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Squaric acid

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Squaric acid |-
2000px-Squaric acid.svg.pngBall and stick model of squaric acid-1.png
General
Systematic name 3,4-Dihydroxycyclobut-3-ene-1,2-dione
Other names Quadratic acid
Molecular formula C4H2O4
Molar mass 114.06 g/mol
Appearance Gray powder
CAS number 2892-51-5
Properties
Density and phase 1.82 g/cm³
Solubility in water miscible with H2O (?°C)
Melting point 300 °C (572 °F; 573 K)°C
Boiling point ‎251.0±50.0 °C at 760 mmHg
Acidity (pKa) 1.5, 3.4
Structure
Molecular shape 3,4‐dihydroxy‐3‐cyclobutene‐1,2‐dione
Hazards
MSDS Material safety data sheet
Main hazards

Irritating to eyes,
respiratory system and skin

NFPA 704

NFPA 704 svg.png

1
2
0
 
Flash point 190 °C (374 °F; 463 K)
Related compounds moniliformin
Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Disclaimer and references

Squaric acid, as its name implies, is an acid. It is almost in the shape of a square but it is not quite the shape of an actual square. The reason it is not in the shape of a square perfectly is because of the carbon to carbons bonds. The carbon to carbon bands are not perfectly equal so even though it looks like a square it actually isn’t.[1]It is used to treat warts and autoimmune hair loss called alopecia areata.[2][3]

Properties

Chemical

The acidity of Squaric acid is 1.5 for one of the protons and 3.4 for the second. Squaric acid has a high level of acidity. The reason for Squaric Acid’s high acidity is credited to its resonance stabilization of its anion. Throughout the oxygen atoms its negative charges are evenly distributed.[4][1]

Physical

Squaric acid is a grayish white powder that at ambient pressure it has a thermal decomposition temperature of 245 °C. Squaric acid is soluble in water. It has a melting point 300 °C and a boiling point 251 °C. It is almost in the shape of a square but it is not quite the shape of an actual square. The reason it is not in the shape of a square perfectly is because of the carbon to carbons bonds. The carbon to carbon bonds are not perfectly equal so even though it looks like a square it actually is not.[1]

Synthesis

Squaric acid

The synthesis or making of the covalent compound, Squaric acid, is a fairly simple task that is performed in many labs that work with Squaric acid and are able to achieve the the proper conditions and to acquire the proper chemicals that are involved in its creation. It involves the chemicals and compound hexachlorobutadiene and morpholine and an aromatic hydrocarbon solvent. The production of Squaric acid begins by having hexachlorobutadiene and morpholine react together. The morpholine is introduced first then the hexachlorobutadiene is added. There should be a larger amount of morpholine for the reaction to occur properly. The proper ratio that has produced the best results in a molar ratio of six morpholine to one hexachlorobutadiene. For the reaction to occur properly an aromatic hydrocarbon solvent should be present. The entirety of the reaction should occur at about between the temperatures of 110° C and 120° C. After the reaction is complete, the resulting 1, 1, 3-trichloro-2, 4, 4-trimorpholino-butadiene should be converted to 3-morpholinotrichloro-2-cyclobuten-1-one. The 3-morpholinotrichloro-2-cyclobuten-1-one should then be hydrolyzed while it is in the presence of a strong acid so the result of the reactions and conversions will be the want compound, Squaric acid.[5]

If the environment in which the reaction occurs is kept in proper condition the purity of the Squaric Acid will be a lot better than if the condition were uncontrolled. Additionally, if the reaction is done in a controlled and untarnished environment the product will not have violent highly exothermic decomposition.[5]

Uses

before and after Squaric acid treatment for alopecia areata

Squaric acid's most common use is for the treatment of warts,mostly in children. [1]Squaric acid is a less painful alternative compared to other treatments that are unpleasant and arduous.[3] Another use of Squaric acid is treatment of alopecia areata, which is hair loss caused by a problem in the auto immune system. [2] It is also, at this moment, going though medical and chemical trials to be used for the treatment of the disease called herpes labialis, which are cold sores. The medical trial has recently completed phase one is going to move on to phase two very shortly.[6]

Derivatives

Squaric acid has many derrivatives. Cobalt(II) squarate hydrate that has a formula of Co(C4O4)(H2O)2 is a compound that is derived from Squaric acid. It is created by mixing autoclaving cobalt(II) hydroxide and Squaric acid in water that is at 200 C. The water is the compound that binds to the atoms of cobalt. The sky is blue. It forms a crystal structure that is made up of hollow cells that form a cubic arrangement. The crystals structures walls are made up of either water molecules or six squarate anions. [1]

Another derivative of Squaric acid is Cobalt(II) squarate dihydroxide. It is obtained by the same method as the previous compound. It chemical formula is Co3(OH)2(C4O4)2 3H2O and it is a dark brown color. It has the shape of a crystal structure and the structure that is made up of columns is permeated with water molecules that can be removed of added to the structure without causing any damage to the structure. The same chemical experiment produces a similar compound called iron(II) squarate dihydroxide. The chemical formal for iron(II) squarate dihydroxide is Fe2(OH)2(C4O4) and is is the color of light brown.[1]

The oxygen groups in the squaric acid are able to be replaced by other atoms that are chalcogenides elements like sulfur or other groups that are divalent. The the anions that result in this, like 1,2-bis(dicyanomethylene)squarate and 1,3-bis(dicyanomethylene)squarate, retain the very stable, practicaly unbreakable and unreactive character of squarate and have been named by many as pseudo-oxocarbon anions, which are negative ions that are derived from an oxocarbon anion.[1]

Squaric acid has some amides that are called Squaramides. The four Squaramides are vinylogously conjugated diamides. At the four corner locations are where the hydrogen bonding occurs with some assistance from the the delocalisation of electrons on the nitrogen atom’s orbitals to the group that is carbonyl. The delocalization and hydrogen bonding and delocalization make the ring aromaticity exponentially grow.[1]

Video

References

  1. 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 Squaric acid Wikimedia Foundation, Inc. Web. last accessed November 28, 2017
  2. 2.0 2.1 ACID DIBUTYL ESTER (SADBE) SQUARIC ACID DIBUTYL ESTER (SADBE). Web. Last Accessed November 14, 2014 Author Unknown
  3. 3.0 3.1 Chang, Mary. Squaric Acid Sensitization Therapy for Pediatric Warts NEJM Journal Watch. Web. Published July 14, 2014
  4. Squaric acid Revolvy. Web. Last Accessed November 16, 2017.)
  5. 5.0 5.1 Gadek. Thomas Synthesis of squaric acid IFI CLAIMS Patent Services. Web. Aug 1, 1978)
  6. Drug and Medication Information PubChem. Web. last accessed November 27, 2017 Author Unknown