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393770

Sigma-Aldrich

1,3-Benzodithiolylium tetrafluoroborate

98%

Sinonimo/i:

BDTF

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About This Item

Formula empirica (notazione di Hill):
C7H5BF4S2
Numero CAS:
57842-27-0
Peso molecolare:
240.05
Beilstein:
4731453
Numero MDL:
MFCD00070613
Codice UNSPSC:
12352100
ID PubChem:
24864541
NACRES:
NA.22

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]

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H315,H319,H335

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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Certificati d'analisi (COA)

Lot/Batch Number
MKBN6902V
14231EH
22229CA
13416TS
10313EC

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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)
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)
Masashi Mamada et al.
Acta crystallographica. Section E, Structure reports online, 65(Pt 9), o2083-o2083 (2009-01-01)
Crystals of the title compound (DBTTF), C(14)H(8)S(4), feature a triclinic polymorph different from two known monoclinic polymorphs. In this form, there are two independent centrosymmetric half-mol-ecules in the asymmetric unit. Although the mol-ecular orientations are relatively similar to one of
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
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)
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