3-Pentenenitrile

Base Information

• Chemical Name: 3-Pentenenitrile
• CAS No.: 16529-66-1
• Molecular Formula: C5H7 N
• Molecular Weight: 81.1173
• European Community (EC) Number: 225-060-7,605-402-5
• UN Number: 3275
• UNII: 80L2GJH2P2
• DSSTox Substance ID: DTXSID901019314
• Nikkaji Number: J298.912C,J38.121G
• Wikidata: Q27269157
• Metabolomics Workbench ID: 123305
• ChEMBL ID: CHEMBL1322495
• Mol file: 16529-66-1.mol

Synonyms:4 pentenenitrile;4-pentenenitrile;trans-3-pentenenitrile

Chemical Property of 3-Pentenenitrile

Chemical Property:

• Vapor Pressure: 24.9 mm Hg ( 50 °C)
• Refractive Index: n20/D 1.422
• Boiling Point: 112°Cat760mmHg
• Flash Point: 28.5°C
• PSA: 23.79000
• Density: 0.827g/cm³
• LogP: 1.47618
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 81.057849228
• Heavy Atom Count: 6
• Complexity: 83.4
• Transport DOT Label: Poison Flammable Liquid

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Pentenenitrile, predominately trans 95% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 10-23/24/25-36/37/38-23-22
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: CC=CCC#N
• Isomeric SMILES: C/C=C/CC#N
• Uses: trans-3-Pentenenitrile can be used for insecticidal properties against insect pests of stored grains.

Technology Process of 3-Pentenenitrile

There total 41 articles about 3-Pentenenitrile 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: 17.8%

thiophene (188290-36-0,8014-23-1,25233-34-5) + buta-1,3-diene (106-99-0,130983-70-9,29406-96-0,9003-17-2) → 3-Pentenenitrile (16529-66-1) + 2-METHYL-3-BUTENENITRILE (16529-56-9)

Guidance literature:

With hydrogen isocyanide; copper(I) bromide;

Reference yield: 6.1%

2-METHYL-3-BUTENENITRILE (16529-56-9) → cis-2-pentenenitrile (25899-50-7) + 2-pentenenitrile (26294-98-4) + 3-Pentenenitrile (16529-66-1) + (Z)-2-methyl-2-butenenitrile (20068-02-4) + tiglonitrile (30574-97-1) + 4-Pentenenitrile (592-51-8) + (Z)-pent-2-enenitrile (16545-78-1)

Guidance literature:

With C₁₄H₃₂P₂*2H^(1-)*2Ni⁽¹⁺⁾; In decane; at 100 ℃; for 3h; Solvent; Temperature; Reagent/catalyst; Kinetics; Inert atmosphere;

DOI:10.1021/ja8000216

Reference yield:

hydrogen cyanide (74-90-8) + buta-1,3-diene (106-99-0,130983-70-9,29406-96-0,9003-17-2) → 2-pentenenitrile (13284-42-9) + 3-Pentenenitrile (16529-66-1) + 4-Pentenenitrile (592-51-8) + 2-METHYL-3-BUTENENITRILE (16529-56-9)

Guidance literature:

(Phosphite A)Ni(crotyl)CN; at 110 - 130 ℃; for 14 - 48.2h; under 5171.62 - 6723.1 Torr; Product distribution / selectivity;

upstream raw materials:

2-chloro-3-butene

hydrogen cyanide

(E)-diethyl (but-2-en-1-yl)malonate

(E)-1-Bromo-2-butene

Downstream raw materials:

5-methyl-dihydro-furan-2-one

5-methyl-5H-furan-2-one

dihydro-4-acetoxy-5-methyl-2(3H)-furanone

(E)-3-pentenoic acid

Refernces

• 1、 Bini, Laura,Houben, Erwin J.E.,Pidko, Evgeny A.,Müller, Christian,Vogt, Dieter. "Nickel-catalyzed isomerization of 2-methyl-3-butenenitrile to 3-pentenenitrile: A kinetic study using in situ FTIR-ATR spectroscopy". . p. 271 - 278. Retrieved 2010.
• 2、 Durig,Gounev,Zhen,Drew,Shen,Guirgis. "Raman and infrared spectra, conformational stability, normal coordinate analysis, vibrational assignment, and ab initio calculations of trans-3-pentenenitrile". . p. 221 - 234. Retrieved 2000.
• 3、 -. "AIR-STABLE NI(0)-OLEFIN COMPLEXES AND THEIR USE AS CATALYSTS OR PRECATALYSTS". Page/Page column 23. . Retrieved 2021/02/05.
• 4、 -. "PROCESS FOR ISOMERIZATION OF CIS-2-PENTENENITRILE TO 3-PENTENENITRILES". Paragraph 0066-0068. . Retrieved 2017/01/02.