Trimethylolethane

Trimethylolethane
Names
	Preferred IUPAC name 2-(Hydroxymethyl)-2-methylpropane-1,3-diol
	Other names TME; trimet; metriol; methriol; pentaglycerol; pentaglycerine; methyltrimethanolmethane; methyltrimethylolmethane; tris(hydroxymethyl)ethane, 1,1,1-tris(hydroxymethyl)ethane, 1,1,1-trimethanolethane; lidaprim [1], TME, trimet, metriol, ,[2]
Identifiers
CAS Number	77-85-0 ;
3D model ( JSmol)	Interactive image;
ChemSpider	6256;
ECHA InfoCard	100.000.968
EC Number	201-063-9;
PubChem CID	6502;
UNII	5D10NYN23W ;
CompTox Dashboard (EPA)	DTXSID2026444 ;
	InChI InChI=1S/C5H12O3/c1-5(2-6,3-7)4-8/h6-8H,2-4H2,1H3 Key: QXJQHYBHAIHNGG-UHFFFAOYSA-N;
	SMILES CC(CO)(CO)CO;
Properties
Chemical formula	C5H12O3
Molar mass	120.15 g/mol
Density	1.22 g/mL
Melting point	180 °C (356 °F; 453 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)	3
Flash point	150 °C (302 °F; 423 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Trimethylolethane (TME) is the

oxidation. More important than TME and closely related is trimethylolpropane

Production

CH₃CH₂CHO + 2 CH₂O → CH₃C(CH₂OH)₂CHO

The second step entails a Cannizzaro reaction:

CH₃C(CH₂OH)₂CHO + CH₂O + NaOH → CH₃C(CH₂OH)₃ + NaO₂CH

A few thousand tons are produced annually in this way.^[1]

TME is an intermediate in the production of

heat of fusion 218 kJ/kg. Nitration of trimethylolethane gives trimethylolethane trinitrate, an explosive, monopropellant

^ Peter Werle, Marcus Morawietz, Stefan Lundmark, Kent Sörensen, Esko Karvinen, Juha Lehtonen “Alcohols, Polyhydric” in Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2008.