2,6-Bis(hydroxymethyl)-p-cresol Chemical Properties

Melting point:

128-130 °C(lit.)

Boiling point:

237.12°C (rough estimate)

Density 

1.0812 (rough estimate)

vapor density 

5.8 (vs air)

refractive index 

1.4371 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

very faint turbidity in THF

form 

powder to crystal

pka

10.20±0.23(Predicted)

color 

White to Yellow to Orange

BRN 

1240237

InChI

InChI=1S/C9H12O3/c1-6-2-7(4-10)9(12)8(3-6)5-11/h2-3,10-12H,4-5H2,1H3

InChIKey

KUMMBDBTERQYCG-UHFFFAOYSA-N

SMILES

C1(CO)=CC(C)=CC(CO)=C1O

CAS DataBase Reference

91-04-3(CAS DataBase Reference)

NIST Chemistry Reference

A1,a3-mesityllenediol, 2-hydroxy-(91-04-3)

EPA Substance Registry System

1,3-Benzenedimethanol, 2-hydroxy-5-methyl- (91-04-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

RTECS 

CZ6440000

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29072990

MSDS

• Language:English Provider:2,6-Bis(hydroxymethyl)-p-cresol
• Language:English Provider:SigmaAldrich
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2,6-Bis(hydroxymethyl)-p-cresol Usage And Synthesis

Chemical Properties

brown crystalline powder

Uses

2,6-Bis(hydroxymethyl)-p-cresol was used as a bridging ligand in binuclear oxovanadium(V) compound, which on exposure to white light and aerial oxygen forms an oligomeric compound.

Preparation

The synthesis method for 2,6-Bis(hydroxymethyl)-p-cresol is as follows:
Aqueous formaldehyde (21.5 g, 37%) is added to a solution of p-cresol (10.8 g, 0.1 mol) and NaOH (5.0 g) in HO (20 mL).
The mixture is stirred at room temperature for 24 hours.
The mixture is filtered and washed with saturated aqueous NaCl (100 mL).
The resulting salt is dissolved in water (400 mL) and neutralized with acetic acid.
Pale pink crystals are obtained and filtered.
The crystals are washed with H2O and dissolved in hot ethyl acetate (40 mL).
The solution is dried over Na2SO4 and filtered while still hot.
The solution is concentrated to 27 mL and recrystallized overnight.
The product crystals are filtered and washed with cold ethyl acetate.
The crystals are air dried.

Properties and Applications

Rammal et al. report the study on the reaction between titanium(IV) alkoxides, known to be tetrameric [Ti4- (OR)16] (1) in the solid state, and an aromatic ligand such as 2,6-bis(hydroxymethyl)-p-cresol (BHMPC 2). Starting from the same planar tetrameric structure, a perfect geometrical match between octahedral edges of (1) and hydroxo moieties of (2) could be anticipated. Upon reaction of the ligand (2) with Ti(OEt)4, a new complex for which the tetrameric structure of (1) was preserved but with all edges occupied by sic molecules of (2) was obtained. The inorganic core of this tetranuclear complex (3) is composed of two μ3-oxo groups bridging the four titanium atoms. The tetranuclear titanium core is surrounded by six ligands (2) acting in groups of two, either as chelating, chelating-bridging, or tridentate units[1].

References

[1] Adel Rammal, Marc Henry, Frédéric Brisach. “Molecular Recognition of Titanium(IV) Alkoxides by 2,6-Bis(hydroxymethyl)-p-cresol in the Crystal Engineering of Hybrid Organic?Inorganic Networks.” Journal of the American Chemical Society 123 23 (2001): 5612–5613.

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