86849
Tetrabutylammonium acetate
≥90% (T), powder, technical grade
Synonym(s):
TBAAc
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About This Item
Linear Formula:
(CH3CH2CH2CH2)4N(OCOCH3)
CAS Number:
Molecular Weight:
301.51
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352116
EC Number:
234-101-8
MDL number:
Beilstein/REAXYS Number:
3599376
Product Name
Tetrabutylammonium acetate, technical, ≥90% (T)
grade
technical
Quality Level
assay
≥90% (T)
form
powder
reaction suitability
core: ammonium
mp
95-98 °C (lit.)
SMILES string
CC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC
InChI
1S/C16H36N.C2H4O2/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;1-2(3)4/h5-16H2,1-4H3;1H3,(H,3,4)/q+1;/p-1
InChI key
MCZDHTKJGDCTAE-UHFFFAOYSA-M
General description
Tetrabutylammonium acetate is an effective alternative for sodium acetate (NaOAc) due to its good solubility in organic solvents.
Application
Tetrabutylammonium acetate (TBAAc) is a good source of nucleophilic acetate ion for SN2 substitution reactions. It is commonly used to displace sulfonates and allylic halides to get corresponding acetates. Additionally, TBAAc can also be used as a mild, soluble base in Sonogashira reaction and Heck arylation.
Other Notes
Reagent for the epimerization of hydroxyl groups; base-molten salt for directing Heck-type reactions
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signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Ligand-, copper-, and amine-free Sonogashira reaction of aryl iodides and bromides with terminal alkynes.
Urgaonkar S and Verkade JG
The Journal of Organic Chemistry, 69(17), 5752-5755 (2004)
Pd nanoparticle catalyzed Heck arylation of 1, 1-disubstituted alkenes in ionic liquids. Study on factors affecting the regioselectivity of the coupling process.
Calo V, et al.
Organometallics, 22(21), 4193-4197 (2003)
T. Jeffery, M. David
Tetrahedron Letters, 39, 5751-5751 (1998)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 86849-50G | 04061833041857 |
| 86849-10G | 04061833041833 |