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Sigma-Aldrich

Glutaronitrile

99%

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Synonym(s):
1,3-Dicyanopropane
Linear Formula:
NC(CH2)3CN
CAS Number:
544-13-8
Molecular Weight:
94.11
Beilstein:
1738385
EC Number:
208-861-6
MDL number:
MFCD00001970
PubChem Substance ID:
24847973
NACRES:
NA.22

Quality Level

200

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
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

233.6 °F

Flash Point(C)

112 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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C Cabezas et al.
Astronomy and astrophysics, 636 (2020-05-28)
Nitriles constitute almost 15% of the molecules observed in the interstellar medium (ISM), surprisingly only two dinitriles have been detected in the ISM so far. The lack of astronomical detections for dinitriles may be partly explained by the absence of
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)
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
Hydrothermal synthesis of single-crystalline zinc glutarate and its structural determination
Kim Jong-Seong, et al.
Chemistry of Materials, 16(16), 2981-2983 (2004)
The BF3.OEt2-Assisted Conversion of Nitriles into Thioamides with Lawesson?s Reagent
Nagl Michael, et al.
Synthesis, 2008(24), 4012-4018 (2008)
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