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110-86-1

Basic Information
CAS No.: 110-86-1
Name: Pyridine
Article Data: 916
Cas Database
Molecular Structure:
Molecular Structure of 110-86-1 (Pyridine)
Formula: C5H5N
Molecular Weight: 79.1014
Synonyms: NCI-C55301;Pyridin;Pyridine ring;Azine;Azabenzene;CP 32;Piridina;py;Pirydyna;Pyridine,crude,light;
EINECS: 203-809-9
Density: 0.978 g/cm3
Melting Point: -42 °C
Boiling Point: 115.3 °C at 760 mmHg
Flash Point: 17 °C
Solubility: Miscible with water
Appearance: Colorless to light yellow liquid
Hazard Symbols: ToxicT,DangerousN,FlammableF,HarmfulXn
Risk Codes: 11-20/21/22-39/23/24/25-23/24/25
Safety: 36/37/39-38-45-61-28A-26-28-24/25-22-36/37-16-7
Transport Information: UN 1282 3/PG 2
PSA: 12.89000
LogP: 1.08160
Synthetic route
694-59-7

pyridine N-oxide

110-86-1

pyridine

Conditions
ConditionsYield
With triphenylphosphine; molybdenum In benzene at 40℃; for 12h;100%
With carbon monoxide; 1 wt% Au/TiO2; water In acetone at 60℃; under 7600.51 Torr; for 10h; Autoclave;99%
With sodium tetrahydroborate; zirconium(IV) chloride In tetrahydrofuran at 0 - 35℃; for 0.25h; Product distribution; Further Variations:; Reaction partners; reaction time; Reduction;98%
29181-50-8

2,4-Dicyanopyridine

110-86-1

pyridine

Conditions
ConditionsYield
With sodium hydroxide; titanium(III) chloride; acetic acid In water at 0℃; C7H3N3:TiCl3 in 1:2 molar ratio, pH=10-11;100%
100-48-1

pyridine-4-carbonitrile

A

110-86-1

pyridine

B

CN(1-)

CN(1-)

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; titanium(III) chloride In water at 0℃; Mechanism; in the absence and in the presence of complex forming agents;A 100%
B n/a
626-60-8

3-Chloropyridine

110-86-1

pyridine

Conditions
ConditionsYield
With ammonium formate In water; isopropyl alcohol at 20℃; for 3h;99%
With ammonium formate In water at 20℃; for 6h;99%
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran at 20℃; for 1h;97 % Spectr.

pyridinium tetrafluoroborate

74-89-5

methylamine

A

110-86-1

pyridine

B

methylammonium tetrafluoroborate

Conditions
ConditionsYield
In water keeping C5H5NHBF4 in ice-cooled water, dropwise addn. of the amine with stirring; extn. of pyridine with CHCl3, concn. of the aq. soln. to dryness on a water-bath at 50 - 60°C, drying over P2O5, elem. anal.;A n/a
B 98%
6206-57-1

2,3-Dibromo-N-[2-(2,3-dibromo-2-methyl-propionylamino)-ethyl]-2-methyl-propionamide

110-86-1

pyridine

Conditions
ConditionsYield
With sodium hydroxide; Duolite A-109 In dichloromethane for 3h; Product distribution; Ambient temperature; bis-β-halocarboxamides to prepare bis-β-lactams;97%

rubidium bromide

pyridinium tetrafluoroborate

A

110-86-1

pyridine

B

18909-68-7

rubidium tetrafluoroborate

Conditions
ConditionsYield
In water addn. of RbBr to C5H5NHBF4; extn. of pyridine with CHCl3, pptn., filtration, washing with a water-alcohol mixture, drying in a hot air oven (about 105°C), elem. anal.;A n/a
B 96%

potassium chloride

pyridinium tetrafluoroborate

A

110-86-1

pyridine

B

14075-53-7

potassium tetrafluoroborate

Conditions
ConditionsYield
In water addn. of KCl to C5H5NHBF4; extn. of pyridine with CHCl3, pptn., filtration, washing with a water-alcohol mixture, drying in a hot air oven (about 105°C), elem. anal.;A n/a
B 96%
109-06-8

α-picoline

A

110-86-1

pyridine

B

100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With air; ammonia; water; vanadia; titanium(IV) oxide; tin(IV) oxide at 380℃; for 0.000105556h; Product distribution; var. reagents ratios, temp. and contact time;A 3%
B 95%
With air; ammonia; water; vanadia; titanium(IV) oxide; tin(IV) oxide at 380℃; for 0.000105556h;A 3%
B 95%
With air; water; vanadia at 380℃; for 0.000508333h;A 86%
B 3.2%
3337-17-5

1,4-dihydropyridine

110-86-1

pyridine

Conditions
ConditionsYield
With dipotassium peroxodisulfate In acetonitrile for 0.25h; Heating;95%
With manganese(IV) oxide; Bentonite A for 0.133333h; Irradiation;100 % Chromat.
With manganese(IV) oxide; Bentonite A for 0.166667h; Irradiation; other 4-aryl-1,4-dihydropyridines; Bentonite B; var. time;100 % Chromat.
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    110-86-1

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Consensus Reports

Community Right-To-Know List. Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.
 

Standards and Recommendations

OSHA PEL: TWA 5 ppm
ACGIH TLV: TWA 5 ppm; (Proposed: TWA 1 ppm, Confirmed Animal Carcinogen.)
DFG MAK: 5 ppm (16 mg/m3)
DOT Classification:  3; Label: Flammable Liquid, Poison

Analytical Methods

For occupational chemical analysis use NIOSH: Pyridine, 1613.

Specification

The Pyridine is an organic compound with the formula C5H5N. The IUPAC name of this chemical is pyridine. With the CAS registry number 110-86-1, it is also named as Azabenzene. The product's categories are Pyridine; Organohalides; Boronic ester; Organoborons; Halogenated; Fluorinated; Building Blocks; Boronic Acid; Carboxy; Alkoxy; Organosilane; Organostannes; Tributylstanny; Chemistry; Alphabetic; P; PU - PZ; Chromasolv PlusChromasolv Solvents (HPLC, LC-MS); Chromasolv(R) Plus; LC-MS Plus and Gradient; Amber Glass Bottles; ReagentPlus(R) Solvent Grade Products; ReagentPlus(R)Solvents; ACS Grade Solvents; ACS GradeSemi-Bulk Solvents; ACS GradeSolvents; Carbon Steel Cans with NPT Threads; Returnable Container Solvents; Biotech SolventsSolvents; Solvent Bottles; Solvents; Sure/Seal Bottles; P-S; Alpha Sort; Volatiles/ Semivolatiles; Aluminum Bottles; O-P, Puriss p.a. ACS; Puriss p.a. ACS; Analytical Reagents for General Use; O-P, Puriss p.a.; Puriss p.a.; Alphabetical Listings; Flavors and Fragrances; O-P; Spectrophotometric Grade Solvents; Spectrophotometric GradeSolvents; PVC Coated Bottles; ReagentPlus(R) Solvent Grade ProductsSolvents; Anhydrous Grade SolventsSolvents; AnhydrousSolvents. Besides, it is colorless to light yellow liquid, which should be stored in a cool and well-ventilated place.

Physical properties about Pyridine are: (1)ACD/LogP: 0.84; (2)ACD/LogD (pH 5.5): 0.65; (3)ACD/LogD (pH 7.4): 0.833; (4)ACD/BCF (pH 5.5): 1.657; (5)ACD/BCF (pH 7.4): 2.524; (6)ACD/KOC (pH 5.5): 44.252; (7)ACD/KOC (pH 7.4): 67.393; (8)#H bond acceptors: 1; (9)Polar Surface Area: 12.89 Å2; (10)Index of Refraction: 1.501; (11)Molar Refractivity: 24.344 cm3; (12)Molar Volume: 82.657 cm3; (13)Polarizability: 9.651×10-24cm3; (14)Surface Tension: 35.263 dyne/cm; (15)Density: 0.957 g/cm3; (16)Flash Point: 20 °C; (17)Enthalpy of Vaporization: 35.09 kJ/mol; (18)Boiling Point: 115.259 °C at 760 mmHg; (19)Vapour Pressure: 22.779 mmHg at 25°C.

Preparation: the Chichibabin pyridine synthesis was reported in 1924 and is still in use industrially. In its general form, the reaction can be described as a condensation reaction of aldehydes, ketones, α,β-Unsaturated carbonyl compounds, or any combination of the above, in ammonia or ammonia derivatives. First, acrolein is formed in a Knoevenagel condensation from the acetaldehyde and formaldehyde. It is then condensed with acetaldehyde and ammonia into dihydropyridine, and then oxidized with a solid-state catalyst to pyridine. This process is carried out in a gas phase at 400–450 °C. The product consists of a mixture of pyridine, simple methylated pyridines (picoline) and lutidine; its composition depends on the catalyst used and can be adapted to the needs of the manufacturer. The catalyst is usually a transition metal salt such as cadmium(II) fluoride or manganese(II) fluoride, but cobalt and thallium compounds can also be used. The recovered pyridine is separated from by-products in a multistage process.

Uses of Pyridine: it is an important raw material in of the chemical industry. Pyridine is used as polar, basic, low-reactive solvent, for example in Knoevenagel condensations. It is especially suitable for the dehalogenation, where it acts as the base of the elimination reaction and bonds the resulting hydrogen halide to form a pyridinium salt. In esterifications and acylations pyridine activates the carboxylic acid halides or anhydrides. Even more active in these reactions are the pyridine derivatives 4-dimethylaminopyridine (DMAP) and 4-(1-pyrrolidinyl) pyridine. Pyridine is also used as a base in condensation reactions.

When you are using this chemical, please be cautious about it as the following:
It is highly flammable and harmful by inhalation, in contact with skin and if swallowed. Please keep away from sources of ignition - No smoking. After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer). In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed. When you are using it, wear suitable gloves and eye/face protection, do not breathe dust and avoid contact with skin and eyes. In case of insufficient ventilation wear suitable respiratory equipment. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: c1ccncc1
(2)InChI: InChI=1/C5H5N/c1-2-4-6-5-3-1/h1-5H
(3)InChIKey: JUJWROOIHBZHMG-UHFFFAOYAY
(4)Std. InChI: InChI=1S/C5H5N/c1-2-4-6-5-3-1/h1-5H
(5)Std. InChIKey: JUJWROOIHBZHMG-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 880mg/kg (880mg/kg) CARDIAC: CHANGE IN RATE

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Toxicology. Vol. 4, Pg. 165, 1975.
frog LDLo parenteral 870mg/kg (870mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 695, 1948.
guinea pig LD50 skin 1gm/kg (1000mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 839, 1986.
guinea pig LDLo intraperitoneal 870mg/kg (870mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: TREMOR

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Journal of Physiology. Vol. 17, Pg. 272, 1894.
guinea pig LDLo oral 4gm/kg (4000mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: TREMOR

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Journal of Physiology. Vol. 17, Pg. 272, 1894.
mammal (species unspecified) LC50 inhalation 10gm/m3 (10000mg/m3)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 32(10), Pg. 25, 1988.
mammal (species unspecified) LD50 oral 1500mg/kg (1500mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 32(10), Pg. 25, 1988.
mouse LD50 intraperitoneal 950mg/kg (950mg/kg)   Progress in Biochemical Pharmacology. Vol. 1, Pg. 542, 1965.
mouse LD50 intravenous 420mg/kg (420mg/kg) BEHAVIORAL: SLEEP

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Pharmacological Research Communications. Vol. 5, Pg. 341, 1973.
mouse LD50 oral 1500mg/kg (1500mg/kg) BEHAVIORAL: SLEEP

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Pharmacological Research Communications. Vol. 5, Pg. 341, 1973.
mouse LD50 subcutaneous 1250mg/kg (1250mg/kg) BEHAVIORAL: SLEEP

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Pharmacological Research Communications. Vol. 5, Pg. 341, 1973.
rabbit LD50 skin 1121mg/kg (1121mg/kg) BEHAVIORAL: ATAXIA

LIVER: OTHER CHANGES

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
BIOFAX Industrial Bio-Test Laboratories, Inc., Data Sheets. Vol. 14-4/1970,
rabbit LDLo intraperitoneal 15mg/kg (15mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BEHAVIORAL: GENERAL ANESTHETIC
Journal of Infectious Diseases. Vol. 42, Pg. 473, 1928.
rabbit LDLo subcutaneous 800mg/kg (800mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 695, 1948.
rat LC50 inhalation 28500mg/m3/1H (28500mg/m3) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
BIOFAX Industrial Bio-Test Laboratories, Inc., Data Sheets. Vol. 14-4/1970,
rat LD50 intraperitoneal 866mg/kg (866mg/kg)   National Technical Information Service. Vol. PB195-158,
rat LD50 intravenous 360mg/kg (360mg/kg) BEHAVIORAL: SLEEP

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Pharmacological Research Communications. Vol. 5, Pg. 341, 1973.
rat LD50 oral 891mg/kg (891mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: COMA
BIOFAX Industrial Bio-Test Laboratories, Inc., Data Sheets. Vol. 14-4/1970,
rat LD50 subcutaneous 866mg/kg (866mg/kg)   Clinical Toxicology. Vol. 4, Pg. 185, 1971.

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