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{{Short description|Hypothetical molecule with the formula HC(OH)3}}
{{redirect-distinguish|Methanetriol|Methanethiol}}
{{Chembox
{{Chembox
|Verifiedfields = changed
⚫
| verifiedrevid = 430724043
|Watchedfields = changed
⚫
| ImageFile = Methanetriol.svg
⚫
|verifiedrevid = 476994446
⚫
| ImageFile_Ref = {{Chemboximage|correct|??}}
⚫
|ImageFile = Methanetriol.svg
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| ImageSize = 121
⚫
|ImageFile_Ref = {{Chemboximage|correct|??}}
⚫
| ImageName = Stereo skeletal formula of orthoformic acid
⚫
|ImageSize = 121
| IUPACName = Orthoformic acid
⚫
|ImageName = Stereo skeletal formula of orthoformic acid
| SystematicName = Methanetriol<ref name="pubchem.ncbi.nlm.nih.gov">{{Cite web | last = | first = | title = Methanetriol - PubChem | url = http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5231666&loc=ec_rcs | publisher =NCBI | date = | accessdate = 22 April 2013 }}</ref>
|PIN = Methanetriol<ref name="pubchem.ncbi.nlm.nih.gov">{{Cite web | last = | first = | title = Methanetriol - PubChem | url = https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5231666&loc=ec_rcs | publisher =NCBI| accessdate = 22 April 2013}}</ref>
| OtherNames = Trihydroxymethane
|OtherNames = Orthoformic acid<br>Trihydroxymethane
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo = 463-78-5
| CASNo_Ref = {{cascite|correct|??}}
|CASNo = 463-78-5
|CASNo_Ref = {{cascite|correct|CAS}}
|UNII_Ref = {{fdacite|correct|FDA}}
⚫
| PubChem = 5231666
|UNII = WIU6G972U6
| PubChem_Ref = {{Pubchemcite|correct|PubChem}}
⚫
|PubChem = 5231666
| ChemSpiderID = 4401409
|ChemSpiderID = 4401409
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| SMILES = OC(O)O
| StdInChI = 1S/CH4O3/c2-1(3)4/h1-4H
|SMILES = OC(O)O
|StdInChI = 1S/CH4O3/c2-1(3)4/h1-4H
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| InChI = 1/CH4O3/c2-1(3)4/h1-4H
|InChI = 1/CH4O3/c2-1(3)4/h1-4H
| StdInChIKey = RLAHWVDQYNDAGG-UHFFFAOYSA-N
|StdInChIKey = RLAHWVDQYNDAGG-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| InChIKey = RLAHWVDQYNDAGG-UHFFFAOYAS
|InChIKey = RLAHWVDQYNDAGG-UHFFFAOYAS
}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| Formula = {{chem2|HC(OH)3}}
| C = 1
| H = 4
| C=1 | H=4 | O=3
| O = 3
| ExactMass = 64.016043994 g mol<sup>-1</sup>
}}
}}
}}
}}


'''Orthoformic acid''' or '''methanetriol''' is a hypothetical compound with the formula HC(OH)<sub>3</sub>. In this molecule, the central carbon is bound to one [[hydrogen]] and three [[hydroxyl]] groups.
'''Orthoformic acid''' or '''methanetriol''' is a chemical compound with the formula {{chem2|HC(OH)3|auto=1}}. In this molecule, the central carbon atom is bound to one [[hydrogen]] and three [[hydroxyl]] groups.


Orthoformic acid was long held to be a [[hypothetical chemical compound]], as it was expected to decompose instantly into [[formic acid]] and water, making it too unstable to isolate or observe.<ref name=Bohm>{{cite journal |last1=Bohm |first1=Stanislav |last2=Antipova |first2=Diana |last3=Kuthan |first3=Josef |title=Study of methanetriol decomposition mechanisms |journal=International Journal of Quantum Chemistry |date=15 October 1996 |volume=60 |issue=2 |pages=649–655 |doi=10.1002/(SICI)1097-461X(1996)60:2<649::AID-QUA3>3.0.CO;2-X}}</ref> However, observation was shown to be possible in 2024, when it was identified by [[mass spectrometry]]. This involved the electron-irradiation of a frozen mixture of [[methanol]] and [[oxygen]].<ref name=Marks>>{{cite journal |last1=Marks |first1=Joshua H. |last2=Bai |first2=Xilin |last3=Nikolayev |first3=Anatoliy A. |last4=Gong |first4=Qi’ang |last5=Zhu |first5=Cheng |last6=Kleimeier |first6=N. Fabian |last7=Turner |first7=Andrew M. |last8=Singh |first8=Santosh K. |last9=Wang |first9=Jia |last10=Yang |first10=Jiuzhong |last11=Pan |first11=Yang |last12=Yang |first12=Tao |last13=Mebel |first13=Alexander M. |last14=Kaiser |first14=Ralf I. |title=Methanetriol─Formation of an Impossible Molecule |journal=Journal of the American Chemical Society |date=17 April 2024 |doi=10.1021/jacs.4c02637}}</ref>
Orthoformic acid has not been isolated to date, and is believed to be unstable, decomposing into [[water]] and [[formic acid]].<ref name=Bohm>Böhm, S., Antipova, D. and Kuthan, J. (1996), "Study of methanetriol decomposition mechanisms". ''International Journal of Quantum Chemistry'', volume 60, pages 649–655. {{doi|10.1002/(SICI)1097-461X(1996)60:2<649::AID-QUA3>3.0.CO;2-X}}</ref>


==Esters==
==Esters==
{{main|Ortho ester}}
Methanetriol [[ester]]s, known as '''orthoformates''', are well known and commercially available.<ref name=Sah37>Peter P. T. Sah, Tsu Sheng Ma (1932), ""ESTERS OF ORTHOFORMIC ACID". ''J. Am. Chem. Soc.'', volume 54, issue 7, pages 2964–2966 {{doi|10.1021/ja01346a048}}</ref><ref name=Post43>H. W. Post (1943), "The Chemistry of the Aliphatic Orthoesters", Reinhold, 188 pages</ref> Like [[acetal]]s, they are stable towards bases but easily hydrolyzed in acidic conditions to the alcohol and an ester of formic acid. They are used are as mild dehydrating agent. Especially well known are [[trimethyl orthoformate]], [[triethyl orthoformate]], and [[triisopropyl orthoformate]].
Methanetriol [[ester]]s, known as '''orthoformates''' or '''ortho esters''', are well known and commercially available.<ref name=Sah37>{{cite journal |last1=Sah |first1=Peter P. T. |last2=Ma |first2=Tsu Sheng |title=ESTERS OF ORTHOFORMIC ACID |journal=Journal of the American Chemical Society |date=July 1932 |volume=54 |issue=7 |pages=2964–2966 |doi=10.1021/ja01346a048}}</ref><ref name=Post43>H. W. Post (1943), "The Chemistry of the Aliphatic Orthoesters", Reinhold, 188 pages</ref> Like [[acetal]]s, they are stable towards bases but easily [[hydrolyzed]] in [[Acid|acidic conditions]] to the [[alcohol (chemistry)|alcohol]] and an ester of [[formic acid]]. They are used as mild [[Dehydration reaction|dehydrating agent]]s. Especially well known are [[trimethyl orthoformate]], [[triethyl orthoformate]], and [[triisopropyl orthoformate]].


==See also ==
==See also ==
* [[Methanol]]
* [[Methanol]]
* [[Methanediol]]
* [[Methanediol]]
* [[Orthocarbonic acid]] (methanetetraol)
* [[Orthoacetic acid]]
* [[Orthocarbonic acid]] (methanetetrol)


==References==
==References==
{{Reflist}}
{{Reflist}}


⚫
{{DEFAULTSORT:Orthoformic Acid}}
{{Alcohol-stub}}

⚫
{{DEFAULTSORT:Orthoformic Acid, Trihydroxymethane, Methanetriol}}

[[Category:Organic acids]]
[[Category:Organic acids]]
[[Category:Dehydrating agents]]
[[Category:Dehydrating agents]]
[[Category:Orthoesters]]
[[Category:Hypothetical chemical compounds]]

Latest revision as of 23:58, 21 May 2024

"Methanetriol" redirects here. Not to be confused with Methanethiol.
Orthoformic acid
Stereo skeletal formula of orthoformic acid
Names
Preferred IUPAC name
Methanetriol[1]
Other names
Orthoformic acid
Trihydroxymethane
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/CH4O3/c2-1(3)4/h1-4H checkY
    Key: RLAHWVDQYNDAGG-UHFFFAOYSA-N checkY
  • InChI=1/CH4O3/c2-1(3)4/h1-4H
    Key: RLAHWVDQYNDAGG-UHFFFAOYAS
  • OC(O)O
Properties
HC(OH)3
Molar mass 64.040 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Orthoformic acid or methanetriol is a chemical compound with the formula HC(OH)3. In this molecule, the central carbon atom is bound to one hydrogen and three hydroxyl groups.

Orthoformic acid was long held to be a hypothetical chemical compound, as it was expected to decompose instantly into formic acid and water, making it too unstable to isolate or observe.[2] However, observation was shown to be possible in 2024, when it was identified by mass spectrometry. This involved the electron-irradiation of a frozen mixture of methanol and oxygen.[3]

Esters

[edit]
Main article: Ortho ester

Methanetriol esters, known as orthoformates or ortho esters, are well known and commercially available.[4][5] Like acetals, they are stable towards bases but easily hydrolyzed in acidic conditions to the alcohol and an ester of formic acid. They are used as mild dehydrating agents. Especially well known are trimethyl orthoformate, triethyl orthoformate, and triisopropyl orthoformate.

See also

[edit]

References

[edit]
  1. ^ "Methanetriol - PubChem". NCBI. Retrieved 22 April 2013.
  2. ^ Bohm, Stanislav; Antipova, Diana; Kuthan, Josef (15 October 1996). "Study of methanetriol decomposition mechanisms". International Journal of Quantum Chemistry. 60 (2): 649–655. doi:10.1002/(SICI)1097-461X(1996)60:2<649::AID-QUA3>3.0.CO;2-X.
  3. ^ >Marks, Joshua H.; Bai, Xilin; Nikolayev, Anatoliy A.; Gong, Qi’ang; Zhu, Cheng; Kleimeier, N. Fabian; Turner, Andrew M.; Singh, Santosh K.; Wang, Jia; Yang, Jiuzhong; Pan, Yang; Yang, Tao; Mebel, Alexander M.; Kaiser, Ralf I. (17 April 2024). "Methanetriol─Formation of an Impossible Molecule". Journal of the American Chemical Society. doi:10.1021/jacs.4c02637.
  4. ^ Sah, Peter P. T.; Ma, Tsu Sheng (July 1932). "ESTERS OF ORTHOFORMIC ACID". Journal of the American Chemical Society. 54 (7): 2964–2966. doi:10.1021/ja01346a048.
  5. ^ H. W. Post (1943), "The Chemistry of the Aliphatic Orthoesters", Reinhold, 188 pages
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