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2-Picoline
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Name

2-Picoline

 EINECS 203-643-7
CAS No. 109-06-8 Density 0.94 g/cm3
PSA 12.89000 LogP 1.39000
Solubility miscible with water Melting Point -70 °C(lit.)
Formula C6H7N Boiling Point 127.544 °C at 760 mmHg
Molecular Weight 93.1283 Flash Point 26.111 °C
Transport Information UN 2313 3/PG 3 Appearance colourless to yellow liquid with an unpleasant smell
Safety 26-36 Risk Codes 10-20/21/22-36/37
Molecular Structure Molecular Structure of 109-06-8 (2-Picoline) Hazard Symbols HarmfulXn
Synonyms

RCRA waste number U191;CCRIS 1721;AI3-24109;AI3-2409;alpha-Methylpyridine;o-Picoline;

Article Data 276

2-Picoline Synthetic route

(C5H5)2Zr(NC5H3CH3)(NC5H4CH3)(1+)*B(C6H5)4(1-)=(C5H5)2Zr(NC5H3CH3)(NC5H4CH3)B(C6H5)4

187737-37-7

propene

A

109-06-8

α-picoline

B

(C5H5)2ZrCH2CH(CH3)NC5H3CH3(1+)*B(C6H5)4(1-)=(C5H5)2ZrCH2CH(CH3)NC5H3CH3B(C6H5)4

Conditions
ConditionsYield
<10 min, 23°C, 1 atm.; monitored by NMR;A n/a
B 100%
931-19-1

2-methylpyridine N-oxide

109-06-8

α-picoline

Conditions
ConditionsYield
With benzyl alcohol at 120℃; for 6h; Inert atmosphere;99%
With cis-Cyclooctene; trans-dioxo(5,10,15,20-tetramesitylporphirinato)ruthenium(VI) In benzene at 80℃; for 15h;96%
With diphosphorus tetraiodide In dichloromethane Heating; 10-20 min;95%
75-05-8

acetonitrile

74-86-2

acetylene

109-06-8

α-picoline

Conditions
ConditionsYield
at 150℃; for 22h; Autoclave;94.3%
With decaethylene glycol mono n-hexadecyl ether; cyclopentadienyl-cyclooctadienyl-cobalt(I) In water for 4h; Ambient temperature; Irradiation;18%
(η5-cyclopentadienyl)-η4-cycloocta-1,5-dienecobalt(I) at 40℃; for 2h; Irradiation; Yield given;
trimethylsilyl modified Cp-CO catalyst at 130 - 152℃; under 15001.2 Torr; for 2h;
η5-cyclopentadienylbis(ethene)cobalt at 40℃; for 3h; Product distribution; in the dark; variation of reaction time, temperature, catalyst. The influence of light and irradiation was investigated.;
5315-25-3

2-bromo-6-methylpyridine

A

109-06-8

α-picoline

B

4411-80-7

6,6'-dimethyl-2,2'-bipyridine

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride In 2-pentanol at 100℃; for 18h; Inert atmosphere;A 93.1%
B 6.9%
110-86-1

pyridine

A

110-89-4

piperidine

B

109-06-8

α-picoline

C

24362-44-5

1,5-di-(1-piperidyl)pentane

Conditions
ConditionsYield
With hydrogen; Ni-Cr catalyst at 160℃; under 30400 Torr; for 8h; Product distribution; temperatures from 140 to 192 deg C, pressure 20 to 65 atm, reaction time 5 - 8 h;A 91.8%
B n/a
C 0.1%
110-86-1

pyridine

67-56-1

methanol

109-06-8

α-picoline

Conditions
ConditionsYield
With Fe-MnOx-Yb at 475℃; Gas phase;89.5%
nickel(II) nitrate for 8h; Ambient temperature; Irradiation;37.1%
With nano-diatomite modified magnesium aluminum hydrotalcite at 140 - 500℃; Temperature;
1452-77-3

pyridine-2-carboxylic acid amide

109-06-8

α-picoline

Conditions
ConditionsYield
With samarium diiodide; phosphoric acid In tetrahydrofuran for 0.000555556h; Ambient temperature;88%
126963-92-6

benzyltri(2-(6-methylpyridyl))phosphonium bromide

A

109-06-8

α-picoline

B

4411-80-7

6,6'-dimethyl-2,2'-bipyridine

C

C19H19N2OP

Conditions
ConditionsYield
With hydrogenchloride In water for 10h; Heating;A 68%
B 87%
C n/a
With hydrogenchloride In water for 10h; Product distribution; Heating; variation of pH, temp. and time;A 68%
B 87%
C n/a
With hydrogenchloride In water for 10h; Heating;A 68%
B 68%
C n/a
14402-20-1

N-cetyl-α-methylpyridinium iodide

109-06-8

α-picoline

Conditions
ConditionsYield
With triethylammonium hydrogensulfite at 150℃; for 30h; Mechanism;86%
38700-15-1

triphenyl-(2-pyridylmethyl)phosphonium chloride

109-06-8

α-picoline

Conditions
ConditionsYield
With potassium tert-butylate; benzyl alcohol In tetrahydrofuran at 40℃; for 6h; Inert atmosphere;80%

2-Picoline Specification

The 2-Methylpyridine, or 2-Picoline, is the compound described with formula C6H7N. With the CAS registry number 109-06-8, it is a colorless liquid. This chemical's classification codes are Mutation Data; Skin / Eye Irritant. Its EINECS registry number is 203-643-7. In addition, its IUPAC name is called 2-methylpyridine.

Physical properties of 2-Methylpyridine: (1)ACD/LogP: 1.22; (2)ACD/LogD (pH 5.5): 0.64; (3)ACD/LogD (pH 7.4): 1.204; (4)ACD/BCF (pH 5.5): 1.31; (5)ACD/BCF (pH 7.4): 4.798; (6)ACD/KOC (pH 5.5): 28.898; (7)ACD/KOC (pH 7.4): 105.888; (8)#H bond acceptors: 1; (9)Index of Refraction: 1.501; (10)Molar Refractivity: 29.169 cm3; (11)Molar Volume: 98.932 cm3; (12)Surface Tension: 34.098 dyne/cm; (13)Density: 0.941 g/cm3; (14)Flash Point: 26.111 °C; (15)Enthalpy of Vaporization: 36.17 kJ/mol; (16)Boiling Point: 127.544 °C at 760 mmHg; (17)Vapour Pressure: 13.468 mmHg at 25°C.

Preparation: 2-Methylpyridine was the first pyridine compound reported to be isolated in pure form. It is now mainly produced by two principal routes, the condensation of acetaldehyde, formaldehyde, and ammonia and the cyclization of nitriles and acetylene. One example of such reaction is the combination of acetaldehyde and ammonia:

such reaction is the combination of acetaldehyde and ammonia

Uses of 2-Methylpyridine: it is a versatile building block and can be used as a precursor to a variety of derivatives. For example, oxidation by potassium permanganate affords picolinic acid:

oxidation by potassium permanganate affords picolinic acid

When you are using this chemical, please be cautious about it as the following:
This chemical may cause damage to health. It is harmful by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)SMILES: Cc1ccccn1
(2)InChI: InChI=1/C6H7N/c1-6-4-2-3-5-7-6/h2-5H,1H3
(3)InChIKey: BSKHPKMHTQYZBB-UHFFFAOYAR

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 900mg/kg (900mg/kg)   Hygiene and Sanitation Vol. 33(10-12), Pg. 341, 1968.
mouse LC50 inhalation 9gm/m3 (9000mg/m3)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 57(9-10), Pg. 64, 1992.
mouse LD50 intraperitoneal 529mg/kg (529mg/kg)   Toxicon. Vol. 23, Pg. 815, 1985.
mouse LD50 oral 674mg/kg (674mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT		 Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 45(12), Pg. 62, 1980.
rabbit LD50 skin 410uL/kg (0.41mL/kg)   AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 4, Pg. 119, 1951.
rat LCLo inhalation 4000ppm/4H (4000ppm)   AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 4, Pg. 119, 1951.
rat LD50 intraperitoneal 200mg/kg (200mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Fundamental and Applied Toxicology. Vol. 5, Pg. 920, 1985.
rat LD50 oral 790mg/kg (790mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT		 Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 45(12),

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