceryl phosphates,[6] and spiropyrans.[7]

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

174.2 °F - closed cup

Flash Point(C)

79 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBL4148
STBL3843
STBL1678
STBK6203
STBJ3308

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Sigma-Aldrich

550604

4-Chloromethyl-2,2-dimethyl-1,3-dioxolane

S-Aryl-L-cysteine S,S-dioxides: design, synthesis, and evaluation of a new class of inhibitors of kynureninase
Rajesh K. Dua,
Journal of the American Chemical Society, 115, 4, 1264-1270 (1993)
European Journal of Organic Chemistry, 4805-4805 (2006)
Synthesis of a `reverse ester? analogue of 1,2-sn-diglycerides from (S)-1,2-di-O-isoprophylideneglycerol; efficient, stereospecific nucleophilic displacement via a triflate at glycerol C-2
Bernard T Golding, et al.
Tetrahedron Letters, 34, 6459-6462 (1993)
René Pemha et al.
Marine drugs, 18(2) (2020-02-23)
A series of novel substituted 1-O-alkylglycerols (AKGs) containing methoxy (8), gem-difluoro (9), azide (10) and hydroxy (11) group at 12 position in the alkyl chain were synthesized from commercially available ricinoleic acid (12). The structures of these new synthesized AKGs
A cytosine analogue containing a conformationally flexible acyclic linker for triplex formation at sites with contiguous GC base pairs.
Xiang G and McLaughlin LW.
Tetrahedron, 54(3), 375-392 (1998)
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