(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: 2024-10-29 11:48:30
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
1,2-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) |
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
Abamectin manufacturer
JSK Chemicals
Synaptics Labs Private Limited
ADAARSH PHARMA
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