trans-2-Phenylcyclopropylamine

Base Information

• Chemical Name: trans-2-Phenylcyclopropylamine
• CAS No.: 3721-28-6
• Molecular Formula: C9H11 N
• Molecular Weight: 133.193
• Hs Code.: 2921499090
• European Community (EC) Number: 205-841-9
• DSSTox Substance ID: DTXSID801315454
• Nikkaji Number: J9.123E
• Wikipedia: Tranylcypromine
• Wikidata: Q100429558
• NCI Thesaurus Code: C61979
• RXCUI: 10734
• ChEMBL ID: CHEMBL257990
• Mol file: 3721-28-6.mol

Synonyms:Jatrosom;Parnate;Sulfate, Tranylcypromine;trans 2 Phenylcyclopropylamine;trans-2-Phenylcyclopropylamine;Transamine;Tranylcypromine;Tranylcypromine Sulfate

Chemical Property of trans-2-Phenylcyclopropylamine

Chemical Property:

• Refractive Index: 1.5690 (estimate)
• Boiling Point: 218.3°Cat760mmHg
• PKA: 8.24±0.10(Predicted)
• Flash Point: 90.8°C
• PSA: 26.02000
• Density: g/cm³
• LogP: 2.20150
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 133.089149355
• Heavy Atom Count: 10
• Complexity: 116

Purity/Quality:

99% ^*data from raw suppliers

(1S,2R)-(+)-2-Phenylcyclopropan-1-amine ^*data from reagent suppliers

Safty Information:

• Safety Statements: Poison by ingestion, intraperitoneal, and subcutaneous routes. Experimental reproductive ef"> x. See also AMINES." target="_blank">Poison by ingestion, intraperitoneal, and subcutaneous routes. Experimental reproductive ef

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antidepressant Agents
• Canonical SMILES: C1C(C1N)C2=CC=CC=C2
• Isomeric SMILES: C1[C@@H]([C@H]1N)C2=CC=CC=C2
• Recent ClinicalTrials: Study of TCP-ATRA for Adult Patients With AML and MDS
• Recent EU Clinical Trials: Phase I/II pilot trial of ATRA (Tretinoin) and TCP (Tranylcypromine) in patients with relapsed or refractory acute myeloid leukemia (AML) when no intensive treatment is possible

Technology Process of trans-2-Phenylcyclopropylamine

There total 60 articles about trans-2-Phenylcyclopropylamine 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: 97.0%

C17H23NO2 → (1R,2S)-1-amino-2-phenylcyclopropane (95-62-5,155-09-9,3721-26-4,3721-28-6,13531-35-6,24873-95-8,69684-88-4,69684-89-5,54-97-7)

Guidance literature:

With trifluoroacetic acid; In 1,4-dioxane; water; for 21h;

DOI:10.1055/s-2008-1072786

Reference yield: 79.0%

(RS)-2-phenylcyclohexanone (1444-65-1) + 1-phenylethyl acetate (93-92-5,50373-55-2) → (1R,2S)-1-amino-2-phenylcyclopropane (95-62-5,155-09-9,3721-26-4,3721-28-6,13531-35-6,24873-95-8,69684-88-4,69684-89-5,54-97-7) + (+)-(1S,2R)-2-Phenylcyclohexanamine (37982-23-3) + (1R,2S)-N-(2-phenylcyclohexyl)acetamide (312611-48-6) + cis-1-amino-2-phenylcyclohexane (1011-11-6,17293-45-7,22147-09-7,37982-23-3,37982-28-8,37982-29-9,40960-61-0,46175-82-0,69743-67-5)

Guidance literature:

(RS)-2-phenylcyclohexanone; With ammonium formate; palladium on activated charcoal; In methanol; water; at 20 ℃;

1-phenylethyl acetate; With Novozyme 435 immobilized on polyacrylamide;

DOI:10.1016/j.tetasy.2005.07.033

Reference yield: 68.0%

(-)-(1R,2S)-trans (2-phenyl-cyclopropyl)carbaminic acid tert-butyl ester (185256-47-7,847644-86-4) → (1R,2S)-1-amino-2-phenylcyclopropane (95-62-5,155-09-9,3721-26-4,3721-28-6,13531-35-6,24873-95-8,69684-88-4,69684-89-5,54-97-7)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 40 ℃; for 0.5h;

DOI:10.1016/S0957-4166(96)00457-0

upstream raw materials:

trans-2-phenylcyclopropylamine

(-)-(1R,2S)-trans (2-phenyl-cyclopropyl)carbaminic acid tert-butyl ester

(RS)-2-phenylcyclohexanone

1-phenylethyl acetate

Downstream raw materials:

N⁶-[(1R,2S)-2-phenyl-1-cyclopropyl]adenosine

C₂₁H₂₂Cl₂N₄O₂

C₂₁H₂₂Cl₂N₄O₂

(8aS)-N-(2,3-dichlorophenyl)-1,3-dioxo-2-[(1R,2S)-2-phenylcyclopropyl]hexahydroimidazo[1,5-a]pyrazine-7(1H)-carboxamide

Refernces

• 1、 -. "SALT OF LSD1 INHIBITOR AND A POLYMORPH THEREOF". Paragraph 0038-0040. . Retrieved 2021/10/15.
• 2、 Bajaj, Priyanka,Sreenilayam, Gopeekrishnan,Tyagi, Vikas,Fasan, Rudi. "Gram-Scale Synthesis of Chiral Cyclopropane-Containing Drugs and Drug Precursors with Engineered Myoglobin Catalysts Featuring Complementary Stereoselectivity". . p. 16110 - 16114. Retrieved 2016/12/26.