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| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
technical grade, ≥90%(T) Technical grade for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Room temperature,Argon charged Ships Normal Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 13 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
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 SN 2 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
| Canonical Smiles | CCCC[N+](CCCC)(CCCC)CCCC.CC(=O)[O-] |
|---|---|
| IUPAC Name | tetrabutylazanium;acetate |
| InChIKey | MCZDHTKJGDCTAE-UHFFFAOYSA-M |
| 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 |
| Isomeric SMILES | CCCC[N+](CCCC)(CCCC)CCCC.CC(=O)[O-] |
| WGK Germany | 3 |
| Molecular Weight | 301.51 |
| Beilstein | 3599376 |
| Reaxy-Rn | 3599376 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
Download SDS →Lot-specific quality data. Enter your lot number to retrieve the exact COA.
Look up COA →Full quality attributes and acceptance criteria for this grade.
View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic nitrogen compounds |
| Class | Organonitrogen compounds |
| Subclass | Quaternary ammonium salts |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Tetraalkylammonium salts |
| Alternative Parents | Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organic salts Organic oxides Hydrocarbon derivatives Carbonyl compounds Amines |
| Molecular Framework | Not available |
| Substituents | Tetraalkylammonium salt - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organic salt - Organooxygen compound - Carbonyl group - Amine - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as tetraalkylammonium salts. These are organonitrogen compounds containing a quaternary ammonium substituted with four alkyl chains. |
| External Descriptors | Not available |
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Solubility | Soluble in water |
|---|---|
| Sensitivity | Moisture and air sensitive |
| Refractive Index | 1.389 |
| Flash Point(°F) | 100^C |
| Flash Point(°C) | 100^C |
| Boil Point(°C) | 100°C |
| Melt Point(°C) | 95-98°C |
| Molecular Weight | 301.500 g/mol |
| XLogP3 | |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 12 |
| Exact Mass | 301.298 Da |
| Monoisotopic Mass | 301.298 Da |
| Topological Polar Surface Area | 40.100 Ų |
| Heavy Atom Count | 21 |
| Formal Charge | 0 |
| Complexity | 142.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 2 |
| 1. Hang Zhong, Wenbo Li, Yin Huang, Duoling Cao, Congqiang Zhang, Huaxi Bao, Zhiguang Guo, Li Wan, Xu Zhang, Xiuhua Zhang, Yuebin Li, Xiaoming Ren, Xianbao Wang, Dominik Eder, Kai Wang, Shengzhong Frank Liu, Shimin Wang. (2022) All-Inorganic Perovskite Solar Cells with Tetrabutylammonium Acetate as the Buffer Layer between the SnO2 Electron Transport Film and CsPbI3. ACS Applied Materials & Interfaces, [PMID:35073689] [10.1021/acsami.1c18375] |
| 2. Zhu Kaijie, Zheng Xiongjie, Ye Junli, Huang Yue, Chen Hongyan, Mei Xuehan, Xie Zongzhou, Cao Lixin, Zeng Yunliu, Larkin Robert M., Xu Qiang, Perez-Roman Estela, Talón Manuel, Zumajo-Cardona Cecilia, Wurtzel Eleanore T., Deng Xiuxin. (2021) Regulation of carotenoid and chlorophyll pools in hesperidia, anatomically unique fruits found only in Citrus. PLANT PHYSIOLOGY, 187 (2): (829-845). [PMID:34608960] [10.1093/plphys/kiab291] |
| 3. Aiqing Feng, Yongmei Jia, Liping Huang, Lin Wang, Guohua Zhou, Sheng Wang, Peilian Liu. (2019) 1,6-Elimination reaction induced detection of fluoride ions in vitro and in vivo based on a NIR fluorescent probe. SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, [PMID:31146206] [10.1016/j.saa.2019.05.013] |
| 4. Xuefang Shang, Xuejing Yue, Yanmei Chen, Congshu Li, Hongli Chen, Tianyun Wang. (2018) Design, synthesis, crystal structure and cytotoxicity studies of colorimetric fluorescent “OFF-ON” probes for rapid detection of hydrogen sulfide based on Cu(II) complex. INORGANIC CHEMISTRY COMMUNICATIONS, [PMID:] [10.1016/j.inoche.2018.10.030] |
| 5. Chen Yanmei, Shang Xuefang, Li Congshu, Xue Zhenzhen, Chen Hongli, Wu Hongwei, Wang Tianyun. (2018) The synthesis, crystal, hydrogen sulfide detection and cell assement of novel chemsensors based on coumarin derivatives. Scientific Reports, 8 (1): (1-9). [PMID:30385799] [10.1038/s41598-018-34331-9] |
| 6. Shang Xuefang, Li Jie, Feng Yaqian, Chen Hongli, Guo Wei, Zhang Jinlian, Wang Tianyun, Xu Xiufang. (2018) Low-Cytotoxicity Fluorescent Probes Based on Anthracene Derivatives for Hydrogen Sulfide Detection. Frontiers in Chemistry, [PMID:29988478] [10.3389/fchem.2018.00202] |
| 7. Yanmei Chen, Xuefang Shang, Xing Zhao, Jie Li, Jianmei Yuan, Hongli Chen, Jinlian Zhang, Tianyun Wang. (2018) Highly selective probes of copper(II) complexes for sulfide detection and cytotoxicity assay. Journal of Sulfur Chemistry, [PMID:] [10.1080/17415993.2018.1425410] |
| 8. Kui Ren, Xuefang Shang, Yanmei Chen, Xueli Zhang, Jiajia Fu, Peipei Zhao, Jinlian Zhang. (2016) Synthesis and crystal structure of a highly selective colorimetric and fluorometric sensor for hydrogen sulfide. LUMINESCENCE, 32 (5): (765-771). [PMID:28026099] [10.1002/bio.3248] |
| 9. Kui Ren, Xuefang Shang, Jiajia Fu, Peipei Zhao, Jinlian Zhang. (2015) Copper complex based on 2-(phenylimino-methyl)-phenol as a high selective fluoresencent probe for hydrogen sulfide. POLYHEDRON, [PMID:] [10.1016/j.poly.2015.11.022] |
| 10. Xuefang Shang, Wanli Li, Yaqian Feng, Xin Li, Xiufang Xu. (2015) Double Properties of Novel Acylhydrazone Nanomaterials Based on a Conjugated System: Anion Binding Ability and Antibacterial Activity. Applied Sciences-Basel, 5 (4): (910-925). [PMID:] [10.3390/app5040910] |
| 11. Xuefang Shang, Wanli Li, Xiaofang Wei, Huanle Zhang, Zhiyuan Fu, Jinlian Zhang, Xiufang Xu. (2014) Synthesis, Bioactivity, and the Anion-Binding Property of 2-Sulfydryl-1,3,4-thiodiazole Derivatives. HETEROATOM CHEMISTRY, 26 (2): (142-149). [PMID:] [10.1002/hc.21239] |
| 12. Wei Lu, Jinting Zhou, Keyuan Liu, Dan Chen, Liming Jiang, Zhiquan Shen. (2013) A polymeric film probe with a turn-on fluorescence response to hydrogen sulfate ions in aqueous media. Journal of Materials Chemistry B, 1 (38): (5014-5020). [PMID:32261091] [10.1039/C3TB20731E] |
| 13. Shuangjun Li, Shengnan Li, Wen Li, Yue Hua, Ruyue Shi, Dongmei Zhao, Jiaxin Wang, Xiuhua Zhao. (2025) Zwitterion-Coated Virus-Like Nanoparticles Enable Oral siRNA Delivery for Tumor Autophagy and Immune Activation. Small, [PMID:40855773] [10.1002/smll.202505955] |
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