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302775

Sigma-Aldrich

(R)-(−)-2-Methoxy-2-phenylethanol

98%

Synonym(s):

(−)-β-Methoxyphenethyl alcohol

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About This Item

Linear Formula:
C6H5CH(OCH3)CH2OH
CAS Number:
17628-72-7
Molecular Weight:
152.19
MDL number:
MFCD00011550
UNSPSC Code:
12352112
PubChem Substance ID:
24858273
NACRES:
NA.22

Assay

98%

form

liquid

optical activity

[α]20/D −133°, c = 1 in acetone

optical purity

ee: 99% (GLC)

refractive index

n20/D 1.52 (lit.)

bp

65 °C/0.1 mmHg (lit.)

density

1.05 g/mL at 25 °C (lit.)

functional group

ether
hydroxyl
phenyl

SMILES string

CO[C@@H](CO)c1ccccc1

InChI

1S/C9H12O2/c1-11-9(7-10)8-5-3-2-4-6-8/h2-6,9-10H,7H2,1H3/t9-/m0/s1

InChI key

JDTUPLBMGDDPJS-VIFPVBQESA-N

Application

(R)-(-)-2-Methoxy-2-phenylethanol can be employed as a precursor to prepare:
  • (−)-3-[(2R)-2-Methoxy-2-phenylethoxy]phenol, a key intermediate for the synthesis of C4-symmetric tetraalkoxy[4]resorcinarenes using boron trifluoride catalyst.[1]
  • N-substituent of the 6,7-benzomorphan scaffold that is used as a potent opioid receptor agonist.[2]
  • Sodium methoxyphenylethoxide (Na-MPE), which is used as an oxy-initiator in the anionic polymerization of n-hexyl isocyanate.[3]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

208.4 °F - closed cup

Flash Point(C)

98 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCK4324
10204LH
11621CN
09014BZ
06109EO

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Effects of different reactive oxyanionic initiators on the anionic polymerizaition of n-hexyl isocyanate.
Min J, et al.
Macromolecules, 44(9), 3211-3216 (2011)
(2S)-N-2-methoxy-2-phenylethyl-6, 7-benzomorphan compound (2S-LP2): Discovery of a biased mu/delta opioid receptor agonist
Pasquinucci L, et al.
European Journal of Medicinal Chemistry, 168(27), 189-198 (2019)
The Diastereoselective Formation of Tetraalkoxy [4] resorcinarenes Derived from (-)-(2R)-2-Methoxy-2-phenylethanol and Proof of Absolute Configurations
Bulman PPC, et al.
European Journal of Organic Chemistry, 2011(27), 5347-5354 (2011)

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