Diethyl (1-cyanoethyl)phosphonate

Base Information

• Chemical Name: Diethyl (1-cyanoethyl)phosphonate
• CAS No.: 29668-61-9
• Molecular Formula: C7H14 N O3 P
• Molecular Weight: 191.167
• Hs Code.: 2931900090
• European Community (EC) Number: 626-587-9
• NSC Number: 135193
• DSSTox Substance ID: DTXSID20300175
• Nikkaji Number: J410.642C
• Mol file: 29668-61-9.mol

Synonyms:Diethyl (1-cyanoethyl)phosphonate;29668-61-9;diethyl(1-cyanoethyl)phosphonate;2-diethoxyphosphorylpropanenitrile;Phosphonic acid, P-(1-cyanoethyl)-, diethyl ester;diethyl 1-cyanoethylphosphonate;NSC135193;(1-Cyanoethyl)phosphonic acid diethyl ester;Phosphonic acid, (1-cyanoethyl)-, diethyl ester;SCHEMBL124930;2-(diethylphosphono)propionitrile;2-diethoxyphosphoryl-propionitrile;diethyl(1-cyanoethyl)-phosphonate;DTXSID20300175;UMLWEPGSWQNXQX-UHFFFAOYSA-N;diethyl-(1-cyanoethyl)-phosphonate;MFCD01457302;AKOS015912609;AB09137;AT32504;NSC-135193;Diethyl (1-cyanoethyl)phosphonate, 97%;AS-68306;BENZYL-2,3,4,5,6-D5CHLORIDE;FT-0737593;Phosphonic acid,p-(1-cyanoethyl)-,diethyl ester;A929559;J-017594

Chemical Property of Diethyl (1-cyanoethyl)phosphonate

Chemical Property:

• Vapor Pressure: 0.004mmHg at 25°C
• Refractive Index: n20/D 1.432(lit.)
• Boiling Point: 279.5°Cat760mmHg
• Flash Point: 122.8°C
• PSA: 69.13000
• Density: 1.094g/cm³
• LogP: 2.16458
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 191.07113031
• Heavy Atom Count: 12
• Complexity: 210

Purity/Quality:

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

Diethyl (1-cyanoethyl)phosphonate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(C(C)C#N)OCC
• Uses: NSC 135193 is an intermediate in the synthesis of 4-(1-Cyanoethyl)-1,2,3,4-tetrahydronaphthalene-1-carbonitrile (C979545), a component of the crude extract resulting from studies on the antifungal activity of Citrullus colocynthis against various plant pathogenic fungi.Oligomeric product in thermal polymerization of acrylonitrile/styrene system.

Technology Process of Diethyl (1-cyanoethyl)phosphonate

There total 5 articles about Diethyl (1-cyanoethyl)phosphonate 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: 94.0%

diethyl chlorophosphate (814-49-3) + propiononitrile (107-12-0) → diethyl (1-cyanoethyl)phosphonate (29668-61-9)

Guidance literature:

propiononitrile; With lithium diisopropyl amide; In tetrahydrofuran; hexane; cyclohexane; at -78 ℃; for 0.25h; Inert atmosphere;

diethyl chlorophosphate; In tetrahydrofuran; hexane; cyclohexane; at -78 - 20 ℃; for 1.16667h; Inert atmosphere;

DOI:10.1021/ja3007929

Reference yield: 74.0%

diethyl 1-cyanomethylphosphonate (2537-48-6) + methyl iodide (74-88-4) → diethyl (1-cyanoethyl)phosphonate (29668-61-9)

Guidance literature:

diethyl 1-cyanomethylphosphonate; With sodium hydride; In 1,2-dimethoxyethane; at -10 ℃; for 0.75h;

methyl iodide; In 1,2-dimethoxyethane; at -10 - 20 ℃; for 17.5h;

DOI:10.1055/s-2000-6315

Reference yield:

triethyl phosphite (122-52-1) + 2-bromopropionitrile (19481-82-4) → diethyl (1-cyanoethyl)phosphonate (29668-61-9)

Guidance literature:

DOI:10.1021/jo00872a043

upstream raw materials:

triethyl phosphite

2-bromopropionitrile

diethyl chlorophosphate

propiononitrile

Downstream raw materials:

2-[3-Methoxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-(17E)-ylidene]-propionitrile

2-[(8R,9S,13S,14S)-3-Methoxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-(17E)-ylidene]-propionitrile

3β-t-Butoxy-20-carbonitrilpregna-5,17(20)-dien

3β-acetoxy-17-hydroxy-5α-pregnan-20-one

Refernces

Synthesis of C15,C14′-ring locked all-trans-β-carotene

10.1016/S0040-4039(02)00663-9

The study presents the synthesis of a C15,C14-ring locked all-trans-β-carotene analog, which is a significant compound due to its role in the production of retinoids, essential for vision and cell differentiation. The synthesis involved the use of various chemicals, including cyclohexenone-3-carboxaldehyde, diethyl(1-cyanoethyl)phosphonate, and β-ionone, which served as starting materials and reagents in the reaction sequences. Key reactions such as Wittig and HWE olefinations were employed to construct the carbon framework, with the final product being synthesized through bis-olefination with a C15 ylide bearing the ionone moiety. This unnatural β-carotene analog preserves molecular connectivity upon oxidative cleavage, which is crucial for isotopic labeling studies to determine the source of oxygen in retinal production. The synthesized compound will be used for enzymatic oxidation studies, furthering understanding of β-carotene-15,15'-dioxygenase (BCDOX), an enzyme vital for retinoid production.