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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

302775-BULK:
302775-VAR:
302775-1G:
302775-250MG:

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Certificates of Analysis (COA)

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

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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)
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)

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