Pyridine-2-carbonitrile

HCID 7522CAS 100-70-9

Basic information

Standard SMILES
N#Cc1ccccn1
InChIKey
FFNVQNRYTPFDDP-UHFFFAOYSA-N
Molecular formula
C6H4N2
Average molar mass
104.11 g/mol
Monoisotopic mass
104.03744813

Overview

2-cyanopyridine is a cyanopyridine carrying the cyano group at position 2.

Names & identifiers

Preferred name
Pyridine-2-carbonitrile
IUPAC
pyridine-2-carbonitrile
English name
2-Cyanopyridine
Molecular formula
C6H4N2
Molecular weight
104.11

Names & synonyms

Pyridine-2-carbonitrileRefChem:4833572-CyanopyridinePicolinonitrile100-70-92-PYRIDINECARBONITRILEPyridinecarbonitrilePicolinic acid nitrile2-Pyridyl nitrilecyanopyridineMFCD0000621829386-66-1
Show more names
NSC 59697picolylnitrile2 cyanopyrimideα-Cyanopyridine
2-Pyridinecarboxylic acid, nitrileDTXSID9021843WHR1DPG7YSCHEMBL3185861CHEBI:27837NSC-59697DTXCID1018432-pyridylnitrile

Database identifiers

CAS
100-70-9、29386-66-1
PubChem CID
7522
DTXSID
DTXSID9021843
ChEMBL
CHEMBL3185861
ChEBI
CHEBI:27837
UNII
WHR1DPG7YS
EC Number
202-880-3
Nikkaji
J58.011B

Properties

Computed structural properties

XLogP
0.4
Topological polar surface area
36.7 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
8

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Nitriles
SpringerMaterials Properties15N nuclear magnetic resonance spectrum
LogP · 2 items

log Kow= 0.45

0.5

Density1.0810 @ 25 °C
Color/FormNEEDLES OR PRISMS FROM ETHER
Solubility · 2 items

Soluble in water, alcohol, ether, and benzene.

Soluble in chloroform; slightly soluble in petroleum ether.

Physicochemical properties

Melting point
24 · 24-27 °C(lit.)
Boiling point
212 · 212-215 °C(lit.)
Density
1.081 g/mL · 1.081 g/mL at 25 °C(lit.)
vapor pressure
11.96 Pa · 11.96Pa at 25℃
refractive index
20 · n20/D 1.529(lit.)
Flash point
193 °F · 193 °F

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H302 (96.5%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 115 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

Hazard information

Regulatory Information · 3 items

Chemical: 2-Pyridinecarbonitrile

Status: Active Update: 26-09-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/25300

2-Pyridinecarbonitrile: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryEmergency treatment: Pyridine; Pyridine is an irritant that causes CNS depression after ingestion of 1/2 cup or inhalation of 6-12 ppm; It can cause liver and kidney injury; [HSDB] An irritant; [MSDSonline] See NITRILES.
TSCA Requirements · 1 item

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 2-Pyridinecarbonitrile is included on this list.

Hazard Classes and Categories · 2 items

Acute Tox. 4 (96.5%)

Acute toxicity (Oral) - Category 4

Skin, Eye, and Respiratory IrritationsPyridine and its derivatives cause local irritation on contact with the skin, mucous membranes and cornea. /Pyridine and its derivatives/

Safety & protection

Disposal Methods · 1 item

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Preventive Measures · 1 item

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Personal Protective Equipment (PPE) · 1 item

Depending on the extent of possible contact, workers should be provided with personal protective equipment. A charcoal gas mask canister respirator has been found to be effective against a 2% pyridine concentration at 30 l/min for 1 hr. Rubber and plastic gloves should not be relied upon to prevent skin contact because pyridine and many of its derivatives penetrate these materials ... . /Pyridine, homologs, and derivatives/

Toxicology

Ecotoxicity Values · 2 items

LC50 Pimephales promelas (fathead minnow) 726 mg/l/96 hr (confidence limit 673 - 783 mg/l), flow-through bioassay with measured concentrations, 25.0 °C, dissolved oxygen 5.7 mg/l, hardness 45.0 mg/l CaCO3, alkalinity 51.3 mg/l CaCO3, and pH 7.58.

EC50 Pimephales promelas (fathead minnow) 726 mg/l/96 hr (confidence limit 673 - 783 mg/l), flow-through bioassay with measured concentrations, 25.0 °C, dissolved oxygen 5.7 mg/l, hardness 45.0 mg/l CaCO3, alkalinity 51.3 mg/l CaCO3, and pH 7.58. Effect: loss of equilibrium.

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 42(SRC), determined from a log Kow of 0.45(2) and a regression-derived equation(3), indicates that 2-pyridinecarbonitrile is expected to have very high mobility in soil(SRC). Volatilization of 2-pyridinecarbonitrile from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.89X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(4). 2-Pyridinecarbonitrile is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.5 mm Hg(SRC), determined from its estimated water solubility, 25,500 mg/l(5), and estimated Henry's law constant(4). In water, the half-life for 2-pyridinecarbonitrile in an anoxic sediment from the Tansui River (Taiwan) was 16.5 hrs based in a pseudo-first-order rate constant of 1.01 per day(6); this suggests that 2-pyridinecarbonitrile may biodegrade in soil under anaerobic conditions(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 42(SRC), determined from a log Kow of 0.45(2) and a regression-derived equation(3), indicates that 2-pyridinecarbonitrile is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 6.89X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). The half-life for 2-pyridinecarbonitrile in an anoxic sediment from the Tansui River (Taiwan) was 16.5 hrs based in a pseudo-first-order rate constant of 1.01 per day(7), which suggests that 2-pyridinecarbonitrile may biodegrade in the environment under anaerobic conditions(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-pyridinecarbonitrile, which has an estimated vapor pressure of 0.5 mm Hg at 25 °C(SRC), determined from its estimated water solubility, 25,500 mg/l(2), and its estimated Henry's law constant, 6.89X10-8 atm/cu m/mole(3), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase 2-pyridinecarbonitrile is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 246 days(SRC), calculated from its rate constant of 6.53X10-14 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(4).

Food Survey Values2-Pyridinecarbonitrile was qualitatively detected in the volatile components of meat(1).
Adverse EffectsNeurotoxin - Other CNS neurotoxin
Effluent ConcentrationsPyridinecarbonitrile (isomer not specified) was detected in 1 of 21 industrial wastewater effluents at a concn between 10 and 100 ug/l(1).
Soil Adsorption/Mobility · 1 item

The Koc of 2-pyridinecarbonitrile is estimated as 42(SRC), using a measured log Kow of 0.45(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2-pyridinecarbonitrile is expected to have very high mobility in soil(SRC).

Regulatory information

TSCA Requirements · 1 item

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 2-Pyridinecarbonitrile is included on this list.

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
ridadr
3276
hs_code
29333999
risk_code
22-36/37/38-20/21/22

Chemistry & industry

Uses & manufacturing

Uses · 3 items

Used as a chemical intermediate for rimiterol hydrobromide (bronchodilator) and other chemicals; [HSDB]

CHEM INT FOR RIMITEROL HYDROBROMIDE, A BRONCHODILATOR

An important chemical intermediate.

Methods of ManufacturingVAPOR PHASE AMMOXIDATION OF 2-METHYLPYRIDINE WITH AMMONIA IN THE PRESENCE OF AIR
General Manufacturing Information2-Pyridinecarbonitrile: ACTIVE
Applications · 3 items

DescriptionThe cyanopyridines are as follows:2-cyano-: A white to tan liquid or solid with an almondodor. Boiling point=about 213℃; Freezing/Meltingpoint=27℃; Flash point=89℃.3-cyano-: A colorless liquid or gray crystalline solid.Molecular weight=104.12; Boiling point=83-84℃;Freezing/Melting point=47-49℃. Hazard Identification(based on NFPA-704 M Rating System): Health 3,Flammability 3, Reactivity 0. Soluble in water.4-cyano-: A beige solid. Freezing/Melting point=75.8℃

Uses2-Cyanopyridine is a cyano substituted pyridine. 2-Cyanopyridine is a related compound of nicotine and is a component of tobacco smoke condensate.

UsesIt is employed as an important chemical intermediate for rimiterol hydrobromide and used as a bronchodilator. It is also used as intermediates of pharmaceutical and dye and pigment. It acts as a precursor of the respective amidate for protein modification via amidation.

Suppliers1 total

Organic Chemicals—

Additional notes

DefinitionChEBI: A cyanopyridine carrying the cyano group at position 2.

Related reactions

230 records

Linked notes

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