94-44-0

Basic information

• Product Name: Benzyl nicotinate
• Synonyms: 3-Pyridinecarboxylic acid, phenylmethyl ester;3-Pyridinecarboxylicacid,phenylmethylester;Benzyl pyridine-3-carboxylate;benzylpyridine-3-carboxylate;Estru benzylowego kwasu nikotynowego;estrubenzylowegokwasunikotynowego;Niacin benzyl ester;niacinbenzylester
• CAS NO: 94-44-0
• Molecular Formula: C₁₃H₁₁NO₂
• Molecular Weight: 213.23
• EINECS: 202-332-3
• Mol File: 94-44-0.mol

Chemical Properties

• Melting Point: 24 °C(lit.)
• Boiling Point: 177 °C8 mm Hg(lit.)
• Flash Point: 170°C
• Appearance: /
• Density: 1,1165 g/cm3
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: n20/D 1.570
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• PKA: 3.16±0.10(Predicted)
• Merck: 14,6526
• BRN: 159169
• CAS DataBase Reference: Benzyl nicotinate(CAS DataBase Reference)
• NIST Chemistry Reference: Benzyl nicotinate(94-44-0)
• EPA Substance Registry System: Benzyl nicotinate(94-44-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26
• WGK Germany: 2
• RTECS: QT0850000
• F: 8
• TSCA: Yes
• Hazardous Substances Data: 94-44-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Benzyl nicotinate is used as a medication for its vasodilating properties, widening blood vessels and oxygenating the skin's capillaries.
Used in Cosmetics Industry:
Benzyl nicotinate is used as an ingredient in cosmetics due to its ability to increase skin oxygenation and stimulate the healing process of wounded skin.
Used in Chemical Synthesis:
Benzyl nicotinate can be used for the synthesis of benzylpalladium complexes to be used as catalysts for the substitution of olefins with benzylic groups.
Used as Certified Reference Materials:
Benzyl nicotinate serves as a secondary standard for use in several analytical applications, including pharmaceutical release testing, method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.

Synthesis Reference(s)

Synthetic Communications, 14, p. 515, 1984 DOI: 10.1080/00397918408059573

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.

InChI:InChI=1/C13H11NO2/c15-13(16)11-7-4-8-14-12(11)9-10-5-2-1-3-6-10/h1-8H,9H2,(H,15,16)/p-1

Upstream product

• 59-67-6 nicotinic acid 
• 500-32-3 N-benzyl-N,N-dimethyl-anilinium; dimethylphenylbenzylammonium hydroxide 
• 100-51-6 benzyl alcohol 
• 10400-19-8 3-pyridinecarbonyl chloride 
• 20260-53-1 pyridine-3-carbonyl chloride hydrochloride 
• 16837-38-0 nicotinic anhydride 
• 100-39-0 benzyl bromide 
• 16518-17-5 potassium nicotinate 
• 100-44-7 benzyl chloride 
• 31139-36-3 dibenzyl dicarbonate 
• 93-60-7 methyl 3-pyridinecarboxylate 
• 108-88-3 toluene 
• 882980-43-0 2-benzyloxy-1-methylpyridinium triflate 
• 54-86-4 sodium nicotinate 

Downstream Products

• 102583-99-3 3-benzyloxycarbonyl-1-methyl-pyridinium; iodide 
• 100727-45-5 1-oxy-nicotinic acid benzyl ester 
• 207672-16-0 6-acetyl-nicotinic acid benzyl ester 
• 207672-27-3 3-(5-Benzyloxycarbonyl-2-pyridyl)-7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoisoquinoline 
• 1007358-73-7 trans-(benzyl)(nicotinato)bis(trimethylphosphine)palladium 
• 100-52-7 benzaldehyde 

Relevant articles and documents

A metal-free iodine-mediated conversion of hydroxamates to esters

A metal-, oxidant-, and additive-free conversion of hydroxamates to esters have been achieved using molecular iodine as the reagent using a novel but not-so-explored heron-type rearrangement. The reaction proceeds with almost equal facility with substrates having either electron-donating or electron-withdrawing substituent. Similarly, α,?-unsaturated, and sterically hindered ortho-substituted hydroxamates also undergo the desired transformation smoothly.

Palladium-Catalyzed Carbonylative Synthesis of Benzyl Benzoates Employing Benzyl Formates as Both CO Surrogates and Benzyl Alcohol Sources

An efficient and convenient palladium-catalyzed carbonylation reaction for the synthesis of benzyl benzoates from aryl bromides has been developed. Benzyl formates have been explored as a new type of efficient and useful CO sources and also reaction partners. A wide range of benzyl benzoates was obtained in good to excellent yields.

NOVEL SINGLE STEP ESTERIFICATION PROCESS OF ALDEHYDES USING A HETEROGENEOUS CATALYST

The present invention relates to a novel simple, efficient and single-step process for esterification of aldehydes using a heterogeneous catalyst with high yields. More particularly, the present invention relates to a novel simple, efficient and single-step process for esterification of aldehydes using Titanium superoxide with greater than 80% yields.

Pyridinium oxidations of benzyl alcohol under microwave-assisted retro-ene conditions

Benzyl alcohol is oxidized to benzaldehyde when heated in sulfolane in the presence of N-benzylnicotinamide and N-benzylpyridinium salts. The oxidation is accelerated in the presence microwaves. Oxidations with related pyridiniums suggest that these oxidations could occur via retro-ene reactions.

Ester manufacturing method (by machine translation)

PROBLEM TO BE SOLVED: To produce an ester compound by transesterification using an inexpensive and low toxic inorganic compound. SOLUTION: Transesterification of an ester compound and an alcohol compound is carried out under the presence of lanthanum nitrate (for example, lanthanum nitrate hexahydrate) and a phosphine compound (for example, tri-n-octylphosphine), thereby obtaining the ester product. For example, transesterification of dimethyl carbonate and benzyl alcohol is carried out under the presence of 1 mol% of lanthanum nitrate hexahydrate, and 2 mol% of tri-n-octylphosphine, thereby obtaining benzyl methylcarbonate at a yield of >99%. COPYRIGHT: (C)2012,JPO&INPIT

Titanium superoxide-a stable recyclable heterogeneous catalyst for oxidative esterification of aldehydes with alkylarenes or alcohols using TBHP as an oxidant

Titanium superoxide efficiently catalysed the oxidative esterification of aldehydes with alkylarenes or alcohols, under truly heterogeneous conditions, to afford the corresponding benzyl and alkyl esters in excellent yields. Mechanistic studies have established that this "one pot" direct oxidative esterification process proceeds through a radical pathway, proven by a FTIR spectral study of a titanium superoxide-aldehyde complex as well as spin trapping experiments with TEMPO. The intramolecular version of this protocol has been successfully demonstrated in the concise synthesis of 3-butylphthalide, an anti-convulsant drug.

N-Heterocyclic Carbene-Mediated Oxidative Electrosynthesis of Esters in a Microflow Cell

An efficient N-heterocyclic carbene (NHC)-mediated oxidative esterification of aldehydes has been achieved in an undivided microfluidic electrolysis cell at ambient temperature. Productivities of up to 4.3 g h-1 in a single pass are demonstrated, with excellent yields and conversions for 19 examples presented. Notably, the oxidative acylation reactions were shown to proceed with a 1:1 stoichiometry of aldehyde and alcohol (for primary alcohols), with remarkably short residence times in the electrolysis cell (13 s), and without added electrolyte. (Chemical Equation Presented).

Electrogenerated N-heterocyclic carbenes in the room temperature parent ionic liquid as an efficient medium for transesterification/acylation reactions

N-Heterocyclic carbenes (NHCs), generated by electrochemical reduction under galvanostatic control of 1,3-dialkylimidazolium-based ionic liquids, were employed as catalysts in transesterification reactions in the parent, room temperature ionic liquids (RTILs) as solvents, without the utilisation of any volatile organic solvent or base. The reaction between isopropenyl or ethyl acetate and an alcohol (not efficient in the absence of catalyst) was induced by the presence of an electrogenerated NHC, which seems to assist the proton transfer from the alcohol to the ester, yielding the corresponding acetate. The reaction also proceeds with methyl nicotinate as starting ester and 2-(diethylamino)ethanol or benzyl alcohol as alcohols and leads to the corresponding biologically active compounds, nicametate and benzyl nicotinate, in good yields. All products were isolated in good to excellent yields and complete recyclability of the ionic liquid as solvent has been demonstrated.

In situ generated "lanthanum(iii) nitrate alkoxide" as a highly active and nearly neutral transesterification catalyst

In situ generated lanthanum(iii) nitrate alkoxide is a highly active and nearly neutral transesterification catalyst, which can promote non-epimerized transesterification of α-substituted chiral carboxylic esters under reflux conditions.

CeO2-catalysed one-pot selective synthesis of esters from nitriles and alcohols

Thirteen kinds of metal oxides were tested for one-pot selective synthesis of esters from nitriles and alcohols. Ceria (CeO2) showed more than two orders of magnitude higher activity than the other oxides. CeO2 acted as a reusable and effective catalyst for the ester synthesis from various nitriles and alcohols under neutral and solvent-free conditions at 160 °C. This method provides a rare example for the synthesis of heteroaromatic esters, which have been difficult to synthesize by conventional catalytic esterification methods. Valuable esters such as picolinic acid alkyl esters and niacin benzyl esters were synthesized, demonstrating a practical aspect of the present method. Kinetic studies suggested the following reaction mechanism: (1) H2O and ROH dissociate on CeO2, (2) nucleophilic attack of hydroxyl species (OHδ-) to the adsorbed nitrile on CeO2, leading to the formation of the primary amide, (3) nucleophilic attack of alkoxide species (ORδ-) to the amide as the rate-limiting step.