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HomeProduct name list(1R,2S)-2-(3,4-difluorophenyl)cyclopropanamine hydrochloride

(1R,2S)-2-(3,4-difluorophenyl)cyclopropanamine hydrochloride

  • CAS NO.:1156491-10-9
  • Empirical Formula: C9H10ClF2N
  • Molecular Weight: 205.63
  • MDL number: MFCD16875501
  • EINECS: 829-852-9
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-14 14:09:35
(1R,2S)-2-(3,4-difluorophenyl)cyclopropanamine hydrochloride Structural

What is (1R,2S)-2-(3,4-difluorophenyl)cyclopropanamine hydrochloride?

The Uses of (1R,2S)-2-(3,4-difluorophenyl)cyclopropanamine hydrochloride

(1S,2R)-2-(3,4-Difluorophenyl)-cyclopropanamine is an intermediate used to prepare ticagrelor (T437700).

Synthesis Reference(s)

Synthesis of 2-(3,4-difluorophenyl)cyclopropanamine derivatives and salts. EU Patent EP2644590A1

Synthesis

(1R trans)-2-(3,4-difluorophenyl)cyclopropane amine1,2-Difluorobenzene is reacted with 3-chloropropionyl chloride to produce 3-chloro-1-(3',4'-difluorophenyl)-propan-1-one, which is by addition of N,N-dimethylformamide, phloroglucinol and sodium iodide in the next step converted to 1-(3',4'-difluorophenyl)-3-nitro-propan-1-one. The keto group of the latter intermediate is in the subsequent step stereochemically reduced to hydroxyl group by the use of chiral oxazaborolidine together with borane dimethyl sulfide or borane-N,N-diethyl aniline complex in the presence of tetrahydrofurane. The obtained (1R)-1-(3',4'-difluorophenyl)-3-nitro-propan-1-ol is then added to a mixture of triphenylphosphine and diethylazodicarboxylate in benzene to yield (1S,2R)-2-(3',4'-difluorophenyl)-1-nitrocyclopropane, which is in the last step converted to 2-(3,4-difluorophenyl)cyclopropane amine by reduction of the nitro group by catalytic hydrogenation with palladium catalyst and zink dust. 

Properties of (1R,2S)-2-(3,4-difluorophenyl)cyclopropanamine hydrochloride

Melting point: >172°C (dec.)
storage temp.  Inert atmosphere,Store in freezer, under -20°C
solubility  DMSO (Slightly), Methanol (Slightly)
form  Solid
color  White

Safety information for (1R,2S)-2-(3,4-difluorophenyl)cyclopropanamine hydrochloride

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for (1R,2S)-2-(3,4-difluorophenyl)cyclopropanamine hydrochloride

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