58157-89-4

Basic information

• Product Name: 1-(5-NITRO-3-THIENYL)ETHAN-1-ONE
• Synonyms: 4-ACETYL-2-NITROTHIOPHENE;1-(5-NITRO-3-THIENYL)ETHAN-1-ONE;1-(5-nitrothiophen-3-yl)ethanone
• CAS NO: 58157-89-4
• Molecular Formula: C6H5NO3S
• Molecular Weight: 171.17
• Product Categories: Thiophene&Benzothiophene
• Mol File: 58157-89-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 59 °C
• Boiling Point: 247.9 °C at 760 mmHg
• Flash Point: 103.7 °C
• Appearance: white to light yellow crystal powder
• Density: 1.399 g/cm³
• Vapor Pressure: 0.025mmHg at 25°C
• Refractive Index: 1.589
• CAS DataBase Reference: 1-(5-NITRO-3-THIENYL)ETHAN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(5-NITRO-3-THIENYL)ETHAN-1-ONE(58157-89-4)
• EPA Substance Registry System: 1-(5-NITRO-3-THIENYL)ETHAN-1-ONE(58157-89-4)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• Hazardous Substances Data: 58157-89-4(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

InChI:InChI=1/C6H5NO3S/c1-4(8)5-2-6(7(9)10)11-3-5/h2-3H,1H3

Upstream product

• 1468-83-3 1-(thiophen-3-yl)-ethanone 

Relevant articles and documents

Meisenheimer-type Adducts from Thiophene Derivates. Part 6. A Kinetic and Thermodynamic Study of Substituent Effects on the Formation of Some non-gem Adducts

The rate and equilibrium constants for the formation of the Meisenheimer-type adducts from some 4-nitro-2-X- (5) or some 2-nitro-4-X-thiophenes (7) and sodium methoxide have been measured at 25 deg C in methanol or methanol-dimethyl sulphoxide mixtures.The observed stability and reactivity patterns have been interpreted in the light of the hyper-ortho relation in the thiophene ring and the special ability of the nitro group to stabilize effectively the adducts from a para-like position also.

Substitution Reactions of Nitrothiophens. IV Limitations in Scope of the SN(AEAE) Reaction in Thienylalkyl Derivatives

The reactions of 5-nitro-3-thienylethyl chloride and acetate with lithium 2-nitropropan-2-ide (1) give excellent yields of the C-alkylate, 4-(1,2-dimethyl-2-nitropropyl)-2-nitrothiophen, by the SN(AEAE) mechanism.The cyano group is not a sufficiently activating substituent to support the SN(AEAE) process and 4-cyano-2-thienyl-methyl and -ethyl chlorides with the salt (1) give O-alkylated products by an SN2 mechanism.The occurence of SN(AEAE) reactions with other nucleophiles is difficult to prove but benzenethiolate and 4-nitro-2-thienylmethyl acetate do react b y this mechanism to give a moderate yield of 4-nitro-2-thienylmethyl phenyl sulfide.