beta-Pinene

Base Information

• Chemical Name: beta-Pinene
• CAS No.: 127-91-3
• Deprecated CAS: 23089-32-9
• Molecular Formula: C10H16
• Molecular Weight: 136.237
• Hs Code.: 2902199090
• European Community (EC) Number: 204-872-5
• NSC Number: 406265,59190,21447
• DSSTox Substance ID: DTXSID7027049
• Nikkaji Number: J2.017F
• Wikipedia: Beta-Pinene
• Wikidata: Q300928
• RXCUI: 1923811
• Metabolomics Workbench ID: 139645
• ChEMBL ID: CHEMBL501351
• Mol file: 127-91-3.mol

Synonyms:beta-pinene;terbenthene;terebenthene

Chemical Property of beta-Pinene

Chemical Property:

• Appearance/Colour: Colorless transparent oily liquid
• Vapor Pressure: 2.399mmHg at 25°C
• Melting Point: -61 °C
• Refractive Index: 1.4782
• Boiling Point: 166 °C at 760 mmHg
• Flash Point: 34.9 °C
• PSA: 0.00000
• Density: 0.88 g/cm³
• LogP: 2.99870
• Water Solubility.: 12mg/L(25 oC)
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 136.125200510
• Heavy Atom Count: 10
• Complexity: 177

Purity/Quality:

95%min , ^*data from raw suppliers

β-Pinene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R10:Flammable.; R36/37/38:Irritating to eyes, respiratory system and skin.
• Hazard Codes: R10:Flammable.; R36/37/38:Irritating to eyes, respiratory system and skin.
• Statements: 10
• Safety Statements: 16

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Terpenes
• Canonical SMILES: CC1(C2CCC(=C)C1C2)C
• Description: Beta-pinene is a component of turpentine. Concentrations vary depending on the source and seem to be high er in European (Portuguese) than in Asian (Indonesian) turpentines.

Technology Process of beta-Pinene

There total 21 articles about beta-Pinene 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: 93.0%

Diethyl (+)-Myrtene-10-phosphonate (74946-99-9) → (1R,5R)-(+)-β-pinene (127-91-3,25719-60-2)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 4h;

DOI:10.1055/s-1980-29049

Reference yield: 92.0%

pinane-2β,10-diol (18680-26-7) → (1R,5R)-(+)-β-pinene (127-91-3,25719-60-2)

Guidance literature:

With bis(cyclopentadienyl)titanium dichloride; manganese; In tetrahydrofuran; for 1.5h; Inert atmosphere; Reflux;

DOI:10.1021/ja906083c

Reference yield: 92.0%

2,6,6-trimethylbicyclo[3.1.1]hept-2-ene (7785-70-8,25766-18-1) → (+)-β-pinene (127-91-3,18172-67-3,19902-08-0,23089-32-9,25719-60-2)

Guidance literature:

With n-butyllithium; Trimethyl borate; potassium tert-butylate; water; Product distribution; var. α-pinene/base ratio, var. time of metalation; (-)-α-pinene;

DOI:10.1021/jo00268a054

upstream raw materials:

(+)-α-pinene

Diethyl (+)-Myrtene-10-phosphonate

ethanol

myrtenal

Downstream raw materials:

(1S)-2-benzyl-6,6-dimethylbicyclo<3.1.1>hept-2-en

(1S,5R)-6,6-Dimethyl-2-[1-phenyl-meth-(E)-ylidene]-bicyclo[3.1.1]heptane

L-diisopinocampheylborane

cis-3-carboxy-2,2-dimethylcyclobutylmethanoic acid

Refernces

• 1、 Brown, Herbert C.,Zaidlewicz, Marek,Bhat, Krishna S.. "Hydroboration of Terpenes. 10. An Improved Procedure for the Conversion of α-Pinene into β-Pinene in High Chemical and Optical Yield Using a Combination of the Schlosser Allylic Metalation of α-Pinene and Allylborane Chemistry". . p. 1764 - 1766. Retrieved 1989.
• 2、 Midland, M. Mark,Petre, Janet E.,Zderic, Stephen A.,Kazubski, Aleksander. "Thermal Reactions of B-Alkyl-9-borabicyclononane (9-BBN). Evidence for Unusually Facile Dehydroboration with B-Pinanyl-9-BBN". . p. 528 - 531. Retrieved 1982.
• 3、 Calva, James,Bec, Nicole,Gilardoni, Gianluca,Larroque, Christian,Cartuche, Luis,Bicchi, Carlo,Montesinos, José Vinicio. "Acorenone B: AChE and BChE inhibitor as a major compound of the essential oil distilled from the ecuadorian species niphogeton dissecta (Benth.) J.F. macbr". . . Retrieved 2017/11/16.
• 4、 Dieguez, Horacio R.,Lopez, Armando,Domingo, Victoriano,Arteaga, Jesus F.,Dobado, Jose A.,Herrador, M. Mar,Quilez Del Moral, Jose F.,Barrero, Alejandro F.. "Weakening C-O bonds: Ti(III), a new reagent for alcohol deoxygenation and carbonyl coupling olefination". supporting information; experimental part. p. 254 - 259. Retrieved 2010/03/25.