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Catalog Number
ACM22306372
Product Name
Bismuth(III) acetate
Structure
CAS
22306-37-2
Synonyms
HSDB 2186; CTK4E9160; bismuth(3+) ion tris(acetate ion); 8AJA86Y692; AKOS015915836; NSC 370498; Bismuth(III) acetate; EINECS 249-426-0; KS-000018GP; Acetic acid, bismuth(3+) salt;
EC Number
249-426-0
UNII
8AJA86Y692
IUPAC Name
bismuth;triacetate;
Molecular Formula
Bi(C2H3O2)3;C6H9BiO6;
Molecular Weight
386.112g/mol
Exact Mass
386.02g/mol
Monoisotopic Mass
386.02g/mol
Topological Polar Surface Area
120A^2
Heavy Atom Count
13
Complexity
25.5
Covalently-Bonded Unit
4
Color/Form
WHITE CRYSTALS;
Solubility
INSOL IN WATER; SOL IN ACETIC ACID;
SMILES
CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].[Bi+3];
InChI
InChI=1S/3C2H4O2.Bi/c3*1-2(3)4;/h3*1H3,(H,3,4);/q;;;+3/p-3;
InChI Key
WKLWZEWIYUTZNJ-UHFFFAOYSA-K;
H-Bond Acceptor
6
Other Experimental Properties
MP: DECOMP;
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1 Bismuth Acetate as a Catalyst for the Sequential Protodeboronation of Di- and Triborylated Indoles.

Shen F1, Tyagarajan S2, Perera D1, Krska SW2, Maligres PE2, Smith MR 3rd1, Maleczka RE Jr1.

Org Lett. 2016 Apr 1;18(7):1554-7. doi: 10.1021/acs.orglett.6b00356. Epub 2016 Mar 21.

Bismuth(III) acetate is a safe, inexpensive, and selective facilitator of sequential protodeboronations, which when used in conjunction with Ir-catalyzed borylations allows access to a diversity of borylated indoles. The versatility of combining Ir-catalyzed borylations with Bi(III)-catalyzed protodeboronation is demonstrated by selectively converting 6-fluoroindole into products with Bpin groups at the 4-, 5-, 7-, 2,7-, 4,7-, 3,5-, and 2,4,7-positions and the late-stage functionalization of sumatriptan.

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Email:
Tel:1-201-478-8534
1-516-662-5404
Fax: 1-516-927-0118
Address: 2200 Smithtown Avenue, Room 1 Ronkonkoma, NY 11779-7329 USA