Benzyl nicotinate

Base Information

• Chemical Name: Benzyl nicotinate
• CAS No.: 94-44-0
• Molecular Formula: C13H11NO2
• Molecular Weight: 213.236
• Hs Code.: 2933.39
• European Community (EC) Number: 202-332-3
• UNII: S497LCF9C9
• DSSTox Substance ID: DTXSID7046542
• Nikkaji Number: J60.115B
• Wikidata: Q3876608
• NCI Thesaurus Code: C83549
• Metabolomics Workbench ID: 67539
• ChEMBL ID: CHEMBL209744
• Mol file: 94-44-0.mol

Synonyms:benzyl nicotinate;nicotinic acid benzyl ester;nicotinic acid benzyl ester, hexafluorosilicate (2-) (2:1);pyridine-3-carboxylic acid benzyl ester

Chemical Property of Benzyl nicotinate

Chemical Property:

• Appearance/Colour: yellow liquid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 24 °C(lit.)
• Refractive Index: 1.570
• Boiling Point: 334.1 °C at 760 mmHg
• PKA: 3.16±0.10(Predicted)
• Flash Point: 155.8 °C
• PSA: 39.19000
• Density: 1.176 g/cm³
• LogP: 2.43860
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 213.078978594
• Heavy Atom Count: 16
• Complexity: 224

Purity/Quality:

99% ^*data from raw suppliers

Benzyl Nicotinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)C2=CN=CC=C2
• Uses: benzyl nicotinate can increase skin oxygenation—thanks to vasodilatation properties—and help stimulate the healing process of wounded skin. It is an ester form of niacin (vitamin B), benzyl alcohol, and nicotinic acid. Benzyl nicotinate can be used for the synthesis of benzylpalladium complexes to be used as catalysts for the substitution of olefins with benzylic groups. These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.
• Clinical Use: Benzyl nicotinate is used in combination with heparin in the treatment of inflammation of vein (thrombophlebitis), pain in dilated veins area, pains and cramps in the leg muscles, disturbances of lymph circulation, traffic and sports related injuries, postoperative and posttraumatic scars, non-joint rheumatism or soft tissue rheumatism.

Technology Process of Benzyl nicotinate

There total 24 articles about Benzyl nicotinate 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: 100.0%

nicotinic acid (59-67-6) + benzyl alcohol (100-51-6,185532-71-2) → benzyl nicotinate (94-44-0)

Guidance literature:

With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; In dichloromethane; for 1h; Ambient temperature;

Reference yield: 99.0%

methyl 3-pyridinecarboxylate (93-60-7) + benzyl alcohol (100-51-6,185532-71-2) → benzyl nicotinate (94-44-0)

Guidance literature:

With lanthanum(III) isopropoxide; 2-(2-methoxyethoxy)ethyl alcohol; at 110 ℃; for 6h; Reagent/catalyst; Molecular sieve;

Reference yield: 96.0%

3-pyridinecarboxaldehyde (500-22-1) + benzyl alcohol (100-51-6,185532-71-2) → benzyl nicotinate (94-44-0)

Guidance literature:

With 3-mesityl-4-methylthiazol-3-ium bis((trifluoromethyl)sulfonyl)imide; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; Electrochemical reaction; Inert atmosphere; Flow reactor;

DOI:10.1021/acs.orglett.5b01459

upstream raw materials:

nicotinic acid

N-benzyl-N,N-dimethyl-anilinium; dimethylphenylbenzylammonium hydroxide

benzyl alcohol

3-pyridinecarbonyl chloride

Downstream raw materials:

trans-(benzyl)(nicotinato)bis(trimethylphosphine)palladium

benzaldehyde

3-(5-Benzyloxycarbonyl-2-pyridyl)-7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoisoquinoline

6-acetyl-nicotinic acid benzyl ester

Refernces

• 1、 Lai, Ming,Qi, Xinxin,Wu, Xiao-Feng. "Palladium-Catalyzed Carbonylative Synthesis of Benzyl Benzoates Employing Benzyl Formates as Both CO Surrogates and Benzyl Alcohol Sources". supporting information. p. 3776 - 3778. Retrieved 2019/06/24.
• 2、 -. "NOVEL SINGLE STEP ESTERIFICATION PROCESS OF ALDEHYDES USING A HETEROGENEOUS CATALYST". Page/Page column 9; 15. . Retrieved 2016/06/20.