Bisoctrizole Chemical Properties

Melting point:

197-199 °C(lit.)

Boiling point:

771.6±70.0 °C(Predicted)

Density 

d20 1.2

vapor pressure 

0Pa at 25℃

Flash point:

>200°C

storage temp. 

Inert atmosphere,Room Temperature

solubility 

almost transparency in THF

form 

Solid

pka

7.62±0.50(Predicted)

color 

White to Orange to Green

Water Solubility 

Insoluble < 5 ng/L at 25 °C

Merck 

14,1294

BRN 

11326835

Stability:

Light Sensitive

InChIKey

ZRFPPIQVEQSFRV-UHFFFAOYSA-N

LogP

4.2 at 20℃

CAS DataBase Reference

103597-45-1(CAS DataBase Reference)

EPA Substance Registry System

Phenol, 2,2'-methylenebis[6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)- (103597-45-1)

Safety Information

Risk Statements 

36/37/38-53

Safety Statements 

26-36/37/39-61

WGK Germany 

1

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

Bisoctrizole Usage And Synthesis

Chemical Properties

White powder

Chemical Properties

Wavelengths covered: about 280-400 nm, which covers both UVB and UVA ranges; peak protection at 303 nm and 358 nm.

Uses

Bisoctrizole is a light stabilizer in polymers and resins. It is majorly used as a UV filter in sunscreens and in photo-luminescent dyes for organic electronic based applications.

Application

Bisoctrizole is a non-FDA-approved combination sunscreen, but is approved in the EU and other parts of the world as a UV filter in sunscreens, day care products, and skin-whitening products at concentrations up to 10%.

Definition

ChEBI: Bisoctrizole is a diarylmethane. It is a broad-spectrum organic UV filter that is marketed as Tinosorb M. It is a benzotriazole-based organic compound that absorbs, reflects, and scatters both UV-A and UV-B rays.

brand name

Tinosorb M (Ciba Specialty Chemicals).

General Description

Bisoctrizole is a benzotriazole based additive that is used as an ultraviolet absorber (UVA). It reduces degradation of the polymeric material by absorbing the UV radiation and converting it to thermal heat. Bisoctrizole is often added to sunscreen formulations that It may protect skin against blue light and other environmental assaults.

Side effects

At present, Bisoctrizole has good safety, photostability and effectiveness, and rarely causes skin irritation. Severe allergic reactions are rare, which may be related to the fact that it is not significantly absorbed by the skin. If you experience symptoms such as difficulty breathing or swallowing, chest tightness, rash, swelling and urticaria, you need to seek medical attention immediately. Due to the lack of clinical studies on Bisoctrizole, long-term use and adverse reactions remain to be investigated.

Safety

Bisoctrizole appears to be relatively non-toxic and rarely causes skin irritation. As with many synthetic chemicals, whether bisoctrizole may produce low-level skin damage or systemic effects with long-term use is unclear. Considering that bisoctrizole is stable, poorly soluble, and minimally absorbed by the skin, the risks appear to be low. Still, more research on bisoctrizole safety is needed.

Synthesis

1. Synthesis procedure: In a 500 mL three-necked flask equipped with a stirrer, thermometer and distillation receiver, 323 g of ultraviolet absorber UV-329, 4 g of powdered sodium hydroxide, 128 g of bis(di-n-propylamino)methane and 15 g of tetrabutylammonium bromide were added sequentially. The reaction mixture was heated to 130°C under reduced pressure at 100 mmHg with continuous stirring. During the reaction, the resulting di-n-propylamine was collected by distillation. After the reaction was carried out for 2 h, the heating was stopped and the vacuum was released. A total of 108 g of di-n-propylamine was recovered (theoretical yield: 122 g) with 88.5% recovery and 98.6% purity. 2. Purification step: When the temperature of the reaction system was lowered to 110°C, 500 g of toluene was slowly added to dissolve all the solids. After complete dissolution, the temperature of the system was lowered to 90°C. About 40 g of 18% aqueous hydrochloric acid was added dropwise slowly and stirred until the reaction system was neutral. The reaction mixture was transferred to a beaker and the crystals were cooled and crystallized in an ice water bath for 4-5 hours. The crystals were collected by filtration and washed twice with 150 mL of deionized water and twice with 250 mL of methanol sequentially. The resulting wet product was dried at 100~110°C to obtain 266 g of ultraviolet absorber UV-360 (theoretical yield: 329 g), the product melting point was 197~198°C, the yield was 80.9% and the purity was 99.6%.

References

[1] Patent: CN106478530, 2017, A. Location in patent: Paragraph 0036-0039
[2] Patent: CN106632111, 2017, A. Location in patent: Paragraph 0033; 0034; 0035; 0036; 0037-0049; 0052; 0053

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