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Sigma-Aldrich

1,3-Benzodithiolylium tetrafluoroborate

98%

Synonym(s):

BDTF

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About This Item

Empirical Formula (Hill Notation):
C7H5BF4S2
CAS Number:
57842-27-0
Molecular Weight:
240.05
Beilstein:
4731453
MDL number:
MFCD00070613
UNSPSC Code:
12352100
PubChem Substance ID:
24864541
NACRES:
NA.22

Assay

98%

form

solid

mp

150 °C (dec.) (lit.)

SMILES string

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

InChI key

CUSWPJQKCZMDPY-UHFFFAOYSA-N

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General description

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.

Application

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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