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77913

Sigma-Aldrich

(R)-(−)-1-Methoxy-2-propanol

≥98.5% (sum of enantiomers, GC)

Synonym(s):

(R)-(−)-Propylene glycol 1-methyl ether

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About This Item

Empirical Formula (Hill Notation):
C4H10O2
CAS Number:
Molecular Weight:
90.12
Beilstein:
1718941
MDL number:
UNSPSC Code:
12352112
PubChem Substance ID:
NACRES:
NA.22

Assay

≥98.5% (sum of enantiomers, GC)

form

liquid

optical activity

[α]20/D −22±2°, c = 10% in chloroform

refractive index

n20/D 1.403

bp

119-121 °C (lit.)

density

0.921 g/mL at 20 °C (lit.)

SMILES string

COC[C@@H](C)O

InChI

1S/C4H10O2/c1-4(5)3-6-2/h4-5H,3H2,1-2H3/t4-/m1/s1

InChI key

ARXJGSRGQADJSQ-SCSAIBSYSA-N

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General description

(R)-(-)-1-Methoxy-2-propanol is a chiral secondary alcohol. It is formed during the hydrolysis of (R)-1-methoxy-2-propyl-acetate in the presence of Candida antarctica lipase B.

Application

(R)-(-)-1-Methoxy-2-propanol can be used as a reactant to prepare:
  • (S)-3-(ethoxycarbonyl)-5-((1-methoxypropan-2-yl)oxy)benzoic acid, a key intermediate to synthesize phenylethyl benzamide derivatives, which can be used as glucokinase activators.
  • Chiral pyrazolopyrimidinone derivatives as potential phosphodiesterase enzyme (PDE5) inhibitors.
  • Aryl or alkyl ethers via etherification reaction.

Pictograms

Flame

Signal Word

Warning

Hazard Statements

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

91.4 °F - closed cup

Flash Point(C)

33 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Highly potent and selective chiral inhibitors of PDE5: an illustration of Pfeiffer?s rule
Bunnage ME, et al.
Bioorganic & medicinal chemistry letters, 18(23), 6033-6036 (2008)
Kinetic modeling of lipase catalyzed hydrolysis of (R/S)-1-methoxy-2-propyl-acetate as a model reaction for production of chiral secondary alcohols.
Berendsen WR, et al.
Journal of Biotechnology, 121(2), 213-226 (2006)
Nucleophilic Amination and Etherification of Aryl Alkyl Thioethers
Wang X, et al.
Organic Letters, 20(16), 4749-4753 (2018)
Kaapjoo Park et al.
Bioorganic & medicinal chemistry letters, 23(2), 537-542 (2012-12-12)
Novel benzamide derivatives were synthesized and tested at in vitro assay by measuring fold increase of glucokinase activity at 5.0 mM glucose concentration. Among the prepared compounds, YH-GKA was found to be an active glucokinase activator with EC(50) of 70

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