77913
(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/REAXYS Number:
1718941
UNSPSC Code:
12352112
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Assay:
≥98.5% (sum of enantiomers, GC)
Form:
liquid
InChI key
ARXJGSRGQADJSQ-SCSAIBSYSA-N
SMILES string
COC[C@@H](C)O
InChI
1S/C4H10O2/c1-4(5)3-6-2/h4-5H,3H2,1-2H3/t4-/m1/s1
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.)
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.
signalword
Warning
hcodes
Hazard Classifications
Flam. Liq. 3
Storage Class
3 - Flammable liquids
wgk
WGK 1
flash_point_f
91.4 °F - closed cup
flash_point_c
33 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
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Nucleophilic Amination and Etherification of Aryl Alkyl Thioethers
Wang X, et al.
Organic Letters, 20(16), 4749-4753 (2018)
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)
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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