(R)-(+)-Bornylamine

Base Information

• Chemical Name: (R)-(+)-Bornylamine
• CAS No.: 464-42-6
• Molecular Formula: C10H19 N
• Molecular Weight: 153.268
• European Community (EC) Number: 251-076-9
• DSSTox Substance ID: DTXSID30947530
• Nikkaji Number: J1.251.144B
• ChEMBL ID: CHEMBL3735331
• Mol file: 464-42-6.mol

Synonyms:(R)-(+)-Bornylamine;32511-34-5;(1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-amine;(+)-bornylamine;SCHEMBL542034;Bicyclo(2.2.1)heptan-2-amine, 1,7,7-trimethyl-, (1R-endo)-;CHEMBL3735331;(R)-(+)-Bornylamine, 97%;DTXSID30947530;MDFWXZBEVCOVIO-WEDXCCLWSA-N;AKOS015915781;AS-81150;(R)-(+)-Bornylamine, purum, >=97.0% (NT)

Chemical Property of (R)-(+)-Bornylamine

Chemical Property:

• Boiling Point: 188.7°Cat760mmHg
• PKA: 10.17(at 25℃)
• Flash Point: 48.5°C
• PSA: 26.02000
• Density: 0.923g/cm³
• LogP: 2.86020
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 153.151749610
• Heavy Atom Count: 11
• Complexity: 185

Purity/Quality:

99% ^*data from raw suppliers

1,7,7-trimethylbicyclo[2.2.1]heptan-2-amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2CCC1(C(C2)N)C)C
• Isomeric SMILES: C[C@@]12CC[C@@H](C1(C)C)C[C@@H]2N

Technology Process of (R)-(+)-Bornylamine

There total 7 articles about (R)-(+)-Bornylamine 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: 33.0%

(1S,4S)-N-benzyl-1,7,7-trimethylbicycto[2,2.1]heptan-2-amine → (1S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-amine (464-42-6,2223-67-8,4481-88-3,32511-34-5,32511-35-6,37606-04-5,94319-59-2,122038-71-5,128574-40-3)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 4h; under 775.743 Torr;

Reference yield:

isoborneol (24393-70-2) → bornane (464-15-3) + 1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one (736109-58-3,787517-91-3,68546-28-1) + 1,7,7-trimethylbicyclo[2.2.1]heptan-exo-2-amine (2223-67-8) + rac-endo-borneol (6627-72-1) + (1S,2R,4S)-1,7,7-Trimethyl-bicyclo[2.2.1]hept-2-ylamine (464-42-6)

Guidance literature:

With ammonia; hydrogen; RPFIC; Product distribution; other substrate, other temperature;

DOI:10.1007/BF00958285

Reference yield:

(1S)-camphor (464-48-2,68546-28-1) → (1S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-amine (464-42-6,2223-67-8,4481-88-3,32511-34-5,32511-35-6,37606-04-5,94319-59-2,122038-71-5,128574-40-3)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene-4-sulfonic acid / toluene / 12 h / 130 °C / Inert atmosphere

2: sodium tetrahydroborate; nickel dichloride / methanol / 12 h / 0 - 20 °C

3: palladium 10% on activated carbon; hydrogen / methanol / 4 h / 20 °C / 775.74 Torr

With sodium tetrahydroborate; palladium 10% on activated carbon; hydrogen; toluene-4-sulfonic acid; nickel dichloride; In methanol; toluene;

upstream raw materials:

(1S)-camphor

isoborneol

Downstream raw materials:

Acetic acid (1S,2S,4S,5R)-5-(benzoyl-methyl-amino)-4,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester

2-endo benzoylamino, 5-exo-hydroxy, N-methyl, bornane

2-endo-benzoylamino, N-methyl, bornane

2-endo-benzoylamino, bornane

Refernces

• 1、 Glebov, L. S.,Shuikin, A. N.,Kliger, G. A.,Loktev, S. M.. "EPIMERIZATION OF ENDO- AND EXO-BORNEOLS IN THE PRESENCE OF AMMONIA AND/OR HYDROGEN ON A FUSED IRON CATALYST". . p. 1985 - 1987. Retrieved 2007/10/02.