Ethyl 3-bromo-2-oxocyclohexanecarboxylate

Base Information

• Chemical Name: Ethyl 3-bromo-2-oxocyclohexanecarboxylate
• CAS No.: 30132-23-1
• Molecular Formula: C9H13 Br O3
• Molecular Weight: 249.104
• Hs Code.: 2918300090
• European Community (EC) Number: 250-065-6
• DSSTox Substance ID: DTXSID60952551
• Nikkaji Number: J249.930D
• Mol file: 30132-23-1.mol

Synonyms:Ethyl 3-bromo-2-oxocyclohexanecarboxylate;30132-23-1;ethyl 3-bromo-2-oxocyclohexane-1-carboxylate;Cyclohexanecarboxylicacid, 3-bromo-2-oxo-, ethyl ester;ethyl 6-bromocyclohexanone-2-carboxylate;EINECS 250-065-6;C9H13BrO3;Cyclohexanecarboxylic acid, 3-bromo-2-oxo-, ethyl ester;SCHEMBL1617437;C9-H13-Br-O3;2-carbethoxy-6-bromocyclohexanone;DTXSID60952551;2-bromo-6-carboethoxycyclohexanone;CS-M0083;2-bromo-6-(carbethoxy)-cyclohexanone;2-bromo-6-ethoxycarbonyl-cyclohexanone;AKOS005137985;AS-76071;ethyl?3-bromo-2-oxocyclohexanecarboxylate;Ethyl 3-bromo-2-oxo-cyclohexanecarboxylate;ethyl 3-bromo-2-oxocyclohexane-carboxylate;FT-0690125;A23014;D77362;EN300-127399;2-Oxo-3-bromocyclohexanecarboxylic acid ethyl ester;J-521177;3-bromo-2-oxo-cyclohexane carboxylic acid ethyl ester

Chemical Property of Ethyl 3-bromo-2-oxocyclohexanecarboxylate

Chemical Property:

• Vapor Pressure: 0.00148mmHg at 25°C
• Refractive Index: 1.5280
• Boiling Point: 295.9°Cat760mmHg
• PKA: 10.39±0.40(Predicted)
• Flash Point: 132.7°C
• PSA: 43.37000
• Density: 1.453g/cm³
• LogP: 1.68220
• Storage Temp.: -20°C Freezer
• Solubility.: Acetone; Dichloromethane; Ethyl Acetate; Methanol
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 248.00481
• Heavy Atom Count: 13
• Complexity: 215

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl3-Bromo-2-oxocyclohexanecarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1CCCC(C1=O)Br
• Uses: Ethyl 3-Bromo-2-oxocyclohexanecarboxylate is an intermediate in the synthesis of trans-1,2-Dimethylcyclopentane (D464925). trans-1,2-Dimethylcyclopentane was found in sedimentary rocks and was one of the hydrocarbons used to determine its maturation history.

Technology Process of Ethyl 3-bromo-2-oxocyclohexanecarboxylate

There total 6 articles about Ethyl 3-bromo-2-oxocyclohexanecarboxylate 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: 100.0%

ethyl 2-oxocyclohexane carboxylate (1655-07-8) → ethyl 3-bromo-2-oxocyclohexanecarboxylate (30132-23-1)

Guidance literature:

With bromine; In diethyl ether; at 0 - 20 ℃; for 1.5h;

DOI:10.1021/jm050522v

Reference yield:

ethyl 2-oxocyclohexane carboxylate (1655-07-8) → ethyl 3-bromo-2-oxocyclohexanecarboxylate (30132-23-1)

Guidance literature:

Multi-step reaction with 2 steps

1: p-toluenesulfonic acid monohydrate / benzene / 120 h / Heating

2: 1.) Br₂, N(C₂H₅)3, 2.) 5percent HCl / 1.) CH₂Cl₂, -95 deg C, 2 h, 2.) CH₂Cl₂, room temperature, overnight

With hydrogenchloride; bromine; triethylamine; toluene-4-sulfonic acid; In benzene;

Reference yield:

ethyl-2-(1-piperidinyl)-2-cyclohexenecarboxylate (35244-51-0) → ethyl 3-bromo-2-oxocyclohexanecarboxylate (30132-23-1)

Guidance literature:

With hydrogenchloride; bromine; triethylamine; Yield given. Multistep reaction; 1.) CH₂Cl₂, -95 deg C, 2 h, 2.) CH₂Cl₂, room temperature, overnight;

upstream raw materials:

ethyl 2-oxocyclohexane carboxylate

ethyl-2-(1-piperidinyl)-2-cyclohexenecarboxylate

ethyl-2-(1-piperidinyl)-1-cyclohexenecarboxylate

bromine

Downstream raw materials:

2-(3-Chloro-phenylamino)-4,5,6,7-tetrahydro-benzothiazole-4-carboxylic acid ethyl ester

2-(4-Bromo-phenylamino)-4,5,6,7-tetrahydro-benzothiazole-4-carboxylic acid ethyl ester

9-benzyl-6,7-dimethoxy-1,2,3,4-tetrahydro-carbazole-4-carboxylic acid

2-o-Tolylamino-4,5,6,7-tetrahydro-benzothiazole-4-carboxylic acid ethyl ester

Refernces

• 1、 Sheehan,Mumaw. "-". . p. 2127. Retrieved 1950.
• 2、 Hagiwara, Koichi,Tabuchi, Toshiki,Urabe, Daisuke,Inoue, Masayuki. "Expeditious synthesis of the fused hexacycle of puberuline C: Via a radical-based cyclization/translocation/cyclization process". . p. 4372 - 4378. Retrieved 2016.
• 3、 -. "Tetrahydrocarbazole small molecular organic compounds, application thereof to preparation of antibacterial medicines and preparation method thereof". Paragraph 0160; 0161. . Retrieved 2018/04/03.
• 4、 Krall, Jacob,Brygger, Benjamin M.,Sigureardóttir, Sara B.,Ng, Clarissa K. L.,Bundgaard, Christoffer,Kehler, Jan,Nielsen, Birgitte,Bek, Toke,Jensen, Anders A.,Fr?lund, Bente. "Discovery of α-Substituted Imidazole-4-acetic Acid Analogues as a Novel Class of ρ1γ-Aminobutyric Acid Type A Receptor Antagonists with Effect on Retinal Vascular Tone". . p. 2299 - 2310. Retrieved 2016/10/25.