Valeronitrile

Base Information

• Chemical Name: Valeronitrile
• CAS No.: 110-59-8
• Molecular Formula: C5H9N
• Molecular Weight: 83.1332
• Hs Code.: 29332100
• European Community (EC) Number: 203-781-8
• UN Number: 3273
• UNII: X44H3R47D4
• DSSTox Substance ID: DTXSID3026275
• Nikkaji Number: J5.095D
• Wikipedia: Pentanenitrile
• Wikidata: Q27293542
• Metabolomics Workbench ID: 48874
• ChEMBL ID: CHEMBL1503158
• Mol file: 110-59-8.mol

Synonyms:n-valeronitrile

Chemical Property of Valeronitrile

Chemical Property:

• Appearance/Colour: Clear liquid
• Vapor Pressure: 7.0 hPa (20 °C)
• Melting Point: -96 °C(lit.)
• Refractive Index: n20/D 1.397(lit.)
• Boiling Point: 141.7 °C at 760 mmHg
• Flash Point: 40.6 °C
• PSA: 23.79000
• Density: 0.795 g/cm³
• LogP: 1.70018
• Storage Temp.: Store below +30°C.
• Solubility.: 10.0g/l
• Water Solubility.: 0.1-0.5 g/100 mL at 22.5 ºC
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 83.073499291
• Heavy Atom Count: 6
• Complexity: 57.6
• Transport DOT Label: Flammable Liquid Poison

Purity/Quality:

99% ^*data from raw suppliers

Valeronitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 10-25-2017/10/25
• Safety Statements: 36/37/39-45-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: CCCCC#N
• Uses: Valeronitrile is used as building block in organic synthesis. Product Data Sheet Solvent. Valeronitrile is used in the preparation of valeric acid. It is also used to enhance the nitrilase activity in many strains.

Technology Process of Valeronitrile

There total 104 articles about Valeronitrile 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: 81.0%

valeraldoxime (5775-76-8,5780-42-7,628-79-5) + dimethylbromosulphonium bromide (50450-21-0) → pentanonitrile (110-59-8) + dimethyl sulfoxide (67-68-5,8070-53-9)

Guidance literature:

In acetonitrile; at 20 ℃; for 4.5h;

DOI:10.1016/j.tetlet.2009.07.100

Reference yield: 76.0%

N'-hydroxypentanimidamide (67015-06-9) → pentanonitrile (110-59-8) + pentamide (626-97-1)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In water; acetonitrile; at 20 ℃; for 0.666667h;

DOI:10.3998/ark.5550190.0011.209

Reference yield: 40.4%

Cyclopentanone oxime (1192-28-5) → pentanonitrile (110-59-8) + δ-chlorovaleronitrile (6280-87-1) + cyclopentanone (120-92-3)

Guidance literature:

With phosphorus pentachloride; 1-butyl-3-methylimidazolium Tetrafluoroborate; at 80 ℃; for 2h;

DOI:10.1016/S0040-4039(00)01974-2

upstream raw materials:

1-bromo-butane

sodium cyanide

butyl para-toluenesulfonate

potassium cyanide

Downstream raw materials:

tri-n-butyl-carbinol

nonanone-5

4-propylheptane

4-Cyan-4-propylheptan

Refernces

• 1、 Peng, Jiajian,Deng, Youquan. "Catalytic Beckmann rearrangement of ketoximes in ionic liquids". . p. 403 - 405. Retrieved 2001.
• 2、 Nagaki, Aiichiro,Yamashita, Hiroki,Hirose, Katsuyuki,Tsuchihashi, Yuta,Yoshida, Jun-ichi. "Alkyllithium Compounds Bearing Electrophilic Functional Groups: A Flash Chemistry Approach". . p. 4027 - 4030. Retrieved 2019.
• 3、 SUGIMOTO,FUJITA,SHIGEMATSU,AYADA. "A new method for preparation of alkylnitriles from alkyl halide and alkylammonium cyanide.". . p. 427 - 429. Retrieved 1962.
• 4、 Limburg, Bart,Gloaguen, Yann,de Bruijn, Hans M.,Drent, Eite,Bouwman, Elisabeth. "Palladium-Catalyzed Isomerization/(Cyclo)carbonylation of Pentenamides: a Mechanistic Study of the Chemo- and Regioselectivity". . p. 2961 - 2971. Retrieved 2017.
• 5、 Hart-Davis, Jason,Battioni, Pierrette,Boucher, Jean-Luc,Mansuy, Daniel. "New catalytic properties of iron porphyrins: Model systems for cytochrome P450-catalyzed dehydration of aldoximes". . p. 12524 - 12530. Retrieved 1998.
• 6、 Smiley,Arnold. "". . p. 257. Retrieved 1960.
• 7、 -. "Method for preparing valeronitrile through hydrogenation of pentenenitrile". Paragraph 0032-0036. . Retrieved 2021/07/21.
• 8、 Sarvi, Iraj,Zahedi, Ehsan. "Zinc Oxide/Graphene Oxide as a Robust Active Catalyst for Direct Oxidative Synthesis of Nitriles from Alcohols in Water". . . Retrieved 2021/08/30.