Glutaronitrile

Base Information

• Chemical Name: Glutaronitrile
• CAS No.: 544-13-8
• Molecular Formula: C5H6 N2
• Molecular Weight: 94.116
• Hs Code.: 29269090
• European Community (EC) Number: 208-861-6
• NSC Number: 3807
• UNII: 01ZI68F3CQ
• DSSTox Substance ID: DTXSID6060266
• Nikkaji Number: J54.244J
• Wikipedia: Glutaronitrile
• Wikidata: Q3059923
• Mol file: 544-13-8.mol

Synonyms:Glutaronitrile;PENTANEDINITRILE;544-13-8;1,3-Dicyanopropane;Glutarodinitrile;Glutaric acid dinitrile;1,3-Trimethylenedinitrile;Pyrotartaric acid nitrile;Glutaric dinitrile;Trimethylene dicyanide;903903-26-4;NSC 3807;EINECS 208-861-6;BRN 1738385;UNII-01ZI68F3CQ;AI3-07024;01ZI68F3CQ;NSC-3807;4-02-00-01941 (Beilstein Handbook Reference);Glutaronitrle;MFCD00001970;Glutaronitrile, 99%;WLN: NC3CN;GLUTARONITRILE [MI];DTXSID6060266;NSC3807;AKOS000156040;LS-157460;FT-0626736;FT-0657164;G0072;D95363;EN300-300474;A830168;A843532;Q3059923;F0001-1431

Chemical Property of Glutaronitrile

Chemical Property:

• Appearance/Colour: clear colorless to pale yellow liquid.
• Vapor Pressure: 0.00251mmHg at 25°C
• Melting Point: -29 ºC
• Refractive Index: n20/D 1.434(lit.)
• Boiling Point: 285-287 ºC
• Flash Point: >230 °F
• PSA: 47.58000
• Density: 0.995
• LogP: 1.20386
• Storage Temp.: Store below +30°C.
• Sensitive.: Hygroscopic
• Solubility.: H2O: soluble
• Water Solubility.: soluble
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 94.053098200
• Heavy Atom Count: 7
• Complexity: 104

Purity/Quality:

Glutaronitrile ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22-36/38
• Safety Statements: 36/37-36/37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(CC#N)CC#N
• Uses: Chemical intermediate 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).

Technology Process of Glutaronitrile

There total 24 articles about Glutaronitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

potassium cyanide (151-50-8) + 1,3-dibromo-propane (109-64-8) → Glutaronitrile (544-13-8)

Guidance literature:

With 18-crown-6 ether; In acetonitrile; at 83 ℃; for 27h;

DOI:10.1002/hlca.19950780604

Reference yield: 86.0%

Glutaraldehyde (111-30-8,29257-65-6,79215-57-9) → Glutaronitrile (544-13-8)

Guidance literature:

With acetic acid; hydroxylamine-O-sulfonic acid; In water; at 50 ℃; for 6h;

DOI:10.1016/j.tetlet.2016.07.047

Reference yield: 83.0%

5-Oximinopentanenitrile → Glutaronitrile (544-13-8)

Guidance literature:

With triethylamine; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate; In ethyl acetate; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1055/s-0034-1378881

upstream raw materials:

gloutaric dichloride

(phenylsulfonyl)phosphorimidic trichloride

(E)-Pent-2-endinitril

ethanol

Downstream raw materials:

Undecandion-(4,8)

2,6-di(phenylimino)piperidine

glutaramidine

6-Phenyl-1,2,3,4-tetrahydropyridin-2-on

Refernces

• 1、 Quinn, Dylan J.,Haun, Graham J.,Moura-Letts, Gustavo. "Direct synthesis of nitriles from aldehydes with hydroxylamine-O-sulfonic acid in acidic water". supporting information. p. 3844 - 3847. Retrieved 2016/08/02.
• 2、 Poldy, Jacqueline,Peakall, Rod,Barrow, Russell A.. "Pheromones and analogs from Neozeleboria wasps and the orchids that seduce them: a versatile synthesis of 2,5-dialkylated 1,3-cyclohexanediones". . p. 2446 - 2449. Retrieved 2008/09/20.