69753-43-1

Basic information

• Product Name: 1-Chloro-1-(phenylthio)-2-propanone
• Synonyms: 1-Chloro-1-(phenylthio)-2-propanone
• CAS NO: 69753-43-1
• Molecular Formula: C₉H₉ClOS
• Molecular Weight: 200.69
• Mol File: 69753-43-1.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Chloro-1-(phenylthio)-2-propanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Chloro-1-(phenylthio)-2-propanone(69753-43-1)
• EPA Substance Registry System: 1-Chloro-1-(phenylthio)-2-propanone(69753-43-1)

Safety Data

• Hazardous Substances Data: 69753-43-1(Hazardous Substances Data)

Upstream product

• 5042-53-5 1-(phenylsulfanyl)acetone 
• 22198-54-5 1-chloro-3-phenylsulfanylpropan-2-one 
• 64-19-7 acetic acid 
• 108-98-5 thiophenol 
• 69753-44-2 α,α-Bis(phenylthio)acetone 
• 2684-62-0 diazoacetone 
• 931-59-9 benzenesulfenyl chloride 

Downstream Products

• 81358-61-4 3-methyl-5-phenyl-2-(phenylsulfanyl)furan 
• 10371-49-0 1-phenyl-1-(phenylthio)-2-propenone 
• 5042-53-5 1-(phenylsulfanyl)acetone 
• 77128-60-0 3-Methyl-2-phenylsulfanyl-benzo[b]thiophene 
• 77128-53-1 (2R,3R)-3-Methyl-2-phenylsulfanyl-2,3-dihydro-benzo[b]thiophen-3-ol 
• 882-33-7 diphenyldisulfane 
• 65755-66-0 3-phenylthiohex-5-ene-2-one 
• 344306-21-4 2-(2-Oxo-1-phenylsulfanyl-propyl)-cyclopentanone 
• 87143-64-4 3-Phenylsulfanyl-4-vinyl-nonan-2-one 
• 22198-56-7 1-acetoxy-1-phenylthio-2-propanone 
• 22198-57-8 acetate of 1-hydroxy-3-phenylthio-2-propanone 
• 82834-09-1 2-methoxy-2-(phenylthio)propanal 
• 344338-62-1 2-Methyl-2-(2-oxo-1-phenylsulfanyl-propyl)-cyclohexanone 
• 98910-26-0 2-(2-Oxo-1-phenylsulfanyl-propyl)-cyclohexanone 

Relevant articles and documents

Cationic Polar Cycloadditions of Phenylthionium Ions with Olefines: A New Route to Thiochromans

Reaction of 2-chloro-N,N-dimethyl-2-(phenylthio)acetamide (1a) with styrene in the presence of stannic chloride gave 3,4-dihydro-N,N-dimethyl-4-phenyl-2H-1-benzothiopyran-2-carboxamide.The same benzothiopyran was also obtained from N,N-dimethyl-2-(phenylsulfinyl)acetamide and styrene under the Pummerer reaction conditions, but in lower yield.Similarly, α-chlorosulfides derived from ethyl 2-(phenylthio)acetate, 2-(phenylthio)acetonitrile, 1-(phenylthio)-2-propanone, and thioanisole reacted with styrene to give the corresponding 4-phenylbenzothiopyrans in variable yields.The reaction of 1a with trans-stilbene gave the expected benzothiopyran derivative, but the reaction of 1a with 1,1-diphenylethylene and phenylacetylene showed some variation of the reaction course.This cycloaddition reaction was extended to the intramolecular case.A possible mechanism for the formation of the benzothiopyran is discussed.

REGIOSPECIFIC SYNTHESIS OF α-(PHENYLTHIO)CYCLOALKENONES AND OF α-PHENYL-α-(PHENYLTHIO)KETONES VIA αα-ADDITION OF PHENYLSULPHENYL CHLORIDE TO α-DIAZOKETONES

Cyclic α-diazoketones react with phenylsulphenyl chloride at room temperature to furnish α-chloro-α-(phenylthio)cycloalkanones which undergo ready dehydrochlorination to α-(phenylthio)cycloalkenones when treated with triethylamine; acyclic, terminal α-diazoketones also furnish α-chloro-α-(phenylthio)adducts which are useful electrophiles in the synthesis of α-phenyl-α-(phenylthio)ketones.

PHOTOCHEMICAL RING CLOSURE OF α,α-BISULFENYLATED CARBONYL COMPOUNDS STEREOSELECTIVE FORMATION OF CIS-DIHYDROBENZOTHIOPHENES

Photochemistry of α,α-bisulfenylated ketone has been investigated.Irradiation of 2-phenylthiodihydrothiophen-3-one (1) in benzene gave the radical recombination products 9 (63percent) and 10 (49percent).In a polar solvent, the ionic chemistry became predominant.Brief irradiation of 1 in acetonitrile and methanol gave the cis-fused dihydrothiophene 11 as the major product in 43percent and 20percent yields, respectively.The stereoselective photocyclization was generally observed for other ketones (2-8) in acetonitrile solution (Table 1).The photoproducts were easily dehydrated by treating with boron trifluoride etherate to give the corresponding benzothiophenes in high yields.Simple α-phenylthioketones are photoinert under the same conditions.The mechanism of this novel photocyclization of bisulfenylated ketones is also discussed.