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

Base Information

• Chemical Name: (1S,2S,4R)-Bicyclo[2.2.1]heptan-2-amine
• CAS No.: 7242-92-4
• Molecular Formula: C7H13 N
• Molecular Weight: 111.187
• Hs Code.: 2921300090
• DSSTox Substance ID: DTXSID30433660
• Nikkaji Number: J215.861B
• Wikidata: Q82247858
• ChEMBL ID: CHEMBL3736187
• Mol file: 7242-92-4.mol

Synonyms:(1S,2S,4R)-Bicyclo[2.2.1]heptan-2-amine;84235-33-6;SCHEMBL353876;CHEMBL3736187;DTXSID30433660;(1beta,2beta,4beta)-2-Aminonorbornane;CS-0119831

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

Chemical Property:

• Vapor Pressure: 0.591mmHg at 25°C
• Melting Point: >345 °C
• Refractive Index: n20/D 1.4807(lit.)
• Boiling Point: 160°Cat760mmHg
• PKA: 10.96±0.20(Predicted)
• Flash Point: 35°C
• PSA: 26.02000
• Density: 0.985g/cm³
• LogP: 1.83400
• Storage Temp.: 2-8°C(protect from light)
• 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:

98%,99%, ^*data from raw suppliers

exo-2-Aminonorbornane 99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC2CC1CC2N
• Isomeric SMILES: C1C[C@H]2C[C@@H]1C[C@@H]2N
• Uses: exo-2-Aminonorbornane is used in preparation of heterocyclic compounds as CDK kinase inhibitors for the treatment of cancer.

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

There total 35 articles about (1S,2S,4R)-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: 90.0%

N-benzyl-N-exo-hydroxybicyclo[2.2.1]heptan-2-amine → exo-2-aminonorbornane (7242-92-4)

Guidance literature:

With formic acid; palladium on activated charcoal; In methanol; at 20 ℃; for 0.75h; Inert atmosphere;

DOI:10.1021/ja806300r

Reference yield: 61.0%

Bicyclo[2.2.1]hept-2-yl-dimethyl-borane (127146-35-4) → exo-2-aminonorbornane (7242-92-4)

Guidance literature:

With ammonium hydroxide; sodium hypochlorite; In water; 1.) 0 deg C, 5-10 min, 2.) 0 deg C -> room temperature;

Reference yield:

exo-2-norbornyl brosylate (61209-50-5) → exo-2-aminonorbornane (7242-92-4)

Guidance literature:

Multi-step reaction with 2 steps

1: tributylhexadecylphosphonium azide / toluene / 65 °C / rate constants determination at various temperatures

2: hydrogen / PtO₂ / toluene

With hydrogen; tributylhexadecylphosphonium azide; platinum(IV) oxide; In toluene;

DOI:10.1021/ja00377a057

upstream raw materials:

norbornene-2-carboxylate methyl ester

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

C₇H₁₁BrZn

exo-bicyclo[2.2.1]heptane-2-carboxamide

Downstream raw materials:

exo-2-nitronorbornane

2-exo-(Dichloroamino)norbornane

1,3-bis(naphthalen-1-yloxy)propan-2-ol

N-exo-bicyclo[2.2.1]hept-2-yl-aniline

Refernces

• 1、 Brunilin, R. V.,Mkrtchyan, A. S.,Nawrozkij, M. B.,Novakov, I. A.,Vernigora, A. A.,Voloboev, S. N.,Vostrikova, O. V.. "Potential Synthetic Adaptogens: V. Synthesis of Cage Monoamines by the Schwenk–Papa Reaction". . p. 1742 - 1748. Retrieved 2020/01/11.
• 2、 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.