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Merck

241806

(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
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
24854331
MDL number:
MFCD00003213
Beilstein/REAXYS Number:
80117
Assay:
98%
Form:
liquid

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InChI

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

SMILES string

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

InChI key

RNVYQYLELCKWAN-RXMQYKEDSA-N

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

Quality Level

100

Related Categories

Application

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

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

174.2 °F - closed cup

flash_point_c

79 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB7308
SDBB4561
STBL4148
STBL3843
STBL1678

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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)
Enantioselective synthesis of N1999A2.
Ji N, et al.
Journal of the American Chemical Society, 128(46), 14825-14825 (2006)
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