Thianaphthene

Thianaphthene Basic information
Product Name:Thianaphthene
Synonyms:THIANAPHTHENE;THIONAPHTHENE;2,3-BENZOTHIOPHENE;BZT;BBT;BENZO2,3THIOPHENE;BENZO[B]THIOPHENE;BENZOTHIOPHENE
CAS:95-15-8
MF:C8H6S
MW:134.2
EINECS:202-395-7
Product Categories:Heterocycle-oher series;Benzothiophenes;Thiophenes & Benzothiophenes;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Benzothiophene;Halogenated;Organoborons;Thiophenes & Benzothiophenes;bc0001
Mol File:95-15-8.mol
Thianaphthene Structure
Thianaphthene Chemical Properties
Melting point 30-33 °C
Boiling point 221-222 °C(lit.)
density 1.149 g/mL at 25 °C(lit.)
refractive index 1.6332 (estimate)
Fp >230 °F
storage temp. Store below +30°C.
solubility 0.13g/l
form Crystalline Solid
pka32.4
Specific Gravity1.149
color White to pink or yellow
Water Solubility insoluble
Merck 14,9303
BRN 80580
InChIKeyFCEHBMOGCRZNNI-UHFFFAOYSA-N
LogP3.120
CAS DataBase Reference95-15-8(CAS DataBase Reference)
NIST Chemistry ReferenceBenzo[b]thiophene(95-15-8)
EPA Substance Registry SystemBenzo[b]thiophene (95-15-8)
Safety Information
Hazard Codes Xn,Xi,N
Risk Statements 22-36/37/38-20/21/22-51/53
Safety Statements 22-24/25-36-26-61
RIDADR UN3077
WGK Germany 3
Hazard Note Irritant
TSCA Yes
HazardClass 9
PackingGroup III
HS Code 29349990
MSDS Information
ProviderLanguage
ThianaphtheneEnglish
SigmaAldrichEnglish
ACROSEnglish
ALFAEnglish
Thianaphthene Usage And Synthesis
Chemical PropertiesWHITE TO RED CRYSTALLINE LOW MELTING SOLID
UsesBenzo[b]thiophene has application in organic as well as pharmaceutical industry as a component in the synthesis of Raloxifene, a breast cancer therapeutic, or hydrodesulfurization reactions.
Usesmanufacture of pharmaceuticals, thioindigo.
UsesBenzo[b]thiophene is used in the preparation of 2-thianapthenylphenyllithium, via metalation by n-butyllithium. It is used in organic as well as pharmaceutical industry as a component in the synthesis of raloxifene, a breast cancer therapeutic, or hydrodesulfurization reactions.
UsesThianaphthene may be used in the preparation of 2-thianapthenylphenyllithium, via metalation by n-butyllithium.
ApplicationThianaphthene may be used in the preparation of 2-thianapthenylphenyllithium, via metalation by n-butyllithium.
Reaction of ethyl diazoacetate with thianaphthene has been reported.
DefinitionChEBI: 1-benzothiophene is a benzothiophene and a member of 1-benzothiophenes.
Synthesis Reference(s)Journal of the American Chemical Society, 69, p. 2008, 1947 DOI: 10.1021/ja01200a053
Tetrahedron, 27, p. 1253, 1971 DOI: 10.1016/S0040-4020(01)90874-9
General DescriptionReaction of ethyl diazoacetate with thianaphthene has been reported.
Purification Methods1-Benzothiophene has the odour of naphthalene. If the IR spectrum is not very good, then suspend it in a faintly alkaline aqueous solution and steam distil it. Extract the distillate with Et2O, dry the extract (CaCl2), filter, evaporate the solvent and fractionate the residue. The distillate sets solid. The sulfoxide has m 142o, the picrate has m 148-149o (yellow crystals from EtOH) and the styphnate has m 136-137o. [Hansch & Lindwall J Org Chem 10, 381 1945, Meyer & Meyer Chem Ber 52B 1249 1919, Weisgerber & Kruber 53 1551 1920, Iddon & Scrowston Adv Heterocycl Chem 11 177 1970, Beilstein 17/2 V 6.]
Thianaphthene Preparation Products And Raw materials
Raw materialsSodium hydroxide–>Methanol–>Sulfuric acid–>Tetrahydrofuran–>Thionyl chloride–>Aluminum chloride–>Sodium borohydride–>Ethyl acetoacetate–>Acetylacetone–>Tetrabutylammonium bromide–>Bromoacetaldehyde diethyl acetal–>Thiophenol–>Bromoacetic acid–>Thiosalicylic acid
Preparation ProductsBenzothiophene-3-boronic acid–>BENZO[B]THIOPHENE-3-ACETIC ACID–>Thianaphthene-2-carboxylic acid–>2-(1-HYDROXYLAMINOETHYL)-BENZOTHIOPHENE–>1-BENZOTHIOPHENE-3-CARBONYL CHLORIDE–>3-Bromo-1-benzothiophene–>1-Benzothiophene-3-carboxylic acid–>Raloxifene–>1-Benzothiophene-3-carbaldehyde–>THIANAPHTHENE-2-CARBOXAMIDE–>1-Benzo[b]thiophen-3-yl-2-bromoethan-1-one–>2-Acetylbenzo[b]thiophene–>BENZO[B]THIOPHENE-3-CARBONITRILE–>Sertaconazole nitrate–>BENZO[B]THIOPHENE-2-CARBONYL CHLORIDE–>2-(HYDROXYMETHYL)BENZO[B]THIOPHENE–>METHYL BENZO[B]THIOPHENE-2-CARBOXYLATE–>BENZO[B]THIOPHENE-2-CARBOXALDEHYDE–>Benzo[b]thien-2-ylboronic acid–>3-Acetylthianaphthene–>1-BENZOTHIOPHENE-2-SULFONYL CHLORIDE–>[2-[4-(dihexylamino)-2-methylbenzylidene]benzo[b]thien-3(2H)-ylidene]malononitrile S,S-dioxide–>1-BENZOTHIOPHENE-3-SULFONYL CHLORIDE

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