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Pyridine-2-carbonitrile

HCID 7522
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Basic information

CAS
100-70-9
Standard SMILES
N#Cc1ccccn1
InChIKey
FFNVQNRYTPFDDP-UHFFFAOYSA-N
Molecular formula
C6H4N2
Average molar mass
104.11 g/mol
Monoisotopic mass
104.03744814

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 nitrilecyanopyridine29386-66-12-Pyridinecarboxylic acid, nitrile
Show more names
NSC 59697picolylnitrile2 cyanopyrimideα-Cyanopyridine
MFCD00006218DTXSID9021843WHR1DPG7YSCHEMBL3185861CHEBI: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
Formal charge
0
Complexity
111

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.

Boiling Point224.5 °C
Melting Point29 °C
Vapor Pressure0.09 [mmHg]
Refractive IndexIndex of refraction: 1.5242 @ 25 °C/D
Physical DescriptionSolid; [HSDB] Low melting solid; mp = 26-28 deg C; [MSDSonline]
Dissociation ConstantspKa = 0.26 (conjugate acid)

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
storage temp.
Inert atmosphere,Room Temperature
solubility
67 g/l · 67g/l
form
Low Melting Crystalline Solid
pka
1 · pK1:-0.26(+1) (25°C)
color
White to brown
PH
8.4 · 8.4 (100g/l, H2O)
Water Solubility
immiscible
BRN
107710 · 107710
Henry's Law Constant
1.4 · 1.4×102 mol/(m3Pa) at 25℃, HSDB (2015)
Exposure limits
25 mg/m3 · NIOSH: IDLH 25 mg/m3
Dielectric constant
93.77 · 93.769999999999996
InChI
1S/C6H4N2/c7-5-6-3-1-2-4-8-6/h1-4H
InChIKey
FFNVQNRYTPFDDP-UHFFFAOYSA-N
SMILES
N#Cc1ccccn1
LogP
0.45 at · 0.45 at 25℃
CAS DataBase Reference
100 · 100-70-9(CAS DataBase Reference)
FDA UNII
1 DPG7YS · WHR1DPG7YS
NIST Chemistry Reference
2 · 2-Pyridinecarbonitrile(100-70-9)
EPA Substance Registry System
2 · 2-Pyridinecarbonitrile (100-70-9)
UNSPSC Code
12352100 · 12352100
NACRES
22 · NA.22
Symbol(GHS)
6 · GHS06
Signal word
Danger
Hazard statements
302 · H302-H311
Precautionary statements
264 · P264-P270-P280-P301+P312-P302+P352+P312-P361+P364
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xn
Risk Statements
22 · 22-36/37/38-20/21/22
Safety Statements
26 · 26-24/25
RIDADR
3276 · 3276
WGK Germany
3 · 3
TSCA
TSCA listed
HazardClass
6.1 · 6.1
PackingGroup
III
HS Code
29333999 · 29333999
Storage Class
6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
3 DermalAcute · Acute Tox. 3 DermalAcute Tox. 4 Oral
Hazardous Substances Data
100 · 100-70-9(Hazardous Substances Data)
REACH Registrations
Active

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

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

REACH registered substance: Pyridine-2-carbonitrile (EC: 202-880-3)

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).

Atmospheric Concentrations2-Pyridinecarbonitrile was qualitatively listed as a contaminant of the ambient air at Houston, TX(1).
Artificial Pollution Sources2-Pyridinecarbonitrile's production and use as a chemical intermediate(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1 item

ANAEROBIC: The maximum pseudo-first-order rate constant and half-life for 2-pyridinecarbonitrile in an anoxic sediment slurry from the estuary of the Tansui River (Guandu, Taipei) were 1.01 per day and 16.5 hrs, respectively(1). 2-Pyridinecarbonitrile was not transformed in the sterile control sediment slurry(1) which suggests that 2-pyridinecarbonitrile may degrade in the environment, at least under anaerobic conditions(SRC).

Environmental Bioconcentration · 1 item

An estimated BCF of 3 was calculated for 2-pyridinecarbonitrile(SRC), using a log Kow of 0.45(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil · 1 item

The Henry's Law constant for 2-pyridinecarbonitrile is estimated as 6.89X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2-pyridinecarbonitrile is expected to be essentially nonvolatile from water surfaces(2). 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(3), and its estimated Henry's law constant(1).

Environmental Abiotic Degradation · 1 item

The rate constant for the vapor-phase reaction of 2-pyridinecarbonitrile with photochemically-produced hydroxyl radicals has been estimated as 6.53X10-14 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 246 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2-Pyridinecarbonitrile is expected to undergo slow hydrolysis in the environment based upon the slow hydrolysis of other aromatic nitriles, eg benzonitrile(2). 2-Pyridinecarbonitrile will not directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm)(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
Signal word
Danger
Symbol(GHS)
GHS06
hazard_code
Xn
safety_code
26-24/25
hazard_class
6.1
Storage Class
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
packing_group
III
Hazard statements
H302-H311
REACH Registrations
Active
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 4 Oral
Precautionary statements
P264-P270-P280-P301+P312-P302+P352+P312-P361+P364
Hazardous Substances Data
100-70-9(Hazardous Substances Data)

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.

Upstream & downstream products

Upstream raw materials

2-(2-Pyridinyl)-1,3,4-oxadiazole2-Iodopyridine4-Chloro-pyridine-2-carbonitrile2-Pyridinecarbaldehyde oximePropanedinitrile, 2-(dimethylamino)-2-(Hydroxymethyl)pyridineZINC CYANIDETrimethylacetonitrilePOTASSIUM CYANIDE2-Bromopyridine2-Chloropyridine

Downstream products

2-Pyridylamid oximeDi-2-pyridyl ketone2,2'-Dipicolylamine2-Cyanopyridin-3-ylboronic acidPyridine-2-carboxamidePyridine-2-carboximidamide hydrochloride2-Picolylamine

Additional notes

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

Related reactions

230 records
New reaction record
HRID 17112 reaction equation
HRID 17112As reactantuspto-grants-2010_06
HRID 19711 reaction equation
HRID 19711As reactantuspto-grants-2010_06
HRID 35895 reaction equation
HRID 35895As reactantuspto-grants-1995_05
HRID 42280 reaction equation
HRID 42280As reactantuspto-grants-2013_09
HRID 52339 reaction equation
HRID 52339As reactantuspto-grants-1997_04
HRID 52568 reaction equation
HRID 52568As reactantuspto-grants-1997_04
HRID 125715 reaction equation
HRID 125715As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 138948 reaction equation
HRID 138948As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
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