1,4-Dicyanobutane

Base Information

• Chemical Name: 1,4-Dicyanobutane
• CAS No.: 111-69-3
• Deprecated CAS: 55462-97-0,68511-79-5
• Molecular Formula: C6H8N2
• Molecular Weight: 108.143
• Hs Code.: 29269090
• European Community (EC) Number: 203-896-3,270-153-8
• ICSC Number: 0211
• NSC Number: 7617
• UN Number: 2205
• UNII: SYT33B891I
• DSSTox Substance ID: DTXSID3021936
• Nikkaji Number: J2.456B
• Wikipedia: Adiponitrile
• Wikidata: Q84062
• ChEMBL ID: CHEMBL2132938
• Mol file: 111-69-3.mol

Synonyms:Adiponitrile(8CI);Adipic acid dinitrile;Adipic acid nitrile;Adipicdinitrile;Hexanedinitrile;Butanedicarbonitrile;NSC 7617;

Chemical Property of 1,4-Dicyanobutane

Chemical Property:

• Appearance/Colour: clear colorless to slightly yellow liquid
• Vapor Pressure: 0.01 mm Hg ( 40 °C)
• Melting Point: 1-3 °C(lit.)
• Refractive Index: 1.438
• Boiling Point: 296.1 °C at 760 mmHg
• Flash Point: 149 °C
• PSA: 47.58000
• Density: 0.945 g/cm³
• LogP: 1.59396
• Storage Temp.: Store below +30°C.
• Solubility.: 50g/l
• Water Solubility.: 90 g/L (20 ºC)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 108.068748264
• Heavy Atom Count: 8
• Complexity: 113
• Transport DOT Label: Poison

Purity/Quality:

98% ^*data from raw suppliers

Adipodinitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-36/37/38-36/38-23/25
• Safety Statements: 26-36-45-39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: C(CCC#N)CC#N
• Inhalation Risk: A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes and skin. Exposure could cause convulsions, unconsciousness and death. Medical observation is indicated.
• Effects of Long Term Exposure: The substance may have effects on the blood and adrenals. This may result in anaemia and tissue lesions.
• Uses: Adiponitrile is mainly used in the production of hexamethylenediamine for manufacturing nylon 6,6. Lesser uses include that in organic synthesis and in the preparation of adipoguanamine, which is used as an extractant for aromatic hydrocarbons. This chemical is an important intermediate for the manufacture of synthetic fiber.

Technology Process of 1,4-Dicyanobutane

There total 114 articles about 1,4-Dicyanobutane 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: 19.0%

3-pentenenitrile (4635-87-4) + 2-hydroxy-2-methylpropanenitrile (75-86-5) → 4-Pentenenitrile (592-51-8) + hexanedinitrile (111-69-3)

Guidance literature:

With Lewis acid; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; C₇₀H₈₄O₈P₂; In tetrahydrofuran; at 90 ℃; for 4h; Product distribution / selectivity;

Reference yield: 10.0%

3-pentenenitrile (4635-87-4) + 2-hydroxy-2-methylpropanenitrile (75-86-5) → 2-pentenenitrile (13284-42-9) + hexanedinitrile (111-69-3)

Guidance literature:

With Lewis acid; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; C₆₈H₈₀O₆P₂; In tetrahydrofuran; at 90 ℃; for 4h;

Reference yield:

hydrogen cyanide (74-90-8) + cis-2-pentenenitrile (25899-50-7) + 2-pentenenitrile (26294-98-4) + 3-Pentenenitrile (16529-66-1) + tiglonitrile (30574-97-1) + 4-Pentenenitrile (592-51-8) + (Z)-pent-2-enenitrile (16545-78-1) → pentanonitrile (110-59-8) + hexanedinitrile (111-69-3) + 2-methylglutaronitrile (4553-62-2) + 4-ethenylcyclohexene (100-40-3)

Guidance literature:

C₄₈H₅₂O₄P₂; (m-tolyl-O-)(p-tolyl-O-)2P; (m-tolyl-O-)2(p-tolyl-O-)P; tri-m-tolyl phosphite; tri-p-tolylphosphite; zinc(II) chloride; Product distribution / selectivity;

upstream raw materials:

1,4-dibromo-butane

potassium cyanide

1,4-Diiodobutane

Adipic acid

Downstream raw materials:

1,6-bis-(2,4,6-trihydroxy-phenyl)-hexane-1,6-dione

2-iminocyclopentanecarbonitrile

diisopentyl adipate

hexanediyldiformamide

Refernces

• 1、 Leonard,Barthel. "-". . p. 3098. Retrieved 1949.
• 2、 Rosen et al.. "". . p. 1425. Retrieved 1969.
• 3、 Fey, Natalie,Garland, Michael,Hopewell, Jonathan P.,McMullin, Claire L.,Mastroianni, Sergio,Orpen, A. Guy,Pringle, Paul G.. "Stable fluorophosphines: Predicted and realized ligands for catalysis". . p. 118 - 122. Retrieved 2012.
• 4、 Endo, Takeshi,Ageishi, Kentaro,Okawara, Makoto. "Reduction of Acrylonitrile in the Presence of Viologen Derivatives". . p. 4309 - 4310. Retrieved 1986.
• 5、 Maldonado, Ana G.,Hageman, Jos A.,Mastroianni, Sergio,Rothenberg, Gadi. "Backbone diversity analysis in catalyst design". . p. 387 - 396. Retrieved 2009.
• 6、 Agnes et al.. "". . p. 1515. Retrieved 1968.
• 7、 Park, Hwa-Kun,Kim, In Bum,Chin, Chong Shik. "1,4-DICYANOBUTENE-BRIDGED BINUCLEAR RHODIUM(I) COMPLEXES AND THEIR CATALYTIC ACTIVITIES". . p. 431 - 436. Retrieved 1987.
• 8、 Cook et al.. "-". . p. 3416. Retrieved 1974.
• 9、 Druliner, J. D.,Blackstone, R. C.. "STUDIES OF A COBALT-PROMOTED ACRYLONITRILE COUPLING REACTION". . p. 277 - 284. Retrieved 1982.
• 10、 -. "METHOD FOR PRODUCING NITRILE". Paragraph 0080; 0084. . Retrieved 2021/02/05.