4-Pentenoic acid, 2-cyano-, ethyl ester

Base Information

• Chemical Name: 4-Pentenoic acid, 2-cyano-, ethyl ester
• CAS No.: 3509-01-1
• Molecular Formula: C8H11NO2
• Molecular Weight: 153.181
• Hs Code.: 2926909090
• Mol file: 3509-01-1.mol

Synonyms:Ethyl-2-cyanopent-4-enoate;ethyl 2-cyano-4-pentenoate;ethyl (prop-2'-en-1'-yl)cyanoacetate;ethyl α-allylcyanoacetate;

Chemical Property of 4-Pentenoic acid, 2-cyano-, ethyl ester

Chemical Property:

• PSA: 50.09000
• LogP: 1.26538

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Pentenoic acid, 2-cyano-, ethyl ester

There total 2 articles about 4-Pentenoic acid, 2-cyano-, ethyl ester 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:

(?-allyl)(dicarbonylnitrosyl)iron + sodium cyanoacetic acid ethyl ester (18852-51-2) + sodium diethylmalonate (996-82-7) → sodium tricarbonylnitrosylferrate(-1) + (2-propenyl)propanedioic acid diethyl ester (2049-80-1) + 2-cyano-pent-4-enoic acid ethyl ester (3509-01-1) + diallylmalonic acid diethyl ester (3195-24-2) + ethyl 2-allyl-2-cyanopent-4-enoate (3509-02-2)

Guidance literature:

In tetrahydrofuran; suspension of Fe-complex and NaNCCHCO2Et in THF at 20°C for 15 min; then addn. of NaCH(CO2Et)2 in THF; agitation at 20°C for 24 h; NaFe(CO)3(NO) detected by IR; distribution of products detd. by GC;;

DOI:10.1016/0022-328X(88)83066-3

Reference yield:

ethyl 2-cyanoacetate (105-56-6) → (2-propenyl)propanedioic acid diethyl ester (2049-80-1) + 2-cyano-pent-4-enoic acid ethyl ester (3509-01-1) + ethyl 2-allyl-2-cyanopent-4-enoate (3509-02-2)

Guidance literature:

Yield given. Multistep reaction. Yields of byproduct given;

DOI:10.1016/0022-328X(88)83066-3

Reference yield: 89.0%

2-cyano-pent-4-enoic acid ethyl ester (3509-01-1) + ortho-nitrofluorobenzene (1493-27-2,127723-77-7) → ethyl 2-cyano-2-(2-nitrophenyl)-4-pentenoate

Guidance literature:

With triethylsilane; t-Bu-P₄; In hexane; N,N-dimethyl-formamide; at 80 ℃; for 3h;

DOI:10.1039/b700140a

upstream raw materials:

ethyl 2-cyanoacetate

sodium cyanoacetic acid ethyl ester

sodium diethylmalonate

Downstream raw materials:

4-Pentenenitrile

5-Allyl-2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-4-N-dimethylformamidine-6-oxocytidine

5-Allyl-5'-O-(4,4'-dimethoxytriphenylmethyl)-4-N-dimethylformamidine-2'-O-methyl-6-oxocytidine

5-Allyl-5'-O-(4,4'-dimethoxytriphenylmethyl)-4-N-dimethylformamidine-6-oxocytidine