Diethoxyacetonitrile

Base Information

• Chemical Name: Diethoxyacetonitrile
• CAS No.: 6136-93-2
• Molecular Formula: C6H11NO2
• Molecular Weight: 129.159
• Hs Code.: 2926909090
• European Community (EC) Number: 228-111-1
• DSSTox Substance ID: DTXSID0064121
• Nikkaji Number: J227.318G
• Wikidata: Q72468866
• Mol file: 6136-93-2.mol

Synonyms:Diethoxyacetonitrile;2,2-diethoxyacetonitrile;6136-93-2;Acetonitrile, diethoxy-;MFCD00043982;Acetonitrile, 2,2-diethoxy-;EINECS 228-111-1;cyanodiethoxymethane;Diethoxyacetonitrile, 97%;SCHEMBL442012;DTXSID0064121;STL451532;AKOS015843383;AB01964;CS-W013452;AS-18953;BP-11391;SY036025;AM20100495;FT-0635990;EN300-69752;Z1117910237

Chemical Property of Diethoxyacetonitrile

Chemical Property:

• Vapor Pressure: 1.73mmHg at 25°C
• Melting Point: ?19-?18 °C(lit.)
• Refractive Index: n20/D 1.4(lit.)
• Boiling Point: 167.1 °C at 760 mmHg
• Flash Point: 49.4 °C
• PSA: 42.25000
• Density: 0.963 g/cm³
• LogP: 0.90908
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 129.078978594
• Heavy Atom Count: 9
• Complexity: 98.9

Purity/Quality:

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

Diethoxyacetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 10-20/21/22-36/37/38
• Safety Statements: 16-26-27-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(C#N)OCC
• Uses: Diethoxyacetonitrile may be used in the preparation of methyl 5-diethoxymethylimidazole-4-carboxylate, via anionic cycloaddition reaction with methyl isocyanoacetate.

Technology Process of Diethoxyacetonitrile

There total 10 articles about Diethoxyacetonitrile 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%

2,2-diethoxy-ethanamine (645-36-3) → 2,2-diethoxyacetonitrile (6136-93-2)

Guidance literature:

With pyridine; Oxone; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; Pyridine hydrobromide; In dichloromethane; at 20 ℃; for 12h; Green chemistry;

DOI:10.1002/chem.201600549

Reference yield: 89.0%

diethoxyacetamide (61189-99-9) → 2,2-diethoxyacetonitrile (6136-93-2)

Guidance literature:

With trichlorophosphate; In pyridine; at -18 ℃; for 0.5h;

DOI:10.1246/bcsj.58.352

Reference yield: 84.0%

N,N-dicyclohexylaminoacetonitrile + orthoformic acid triethyl ester (122-51-0) → 2,2-diethoxyacetonitrile (6136-93-2)

Guidance literature:

With Trichloro(trifluoromethylsulfonyloxy)silane; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere; Sealed tube;

DOI:10.1002/ejoc.201501084

upstream raw materials:

diethoxyacetamide

hydrogen cyanide

orthoformic acid triethyl ester

ethanol

Downstream raw materials:

2,2-diethoxy-ethanimidic acid methyl ester

methyl 5-diethoxymethylimidazole-4-carboxylate

1,1-Diethoxy-4-phenyl-but-3-yn-2-one

N-[(4-bromo-2-chloro-phenyl)methyl]-2,2-diethoxy-acetamidine

Refernces

• 1、 Kotani, Shunsuke,Sakamoto, Midori,Osakama, Kazuki,Nakajima, Makoto. "A Sterically Congested α-Cyanoamine as a Cyanating Reagent: Cyanation of Acetals and Orthoesters". supporting information. p. 6606 - 6609. Retrieved 2015/10/29.
• 2、 Stambouli, Abdelhamid,Hamedi-Sangsari, Farid,Amouroux, Roger,Chastrette, Francine,Blanc, Alain,Mattioda, Georges. "Les dialkoxy-2,2 ethanals, synthons difonctionnels a deux carbones : preparation par acetalisation du glyoxal et quelques applications en synthese". . p. 95 - 100. Retrieved 2007/10/02.