Ethyl 2-amino-1-cyclopentene-1-carboxylate

Base Information

• Chemical Name: Ethyl 2-amino-1-cyclopentene-1-carboxylate
• CAS No.: 7149-18-0
• Molecular Formula: C8H13 N O2
• Molecular Weight: 155.197
• Hs Code.: 2922499990
• European Community (EC) Number: 696-381-1
• NSC Number: 52925
• DSSTox Substance ID: DTXSID10287860
• Nikkaji Number: J1.494.589J
• Wikidata: Q72472336
• Mol file: 7149-18-0.mol

Synonyms:7149-18-0;Ethyl 2-amino-1-cyclopentene-1-carboxylate;ethyl 2-aminocyclopent-1-enecarboxylate;2-Amino-cyclopent-1-enecarboxylic acid ethyl ester;ethyl 2-aminocyclopentene-1-carboxylate;ethyl 2-aminocyclopent-1-ene-1-carboxylate;NSC52925;Oprea1_395378;SCHEMBL3456275;1-Cyclopentene-1-carboxylic acid, 2-amino-, ethyl ester;2-amino-1-cyclopentenecarboxylate;DTXSID10287860;MFCD00216929;NSC-52925;AKOS015994949;AB04907;AT23521;BS-32726;ethyl trans-2-aminocyclopentenecarboxylate;A9357;CS-0151816;FT-0762811;Ethyl 2-amino-1-cyclopentene-1-carboxylate #;J-508039;Cyclopentene-1-carboxylic acid, 2-amino-, ethyl ester;Ethyl 2-amino-1-cyclopentene-1-carboxylate, AldrichCPR

Chemical Property of Ethyl 2-amino-1-cyclopentene-1-carboxylate

Chemical Property:

• Appearance/Colour: light yellow crystalline powder
• Vapor Pressure: 0.006mmHg at 25°C
• Melting Point: 57-60 °C
• Refractive Index: 1.4890 (estimate)
• Boiling Point: 272.5°Cat760mmHg
• Flash Point: 118.6°C
• PSA: 52.32000
• Density: 1.17g/cm³
• LogP: 1.64650
• Water Solubility.: soluble
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 155.094628657
• Heavy Atom Count: 11
• Complexity: 196

Purity/Quality:

99%, ^*data from raw suppliers

Ethyl2-Amino-1-cyclopentene-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(CCC1)N

Technology Process of Ethyl 2-amino-1-cyclopentene-1-carboxylate

There total 7 articles about Ethyl 2-amino-1-cyclopentene-1-carboxylate 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: 99.0%

2-ethoxycarbonyl-1-cyclopentanone (611-10-9) → ethyl 2-amino-1-cyclopentene-1-carboxylate (7149-18-0)

Guidance literature:

With ammonia; silica gel; at 20 ℃; for 0.166667h;

DOI:10.1081/SCC-120028364

Reference yield: 68.0%

4-Chlorobutyronitrile (628-20-6) + ethyl bromoacetate (105-36-2) → ethyl 2-amino-1-cyclopentene-1-carboxylate (7149-18-0) + (Z)-ethyl 2-(pyrrolidin-2-ylidene)acetate (35150-22-2)

Guidance literature:

4-Chlorobutyronitrile; ethyl bromoacetate; With methanesulfonic acid; zinc; In tetrahydrofuran; for 1h; Reflux; Inert atmosphere;

With potassium tert-butylate; In tetrahydrofuran; at 0 - 20 ℃; for 5h; chemoselective reaction; Inert atmosphere;

DOI:10.1021/jo201964a

Reference yield: 40.0%

ethyl bromoacetate (105-36-2) + 4-bromobutanenitrile (5332-06-9) → ethyl 2-amino-1-cyclopentene-1-carboxylate (7149-18-0)

Guidance literature:

With methanesulfonic acid; zinc; In tetrahydrofuran; for 8h; chemoselective reaction; Reflux; Inert atmosphere;

DOI:10.1021/jo201964a

upstream raw materials:

2-ethoxycarbonyl-1-cyclopentanone

diethyl adipate

ethyl 2-[(ethoxycarbonyl)amino]-1-cyclopentene-1-carboxylate

4-Chlorobutyronitrile

Downstream raw materials:

2,4-dihydroxy-6,7-dihydro-5H-[1]pyrindine-3-carboxylic acid ethyl ester

2,3-cyclopentenopyridine

(+/-)-trans-octahydro[1]pyrindine

2,4-dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine

Refernces

• 1、 He, Tian,Gao, Wen-Chao,Wang, Wei-Kun,Zhang, Chi. "Synthesis of oxazolidin-2-ones and imidazolidin-2-ones directly from 1,3-diols or 3-amino alcohols using iodobenzene dichloride and sodium azide". supporting information. p. 1113 - 1118. Retrieved 2014/04/03.
• 2、 Kim, Juhyun,Chun, Yusung,Shin, Hyunik,Lee, Sang-Gi. "Tandem transformations of nitriles into N-heterocyclic compounds by electrophilic trapping of Blaise reaction intermediates". experimental part. p. 1809 - 1817. Retrieved 2012/08/08.