Methoxymethanol

Methoxymethanol
Names
	Preferred IUPAC name Methoxymethanol
	Other names Formaldehyde methyl hemiacetal
Identifiers
CAS Number	4461-52-3;
3D model (JSmol)	Interactive image;
Beilstein Reference	1900186
ChEBI	CHEBI:46791;
ChemSpider	56311;
ECHA InfoCard	100.022.476
EC Number	224-722-2;
PubChem CID	62540;
UNII	9T7K15960E;
CompTox Dashboard (EPA)	DTXSID4027571;
	InChI InChI=1S/C2H6O2/c1-4-2-3/h3H,2H2,1H3 Key: VHWYCFISAQVCCP-UHFFFAOYSA-N;
	SMILES COCO;
Properties
Chemical formula	C2H6O2
Molar mass	62.068 g·mol−1
Density	0.948
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H226, H302, H371
Precautionary statements	P210, P233, P240, P241, P242, P243, P260, P264, P270, P280, P301+P312, P303+P361+P353, P309+P311, P330, P370+P378, P403+P235, P405, P501
Flash point	39.9 °C (103.8 °F; 313.0 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Methoxymethanol is a chemical compound which is both an ether and an alcohol, a hemiformal.^[1] The structural formula can be written as CH₃OCH₂OH. It has been discovered in space.^[2]

Formation

Methoxymethanol forms spontaneously when a water solution of formaldehyde and methanol are mixed.^[3]^[1] or when formaldehyde is bubbled through methanol.^[4]

In space methoxymethanol can form when methanol radicals (CH₂OH or CH₃O) react. These are radiolysis products derived when ultraviolet light or cosmic rays hit frozen methanol.^[3]

Methanol can react with carbon dioxide and hydrogen at 80°C and some pressure with a ruthenium or cobalt catalyst, to yield some methoxymethanol.^[5]

Properties

Different conformations of the molecule are Gauche-gauce (Gg), Gauche-gauce' (Gg'), and Trans-gauche (Tg).^[6]

References

^ ^a ^b Maiwald, Michael; Fischer, Holger H.; Ott, Michael; Peschla, Roger; Kuhnert, Christian; Kreiter, Cornelius G.; Maurer, Gerd; Hasse, Hans (January 2003). "Quantitative NMR Spectroscopy of Complex Liquid Mixtures: Methods and Results for Chemical Equilibria in Formaldehyde−Water−Methanol at Temperatures up to 383 K". Industrial & Engineering Chemistry Research. 42 (2): 259–266. doi:10.1021/ie0203072.
^ McGuire, Brett A.; Shingledecker, Christopher N.; Willis, Eric R.; Burkhardt, Andrew M.; El-Abd, Samer; Motiyenko, Roman A.; Brogan, Crystal L.; Hunter, Todd R.; Margulès, Laurent; Guillemin, Jean-Claude; Garrod, Robin T.; Herbst, Eric; Remijan, Anthony J. (2017). "ALMA Detection of Interstellar Methoxymethanol (CH3OCH2OH)". The Astrophysical Journal. 851 (2): L46. arXiv:1712.03256. Bibcode:2017ApJ...851L..46M. doi:10.3847/2041-8213/aaa0c3. S2CID 119211919.
^ ^a ^b Hays, Brian M.; Widicus Weaver, Susanna L. (6 May 2013). "Theoretical Examination of O(¹D) Insertion Reactions to Form Methanediol, Methoxymethanol, and Aminomethanol". The Journal of Physical Chemistry A. 117 (32): 7142–7148. Bibcode:2013JPCA..117.7142H. doi:10.1021/jp400753r. PMID 23646865.
^ Celik, Fuat E.; Lawrence, Henry; Bell, Alexis T. (June 2008). "Synthesis of precursors to ethylene glycol from formaldehyde and methyl formate catalyzed by heteropoly acids". Journal of Molecular Catalysis A: Chemical. 288 (1–2): 87–96. doi:10.1016/j.molcata.2008.03.029.
^ Dixneuf, Pierre H.; Soulé, Jean-François (2019). Organometallics for Green Catalysis. Springer. pp. 69–70. ISBN 978-3-030-10955-4.
^ Motiyenko, R. A. (21 June 2016). "Millimeter-wave spectroscopy of methoxymethanol". 71st International Symposium on Molecular Spectroscopy: 1. Bibcode:2016isms.confETH04M. doi:10.15278/isms.2016.TH04. hdl:2142/91121. ISBN 978-1-5330-5390-9.

[mai-1] Maiwald, Michael; Fischer, Holger H.; Ott, Michael; Peschla, Roger; Kuhnert, Christian; Kreiter, Cornelius G.; Maurer, Gerd; Hasse, Hans (January 2003). "Quantitative NMR Spectroscopy of Complex Liquid Mixtures: Methods and Results for Chemical Equilibria in Formaldehyde−Water−Methanol at Temperatures up to 383 K". Industrial & Engineering Chemistry Research. 42 (2): 259–266. doi:10.1021/ie0203072.

[2] McGuire, Brett A.; Shingledecker, Christopher N.; Willis, Eric R.; Burkhardt, Andrew M.; El-Abd, Samer; Motiyenko, Roman A.; Brogan, Crystal L.; Hunter, Todd R.; Margulès, Laurent; Guillemin, Jean-Claude; Garrod, Robin T.; Herbst, Eric; Remijan, Anthony J. (2017). "ALMA Detection of Interstellar Methoxymethanol (CH3OCH2OH)". The Astrophysical Journal. 851 (2): L46. arXiv:1712.03256. Bibcode:2017ApJ...851L..46M. doi:10.3847/2041-8213/aaa0c3. S2CID 119211919.

[hays-3] Hays, Brian M.; Widicus Weaver, Susanna L. (6 May 2013). "Theoretical Examination of O(¹D) Insertion Reactions to Form Methanediol, Methoxymethanol, and Aminomethanol". The Journal of Physical Chemistry A. 117 (32): 7142–7148. Bibcode:2013JPCA..117.7142H. doi:10.1021/jp400753r. PMID 23646865.

[4] Celik, Fuat E.; Lawrence, Henry; Bell, Alexis T. (June 2008). "Synthesis of precursors to ethylene glycol from formaldehyde and methyl formate catalyzed by heteropoly acids". Journal of Molecular Catalysis A: Chemical. 288 (1–2): 87–96. doi:10.1016/j.molcata.2008.03.029.

[5] Dixneuf, Pierre H.; Soulé, Jean-François (2019). Organometallics for Green Catalysis. Springer. pp. 69–70. ISBN 978-3-030-10955-4.

[6] Motiyenko, R. A. (21 June 2016). "Millimeter-wave spectroscopy of methoxymethanol". 71st International Symposium on Molecular Spectroscopy: 1. Bibcode:2016isms.confETH04M. doi:10.15278/isms.2016.TH04. hdl:2142/91121. ISBN 978-1-5330-5390-9.

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