3-Cyanopyridine

HCID 79CAS 100-54-9

Basic information

Standard SMILES
N#Cc1cccnc1
InChIKey
GZPHSAQLYPIAIN-UHFFFAOYSA-N
Molecular formula
C6H4N2
Average molar mass
104.11 g/mol
Monoisotopic mass
104.03744813

Overview

3-cyanopyridine is a cyanopyridine carrying the cyano group at position 3.

Names & identifiers

Preferred name
3-Cyanopyridine
IUPAC
pyridine-3-carbonitrile
English name
3-Cyanopyridine
Molecular formula
C6H4N2
Molecular weight
104.11

Names & synonyms

3-cyanopyridineNicotinonitrile100-54-93-PYRIDINECARBONITRILENicotinic acid nitrile3-Pyridinenitrile3-Pyridylcarbonitrile3-AzabenzonitrileNitryl kwasu nikotynowegoDTXSID10266653-Pyridinecarboxylic acid, nitrileNSC-17558
Show more names
BETA-CYANOPYRIDINENicotinamide EP Impurity Bb-Cyanopyridine
CHEBI:86556X64V0K6260DTXCID606665RefChem:505106202-863-0pyridine-3-carbonitrile3-Cyjanopirydyna3-Pyridyl cyanide

Database identifiers

CAS
100-54-9
PubChem CID
79
DTXSID
DTXSID1026665
ChEMBL
CHEMBL3181972
ChEBI
CHEBI:86556
UNII
X64V0K6260
EC Number
202-863-0
Nikkaji
J149.678F

Properties

Computed structural properties

XLogP
0.2
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 PropertiesBoiling point
LogP · 2 items

log Kow = 0.36

0.36

Density1.1590 @ 25 °C
Color/Form · 2 items

NEEDLES FROM PETROLEUM ETHER

Colorless liquid

Solubility · 3 items

Soluble in hot petroleum ether

Soluble in alcohol, ether, and benzene.

In water, 1.35X10+5 mg/l @ 20 °C

Physicochemical properties

Melting point
48 · 48-52 °C(lit.)
Boiling point
201 °C · 201 °C(lit.)
Density
1.159 · 1.159
refractive index
1.5242 · 1.5242 (estimate)
Flash point
184 °F · 184 °F
storage temp.
Inert atmosphere,Room Temperature

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, 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 85 reports by companies from 9 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 · 4 items

Chemical: 3-Pyridinecarbonitrile

3-Pyridinecarbonitrile is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 3-Pyridinecarbonitrile are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 10-12-2012 https://echa.europa.eu/registration-dossier/-/registered-dossier/5149

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

Hazards Summary · 1 item

A skin, eye, and mucous membrane irritant; Emergency 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] Causes respiratory depression and liver changes in lethal-dose studies of rats; [RTECS] An irritant; Harmful if swallowed; [Alfa Aesar MSDS] See m-Phthalodinitrile.

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. 3-Pyridinecarbonitrile is included on this list.

Hazard Classes and Categories · 2 items

Acute Tox. 4 (100%)

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

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 37(SRC), determined from a measured log Kow of 0.36(2) and a regression-derived equation(3), indicates that 3-pyridinecarbonitrile is expected to have very high mobility in soil(SRC). Volatilization of 3-pyridinecarbonitrile from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 2.74X10-7 atm-cu m/mole(4). 3-Pyridinecarbonitrile is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.296 mm Hg(5). In water, the maximum pseudo-first-order rate constant and half-life for 3-pyridinecarbonitrile in an anoxic sediment slurry from the estuary of the Tansui River (Guandu, Taipei) were 9.41 per day and 1.7 hrs, respectively(6) which suggests that 3-pyridinecarbonitrile may biodegrade in soil at least under anaerobic conditions(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 37(SRC), determined from a measured log Kow of 0.36(2) and a regression-derived equation(3), indicates that 3-pyridinecarbonitrile is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 2.74X10-7 atm-cu m/mole(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 maximum pseudo-first-order rate constant and half-life for 3-pyridinecarbonitrile in an anoxic sediment slurry from the estuary of the Tansui River (Guandu, Taipei) were 9.41 per day and 1.7 hrs, respectively(7) which suggests that 3-pyridinecarbonitrile may degrade in the environment at least under anaerobic conditions(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3-pyridinecarbonitrile, which has a vapor pressure of 0.296 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase 3-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(3).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Soil Adsorption/Mobility · 1 item

The Koc of 3-pyridinecarbonitrile is estimated as 37(SRC), using a measured log Kow of 0.36(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 3-pyridinecarbonitrile is expected to have very high mobility in soil(SRC).

Artificial Pollution Sources3-Pyridinecarbonitrile's production and use in organic synthesis(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 3-pyridinecarbonitrile in an anoxic sediment slurry from the estuary of the Tansui River (Guandu, Taipei) were 9.41 per day and 1.7 hrs, respectively(1). 3-Pyridinecarbonitrile was not transformed in the sterile control sediment slurry(1) which suggests that 3-pyridinecarbonitrile may degrade in the environment at least under anaerobic conditions(SRC).

Environmental Bioconcentration · 1 item

An estimated BCF of 3 was calculated for 3-pyridinecarbonitrile(SRC), using a log Kow of 0.36(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).

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. 3-Pyridinecarbonitrile is included on this list.

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
QT3030000
hs_code
29333999
risk_code
22-36/37/38

Chemistry & industry

Uses & manufacturing

Uses · 3 items

Used for organic synthesis; [HSDB]

Org synthesis

CHEM INT, EG, FOR NICOTINYL ALCOHOL & NIACINAMIDE

U.S. Production · 2 items

2023: <75,000 lb

(1980) PROBABLY GREATER THAN 2.27X10+6 GRAMS

Methods of ManufacturingVAPOR PHASE AMMOXIDATION OF 3-METHYLPYRIDINE WITH AMMONIA IN THE PRESENCE OF AIR
General Manufacturing Information3-Pyridinecarbonitrile: ACTIVE

Applications

Uses3-Cyanopyridine is used in the preparation of arylthiazolines and arylimidazolines via dibromodimethylhydantoin-catalyzed condensation of aryl nitriles with ethylene diamine or aminoethanethiol.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]

Additional notes

DefinitionChEBI: A nitrile that is pyridine substituted by a cyano group at position 3.

Related reactions

199 records

Linked notes

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