(1R trans)-2-(3,4-difluorophenyl)cyclopropane amine

Base Information

• Chemical Name: (1R trans)-2-(3,4-difluorophenyl)cyclopropane amine
• CAS No.: 1156491-10-9
• Molecular Formula: C9H9F2N.ClH
• Molecular Weight: 205.6322
• Mol file: 1156491-10-9.mol

Synonyms:(1r,2s)-rel-2-(3,4-difluorophenyl)cyclopropanamine hydrochloride; (1R,2S)-2-(3,4-difluorophenyl)cyclopropanamine hydrochloride; (1R,2S)-rel-2-(3,4-Difluorophenyl)cyclopropanamine HCl; (1R,2S)-2-(3,4-difluorophenyl)cyclopropanamine HCL; (1R,2S)-rel-2-(3,4-Difluoro phenyl)cyclopropanamine hydrochloride; (1R trans)-2-(3,4-difluorophenyl)cyclopropane amine

Chemical Property of (1R trans)-2-(3,4-difluorophenyl)cyclopropane amine

Chemical Property:

• PSA: 26.02000
• LogP: 3.28170
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99%+ ^*data from raw suppliers

(1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamineHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (1R trans)-2-(3,4-difluorophenyl)cyclopropane amine

There total 4 articles about (1R trans)-2-(3,4-difluorophenyl)cyclopropane amine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2-chloro-1-(3,4-difluorophenyl)ethan-1-one (51336-95-9) → trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine hydrochloride (1402222-66-5,1156491-10-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium tetrahydroborate; Trimethyl borate; (S)-diphenylprolinol / toluene / 0.97 h / 38 °C / Inert atmosphere

2.1: sodium t-butanolate / toluene / 13 h / 38 - 58 °C

3.1: sodium hydroxide / water / 1.5 h / 48 °C

4.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 1.5 h / 30 °C

4.2: 1.5 h

5.1: sodium hydroxide; sodium hypochlorite / water / 4.5 h / 20 - 38 °C

5.2: 1.5 h / 8 °C

With sodium hypochlorite; sodium tetrahydroborate; oxalyl dichloride; Trimethyl borate; (S)-diphenylprolinol; sodium hydroxide; sodium t-butanolate; In dichloromethane; water; N,N-dimethyl-formamide; toluene;

Reference yield:

ortho-difluorobenzene (367-11-3) → trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine hydrochloride (1402222-66-5,1156491-10-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: aluminum (III) chloride / 1.83 h / 50 °C

2.1: sodium tetrahydroborate; Trimethyl borate; (S)-diphenylprolinol / toluene / 0.97 h / 38 °C / Inert atmosphere

3.1: sodium t-butanolate / toluene / 13 h / 38 - 58 °C

4.1: sodium hydroxide / water / 1.5 h / 48 °C

5.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 1.5 h / 30 °C

5.2: 1.5 h

6.1: sodium hydroxide; sodium hypochlorite / water / 4.5 h / 20 - 38 °C

6.2: 1.5 h / 8 °C

With aluminum (III) chloride; sodium hypochlorite; sodium tetrahydroborate; oxalyl dichloride; Trimethyl borate; (S)-diphenylprolinol; sodium hydroxide; sodium t-butanolate; In dichloromethane; water; N,N-dimethyl-formamide; toluene;

Reference yield:

diethyl (3,4-difluoro-benzyl)phosphonate (451455-95-1) → trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine hydrochloride (1402222-66-5,1156491-10-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium t-butanolate / toluene / 2 h / 50 °C / Inert atmosphere

1.2: 16 h / Inert atmosphere; Reflux

2.1: sodium methylate / methanol / 26 h / Reflux

3.1: sodium hydroxide; sodium hypochlorite / water / 6 h / 10 - 65 °C

4.1: hydrogenchloride / 5 °C / pH 8 - 9

With hydrogenchloride; sodium hypochlorite; sodium methylate; sodium hydroxide; sodium t-butanolate; In methanol; water; toluene;

upstream raw materials:

ortho-difluorobenzene

2-chloro-1-(3,4-difluorophenyl)ethan-1-one

diethyl (3,4-difluoro-benzyl)phosphonate

Downstream raw materials:

ticagrelor

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

Refernces

• 1、 -. "Preparation method of ticagrelor". . . Retrieved 2018/04/21.