(1R,2S,4S)-Bicyclo[2.2.1]heptan-2-amine

Base Information

• Chemical Name: (1R,2S,4S)-Bicyclo[2.2.1]heptan-2-amine
• CAS No.: 121055-07-0
• Molecular Formula: C7H13N
• Molecular Weight: 111.187
• European Community (EC) Number: 863-709-1
• Nikkaji Number: J231.949G
• Mol file: 121055-07-0.mol

Synonyms:121055-07-0;(1R,2S,4S)-BICYCLO[2.2.1]HEPTAN-2-AMINE;Bicyclo[2.2.1]heptan-2-amine,(1R,2S,4S)-;Bicyclo[2.2.1]heptan-2-amine, (1R,2S,4S)-;(+)-endo-2-aminonorbornane;SCHEMBL2915075;AKOS006340970;(1alpha,4alpha)-Norbornane-2beta-amine;CS-0376812;EN300-7193269

Chemical Property of (1R,2S,4S)-Bicyclo[2.2.1]heptan-2-amine

Chemical Property:

• Boiling Point: 160.001 °C at 760 mmHg
• Flash Point: 35 ºC
• PSA: 26.02000
• Density: 0.986 g/cm³
• LogP: 1.83400
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 111.104799419
• Heavy Atom Count: 8
• Complexity: 101

Purity/Quality:

99.3% ^*data from raw suppliers

(1R,2S,4S)-BICYCLO[2.2.1]HEPTAN-2-AMINE HYDROCHLORIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2CC1CC2N
• Isomeric SMILES: C1C[C@@H]2C[C@H]1C[C@@H]2N

Technology Process of (1R,2S,4S)-Bicyclo[2.2.1]heptan-2-amine

There total 12 articles about (1R,2S,4S)-Bicyclo[2.2.1]heptan-2-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: 87.0%

N-((1R,2R,4S)-bicyclo[2.2.1]heptan-2-yl)-4-(trifluoromethyl)benzamide (1389327-48-3) → (1R,2R,4S)-bicyclo[2.2.1]hept-2-ylamine (822-98-0,7242-92-4,31002-73-0,84235-33-6,84235-34-7,111137-34-9,121055-07-0,126752-99-6,130463-97-7)

Guidance literature:

With hydrogenchloride; at 120 ℃; for 72h; optical yield given as %ee; Inert atmosphere;

DOI:10.1021/ja3052848

Reference yield:

C7H11BrZn (342029-20-3) → (1R,2R,4S)-bicyclo[2.2.1]hept-2-ylamine (822-98-0,7242-92-4,31002-73-0,84235-33-6,84235-34-7,111137-34-9,121055-07-0,126752-99-6,130463-97-7) + (1R,2R,4S)-2-aminobicyclo<2.2.1>heptane hydrochloride

Guidance literature:

C₇H₁₁BrZn; With 3,3’-di-tert-butyl oxaziridine; In diethyl ether; at 20 ℃; for 6h; Inert atmosphere;

With hydrogenchloride; In water; at 0 ℃; Overall yield = 61 %;

DOI:10.1021/acs.orglett.8b03734

Reference yield:

(1S,2S,4R)-bicyclo[2.2.1]heptan-2-amine → (1R,2R,4S)-bicyclo[2.2.1]hept-2-ylamine (822-98-0,7242-92-4,31002-73-0,84235-33-6,84235-34-7,111137-34-9,121055-07-0,126752-99-6,130463-97-7) + (+)-(1S,2S,4R)-2-norbornylamine (84235-33-6)

Guidance literature:

With chiral stationary phase including isopropyl-functionalized CF₆; In methanol; acetic acid; triethylamine; acetonitrile; at 20 ℃; Purification / work up;

upstream raw materials:

norbornene-2-carboxylate methyl ester

N-((1R,2R,4S)-bicyclo[2.2.1]heptan-2-yl)-4-(trifluoromethyl)benzamide

C₇H₁₁BrZn

norborn-2-ene

Refernces

• 1、 Behnke, Nicole Erin,Kielawa, Russell,Kwon, Doo-Hyun,Ess, Daniel H.,Kürti, László. "Direct Primary Amination of Alkylmetals with NH-Oxaziridine". supporting information. p. 8064 - 8068. Retrieved 2019/01/04.
• 2、 -. "COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS". Page/Page column 45-49; 63. . Retrieved 2010/12/31.