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Sigma-Aldrich

4-Methoxyphenethyl alcohol

99%

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Synonym(s):
2-(4-Methoxyphenyl)ethanol
Linear Formula:
CH3OC6H4CH2CH2OH
CAS Number:
702-23-8
Molecular Weight:
152.19
Beilstein:
2043563
EC Number:
211-866-6
MDL number:
MFCD00002900
PubChem Substance ID:
24849412
NACRES:
NA.22

Quality Level

100

Assay

99%

form

solid

bp

334-336 °C (lit.)

mp

26-28 °C (lit.)

SMILES string

COc1ccc(CCO)cc1

InChI

1S/C9H12O2/c1-11-9-4-2-8(3-5-9)6-7-10/h2-5,10H,6-7H2,1H3

InChI key

AUWDOZOUJWEPBA-UHFFFAOYSA-N

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General description

(R)-1-(4-methoxyphenyl)ethanol {(R)-MOPE, 4-Methoxyphenethyl alcohol, 1-(4-methoxyphenyl)ethanol } is formed during the biocatalytic anti-Prelog enantioselective reduction of 4-methoxyacetophenone (MOAP) using immobilized Trigonopsis variabilis AS2.

Application

4-Methoxyphenethyl alcohol was used as an internal standard in the fluorous biphasic catalysis reaction.
4-Methoxyphenethyl alcohol was used in the preparation of 4-(2-iodoethyl)phenol, by refluxing it with 47% hydriodic acid. It may be used in the preparation of (2R*,4R*)-1-n-butyl-2-methyl-4-(2-oxopyrrolidin-1-yl)-6-methoxy-1,2,3,4-tetrahydroquinoline and (2R*,4S*)-1-n-butyl-2-methyl-4-(2-oxopyrrolidin-1-yl)-6-methoxy-1,2,3,4- tetrahydroquinoline.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Reactions of Azides with Electrophiles: New Methods for the Generation of Cationic 2-Azabutadienes. Synthesis of 1, 2, 3, 4-Tetrahydroquinolines and 1, 2-Dihydroquinolines via a Hetero Diels-Alder Reaction.
Pearson WH and Fang WK
Israel J. Chem., 37(1), 39-46 (1997)
An asymmetric catalytic carbon? carbon bond formation in a fluorous biphasic system based on perfluoroalkyl-BINOL.
Tian Y and Chan KS.
Tetrahedron Letters, 41(45), 8813-8816 (2000)
Biocatalytic anti-Prelog stereoselective reduction of 4'-methoxyacetophenone to (R)-1-(4-methoxyphenyl) ethanol with immobilized Trigonopsis variabilis AS2. 1611 cells using an ionic liquid-containing medium.
Lou W-Y, et al.
Green Chemistry, 11(9), 1377-1384 (2009)
Synthesis of 5-(ω-sulfhydrylalkyl) salicylaldehydes as precursors for the preparation of alkanethiol-modified metal salens.
Ji C and Peters DG
Tetrahedron Letters, 42(35), 6065-6067 (2001)
Min Kyung Song et al.
Journal of agricultural and food chemistry, 67(7), 2028-2035 (2019-01-31)
Caffeic acid phenethyl ester (CAPE) is an ester of a hydroxycinnamic acid (phenylpropanoid) and a phenylethanoid (2-phenylethanol; 2-PE), which has long been used in traditional medicine. Here, we synthesized 54 hydroxycinnamic acid-phenylethanoid esters by feeding 64 combinations of hydroxycinnamic acids

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