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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)

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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)
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
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)
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)
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