393770
1,3-Benzodithiolylium tetrafluoroborate
98%
Sinonimo/i:
BDTF
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About This Item
Formula empirica (notazione di Hill):
C7H5BF4S2
Numero CAS:
Peso molecolare:
240.05
Beilstein:
4731453
Numero MDL:
Codice UNSPSC:
12352100
ID PubChem:
NACRES:
NA.22
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Saggio
98%
Stato
solid
Punto di fusione
150 °C (dec.) (lit.)
Stringa SMILE
F[B-](F)(F)F.c1ccc2[s+]csc2c1
InChI
1S/C7H5S2.BF4/c1-2-4-7-6(3-1)8-5-9-7;2-1(3,4)5/h1-5H;/q+1;-1
CUSWPJQKCZMDPY-UHFFFAOYSA-N
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Descrizione generale
1,3-Benzodithiolylium tetrafluoroborate (BDTF, 1,3-BDYT) is an electrophilic compound.[1] It is a salt of 1,3-benzodithiolylium ion.[2]
1,3-Benzodithiolylium tetrafluoroborate is a carbenium ionic compound.[3] It has been synthesized by reacting 1,3-benzodithiole with trityl tetrafluoroborate.[2] It is widely used as an α-alkylating agent for the enantioselective α-alkylation of aldehydes.[4],[5] The nature of adsorption of 1,3-benzodithiolylium tetrafluoroborate on various carbon nanotubes (CNTs) has been studied.[1] 1,3-Benzodithiolylium tetrafluoroborate reacts with different nucleophilic reagents at the 2-position to form the respective 1,3-benzodithioles.[2]
Applicazioni
1,3-Benzodithiolylium tetrafluoroborate may be used in the synthesis of the following:
- Dibenzotetrathiafulvalene by reacting with 1,8-diazabicyclo[5.4.0]undec-7-ene.[6]
- Substituted arylcarbenium ions by reacting with boronic derivatives.[3]
- α-(1,3-benzodithiol-2-ylidene) ketones and 1,3-benzodithiole by reacting with ketones.[7]
- 2-styryl-1,3-benzodithioles by reacting with styryl-type cobaloximes.[8]
- 2-(3-indolyl)-1,3-benzodithiolylium tetrafluoroborate by reacting with indole.[9]
- 2-(1,3-benzodithiol-2-ylidene)-3,5-cyclohexadien-1-ones and 4-(1,3-benzodithiol-2-ylidene)-2,5-cyclohexadien-1-ones by reacting with 2,4- and 2,6-disubstituted phenols.[10]
Avvertenze
Warning
Indicazioni di pericolo
Consigli di prudenza
Classi di pericolo
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Organi bersaglio
Respiratory system
Codice della classe di stoccaggio
11 - Combustible Solids
Classe di pericolosità dell'acqua (WGK)
WGK 3
Dispositivi di protezione individuale
dust mask type N95 (US), Eyeshields, Gloves
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I documenti relativi ai prodotti acquistati recentemente sono disponibili nell’Archivio dei documenti.
The Facile and Direct Formylation of Organoboron Aromatic Compounds with Benzodithiolylium Tetrafluoroborate.
Petruzziello D, et al
European Journal of Organic Chemistry, 2013(22), 4909-4917 (2013)
1, 3-Benzodithiolylium salts. Synthesis and reactions with nucleophilic reagents.
Nakayama J, et al
Bulletin of the Chemical Society of Japan, 49(12), 3567-3573 (1976)
Reaction of styryl-type bis-dimethylglyoximato (pyridine) cobalt (iii), styryl cobaloximes, with 1, 3-benzodithiolylium tetrafluoroborate.
Miura K and Tada M
Chemistry Letters (Jpn), 7(10), 1139-1142 (1978)
Heterofulvalenes. II. Synthesis and reaction of 2, 3: 7, 8-dibenzo-1, 4-dithia-6-azafulvalene.
Nakayama J, et al
Bulletin of the Chemical Society of Japan, 53(6), 1661-1665 (1980)
Riccardo Porta et al.
ChemSusChem, 7(12), 3534-3540 (2014-10-23)
The use of immobilized metal-free catalysts offers the unique possibility to develop sustainable processes in flow mode. The challenging intermolecular organocatalyzed enantioselective alkylation of aldehydes was performed for the first time under continuous flow conditions. By using a packed-bed reactor
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