Sulisobenzone | Benzophenone-4

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Quality Control of Sulisobenzone Purity: 98% SDS Specification

COA

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NMR

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Product Details of Sulisobenzone

CAS No. :	4065-45-6
Formula :	C₁₄H₁₂O₆S
M.W :	308.31
SMILES Code :	COC1=C(C=C(C(=O)C2=CC=CC=C2)C(O)=C1)S(O)(=O)=O
Synonyms :	Benzophenone-4; 3-Benzoyl-4-hydroxy-6-Methoxybenzenesulfonic Acid; UV-248
MDL No. :	MFCD00024962
InChI Key :	CXVGEDCSTKKODG-UHFFFAOYSA-N
Pubchem ID :	19988

Safety of Sulisobenzone

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of Sulisobenzone

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 4065-45-6 ]

[ 4065-45-6 ] Synthesis Path-Downstream 1~20

1
[ 4065-45-6 ]
[ 1609-47-8 ]
[ 19337-04-3 ]

References: [1]Bulletin de la Societe Chimique de France,1968,p. 329 - 335.

2
[ 4065-45-6 ]
[ 77-78-1 ]
sodium 2,4-dimethoxy-5-benzoylbenzenesulfonate [ No CAS ]

References: [1]Journal of Physical Chemistry,1980,vol. 84,p. 2356 - 2363.

Yield	Reaction Conditions	Operation in experiment
		In a preferred embodiment, the care lotion according to the invention contains a combination of water-soluble and lipid-soluble UV protection factors. Suitable water-soluble UV protection factors are, for example, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid p-methoxycinnamic acid diethanolamine salt p-aminobenzoic acid 2-phenylbenzimidazole-5-sulfonic acid triethanolamine salicylate and lauryl-[3-(p-dimethylamainobenzamido)-propyl]-dimethyl ammonium-p-toluenesulfonate.
		Preparation of 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid (Examples 1 to 3) EXAMPLE 1 22.8 g of 2-hydroxy-4-methoxybenzophenone were introduced into 60 ml of ethyl acetate, 31 g of chlorosulfonic acid were added dropwise in the course of 30 minutes while cooling (internal temperature about 0-5 C.), and the mixture was stirred overnight at room temperature (18-25 C.). Thereafter, the mixture was cooled to 10 C. and the product was filtered off under suction, washed with 10 ml of ethyl acetate and dried at 30 C. under reduced pressure. 26 g of 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid of melting point 193-195 C. and having a water content of 3.7% by weight were obtained.
		The following compounds are particularly preferably used as UV filters: 2-ethoxyhexyl p-(dimethylamino)-benzoate; 2-ethylhexyl p-methoxycinnamate; 3-(4'-methylbenzylidene)-d,1-camphor; 2-hydroxy-5-methoxybenzophenone; 2-hydroxy-4-methoxybenzophenone-5-sulphonic acid; 2-phenylbenzimidazole-5-sulphonic acid.

		Such preferred UV-B absorbers include p-aminobenzoic acid derivatives, camphor derivatives, cinnamates, and salicylates. ... isoamyl 4-methoxycinnamate, diethanolamine 4-methoxycinnamate, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonate, 2,4-dihydroxybenzophenone, 2,2',4,4'-tetrahydroxybenzophenone, 2,2'-dihydroxy-4,4'dimethoxybenzophenone, ...
		Starting from Titanium 5-Benzoyl-4-Hydroxy-2-Methoxybenzene Sulphonate-Tri-Isopropoxide in an Aqueous Medium The [Ti(OC3H7)3(C14H12O6S)]m is obtained by an equimolar reaction between the titanium tetra-isopropoxide [Ti(OC3H7)4] and the 5-benzoyl-4-hydroxy-2-methoxybenzene sulphonic acid (Uvinul MS 40).
		Starting from Titanium 5-benzoyl-4-hydroxy-2-methoxybenzene sulphonate-tri-isopropoxide in an Aqueous Medium The [Ti(OC3H7)3(C14H12O6S)]m is obtained by an equimolar reaction between the titanium tetra-isopropoxide [Ti(OC3H7)4] and the 5-benzoyl-4-hydroxy-2-methoxybenzene sulphonic acid (Uvinul MS 40).
		Broadband filters which are preferably combined with one or more compounds of formula (I) in a preparation according to the present invention are selected from the group consisting of ? 2-ethylhexyl-2-cyano-3,3-diphenyl acrylate (Neo Heliopan303)? ethyl-2-cyano-3,3'-diphenyl acrylate? 2-hydroxy-4-methoxybenzophenone (Neo HeliopanBB)? 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid? dihydroxy-4-methoxybenzophenone? 2,4-dihydroxybenzophenone? tetrahydroxybenzophenone? 2,2'-dihydroxy-4,4'-dimethoxybenzophenone? 2-hydroxy-4-n-octoxybenzophenone...
		Broadband filters which are preferably combined with one or more compounds of formula (I) in a preparation according to the present invention are selected from the group consisting of 2-ethylhexyl-2-cyano-3,3-diphenyl acrylate (Neo Heliopan303)ethyl-2-cyano-3,3'-diphenyl acrylate2-hydroxy-4-methoxybenzophenone (Neo HeliopanBB)2-hydroxy-4-methoxybenzophenone-5-sulfonic aciddihydroxy-4-methoxybenzophenone2,4-dihydroxybenzophenonetetrahydroxybenzophenone2,2'-dihydroxy-4,4'-dimethoxybenzophenone2-hydroxy-4-n-octoxybenzophenone...

5
4-benzoyloxy-2-methoxybenzenesulfonic acid [ No CAS ]
[ 4065-45-6 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; at 35℃; for 0.333333h;UVB irradiation;	A solution containing 5 mg of 4-benzoyloxy-2-methoxybenzenesulfonic acid in 10 mL of methanol was irradiated with UVB lamps (60 W·m-2) for 20 minutes at 35C. The absorption spectrum was then recorded minute by minute. The conversion to sulisobenzone was complete in 10 minutes. The phototransposition kinetics is shown in Figure 4.

References: [1]Patent: EP1707558,2006,A1 .Location in patent: Page/Page column 17; 36.

6
[ 131-57-7 ]
[ 4065-45-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	With chlorosulfonic acid; In ethyl acetate; at 45℃;	Weigh 228g (1mol) 2-hydroxy-4-methoxy-benzophenone dissolved in an appropriate amount of ethyl acetate, fully stirred to dissolve, weighed 232g (2mol) of chlorosulfonic acid dissolved in an appropriate amount of ethyl acetate, The two raw materials were simultaneously pumped into the microreactor in a continuous and constant form, and the continuous reaction was carried out at 45C. The collected reaction liquid was cooled to below 5C and filtered, washed with ethyl acetate solvent, and dried at 30C under vacuum to obtain BP- 4. The yield can reach 96%
	With chlorosulfonic acid; In phthalic acid dimethyl ester;	EXAMPLE 5 11.4 g of 2-hydroxy-4-methoxybenzophenone were dissolved in 30 ml of dimethyl phthalate at 80 C., and 3.5 ml of chlorosulfonic acid were added dropwise at this temperature. Stirring was carried out for a further 4 hours at 80 C., the mixture was cooled to room temperature and 25 ml of ether were added to the solution. The precipitate was filtered off under suction, washed with ether and hexane and dried under reduced pressure at 30 C. 10 g of 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid of melting point 112-114 C. were obtained (water content 7.7%).
	With chlorosulfonic acid; at 25℃; for 20h;Inert atmosphere; Autoclave;	(1) pre-enamel kettle adding solvent and 2-hydroxy-4-methoxy benzophenone;(2) in a nitrogen atmosphere and stirred dropwise chlorosulfonic acid, water bath through the jacket cooling and control acid dropwise speed control of the autoclave temperature is 25 ;(3) chlorosulfonic acid added at the end of the reaction was continued for 20h at 25 , after the end of the reaction, the product was isolated by filtration and centrifugation;(4) with the appropriate solvent washing products, dried under nitrogen, throughout the synthesis process, the solvent used and by-products are to be recycled.

References: [1]Patent: CN110655479,2020,A .Location in patent: Paragraph 0031-0036.
[2]Patent: US5072034,1991,A .
[3]Patent: CN105622465,2016,A .Location in patent: Paragraph 0011.

7
[ 4065-45-6 ]
[ 121715-18-2 ]

Yield	Reaction Conditions	Operation in experiment
		A. Preparation of 5-benzoyl-4-hydroxy-2-methoxy-benzenesulfonyl chloride A solution of 5-benzoyl-4-hydroxy-2-methoxybenzenesulfonic acid (Uvinul MS-40, a product of BASF Wyandotte Corporation) (20.0g, 0.065 mole) and 250 ml of warm tetrahydrofuran was cooled to room temperature. A solution of 8.0g (0.10 mole) of pyridine in 25 ml tetrahydrofuran was added accompanied by an exotherm. The resulting mixture was stirred at room temperature for 30 minutes, then poured into 200 ml pentane and stirred briefly before the sulfonic acid salt (23.5g) was collected by filtration. This salt was added slowly over 15 minutes to 29.0g (0.244 mole) of thionyl chloride at 50 C. under a nitrogen atmosphere. The resulting mixture was stirred at 55 C. for 1 hour 45 minutes. The reaction mixture was poured into 600 ml of ice water to precipitate the product. The product was isolated by filtration and transferred to a separatory funnel with 200 ml chloroform. The mixture was extracted with 125 ml of 2.5 % HCl, 100 ml of 2.5% HCl and 100 ml water. The organic phase was dried with anhydrous magnesium sulfate and stripped of solvent using aspirator and high vacuum systems. The product weighed 16.5g and melted at 165-172 C.

References: [1]Patent: US5041545,1991,A .

8
[ 4065-45-6 ]
[ 108-90-7 ]
[ 817203-48-8 ]

Yield	Reaction Conditions	Operation in experiment
79%		Example 3: Synthesis of the compound (7) ; To a mixture consisting of chlorobenzene (150 mL) and anhydrous aluminum chloride (40 g) was added dropwise thionyl chloride (17.6 g) under nitrogen flow at an internal temperature of 25C or less. The reaction mixture was stirred at 20 to 25C for 1 hr, anhydrous aluminum chloride (30 g) was added thereto, and the reaction mixture was stirred at 120 to 150C for 4 hr. The reaction mixture was cooled to 30C or less and poured into ion exchanged water (2000 mL), and the mixture was stirred at 60C for 1 hr. Thereafter, from the reaction mixture separated into two layers, the water layer was isolated. The water layer was extraction-treated twice with ethyl acetate (200 ml), and the ethyl acetate layer was discarded. To the water layer was added <strong>[4065-45-6]2-hydroxy-4-methoxybenzophenone-5-sulfonic acid</strong> dihydrate (50.8 g), and the mixture was stirred for 4 hr. The precipitated crystals were collected by filtration, washed with ion exchanged water, and dried to give 79 g of the compound (7) as pale yellow crystals. Yield 79%. Melting point 71 to 73C, HPLC purity 99% (total of <strong>[4065-45-6]2-hydroxy-4-methoxybenzophenone-5-sulfonic acid</strong> anion moiety and tris(4-chlorophenyl)sulfonium cation moiety).

References: [1]Patent: EP2042487,2009,A2 .Location in patent: Page/Page column 15.

9
2-[2-[2-chloro-3-[(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)ethylidene]-1-cyclohexen-1-yl]ethenyl]-1,3,3-trimethyl-3H-indolium bromide [ No CAS ]
[ 4065-45-6 ]
2-[2-[2-chloro-3-[(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)ethylidene]-1-cyclohexen-1-yl]ethenyl]-1,3,3-trimethyl-3H-indolium, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		5.6 g of KF654B was dissolved in 100 g of water and 100 g of DOWANOLO PM. 3.1 g OF 2-HYDROXY-4-METHOXYBENZOPHENONE-5-SULFONIC ACID (TCI America, Portland, OR, USA) was dissolved in A mixture of 20 g of water and 30 g of DOWAINIOL PM and neutralized with 0. 85 G of sodium bicarbonate in 10 g of water. The KF654B solution was slowly added to the solution of the SULFONIC acid salt with stirring. The reaction mixture was stirred for another 10 minutes and stored in the dark at room temperature for 2 hours. The resulting precipitate was filtered off, washed with 50 ml of water, and dried at ambient temperature for 24 hours. Yield : 7.4 g. Proton NMR (in DMSO-d6) : 8 1. 66 (12H, S), 1. 85 (2H, br), 2. 71 (4H, t), 3. 68 (6H, s), 3. 84 (3H, s), 6. 30 (2H, D), 6. 57 (1H, S), 7. 20-7. 35 (2H, M), 7. 40-7. 70 (11H, M), 7. 92 (1H, S), 8. 24 (2H, d) AND 12. 29 (1H, S).

References: [1]Patent: WO2004/81117,2004,A2 .Location in patent: Page 26-27.

10
[ 4065-45-6 ]
[ 99-09-2 ]
[ 1243203-31-7 ]

Yield	Reaction Conditions	Operation in experiment
10.73%Chromat.		General procedure: A mixture of nitroaniline (1.38 g, 10.0 mmol), 3.6 mL concentrated hydrochloric acid and 25 mL H2O was stirred vigorously for 0.5 h at 70C. The resultant solution was cooled below 5C with the aid of an ice bath and stirred as NaNO2 (0.73 g, 10.5 mmol) in 5 mL H2O was added rapidly. The reaction mixture was stirred at 5C until a clear solution was formed. This solution was added to 87 mL ethanol and 10 mL H2O containing compound <strong>[4065-45-6]2-hydroxy-4-methoxybenzophenone-5-sulfonic acid</strong> (UV-284) (3.08 g, 10 mmol) and Na2CO3 (2.40 g, 45.4 mmol) while keeping the temperature below -20C. The volume ratio of ethanol and water was 2:1 in the final solution, which was stirred for 2.5 h at -20C. Then, the pH of the reaction solution was adjusted to 3.0 by adding 1 mol/L hydrochloric acid solution. The ethanol was distilled out from the above reaction solution, and the remaining solution was cooled to 0-5C. The solid was filtered and dried to yield a yellow solid. The compounds 1-3 were obtained by silica gel column chromatography using ethyl acetate/petroleum ether (60/90) mixtures as the eluent. The compounds 8 and 9 were synthesized and purified according to the procedures described before.