Tetraacetyl diborate
Basic information
- CAS
5187-37-1- Standard SMILES
CC(=O)OB(OB(OC(C)=O)OC(C)=O)OC(C)=O- InChIKey
ZMJHYNIVOZEJTJ-UHFFFAOYSA-N- Molecular formula
- C8H12B2O9
- Average molar mass
- 273.8 g/mol
- Monoisotopic mass
- 274.0667423
Names & identifiers
- Preferred name
- Tetraacetyl diborate
- IUPAC
- [acetyloxy(diacetyloxyboranyloxy)boranyl] acetate
- English name
- Boron tetraacetate
- Molecular formula
- C8H12B2O9
- Molecular weight
- 273.8
Names & synonyms
Tetraacetyl diborateTetraacetoxy diboroxane5187-37-1[acetyloxy(diacetyloxyboranyloxy)boranyl] acetateTetraacetoxy diboroxane, 97%SCHEMBL9452576DTXSID80416100FAA187371,1'-{[3,3-Bis(acetyloxy)diboroxane-1,1-diyl]bis(oxy)}di(ethan-1-one)InChI=1/C8H12B2O9/c1-5(11)15-9(16-6(2)12)19-10(17-7(3)13)18-8(4)14/h1-4HBoron tetraacetatePyroboron tetraacetate
Show more names
Tetraacetoxy diboroxane 97%Acetic acid, tetraanhydride with boric acid (H4B2O5)
Database identifiers
- CAS
5187-37-1- PubChem CID
- 5326258
- DTXSID
DTXSID80416100- Nikkaji
- J1.661.822E
Properties
Computed structural properties
- Topological polar surface area
- 114 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 10
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 303
Physicochemical properties
- Melting point
- 147 · 147-150°C
- Boiling point
- 285.5 · 285.5±23.0 °C(Predicted)
- Density
- 1.218 · 1.218±0.06 g/cm3(Predicted)
- solubility
- 4 · nearly insol petroleum ether, CCl4, CS2, Et2O; especially sol dry warm benzene, EtOAc, ethylene bromide, and nitrobenzene (can be recrystallized from these solvents)
- form
- solid
- Sensitive
- moisture sensitive
- InChI
- 1S/C8H12B2O9/c1-5(11)15-9(16-6(2)12)19-10(17-7(3)13)18-8(4)14/h1-4H3
- InChIKey
- ZMJHYNIVOZEJTJ-UHFFFAOYSA-N
- SMILES
- CC(=O)OB(OB(OC(C)=O)OC(C)=O)OC(C)=O
- UNSPSC Code
- 12161600 · 12161600
- NACRES
- 22 · NA.22
- WGK Germany
- nwg
- Storage Class
- 13 · 13 - Non Combustible Solids
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- nwg
- Storage Class
- 13 - Non Combustible Solids
Chemistry & industry
Applications
UsesTetraacetyl Diborate (TADB) is used as a selective acetylating agent for aromatic polyhydroxycarbonyl compounds; mild Lewis acid for Diels-Alder reactions of hydroxyquinones.
Preparation methods
PreparationPreparative Methods of Tetraacetyl Diborate: a mixture of 31 g (0.50 mol) of Boric Acid and 165 mL (1.75 mol) of Acetic Anhydride is heated slowly with an oil bath under N2 in a flask equipped with a reflux condenser and a magnetic stirrer. At about 70 °C a vigorous exotherm (CAUTION) occurs and the reaction mixture becomes a clear solution which, upon cooling, deposits crystals of TADB. The supernatant is drawn off and the crystals either washed with dry ether or recrystallized from 200 mL CHCl3/benzene.[1]
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