cis-Cyclobutane-1,2-dicarboxylic acid

Base Information

• Chemical Name: cis-Cyclobutane-1,2-dicarboxylic acid
• CAS No.: 1461-94-5
• Molecular Formula: C₆H₈O₄
• Molecular Weight: 144.127
• Hs Code.: 2917200090
• European Community (EC) Number: 624-348-3
• DSSTox Substance ID: DTXSID00424909
• Nikkaji Number: J80.118F
• Wikidata: Q82237673
• Mol file: 1461-94-5.mol

Synonyms:cis-Cyclobutane-1,2-dicarboxylic acid;1461-94-5;(1R,2S)-cyclobutane-1,2-dicarboxylic acid;1,2-Cyclobutanedicarboxylic acid, cis-;(1S,2R)-cyclobutane-1,2-dicarboxylic acid;1,2-Cyclobutanedicarboxylic acid, (1R,2S)-rel-;cis-1,2-Cyclobutanedicarboxylic Acid;(1R,2S)-rel-Cyclobutane-1,2-dicarboxylic acid;MFCD00019263;SCHEMBL709492;AMY7603;DTXSID00424909;AKOS006376609;CS-W016394;1,2-Cyclobutanedicarboxylic acid, (Z)-;1alpha,2alpha-Cyclobutanedicarboxylic acid;P15779;A855436;J-008202;cis-Cyclobutane-1,2-dicarboxylic acid, >=97.0% (T)

Chemical Property of cis-Cyclobutane-1,2-dicarboxylic acid

Chemical Property:

• Vapor Pressure: 9.54E-07mmHg at 25°C
• Melting Point: 133-139oC
• Boiling Point: 377.7oC at 760 mmHg
• PKA: pK1:3.90 ;pK2:5.89 (25°C)
• Flash Point: 196.4oC
• PSA: 74.60000
• Density: 1.509g/cm3
• LogP: 0.18180
• Storage Temp.: 2-8°C
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 144.04225873
• Heavy Atom Count: 10
• Complexity: 155

Purity/Quality:

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

cis-Cyclobutane-1,2-dicarboxylic acid ≥97.0% (T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,Xi
• Hazard Codes: C,Xi
• Statements: 34-36/37/38
• Safety Statements: 26-36/37/39-45-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC(C1C(=O)O)C(=O)O
• Isomeric SMILES: C1C[C@@H]([C@@H]1C(=O)O)C(=O)O

Technology Process of cis-Cyclobutane-1,2-dicarboxylic acid

There total 45 articles about cis-Cyclobutane-1,2-dicarboxylic acid 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:

3,3,4,4-Tetrachloro-cyclobut-1-ene-1,2-dicarboxylic acid (89799-95-1) → cis-cyclobutane-1,2-dicarboxylic acid (1124-13-6,3396-14-3,17224-72-5,58616-94-7,58616-97-0,1461-94-5)

Guidance literature:

With hydrogen; platinum(IV) oxide; In water;

Reference yield:

cyclobutane-1,1,2,2-tetracarboxylic acid → cis-cyclobutane-1,2-dicarboxylic acid (1124-13-6,3396-14-3,17224-72-5,58616-94-7,58616-97-0,1461-94-5)

Guidance literature:

at 180 ℃; Behandeln mit Acetylchlorid und Kochen des erhaltenen Anhydrids mit Wasser;

Reference yield:

dimethyl 1-cyanocyclobutane-1,2-dicarboxylate (14132-45-7) → cis-cyclobutane-1,2-dicarboxylic acid (1124-13-6,3396-14-3,17224-72-5,58616-94-7,58616-97-0,1461-94-5)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. HCl / 12 h / Heating

2: 180 °C / water pump

With hydrogenchloride;

DOI:10.1016/S0957-4166(02)00757-7

upstream raw materials:

cis-1,2-divinylcyclobutane

1,2-bis-methanesulfonyl-cyclobutane-1,2-dicarboxylic acid diamide

all-cis-3,4-Dibrom-cyclobutan-dicarbonsaeure-(1,2)-anhydrid

3,3,4,4-Tetrachloro-cyclobut-1-ene-1,2-dicarboxylic acid

Downstream raw materials:

3-oxabicyclo[3.2.0]heptane-2,4-dione

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

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

cis-1,2-cyclobutane dicarboxylic anhydride

Refernces

• 1、 -. "MACROCYCLIC SPIROETHERS AS MCL-1 INHIBITORS". Paragraph 0747; 0748. . Retrieved 2020/07/31.
• 2、 Earl, Harold A.,Stirling, Charles J. M.. "Elimination and Addition Reactions. Part 43. Eliminative Fission of Cyclobutanes and the Relationship between Strain and Reactivity in Cyclobutanes and Cyclopropanes". . p. 1273 - 1280. Retrieved 2007/10/02.