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Glutaronitrile

HCID 10994
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
544-13-8
Standard SMILES
N#CCCCC#N
InChIKey
ZTOMUSMDRMJOTH-UHFFFAOYSA-N
Molecular formula
C5H6N2
Average molar mass
94.11 g/mol
Monoisotopic mass
94.0530982

Overview

Glutaronitrile is a chemical compound of cyanide.

Names & identifiers

Preferred name
Glutaronitrile
IUPAC
pentanedinitrile
English name
Glutaronitrile
Molecular formula
C5H6N2
Molecular weight
94.11

Names & synonyms

GlutaronitrilePENTANEDINITRILE544-13-81,3-DicyanopropaneGlutarodinitrileGlutaric acid dinitrile1,3-TrimethylenedinitrilePyrotartaric acid nitrileTrimethylene dicyanideGlutaric dinitrileNSC 3807UNII-01ZI68F3CQ
Show more names
GlutaronitrleutaronitriLPentanedinitrlieGlutaronitrile>1,3-Dicyanopopane.
EINECS 208-861-601ZI68F3CQBRN 1738385AI3-07024NSC-3807GLUTARONITRILE [MI]4-02-00-01941 (Beilstein Handbook Reference)DTXSID6060266

Database identifiers

CAS
544-13-8
PubChem CID
10994
DTXSID
DTXSID6060266
UNII
01ZI68F3CQ
EC Number
208-861-6
Nikkaji
J54.244J

Properties

Computed structural properties

XLogP
-0.7
Topological polar surface area
47.6 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
7
Formal charge
0
Complexity
104

Experimental & physicochemical properties

SpringerMaterials PropertiesSchoenflies notation
LogP-0.72

Physicochemical properties

Melting point
29 °C · −29 °C(lit.)
Boiling point
285 · 285-287 °C(lit.)
Density
0.995 g/mL · 0.995 g/mL at 25 °C(lit.)
refractive index
20 · n20/D 1.434(lit.)
Flash point
230 °F · >230 °F
storage temp.
30 °C · Store below +30°C.
solubility
2 O: · H2O: soluble
form
clear liquid
color
Colorless to Light yellow
Water Solubility
soluble
Sensitive
Hygroscopic
Merck
14 · 14,4474

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 · 4 items

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P261, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P317, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 44 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationPentanedinitrile: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 3 (100%)

Toxicology

Treatment · 1 item

Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (L97)

Health Effects · 1 item

Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97)

Exposure RoutesOral (L96) ; inhalation (L96) ; dermal (L96)

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)

Uses & manufacturing

General Manufacturing InformationPentanedinitrile: ACTIVE
Applications · 2 items

UsesChemical intermediate

UsesGlutaronitrile can be used as: An electrolyte additive in high energy/power Li-ion batteries. A glutarate ligand source to prepare zinc glutarate (ZnGA) by reacting with zinc perchlorate hexahydrate. A reactant to synthesize pentanedithioamide by reacting with Lawesson′s reagent in the presence of boron trifluoride etherate (BF3.OEt2).

Upstream & downstream products

Upstream raw materials

1,2-Dibromopropane

Downstream products

Diethyl glutarateGlutaric acid1,5-Diaminopentane5-(4-Methoxyphenyl)-5-oxovaleronitrile

Related reactions

2 records
New reaction record
HRID 538088 reaction equation
HRID 538088As reactantuspto-grants-2014_10
HRID 1910464 reaction equation
HRID 1910464As reactantuspto-grants-2013_12

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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BRN
1738385 · 1738385
Henry's Law Constant
7.8 · 7.8×102 mol/(m3Pa) at 25℃, Plyasunov et al. (2006)
InChI
1S/C5H6N2/c6-4-2-1-3-5-7/h1-3H2
InChIKey
ZTOMUSMDRMJOTH-UHFFFAOYSA-N
SMILES
N#CCCCC#N
CAS DataBase Reference
544 · 544-13-8(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
1 ZI68F3CQ · 01ZI68F3CQ
NIST Chemistry Reference
Glutaronitrile(544-13-8)
EPA Substance Registry System
Pentanedinitrile (544-13-8)
UNSPSC Code
12352100 · 12352100
NACRES
22 · NA.22
Symbol(GHS)
6 · GHS06
Signal word
Danger
Hazard statements
301 · H301-H315-H319-H335
Precautionary statements
501 · P501-P270-P261-P271-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P310+P330-P304+P340+P312-P403+P233-P405
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes
Xn
Risk Statements
20 · 20/21/22-36/38
Safety Statements
36 · 36/37-36/37/39-26
RIDADR
2810 · UN 2810 6.1/PG 3
WGK Germany
3 · 3
RTECS
3500000 · YI3500000
F
3 · 3-10
TSCA
TSCA listed
HazardClass
6.1 · 6.1
PackingGroup
III
HS Code
29269090 · 29269090
Storage Class
6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
3 Oral · Acute Tox. 3 Oral
Limited Quantities
5 L · 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Toxicity Summary · 1 item

Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)

Signs and SymptomsCyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (L96, L97)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

F
3-10
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
rtecs
YI3500000
ridadr
UN 2810 6.1/PG 3
hs_code
29269090
risk_code
20/21/22-36/38
Signal word
Danger
Symbol(GHS)
GHS06
hazard_code
Xn
safety_code
36/37-36/37/39-26
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
H301-H315-H319-H335
Limited Quantities
5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Hazard Classifications
Acute Tox. 3 Oral
Precautionary statements
P501-P270-P261-P271-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P310+P330-P304+P340+P312-P403+P233-P405