4795-86-2

Basic information

• Product Name: (1R)-(+)-CIS-PINANE
• Synonyms: (1R,2S)-2,6,6-TRIMETHYLBICYCLO[3.1.1]HEPTANE;(1R)-(+)-CIS-PINANE;PINANE, (1R)-(+)-CIS-;[1R-(1alpha,2beta,5alpha)]-2,6,6-trimethylbicyclo[3.1.1]heptane;(1R)-(+)-CIS-PINANE, TERPENE STANDARD;PINANE(1S,2S)-2,6,6-TRIMETHYLBICYCLO(3.1.1)HEPTANE;(1R,2R,5R)-Pinane;(1R,5R)-2α,6,6-Trimethylbicyclo[3.1.1]heptane
• CAS NO: 4795-86-2
• Molecular Formula: C₁₀H₁₈
• Molecular Weight: 138.25
• EINECS: 225-352-4
• Mol File: 4795-86-2.mol
• Article Data: 47

Chemical Properties

• Melting Point: -53°C
• Boiling Point: 168-169 °C(lit.)
• Flash Point: 48°C
• Appearance: /
• Density: 0.856 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.463
• BRN: 2036204
• CAS DataBase Reference: (1R)-(+)-CIS-PINANE(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-(+)-CIS-PINANE(4795-86-2)
• EPA Substance Registry System: (1R)-(+)-CIS-PINANE(4795-86-2)

Safety Data

• Statements: 10
• Safety Statements: 16
• RIDADR: UN 2319 3/PG 3
• WGK Germany: 3
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 4795-86-2(Hazardous Substances Data)

Usage

General Description

(1R)-(+)-CIS-PINANE is a bicyclic monoterpene hydrocarbon with a molecular formula of C10H16. It is a colorless liquid with a characteristic pine-like odor, and is commonly found in the essential oils of various pine species. (1R)-(+)-CIS-PINANE is used in the production of fragrances, flavors, and as a chiral building block in organic synthesis. It also has potential applications in the pharmaceutical and agrochemical industries due to its unique chemical structure and biological activities. Additionally, (1R)-(+)-CIS-PINANE is used as a chiral auxiliary in asymmetric synthesis and as a chiral resolving agent in enantiomeric separations. Overall, (1R)-(+)-CIS-PINANE is a versatile chemical compound with a wide range of industrial and scientific applications.

InChI:InChI=1/C10H18/c1-7-4-5-8-6-9(7)10(8,2)3/h7-9H,4-6H2,1-3H3/t7?,8?,9-/m1/s1

Upstream product

• 18172-67-3 beta-pinene 
• 7785-70-8 (+)-α-pinene 
• 18492-59-6 (+)-pinocamphone 
• 473-62-1 (1R,2R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one 
• 177698-19-0 Beta-pinene 
• 80-56-8 Pinene 
• 80-56-8 rac-α-pinene 
• 24031-98-9 (1S,4S,5R)-4,6,6-trimethylbicyclo[3.1.1]hept-2-ene 
• 7785-26-4 (-)-α-pinene 
• 127-91-3 (1R,5R)-(+)-β-pinene 
• 473-55-2 2,6,6-trimethylbicyclo[3.1.1]heptane 
• 60-29-7 diethyl ether 
• 64-17-5 ethanol 
• 117227-80-2 (-)(1R)-3ξ-chloro-cis-pinane 

Downstream Products

• 6783-92-2 1,1,2,3-tetramethylcyclohexane 
• 527-84-4 2-methylisopropylbenzene 
• 99-87-6 4-methylisopropylbenzene 
• 95-93-2 1,2,4,5-tetramethylbenzene 
• 54497-05-1 1,1,2,5-tetramethylcyclohexane 
• 4863-59-6 [1R-(1α,2α,5α)]-2,6,6-trimethylbicyclo[3.1.1]heptane 
• 4951-97-7 1-Acetyl-2.2-dimethyl-3-aethyl-cyclobutan 
• 2436-90-0 (S)-(+)-dihydromyrcene 
• 61585-35-1 p-menth-1-ene 
• 110-43-0 n-pentyl methyl ketone 
• 590-67-0 1-Methylcyclohexanol 
• 98-55-5 terpineol 
• 473-54-1 pinan-2α-ol 
• 473-54-1 cis-pinane-2-ol 

Relevant articles and documents

Crabtree's catalyst revisited; Ligand effects on stability and durability

The extent of time-dependent deactivation of monophosphine monoamine iridium hydrogenation catalysts by trimer formation is strongly dependent on ligand structure; attempts to counter this process lead to the observation of an oligomerisation resistant catalyst. The Royal Society of Chemistry.

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A General Approach to Deboronative Radical Chain Reactions with Pinacol Alkylboronic Esters

The generation of carbon-centered radicals from air-sensitive organoboron compounds through nucleohomolytic substitution at boron is a general method to generate non-functionalized and functionalized radicals. Due to their reduced Lewis acidity, alkylboronic pinacol esters are not suitable substrates. We report their in situ conversion into alkylboronic catechol esters by boron-transesterification with a substoichiometric amount of catechol methyl borate combined with an array of radical chain processes. This simple one-pot radical-chain deboronative method enables the conversion of pinacol boronic esters into iodides, bromides, chlorides, and thioethers. The process is also suitable the formation of nitriles and allylated compounds through C?C bond formation using sulfonyl radical traps. The power of combining radical and classical boron chemistry is illustrated with a modular 5-membered ring formation using a combination of three-component coupling and protodeboronative cyclization.

Amine-Borane Dehydrogenation and Transfer Hydrogenation Catalyzed by α-Diimine Cobaltates

Anionic α-diimine cobalt complexes, such as [K(thf)1.5{(DippBIAN)Co(η4-cod)}] (1; Dipp=2,6-diisopropylphenyl, cod=1,5-cyclooctadiene), catalyze the dehydrogenation of several amine-boranes. Based on the excellent catalytic properties, an especially effective transfer hydrogenation protocol for challenging olefins, imines, and N-heteroarenes was developed. NH3BH3 was used as a dihydrogen surrogate, which transferred up to two equivalents of H2 per NH3BH3. Detailed spectroscopic and mechanistic studies are presented, which document the rate determination by acidic protons in the amine-borane.