Cyclobutane-1,2-dicarboxylic anhydride

Base Information

• Chemical Name: Cyclobutane-1,2-dicarboxylic anhydride
• CAS No.: 4462-96-8
• Molecular Formula: C6H6O3
• Molecular Weight: 126.112
• Hs Code.: 2917209090
• NSC Number: 148995,134999,119923
• DSSTox Substance ID: DTXSID30963250
• Nikkaji Number: J1.492.880D
• Mol file: 4462-96-8.mol

Synonyms:1,2-Cyclobutanedicarboxylicanhydride (6CI,7CI,8CI);1,2-Cyclobutanedicarboxylic acid anhydride;NSC119923;NSC 134999;NSC 148995;cis-1,2-Cyclobutanedicarboxylic anhydride;

Chemical Property of Cyclobutane-1,2-dicarboxylic anhydride

Chemical Property:

• Melting Point: 73-76 °C
• Refractive Index: 1.581
• Boiling Point: 271.5 °C at 760 mmHg
• Flash Point: 139.4 °C
• PSA: 43.37000
• Density: 1.412 g/cm³
• LogP: 0.09600
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 126.031694049
• Heavy Atom Count: 9
• Complexity: 165

Purity/Quality:

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

Perhydrocyclobuta[c]furan-1,3-dione ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2C1C(=O)OC2=O

Technology Process of Cyclobutane-1,2-dicarboxylic anhydride

There total 16 articles about Cyclobutane-1,2-dicarboxylic anhydride 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: 96.0%

cyclobut-3-ene-1,2-dicarboxylic acid anhydride (10374-07-9) → cis-1,2-cyclobutane dicarboxylic anhydride (4462-96-8)

Guidance literature:

With hydrogen; palladium on activated charcoal;

DOI:10.1016/S0040-4039(00)95703-4

Reference yield: 84.0%

maleic anhydride (108-31-6) + ethene (74-85-1) → 3-oxabicyclo[3.2.0]heptane-2,4-dione (4462-96-8)

Guidance literature:

With benzophenone; In ethyl acetate; at 25 ℃; under 9000.9 Torr; Concentration; Temperature; Reagent/catalyst; Flow reactor; UV-irradiation;

DOI:10.1021/acs.oprd.8b00375

Reference yield: 80.0%

(RR,SS)-trans-1,2-cyclobutanedicarboxylic acid (3396-14-3) → 3-oxabicyclo[3.2.0]heptane-2,4-dione (4462-96-8)

Guidance literature:

With acetic anhydride; at 150 ℃;

upstream raw materials:

cyclobutane-1,1,2-tricarboxylic acid

cyclobut-3-ene-1,2-dicarboxylic acid anhydride

cis-cyclobutane-1,2-dicarboxylic acid

(+/-)-(1S,2S)-cyclobutane-1,2-dicarboxylic acid

Downstream raw materials:

(+/-)-cis-2-benzoyl-cyclobutane-carboxylic acid-⁽¹⁾

(1R,2S)-(2-hydroxymethylcyclobutyl)methanol

cis-cyclobutane-1,2-dicarboxylic acid

(1R,2S)-cyclobutane-1,2-diylbis(methylene) diacetate

Refernces

• 1、 Bielawski, Christopher W.,Lee, Stanfield Y.,Seo, Jinwon. "Hydrogenated Poly(Dewar benzene): A Compact Cyclic Olefin Polymer with Enhanced Thermomechanical Properties". . . Retrieved 2020.
• 2、 Williams, Jason D.,Nakano, Momoe,Gérardy, Romaric,Rincón, Juan A.,De Frutos, óscar,Mateos, Carlos,Monbaliu, Jean-Christophe M.,Kappe, C. Oliver. "Finding the Perfect Match: A Combined Computational and Experimental Study toward Efficient and Scalable Photosensitized [2 + 2] Cycloadditions in Flow". supporting information. p. 78 - 87. Retrieved 2019/01/24.