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1,3-Benzodithiolylium tetrafluoroborate

98%

Sinônimo(s):

BDTF

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About This Item

Fórmula empírica (Notação de Hill):
C7H5BF4S2
Número CAS:
57842-27-0
Peso molecular:
240.05
Beilstein:
4731453
Número MDL:
MFCD00070613
Código UNSPSC:
12352100
ID de substância PubChem:
24864541
NACRES:
NA.22

Ensaio

98%

forma

solid

pf

150 °C (dec.) (lit.)

cadeia de caracteres SMILES

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

chave InChI

CUSWPJQKCZMDPY-UHFFFAOYSA-N

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Descrição geral

1,3-Benzodithiolylium tetrafluoroborate (BDTF, 1,3-BDYT) is an electrophilic compound. It is a salt of 1,3-benzodithiolylium ion.
1,3-Benzodithiolylium tetrafluoroborate is a carbenium ionic compound. It has been synthesized by reacting 1,3-benzodithiole with trityl tetrafluoroborate. It is widely used as an α-alkylating agent for the enantioselective α-alkylation of aldehydes., The nature of adsorption of 1,3-benzodithiolylium tetrafluoroborate on various carbon nanotubes (CNTs) has been studied. 1,3-Benzodithiolylium tetrafluoroborate reacts with different nucleophilic reagents at the 2-position to form the respective 1,3-benzodithioles.

Aplicação

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.
  • Substituted arylcarbenium ions by reacting with boronic derivatives.
  • α-(1,3-benzodithiol-2-ylidene) ketones and 1,3-benzodithiole by reacting with ketones.
  • 2-styryl-1,3-benzodithioles by reacting with styryl-type cobaloximes.
  • 2-(3-indolyl)-1,3-benzodithiolylium tetrafluoroborate by reacting with indole.
  • 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.

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H315,H319,H335

Classificações de perigo

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

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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
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)
Highly enantioselective α alkylation of aldehydes with 1,3-benzodithiolylium tetrafluoroborate: a formal organocatalytic α alkylation of aldehydes by the carbenium ion.
Andrea Gualandi et al.
Angewandte Chemie (International ed. in English), 50(34), 7842-7846 (2011-06-30)
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