(R)-3-[1-(Dimethylamino)ethyl]phenol

CAS No.

851086-95-8

Synonyms

ent-NAP 226-90; (R)-Decarbamylated rivastigmine; also listed as 3-[(1R)-1-(Dimethylamino)ethyl]phenol

Molecular formula

C10H15NO

Molecular weight

165.24 g/mol

Grade

Reagent grade

Packaging

Aluminum foil laminate bag / Fiber drum with PE liner

Chemical Product Description & Applications

(R)-3-[1-(Dimethylamino)ethyl]phenol is the R-configured counterpart of the phenolic intermediate associated with rivastigmine. It serves as a stereochemical comparator in analytical work and as a phenolic precursor for preparing opposite-configuration carbamate derivatives. The phenol provides the carbamoylation site, while the tertiary dimethylamine and existing stereocenter retain the characteristic aminoethyl substitution pattern.

This material must be distinguished from the S-configured precursor used to obtain rivastigmine with its intended configuration. In analytical development, the R form is useful because ordinary identity tests may not distinguish enantiomers. Its value therefore lies in defined stereochemistry and chemical traceability, rather than an assumed therapeutic role or automatic equivalence to a certified pharmacopoeial reference material.

Typical Applications

  • Chiral chromatographic method development: Used as an identified R-configured comparator to examine separation from the corresponding S phenol in rivastigmine-related intermediate or impurity analysis.
  • Opposite-configuration carbamate preparation: Used in O-carbamoylation sequences to prepare R-configured rivastigmine-related material for analytical investigations of enantiomeric impurities.

Specifications

Parameter Specification Test Method
Appearance Clear liquid; color consistent with the reference sample Visual inspection
Identification Consistent with authenticated reference FTIR fingerprint comparison
Chromatographic purity ≥99.0 area% GC-FID
Total organic impurities ≤1.0 area% GC-FID, area normalization
Water ≤0.20% w/w Karl Fischer titration
Nonvolatile residue ≤0.10% w/w Gravimetric evaporation residue
Stereochemical purity ≥98.0 area% specified stereoisomer Chiral HPLC or stereoisomer-resolving GC

Specifications describe the standard grade. Tolerance, test method and documentation package are confirmed per order.

Documents & Handling

Packaging

Aluminum foil laminate bag / Fiber drum with PE liner

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TDS

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SDS

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