1-[4-(Phenylthio)phenyl]-1,2-octanedione 2-(O-benzoyloxime) CAS#: 253585-83-0; ChemWhat Code: 301293

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

Product Name1-[4-(Phenylthio)phenyl]-1,2-octanedione 2-(O-benzoyloxime)
IUPAC Name[[1-oxo-1-(4-phenylsulfanylphenyl)octan-2-ylidene]amino] benzoate
Molecular Structure1-4-Phenylthiophenyl-12-octanedione-2-O-benzoyloxime-CAS-253585-83-0
CAS Registry Number 253585-83-0
MDL NumberMFCD12911795
Synonyms253585-83-0
1,2-Octanedione, 1-(4-(phenylthio)phenyl)-, 2-(O-benzoyloxime)
1,2-Octanedione, 1-[4-(phenylthio)phenyl]-, 2-(O-benzoyloxime)
[[1-oxo-1-(4-phenylsulfanylphenyl)octan-2-ylidene]amino] benzoate
1-[4-(Phenylthio)phenyl]-1,2-octanedione 2-(O-benzoyloxime)
[(E)-[1-oxo-1-(4-phenylsulfanylphenyl)octan-2-ylidene]amino] benzoate
DTXSID1074969
SB66345
NS00077818
(Z)-{1-OXO-1-[4-(PHENYLSULFANYL)PHENYL]OCTAN-2-YLIDENE}AMINO BENZOATE
Molecular FormulaC27H27NO3S 
Molecular Weight445.6
InChIInChI=1S/C27H27NO3S/c1-2-3-4-11-16-25(28-31-27(30)22-12-7-5-8-13-22)26(29)21-17-19-24(20-18-21)32-23-14-9-6-10-15-23/h5-10,12-15,17-20H,2-4,11,16H2,1H3
InChI KeyLOCXTTRLSIDGPS-UHFFFAOYSA-N
Isomeric SMILESCCCCCCC(=NOC(=O)C1=CC=CC=C1)C(=O)C2=CC=C(C=C2)SC3=CC=CC=C3
Patent Information
Patent IDTitlePublication Date
TW2023/34322Infrared absorbing composition, film, optical filter, solid-state imaging element, image display device, infrared sensor, and camera module2023
CN115260066Method for preparing oxime ester compound from supercritical carbon dioxide2022
TW2022/48363Composition, film, optical filter, solid-state imaging element, image display device, infrared sensor, camera module, compound, and infrared absorbing agent2022
TW2021/4456Photosensitive resin composition, cured film, color filter, solid-state imaging element and image display device2021
US2020/392343COMPOSITION, CURED PRODUCT, COLOR FILTER, METHOD FOR PRODUCING COLOR FILTER, SOLID-STATE IMAGING ELEMENT, IMAGE DISPLAY DEVICE, AND COMPOUND2020

Physical Data

AppearanceOff-white or light yellow powder
Melting Point, °C
42

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)
Chemical shifts1Hchloroform-d1
Description (UV/VIS Spectroscopy)Solvent (UV/VIS Spectroscopy)Absorption Maxima (UV/VIS), nmExt./Abs. Coefficient, l·mol-1cm-1
Absorption maximaH2O, NaOH
methanol32629500
326
Absorption spectrum

Route of Synthesis (ROS)

Route of Synthesis (ROS) of 1-[4-(Phenylthio)phenyl]-1,2-octanedione 2-(O-benzoyloxime) CAS# 253585-83-0
Route of Synthesis (ROS) of 1-[4-(Phenylthio)phenyl]-1,2-octanedione 2-(O-benzoyloxime) CAS# 253585-83-0
ConditionsYield
With triethylamine In chloroform at 0℃; for 2h; Reagent/catalyst; Solvent;

Experimental Procedure
2.c c. Preparation of 1-diphenyl sulfide-1-cyclopentylacetone oxime benzyl ester
A four-necked flask equipped with a motor-driven stirrer and a thermometer was charged with 102.4 g of diphenyl sulfide cyclopentylacetone oxime (0.30 mol)1200 ml of chloroform,39.5 g of triethylamine (0.39 mol),Stir well,After cooling to 0 ° C, a mixed solution of 50.6 g of benzoyl chloride (0.36 mol) and 50 g of chloroform was added dropwise.After completion of the addition, stirring was continued for 2 hours,1500 ml of cold water was added dropwise,Layered,Once with 500 ml of saturated sodium bicarbonate solution,500 ml of water,1000 ml of 0.5 N hydrochloric acid,500ml washing,Dried over 300 g of anhydrous magnesium sulfate,Filtration,The filtrate was evaporated to remove the solvent,A viscous liquid was obtained.To this was added an appropriate amount of ethanol,To precipitate white solid 1-diphenyl sulfide 1-cyclopentyl acetone oxime benzyl ester, filtration, drying product 104.2g, yield 78%, purity greater than 98%.		78%
With triethylamine at 20℃;

Experimental Procedure

Add the triethylamine of 121g,Control the reaction temperature within 10°C, Start stirring, continue to add the benzoyl chloride of 155g; After joining, Warming up to room temperature and continuing the reaction to the end; At room temperature, the reaction solution after the reaction was washed three times with 300 g of ice water;Atmospheric pressure reclaims dichloromethane to dry afterwards;Then add 1080g isopropanol for recrystallization,Filter, dry, finally obtain the OXE01 product of 346g,Has the structure shown in formula 1-1;Yield 78%,The purity is above 99%.		78%

Safety and Hazards

Pictogram(s)exclamation-mark
SignalWarning
GHS Hazard StatementsH317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]
Precautionary Statement CodesP261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501
(The corresponding statement to each P-code can be found at the GHS Classification page.)

Other Data

Transportation
HS Code
StorageSealed and protected from light, store at 25°C
Shelf Life1 year
Market Price
Druglikeness
Lipinski rules component
Molecular Weight445.582
logP8.662
HBA2
HBD0
Matching Lipinski Rules3
Veber rules component
Polar Surface Area (PSA)81.03
Rotatable Bond (RotB)12
Matching Veber Rules1
Use Pattern
1-[4-(Phenylthio)phenyl]-1,2-octanedione 2-(O-benzoyloxime) CAS 253585-83-0 is a highly efficient photoinitiator, especially suitable for applications requiring high photosensitivity and low yellowing. It has an absorption band in the range of 300-400nm, the peak wavelength is 325nm, the absorption edge reaches 400nm, and it is sensitive to light at or below the i-line (365nm). Highly soluble in solvents such as propylene glycol monomethyl ether acetate (PGMEA) and cyclohexanone, which are commonly used in color filter photoresists.
1-[4-(Phenylthio)phenyl]-1,2-octanedione 2-(O-benzoyloxime) has excellent curing properties in highly pigmented photoresist formulations and is commonly used in color filter photoresists and black matrix photoresists. In resist (BM glue): In addition, it can be used in photosensitive polyimide formulations, LCD isolation materials, microlens materials, outer coatings, dielectric layers and insulating layers.

Absorption specture of 1-[4-(Phenylthio)phenyl]-1,2-octanedione 2-(O-benzoyloxime) CAS# 253585-83-0

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