2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical Properties

Melting point:

88-90 °C(lit.)

Boiling point:

405.0±25.0 °C(Predicted)

Density 

1.183±0.06 g/cm3(Predicted)

vapor pressure 

0Pa at 25℃

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

12.96±0.29(Predicted)

color 

White to Light yellow

Water Solubility 

7.6g/L at 25℃

InChI

InChI=1S/C12H16O4/c1-12(2,15)11(14)9-3-5-10(6-4-9)16-8-7-13/h3-6,13,15H,7-8H2,1-2H3

InChIKey

GJKGAPPUXSSCFI-UHFFFAOYSA-N

SMILES

C(C1=CC=C(OCCO)C=C1)(=O)C(O)(C)C

LogP

0.84 at 23℃

CAS DataBase Reference

106797-53-9(CAS DataBase Reference)

EPA Substance Registry System

1-Propanone, 2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methyl- (106797-53-9)

Safety Information

Safety Statements 

24/25

WGK Germany 

2

RTECS 

UC2976000

HS Code 

29145090

MSDS

• Language:English Provider:SigmaAldrich

2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Usage And Synthesis

Description

2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone(Photoinitiator 2959) has been tested for use in UV curing formulations on wood, metal, plastic and paper surfaces.It has lower volatility and odor compared to Irgacure 1173. Importantly, the reactive hydroxyl groups of it are easily grafted onto the polymer molecules, making it more convenient to process. 

Uses

2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone is a photoinitiator allowed by the FDA certification system; it can be used in water-based photocuring systems, with high melting point, and can also be used in UV-curable powder coatings; it is a high-efficiency non-yellowing UV photoinitiator. UV polymerization of saturated prepolymerized systems.

Chemical Properties

Density 1.183 g/cm3, melting point 88-90°C (lit.), boiling point 405℃ at 760 mmH, flash point 155.8℃, refractive index .544, vapor pressure 2.75E-07 mmHg at 25℃.

Uses

2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone is used in the preparation of UV-VIS curable PEG hydrogels for biomedical applications with multi-functionality.

Definition

ChEBI: 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone is an aromatic ketone.

Synthesis

The general procedure for the synthesis of photoinitiator 2959 from the compound (CAS:159119-01-4) was as follows: a 25 mL Schlenk reaction tube was taken and N-bromosuccinimide (NBS) 18 mg (0.1 mmol) was added sequentially as catalyst, 4'-(2-hydroxyethoxy)-2-methylpropiophenone 105 mg (0.5 mmol), and dimethyl sulfoxide (DMSO) 1 mL as oxidizing reagent and solvent. ), and dimethyl sulfoxide (DMSO) 1 mL as oxidizer, carbonylation reagent and solvent. The reaction mixture was stirred at 100 °C for 24 hours. Upon completion of the reaction, 15 mL of ethyl acetate and 3 mL of brine were added to the reaction mixture for extraction, which was then extracted three times with ethyl acetate. All organic phases were combined and purified by column chromatographic separation to give a final purity of 103 mg of 2-hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone in 92% yield.

References

[1] Organic Letters, 2015, vol. 17, # 4, p. 876 - 879
[2] Patent: CN104710256, 2017, B. Location in patent: Paragraph 0174-0177
[3] Angewandte Chemie - International Edition, 2014, vol. 53, # 2, p. 548 - 552
[4] Angew. Chem., 2014, vol. 53, # 2, p. 558 - 562,5
[5] Patent: CN107739303, 2018, A. Location in patent: Paragraph 0017

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