Cyclobutene-1,2-dicarboxylic acid dimethyl ester

Base Information

• Chemical Name: Cyclobutene-1,2-dicarboxylic acid dimethyl ester
• CAS No.: 1128-10-5
• Molecular Formula: C8H10 O4
• Molecular Weight: 170.165
• Hs Code.: 2917209090
• Mol file: 1128-10-5.mol

Synonyms:1-Cyclobutene-1,2-dicarboxylicacid, dimethyl ester (6CI,7CI,8CI,9CI); 1,2-Bis(methoxycarbonyl)cyclobut-1-ene;1,2-Dicarbomethoxycyclobutene; Dimethyl 1-cyclobutene-1,2-dicarboxylate;Dimethyl cyclobutene-1,2-dicarboxylate; NSC 249256

Chemical Property of Cyclobutene-1,2-dicarboxylic acid dimethyl ester

Chemical Property:

• Vapor Pressure: 0.109mmHg at 25°C
• Melting Point: 45-46℃
• Boiling Point: 60-68℃ (0.2 Torr)
• Flash Point: 104.6°C
• PSA: 52.60000
• Density: 1.255g/cm³
• LogP: 0.42280
• Storage Temp.: 2-8°C

Purity/Quality:

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

DimethylCyclobut-1-ene-1,2-dicarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Cyclobutene-1,2-dicarboxylic acid dimethyl ester

There total 13 articles about Cyclobutene-1,2-dicarboxylic acid dimethyl 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: 42.0%

dimethyl 2,5-dibromohexanedioate (868-72-4,53490-47-4,124819-17-6) → 1,2-dicarbomethoxycyclobutene (1128-10-5)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 120 ℃; for 36h; Large scale;

Reference yield:

cis-1,2-cyclobutane dicarboxylic anhydride (4462-96-8) → 1,2-dicarbomethoxycyclobutene (1128-10-5)

Guidance literature:

Multi-step reaction with 2 steps

1: red phosphorus; bromine / Behandeln des Reaktionsprodukts mit Methanol

2: potassium iodide; ethanol

With phosphorus; ethanol; bromine; potassium iodide;

DOI:10.1039/jr9570001733

Reference yield:

1,2-Dichlor-cyclobutan-1,2-dicarbonitril (3496-67-1) → 1,2-dicarbomethoxycyclobutene (1128-10-5)

Guidance literature:

Multi-step reaction with 4 steps

1: Raney-Co / ethanol

2: aq. H₂SO₄ / dioxane

3: SOCl₂

4: Et₃N

With thionyl chloride; sulfuric acid; triethylamine; Raney-Co; In 1,4-dioxane; ethanol;

DOI:10.1002/hlca.19730560839

upstream raw materials:

1,2-dibromo-cyclobutane-1r,2c-dicarboxylic acid dimethyl ester

(+/-)-1,2-dibromo-cyclobutane-1r,2t-dicarboxylic acid dimethyl ester

methanol

cyclobut-1-ene-1,2-dicarbonyl chloride

Downstream raw materials:

(+/-)-1-benzylsulfanyl-cyclobutane-1r,2t-dicarboxylic acid diamide

Refernces

• 1、 Bellus,Von Bredow,Sauter,Weis. "[4+2] Cycloadditions of 1,2 dicyanocyclobutene and its thermal ring opening to 2,3 dicyanobutadiene 1,3". . p. 3004 - 3038. Retrieved 2007/10/06.