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3-Cyanopyridine

HCID 79
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Basic information

CAS
100-54-9
Standard SMILES
N#Cc1cccnc1
InChIKey
GZPHSAQLYPIAIN-UHFFFAOYSA-N
Molecular formula
C6H4N2
Average molar mass
104.11 g/mol
Monoisotopic mass
104.03744814

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 propertiesFilling in

XLogP
0.2
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 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

Flash Point87 °C
Boiling Point206.9 °C
Melting Point51 °C
Vapor Pressure · 2 items

0.29 [mmHg]

0.296 mm Hg @ 25 °C

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

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)

REACH registered substance: Nicotinonitrile (EC: 202-863-0)

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.

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.

Upstream & downstream products

Upstream raw materials

NicotinamideN-PHENYL-1-NAPHTHYLAMINE HYDROBROMIDE4-Chlorobenzaldehyde

Downstream products

Nicotinic acid3-(TERT-BUTOXYCARBONYLAMINO-METHYL)-PYRIDINE-2-CARBOXYLIC ACIDNicotinamide2-(3-PYRIDYL)-1,3-THIAZOLE-4-CARBOXYLIC ACID

Related reactions

199 records
New reaction record
HRID 17764 reaction equation
HRID 17764As reactantuspto-grants-2010_06
HRID 21702 reaction equation
HRID 21702As reactantuspto-grants-1995_06
HRID 21703 reaction equation
HRID 21703As reactantuspto-grants-1995_06
HRID 21704 reaction equation
HRID 21704As reactantuspto-grants-1995_06
HRID 29512 reaction equation
HRID 29512As reactantuspto-grants-2008_09
HRID 42281 reaction equation
HRID 42281As reactantuspto-grants-2013_09
HRID 42282 reaction equation
HRID 42282As reactantuspto-grants-2013_09
HRID 42283 reaction equation
HRID 42283As reactantuspto-grants-2013_09
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Compound notes

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Henry's Law ConstantHenry's Law constant = 2.74X10-7 atm-cu m/mole @ 25 °C
Physical Description · 2 items

Other Solid

Colorless liquid; [Hawley] Off-white crystalline solid; [MSDSonline]

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
solubility
140 g/l · 140g/l
form
Crystalline Mass, Crystals or Chunks
pka
1 · pK1:1.45(+1) (25°C)
color
Colorless or white to yellow
Water Solubility
140 g/L · 140 g/L (20 ºC)
BRN
107711 · 107711
Henry's Law Constant
3.6 · 3.6×101 mol/(m3Pa) at 25℃, Abraham et al. (1994)
Exposure limits
25 mg/m3 · NIOSH: IDLH 25 mg/m3
Stability
Incompatible with strong oxidizing agents, strong reducing agents, strong acids, strong bases.
InChI
1S/C6H4N2/c7-4-6-2-1-3-8-5-6/h1-3,5H
InChIKey
GZPHSAQLYPIAIN-UHFFFAOYSA-N
SMILES
N#Cc1cccnc1
CAS DataBase Reference
100 · 100-54-9(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
64 V0K6260 · X64V0K6260
NIST Chemistry Reference
3 · 3-Pyridinecarbonitrile(100-54-9)
EPA Substance Registry System
3 · 3-Pyridinecarbonitrile (100-54-9)
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
5 · GHS05,GHS07
Signal word
Danger
Hazard statements
302 · H302-H315-H318
Precautionary statements
264 · P264-P270-P280-P301+P312-P302+P352-P305+P351+P338
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xn
Risk Statements
22 · 22-36/37/38
Safety Statements
22 · 22-24/25-36/37/39-26
WGK Germany
3 · 3
RTECS
3030000 · QT3030000
TSCA
TSCA listed
HS Code
29333999 · 29333999
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 OralEye · Acute Tox. 4 OralEye Dam. 1Skin Irrit. 2
Hazardous Substances Data
100 · 100-54-9(Hazardous Substances Data)
REACH Registrations
Active
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).

Volatilization from Water/Soil · 1 item

The Henry's Law constant for 3-pyridinecarbonitrile is 2.74X10-7 atm-cu m/mole(1). This Henry's Law constant indicates that 3-pyridinecarbonitrile is not expected to volatilize from water and moist soil surfaces(2). 3-Pyridinecarbonitrile is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.296 mm Hg(3).

Environmental Abiotic Degradation · 1 item

The rate constant for the vapor-phase reaction of 3-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 concn of 5X10+5 hydroxyl radicals per cu cm(1). 3-Pyridinecarbonitrile is expected to undergo slow hydrolysis in the environment based upon the slow hydrolysis of other aromatic nitriles, eg, benzonitrile(2). 3-Pyridinecarbonitrile is also not expected to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm)(SRC).

Probable Routes of Human ExposureOccupational exposure to 3-pyridinecarbonitrile may occur through inhalation and dermal contact with this compound at workplaces where 3-pyridinecarbonitrile is produced or used. (SRC)
Environmental Fate/Exposure Summary · 1 item

3-Pyridinecarbonitrile's production and use in organic synthesis may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 0.296 mm Hg at 25 °C indicates 3-pyridinecarbonitrile will exist solely as a vapor in the ambient atmosphere. Vapor-phase 3-pyridinecarbonitrile will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 246 days. If released to soil, 3-pyridinecarbonitrile is expected to have very high mobility based upon an estimated Koc of 37. Volatilization from moist soil surfaces is not expected to be an important fate process based upon a Henry's Law constant of 2.74X10-7 atm-cu m/mole. If released into water, 3-pyridinecarbonitrile is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. The maximum pseudo-first-order rate constant and half-life for 3-pyridinecarbonitrile in an anoxic sediment slurry were 9.41 per day and 1.7 hrs, respectively which suggests that 3-pyridinecarbonitrile may rapidly biodegrade in the environment at least under anaerobic conditions(SRC). Volatilization from water surfaces is not expected to be an important fate process based upon this compound's Henry's Law constant. An estimated BCF of 3 suggests the potential for bioconcentration in aquatic organisms is low. Chemical hydrolysis is expected to be slow. Occupational exposure to 3-pyridinecarbonitrile may occur through inhalation and dermal contact with this compound at workplaces where 3-pyridinecarbonitrile is produced or used. (SRC)

EPA Provisional Peer-Reviewed Toxicity Values · 3 items

Nicotinonitrile

PDF Document

2004

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
Signal word
Danger
Symbol(GHS)
GHS05,GHS07
hazard_code
Xn
safety_code
22-24/25-36/37/39-26
Storage Class
11 - Combustible Solids
Hazard statements
H302-H315-H318
REACH Registrations
Active
Hazard Classifications
Acute Tox. 4 OralEye Dam. 1Skin Irrit. 2
Precautionary statements
P264-P270-P280-P301+P312-P302+P352-P305+P351+P338
Hazardous Substances Data
100-54-9(Hazardous Substances Data)
3-[(N-(TERT-BUTYLOXYCARBONYL)AMINO)METHYL]PYRIDINE
3-(Aminomethyl)pyridine
3-CYANOPYRIDIN-4-YLBORONIC ACID
3-PYRIDINECARBOXAMIDINE
3-AMINOMETHYL-PYRIDINE-2-CARBOXYLIC ACID
2-chloro-5-cyanopyridine
3-AMIDINOPYRIDINIUM CHLORIDE
3-Pyridinecarboxaldehyde
ETHYL 4-(TRIFLUOROMETHYL)-2-(PYRIDIN-2-YL)PYRIMIDINE-5-CARBOXYLATE
Benzyltriphenylphosphonium chloride
3-Pyridinemethanol
3-PYRIDYLAMIDOXIME
3-[(Methylamino)methyl]pyridine
Methyl 2-(3-cyanopyridin-4-yl)acetate
2-(2-PYRIDINYL)-4-(TRIFLUOROMETHYL)-5-PYRIMIDINECARBOXYLIC ACID
3,3'-DIPICOLYLAMINE

Additional notes

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