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Sigma-Aldrich

Glutaronitrile

99%

Synonym(s):

1,3-Dicyanopropane

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About This Item

Linear Formula:
NC(CH2)3CN
CAS Number:
Molecular Weight:
94.11
Beilstein/REAXYS Number:
1738385
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

99%

form

liquid

refractive index

n20/D 1.434 (lit.)

bp

285-287 °C (lit.)

mp

−29 °C (lit.)

solubility

H2O: soluble
alcohol: soluble
chloroform: soluble

density

0.995 g/mL at 25 °C (lit.)

SMILES string

N#CCCCC#N

InChI

1S/C5H6N2/c6-4-2-1-3-5-7/h1-3H2

InChI key

ZTOMUSMDRMJOTH-UHFFFAOYSA-N

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Application

Glutaronitrile (1,3-Dicyanopropane) was used in the preparation of dicarbonyl compounds.
Glutaronitrile 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).

pictograms

Skull and crossbones

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 3 Oral

wgk_germany

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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γ-butyrolactone and glutaronitrile as 5 V electrolyte additive and its electrochemical performance for LiNi0. 5Mn1. 5O4
Xu Yun, et al.
Journal of alloys and compounds, 698, 207-214 (2017)
M Zachariah et al.
Physical chemistry chemical physics : PCCP, 17(24), 16053-16057 (2015-06-02)
We probe the ionic conduction and the molecular dynamics in a pure and lithium-salt doped dinitrile molecular plastic crystal. While the diffusion of the Li(+) ions is decoupled from the molecular reorientational dynamics, in the undoped plastic crystal the temperature
Xingyong Wang et al.
The Journal of organic chemistry, 78(11), 5273-5281 (2013-05-15)
A palladium-catalyzed addition of potassium aryltrifluoroborates to aliphatic nitriles has been developed, leading to a wide range of alkyl aryl ketones with moderate to excellent yields. Moreover, several dinitriles (e.g., malononitrile, glutaronitrile, and adiponitrile) were applicable to this process for
Francesco Endrizzi et al.
Dalton transactions (Cambridge, England : 2003), 44(31), 13835-13844 (2015-05-01)
The complex formation between a cyclic ligand glutarimidoxioxime (denoted as HL(III) in this paper) and UO2(2+) is studied by potentiometry and microcalorimetry. Glutarimidoxioxime (HL(III)), together with glutarimidedioxime (H2L(I)) and glutardiamidoxime (H2L(II)), belongs to a family of amidoxime derivatives with prospective
Andreas Hofmann et al.
International journal of molecular sciences, 16(9), 20258-20276 (2015-09-08)
In this study, promising electrolytes for use in Li-ion batteries are studied in terms of interacting and wetting polyethylene (PE) and particle-coated PE separators. The electrolytes are characterized according to their physicochemical properties, where the flow characteristics and the surface

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