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91-02-1

Basic Information
CAS No.: 91-02-1
Name: 2-Benzoylpyridine
Article Data: 212
Molecular Structure:
Molecular Structure of 91-02-1 (2-Benzoylpyridine)
Formula: C12H9NO
Molecular Weight: 183.21
Synonyms: Ketone,phenyl 2-pyridyl (6CI,7CI,8CI);2-Pyridyl phenyl ketone;NSC20887;Phenyl 2-pyridyl ketone;Phenyl(2-pyridinyl)methanone;phenyl(pyridin-2-yl)methanone;methanone, phenyl-2-pyridinyl-;
EINECS: 202-034-3
Density: 1.139 g/cm3
Melting Point: 41-43 °C(lit.)
Boiling Point: 317.7 °C at 760 mmHg
Flash Point: 153.9 °C
Solubility: insoluble in water
Appearance: colourless to slightly yellow crystalline chunks
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
PSA: 29.96000
LogP: 2.31260
Synthetic route
31796-72-2

phenyl(2-pyridinyl)methanol

91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With butyltriphenylphosphonium chlorochromate In acetonitrile for 0.166667h; Heating;100%
With tert.-butylhydroperoxide; tetrabutyl-ammonium chloride; sodium carbonate; copper dichloride; 2,2′‐biquinoline‐4,4′‐dicarboxylic acid dipotassium salt In water at 40℃; for 48h;100%
With dicarbonyl(cyclopentadienyl)iron(II) chloride; sodium hydride In toluene for 20h; Catalytic behavior; Reagent/catalyst; Temperature; Reflux; Inert atmosphere; Schlenk technique;100%
4789-06-4

(1-oxido-2-pyridinyl)phenylmethanone

91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With phosphorus trichloride In chloroform at 0 - 80℃; for 1.16667h;100%
101-82-6

2-Benzylpyridine

91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With pyridine; tert.-butylhydroperoxide; iodine In water at 80℃; chemoselective reaction;99%
With oxygen In 1,2-dichloro-benzene at 110℃; under 760.051 Torr; for 6h; Schlenk technique;99%
With potassium bromate; cerium(IV) oxide In 1,4-dioxane; water; acetic acid at 95℃; for 4h;95%
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In toluene for 3h;99%
With oxygen; potassium carbonate In water; dimethyl sulfoxide Ambient temperature;48%
With oxygen; sodium hydride 1.) THF, 5 min; Yield given. Multistep reaction;

2-benzoylpyridine phenylhydrazone

91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With benzyltriphenylphosphonium dichromate; silica gel for 0.166667h;98%
With 1-benzyl-4-aza-1-azoniabiyclo<2.2.2>octane peroxodisulfate In acetonitrile for 1h; Heating;96%
With benzyltriphenylphosphonium dichromate In acetonitrile for 0.5h; Oxidation; Heating;96%
15260-65-8

2-(1-phenylvinyl)pyridine

91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With oxygen at 110℃; for 8h; Sealed tube;97.3%
With oxygen at 110℃; for 8h; Schlenk technique; Green chemistry;95%
With 1-hydroxy-pyrrolidine-2,5-dione; graphitic carbon nitride; oxygen In acetonitrile at 20℃; Inert atmosphere; Irradiation;75%

phenyl-pyridin-2-yl-methanethione

91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With 3-carboxypyridinium chlorochromate In acetonitrile for 0.0333333h; Product distribution; Further Variations:; Reagents; Temperatures; without microwave irradiation; solvent-free; microwave irradiation;96%
5029-67-4

2-iodopyridine

201230-82-2

carbon monoxide

98-80-6

phenylboronic acid

91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With (bis(tricyclohexyl)phosphine)palladium(II) dichloride; potassium carbonate In tetrahydrofuran at 100℃; under 3750.3 Torr; for 20h;95%
Stage #1: 2-iodopyridine; phenylboronic acid With potassium carbonate In toluene for 0.166667h; Suzuki cross-coupling reaction; Autoclave;
Stage #2: carbon monoxide In toluene at 100℃; under 10343.2 Torr; for 10h; Suzuki cross-coupling reaction; Autoclave;
89%
With Bedford’s palladacycle; potassium carbonate; methoxybenzene at 120℃; under 3750.38 Torr; for 12h; Suzuki-Miyaura Coupling; Autoclave;89%
101-82-6

2-Benzylpyridine

A

91-02-1

phenyl(pyridin-2-yl)methanone

B

[18O]-2-benzoylpyridine

Conditions
ConditionsYield
With N-Bromosuccinimide; (18O)-dimethylsulfoxide at 20 - 120℃; for 24h; Reagent/catalyst; Inert atmosphere; Schlenk technique;A n/a
B 95%

2-(2-phenyl-[1,3]dithian-2-yl)-pyridine

91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With bismuth(III) chloride; benzyltriphenylphosphonium peroxymonosulfate In acetonitrile for 3h; Heating;94%
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Specification

The 2-Benzoylpyridine, with the CAS registry number 91-02-1 and EINECS registry number 202-034-3, has the systematic name of phenyl(pyridin-2-yl)methanone. It is a kind of colourless to slightly yellow crystalline chunks, and belongs to the product category of Pyridines derivates. And the molecular formula of this chemical is C12H9NO. What's more, it is often used in organic synthesis.

The physical properties of 2-Benzoylpyridine are as followings: (1)ACD/LogP: 1.88; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.88; (4)ACD/LogD (pH 7.4): 1.88; (5)ACD/BCF (pH 5.5): 15.74; (6)ACD/BCF (pH 7.4): 15.74; (7)ACD/KOC (pH 5.5): 250.31; (8)ACD/KOC (pH 7.4): 250.34; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 29.96 Å2; (13)Index of Refraction: 1.588; (14)Molar Refractivity: 54.13 cm3; (15)Molar Volume: 160.7 cm3; (16)Polarizability: 21.46×10-24cm3; (17)Surface Tension: 47 dyne/cm; (18)Density: 1.139 g/cm3; (19)Flash Point: 153.9 °C; (20)Enthalpy of Vaporization: 55.91 kJ/mol; (21)Boiling Point: 317.7 °C at 760 mmHg; (22)Vapour Pressure: 0.000379 mmHg at 25°C.

Preparation of 2-Benzoylpyridine: This chemical can be prepared by pyridine and N,N-dimethyl-benzamide. The reaction will need reagents BuLi and N,N-dimethylaminoethanol. And the yield is about 65%. 

2-Benzoylpyridine can be prepared by pyridine and N,N-dimethyl-benzamide

Uses of 2-Benzoylpyridine: It can react with 2-hydrazino-pyridine to produce N-(phenyl-pyridin-2-yl-methylene)-N'-pyridin-2-yl-hydrazine. This reaction will need reagent glacial acetic acid, and the solvent methanol. And the yield is about 70%.  

2-Benzoylpyridine can react with 2-hydrazino-pyridine to produce N-(phenyl-pyridin-2-yl-methylene)-N'-pyridin-2-yl-hydrazine

You should be cautious while dealing with this chemical. It irritates eyes, respiratory system and skin. Therefore, you had better take the following instructions: Wear suitable protective clothing, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(c1ccccc1)c2ncccc2
(2)InChI: InChI=1/C12H9NO/c14-12(10-6-2-1-3-7-10)11-8-4-5-9-13-11/h1-9H
(3)InChIKey: GCSHUYKULREZSJ-UHFFFAOYAK

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 475mg/kg (475mg/kg)   Journal of Medicinal Chemistry. Vol. 14, Pg. 551, 1971.