Octyl cyanoacetate

Base Information

• Chemical Name: Octyl cyanoacetate
• CAS No.: 15666-97-4
• Molecular Formula: C11H19NO2
• Molecular Weight: 197.277
• Hs Code.: 29299090
• European Community (EC) Number: 629-113-9
• DSSTox Substance ID: DTXSID30402694
• Nikkaji Number: J1.386.225G
• Wikidata: Q72497521
• Mol file: 15666-97-4.mol

Synonyms:Octyl 2-cyanoacetate;Octyl cyanoacetate;15666-97-4;n-Octyl cyanoacetate;Acetic acid, cyano-, octyl ester;MFCD00075425;octylcyanoacetate;2-cyanoacetic acid octyl ester;octyl 2-cyanoethanoate;Octyl cyanoacetate, 99%;Cyanoacetic acid, octyl ester;SCHEMBL634649;DTXSID30402694;BCP12781;Acetic acid, 2-cyano-, octyl ester;AKOS015843130;AS-19997;SY037984;CS-0152152;FT-0659706;A809762;J-009330

Chemical Property of Octyl cyanoacetate

Chemical Property:

• Vapor Pressure: 0.000258mmHg at 25°C
• Refractive Index: n20/D 1.449(lit.)
• Boiling Point: 323.7 °C at 760 mmHg
• PKA: 3.11±0.10(Predicted)
• Flash Point: 109.481 °C
• PSA: 50.09000
• Density: 0.953 g/cm³
• LogP: 2.80378
• Storage Temp.: 2-8°C
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 9
• Exact Mass: 197.141578849
• Heavy Atom Count: 14
• Complexity: 193

Purity/Quality:

99% ^*data from raw suppliers

Octyl2-Cyanoacetate ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCOC(=O)CC#N
• Uses: Octyl cyanoacetate may be used in the preparation of a small molecule with a dithienosilole core for the high efficiency solution-processed organic photovoltaic cells. It may be used in the preparation of small molecule DCAO3TBDT with the acceptor-donor-acceptor (A-D-A) structure and benzo[1,2-b:4,5-b′]dithiophene (BDT) as the central building block.

Technology Process of Octyl cyanoacetate

There total 5 articles about Octyl cyanoacetate 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: 95.0%

octanol (111-87-5) + cyanoacetic acid (372-09-8) → octyl 2-cyanoacetate (15666-97-4)

Guidance literature:

With magnesium sulfate; zinc(II) perchlorate; at 80 ℃; for 40h;

DOI:10.1002/adsc.200404171

Reference yield: 65.0%

n-octyl triflate (71091-89-9) + dicyclohexylammonium α-cyanoacrylate → n-octyl 2-cyanoacrylate + di-n-octyl ether (629-82-3) + CHF3O3S*C12H23N (1215021-90-1) + octyl 2-cyanoacetate (15666-97-4) + 2-cyanoacrylic acid (15802-18-3)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 22 ℃; Product distribution / selectivity;

Reference yield:

octyl (3S)-(+)-3-hydroxypentanoate (92445-22-2) → octyl 2-cyanoacetate (15666-97-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 97.2 percent / p-TsOH / CH₂Cl₂ / 1 h / Ambient temperature

2: LiAlH₄ / diethyl ether / 4 h / Ambient temperature

3: 86.8 percent / c.c.H₂SO₄ / benzene / 3 h / Heating

With lithium aluminium tetrahydride; sulfuric acid; toluene-4-sulfonic acid; In diethyl ether; dichloromethane; benzene;

DOI:10.1016/S0040-4020(01)96410-5

upstream raw materials:

octanol

ethyl 2-cyanoacetate

cyanoacetic acid

octyl (3S)-(+)-3-hydroxypentanoate

Downstream raw materials:

malononitrile

Refernces

• 1、 Yang, Jianzhong,He, Wenhan,Denman, Kimberly,Jiang, Ying-Bing,Qin, Yang. "A molecular breakwater-like tetrapod for organic solar cells". . p. 2108 - 2119. Retrieved 2015/02/05.
• 2、 Bartoli,Boeglin,Bosco,Locatelli,Massaccesi,Melchiorre,Sambri. "Highly efficient solvent-free condensation of carboxylic acids with alcohols catalysed by zinc perchlorate hexahydrate, Zn(ClO4) 2·6 H2O". . p. 33 - 38. Retrieved 2007/10/03.