69460-11-3

Basic information

• Product Name: (-)-ISOPINOCAMPHEYLAMINE
• Synonyms: (-)-ISOPINOCAMPHEYLAMINE;(1R,2R,3R,5S)-(-)-ISOPINOCAMPHEYLAMINE;(1R,2R,3R,5S)-3-PINANAMINE;(1R,2R,3R,5S)-(-)-ISOPINOCAMPHEYLAMINE,95%;(-)-Isopinocampheylamine, (1R,2R,3R,5S)-3-Pinanamine;(1R,2R,3R,5S)-2,6,6-;(1R,2R,3R,5S)-(-)-Isopinocampheylamine 95%;(1R,2R,3R,5S)-2,6,6-Trimethyl-bicyclo[3.1.1]heptan-3-amine
• CAS NO: 69460-11-3
• Molecular Formula: C₁₀H₁₉N
• Molecular Weight: 153.26
• Mol File: 69460-11-3.mol

Chemical Properties

• Melting Point: 250 °C
• Boiling Point: 90 °C18 mm Hg(lit.)
• Flash Point: 162 °F
• Appearance: Colorless to yellow/Liquid
• Density: 0.914 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.556mmHg at 25°C
• Refractive Index: n20/D 1.48(lit.)
• PKA: 11.03±0.60(Predicted)
• CAS DataBase Reference: (-)-ISOPINOCAMPHEYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-ISOPINOCAMPHEYLAMINE(69460-11-3)
• EPA Substance Registry System: (-)-ISOPINOCAMPHEYLAMINE(69460-11-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 69460-11-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(-)-ISOPINOCAMPHEYLAMINE is used as a therapeutic agent for conditions associated with STING (Stimulator of Interferon Genes) activity. It modulates the immune response by targeting STING, which plays a crucial role in the body's defense against viral and bacterial infections. (-)-ISOPINOCAMPHEYLAMINE has shown potential in the treatment of various diseases and disorders related to STING activity, making it a valuable asset in the development of new medications.

InChI:InChI=1/C10H19N/c1-6-8-4-7(5-9(6)11)10(8,2)3/h6-9H,4-5,11H2,1-3H3/t6-,7+,8-,9-/m1/s1

Upstream product

• 7785-70-8 (+)-α-pinene 
• 85116-37-6 (-)-diisopinocamphenylborane chloride 

Downstream Products

• 7785-54-8 (4R)-(+)-α-terpinyl acetate 
• 28272-96-0 2-vinylbenzaldehyde 
• 1227473-61-1 C₂₆H₃₅NO₅ 
• 1265628-16-7 (1R,2R,3R,5S)-N-cyclohexyl-2,6,6-trimethylbicyclo[3.1.1]heptan-3-amine hydrochloride 
• 1265628-20-3 (1R,2R,3R,5S,E)-2,6,6-trimethyl-N-(4-methylbenzylidene)bicyclo[3.1.1]heptan-3-amine 
• 1265628-19-0 (1R,2R,3R,5S,E)-N-(4-fluorobenzylidene)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-amine 
• 1259384-23-0 (1R,2R,3R,5S)-N-(4-fluorobenzyl)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-amine hydrochloride 
• 1265628-22-5 4-((E)-(((1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)imino)methyl)phenol 
• 1265628-17-8 4-((((1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)amino)methyl)-phenol hydrochloride 
• 1265628-23-6 2-((E)-(((1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)imino)methyl)phenol 
• 1259384-24-1 3-((E)-(((1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)imino)methyl)phenol 
• 1265628-21-4 (1R,2R,3R,5S,E)-N-(4-(dimethylamino)benzylidene)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-amine 
• 1438288-46-0 1-(3-chlorophenethyl)-3-((1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1438288-47-1 1-(4-chlorophenethyl)-3-((1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)pyrimidine-2,4,6(1H,3H,5H)-trione 

Relevant articles and documents

Organoboranes for synthesis. 16. A convenient synthesis of enantiomerically pure isopinocampheylamine, a chiral derivatizing agent for gas chromatographic analysis of optically active carboxylic acids

Both isomers of enantiomerically pure isopinocampheylamine (1) have been synthesized from the corresponding B-chlorodiisopinocampheylborane by treatment with either methylmagnesium bromide or trimethylaluminum to form B-methyldiisopinocampheylborane, followed by treatment of the intermediate with hydroxylamine-O-sulfonic acid. Application of 1 as a derivatizing agent for the gas chromatographic analysis of optically active carboxylic acids has been demonstrated.

Rearrangement of Pinane Derivatives. Part 8. Deamination of 2αH-Pinan-3α-ylamine

Solvolysis of 2αH-pinan-3α-yl toluene-p-sulphonate has been shown to proceed with concomitant 1,2-hydride shift to give the pinan-2-yl carbocation.Contrary to earlier reports, this species reacts normally to give, in good yield, pinan-2-yl substitution products.In contrast the pinan-3-ylamines react via a similar route, but give much smaller amounts of pinan-2-yl products.The usual reasons for differences between solvolysis and deamination (i.e. the intermediacy of diazonium ions and/or high-energy ions) can be discounted, and possible reasons for the differences in behaviour are discussed.