5,5'-isopropylidenebis(m-xylene-2,alpha,alpha'-triol) Chemical Properties

Boiling point:

564.8±45.0 °C(Predicted)

Density 

1.367±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

10.27±0.10(Predicted)

color 

White to Off-White

InChI

InChI=1S/C19H24O6/c1-19(2,15-3-11(7-20)17(24)12(4-15)8-21)16-5-13(9-22)18(25)14(6-16)10-23/h3-6,20-25H,7-10H2,1-2H3

InChIKey

ZRIRUWWYQXWRNY-UHFFFAOYSA-N

SMILES

C(C1C=C(CO)C(O)=C(CO)C=1)(C1C=C(CO)C(O)=C(CO)C=1)(C)C

EPA Substance Registry System

1,3-Benzenedimethanol, 5,5'-(1-methylethylidene)bis[2-hydroxy- (3957-22-0)

5,5'-isopropylidenebis(m-xylene-2,alpha,alpha'-triol) Usage And Synthesis

Uses

5,5'-isopropylidenebis(m-xylene-2,alpha,alpha'-triol) can be used as organic synthesis intermediate and pharmaceutical intermediate, mainly used in laboratory research and development process and chemical production process.

Synthesis

Preparation Example 3. 2,2-bis[4-trimethylsilyloxy-3,5-bis(trimethylsilyloxymethyl)-phenyl]propane (monomer K). a) 2,2-bis[4-hydroxy-3,5-di(hydroxymethyl)phenyl)]propane. 114.4 of bisphenol A (2,2-bis[4-hydroxyphenyl)]propane) were initially charged in a mixture of 450 g of water and 50 g of NaOH. While cooling (Tmax=25°C), 350 g of 30% formaldehyde solution were added dropwise. After continued reaction at room temperature for 1 h, a clear solution was obtained. The mixture was neutralized by adding solid CO2. The resulting solution was saturated with sodium chloride and extracted 3 times with butanol. The extracts were concentrated on a rotary evaporator at 50°C down to 5 mbar. The product was used in the next step without further purification. colorless oil. 1H-NMR 400 MHz, CDCl3, 25°C, TMS δ [ppm] = 7.03 (s, 4 H, Aromat); 5.00 (s, 6 H, -OH (breit)); 4.63 (s, 8H, -CH2-); 1.60 (s, 6 H, C-CH3).

References

[1] Monatshefte fuer Chemie, 1973, vol. 104, p. 1077 - 1089
[2] Patent: WO2015/84304, 2015, A1. Location in patent: Paragraph 0132; 0133
[3] Patent: US2016/9672, 2016, A1. Location in patent: Paragraph 0083-0084
[4] Patent: US2016/280675, 2016, A1. Location in patent: Paragraph 0458