2-Benzylpyridine

Base Information

• Chemical Name: 2-Benzylpyridine
• CAS No.: 101-82-6
• Molecular Formula: C12H11N
• Molecular Weight: 169.226
• Hs Code.: 29333999
• European Community (EC) Number: 202-979-1
• NSC Number: 4033
• UNII: EW2N4V60MQ
• DSSTox Substance ID: DTXSID5059240
• Nikkaji Number: J36.122D
• Wikidata: Q27277389
• ChEMBL ID: CHEMBL3248606
• Mol file: 101-82-6.mol

Synonyms:2-benzylpyridine

Chemical Property of 2-Benzylpyridine

Chemical Property:

• Appearance/Colour: clear dark brown liquid.
• Vapor Pressure: 0.00829mmHg at 25°C
• Melting Point: 8-10 °C(lit.)
• Refractive Index: n20/D 1.579(lit.)
• Boiling Point: 276 °C at 760 mmHg
• PKA: 5.13(at 25℃)
• Flash Point: 125 °C
• PSA: 12.89000
• Density: 1.044 g/cm³
• LogP: 2.67240
• Storage Temp.: Store below +30°C.
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: insoluble
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 169.089149355
• Heavy Atom Count: 13
• Complexity: 138

Purity/Quality:

99% ^*data from raw suppliers

2-Benzylpyridine >98.0%(GC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36-36/37/38-22
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC2=CC=CC=N2
• Uses: 2-Benzylpyridine is a benzylpyridine with antifungal properties. 2-Benzylpyridine is also used as a chromogenic reagent for micro determination of Molybednum. 2-Benzylpyridine is used in organic synthesis.

Technology Process of 2-Benzylpyridine

There total 139 articles about 2-Benzylpyridine 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: 98.0%

phenylmagnesium bromide (100-58-3) → 2-Benzylpyridine (101-82-6) + S-Phenyl benzenethiosulfonate (1212-08-4) + S-phenyl benzenethiosulfinate (1208-20-4,6930-77-4,133670-27-6) + diphenyldisulfane (882-33-7)

Guidance literature:

With 2-[(1-phenylmethyl)sulfinyl]pyridine; In tetrahydrofuran; Ambient temperature;

Reference yield: 98.0%

2-[(1-phenylmethyl)sulfinyl]pyridine (87577-90-0) + phenylmagnesium bromide → 2-Benzylpyridine (101-82-6) + S-Phenyl benzenethiosulfonate (1212-08-4) + S-phenyl benzenethiosulfinate (1208-20-4,6930-77-4,133670-27-6) + diphenyldisulfane (882-33-7)

Guidance literature:

In tetrahydrofuran; Product distribution; Mechanism; Ambient temperature; investigation of reaction with various Grignard reagents and n-BuLi;

DOI:10.1016/S0040-4039(01)91150-5

Reference yield: 80.0%

2-methylsulfanyl-pyridine (18438-38-5,79639-75-1) + benzyl(bromo)zinc (62673-31-8) → [2,2]bipyridinyl (366-18-7) + 2-Benzylpyridine (101-82-6)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 55 - 60 ℃; for 5h;

upstream raw materials:

pyridine

pyridine hydrochloride

benzyl chloride

iodomethylbenzene

Downstream raw materials:

N,O-dimethyl-N-(3-phenyl-3-[2]pyridyl-propyl)-hydroxylamine

N,O-dimethyl-N-(4-phenyl-4-[2]pyridyl-butyl)-hydroxylamine

N,O-diethyl-N-(3-phenyl-3-[2]pyridyl-propyl)-hydroxylamine

N,O-diethyl-N-(4-phenyl-4-[2]pyridyl-butyl)-hydroxylamine

Refernces

• 1、 Vorbrueggen, Helmut,Krolikiewicz, Konrad. "CONVERSION OF HETEROCYCLIC N-OXIDES INTO α-ALKYLATED HETEROCYCLES. TRIMETHYLSILANOL AS LEAVING GROUP -IV.". . p. 889 - 890. Retrieved 1983.
• 2、 Guha, Somraj,Sekar, Govindasamy. "Metal-Free Halogen(I) Catalysts for the Oxidation of Aryl(heteroaryl)methanes to Ketones or Esters: Selectivity Control by Halogen Bonding". . p. 14171 - 14182. Retrieved 2018.
• 3、 Kato, Yoshiaki,Mase, Toshiaki. "A novel reduction of pyridinemethanols by samarium diiodide". . p. 8823 - 8826. Retrieved 1999.
• 4、 Bonini et al.. "-". . p. 1799. Retrieved 1979.
• 5、 Yakhontov,Leskoeva. "-". . . Retrieved 1975.
• 6、 Antilla, Jon C.,Jing, Hua-qing,Li, Hong-liang. "Acylation of 2-benzylpyridine N-oxides and subsequent in situ [3,3]-sigamatropic rearrangement reaction". . . Retrieved 2020/09/22.
• 7、 Puthanveedu, Mahesh,Polychronidou, Vasiliki,Antonchick, Andrey P.. "Catalytic Selective Metal-Free Cross-Coupling of Heteroaromatic N-Oxides with Organosilanes". supporting information. p. 3407 - 3411. Retrieved 2019/05/10.