Basic information
- CAS
57842-27-0- Standard SMILES
F[B-](F)(F)F.c1ccc2[s+]csc2c1- InChIKey
CUSWPJQKCZMDPY-UHFFFAOYSA-N- Molecular formula
- C7H5BF4S2
- Average molar mass
- 240.1 g/mol
- Monoisotopic mass
- 239.98618544
Names & identifiers
- Preferred name
- 1,3-Benzodithiolylium Tetrafluoroborate (Hydroxyl-Protecting Agent)
- IUPAC
- 1,3-benzodithiol-3-ium tetrafluoroborate
- English name
- 1,3-Benzodithiolylium tetrafluoroborate
- Molecular formula
- C7H5BF4S2
- Molecular weight
- 240.05
Names & synonyms
Show more names
Database identifiers
- CAS
57842-27-0- PubChem CID
- 2735971
- DTXSID
DTXSID70371057- EC Number
- 625-335-5
Properties
Computed structural properties
- Topological polar surface area
- 56.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 0
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 110
Physicochemical properties
- Melting point
- 150 °C · 150 °C (dec.) (lit.)
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- sol MeCN and DMF (slowly reacts); insol ether.
- form
- Solid
- color
- Gray to brown
- BRN
- 4731453 · 4731453
- 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
- InChIKey
- CUSWPJQKCZMDPY-UHFFFAOYSA-N
- SMILES
- F[B-](F)(F)F.c1ccc2[s+]csc2c1
- CAS DataBase Reference
- 57842 · 57842-27-0(CAS DataBase Reference)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05,GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335-H302-H314
- Precautionary statements
- 280 a-P304+P340-P501a-P260-P264-P270-P280-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P405-P501-P261-P305+P351+P338 · P280a-P304+P340-P501a-P260-P264-P270-P280-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P405-P501-P261-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36
- RIDADR
- 1759 · 1759
- WGK Germany
- 3 · 3
- F
- 8 · 8-10-21
- Hazard Note
- Irritant
- HazardClass
- 8 · 8
- PackingGroup
- III
- HS Code
- 2934999090 · 2934999090
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (97.6%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Safety data
- F
- 8-10-21
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- ridadr
- 1759
- hs_code
- 2934999090
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS05,GHS07
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 26-36
- hazard_class
- 8
- Storage Class
- 11 - Combustible Solids
- packing_group
- III
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335-H302-H314
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P280a-P304+P340-P501a-P260-P264-P270-P280-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P405-P501-P261-P305+P351+P338
Chemistry & industry
Applications
Uses1,3-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.
General Description1,3-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.
Preparation methods
PreparationPreparative Method of 1,3-Benzodithiolylium tetrafluoroborate: treatment of 2-(3-methylbutoxy)-1,3-benzodithiole with Tetrafluoroboric Acid in Acetic Anhydride at 0 °C.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers33 total
Related reactions
Compound notes
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