1,4-Di-tert-butyl-2,5-dimethoxybenzene

CAS Number 7323-63-9

Chemistry Building Blocks, Materials, Non-Heterocyclic Building Blocks, Semiconducting Molecules

1,4-Di-tert-butyl-2,5-dimethoxybenzene MSDS

1,4-Di-tert-butyl-2,5-dimethoxybenzene CAS 7323-63-9

1,4-Di-tert-butyl-2,5-dimethoxybenzene (DDB)

A benchmark redox shuttle for lithium ion battery (LIB) systems.

Specifications | MSDS | Literature and Reviews

2,5-Di-tert-butyl-1,4-dimethoxybenzene (DDB, CAS number 7323-63-9), an aromatic compound with two methoxy groups at 2,5-positions and two tert-butyl groups at 1,4-positions of the benzene ring, is a very successful benchmark redox shuttle molecule developed for the lithium ion battery (LIB) systems. With two tert-butyl groups, DDB has rigid molecular structure with an outstanding electrochemical reversibility and stability.

DDB provides high-rate overcharge protection of lithium iron phosphate (LiFePO₄) based Li-ion cells by a reversible and stable redox reaction at 3.9 V vs. Li/Li⁺and more than 200 cycles of 100% overcharge per cycle at C/2 and 1C rate for LiFePO₄ cathode in LIBs.

Despite being a benchmark shuttle, DDB has relatively low solubility in the carbonate electrolyte and the redox potential that is insufficient for 4 V operation of LIBs, due to its low polarity induced from symmetric structure.

General Information

CAS Number	7323-63-9
Chemical Formula	C₁₆H₂₆O₂
Full Name	1,4-Di-tert-butyl-2,5-dimethoxybenzene
Molecular Weight	250.38 g/mol
Synonyms	DDB, 2,5-Di-tert-butyl-1,4-dimethoxybenzene, 1,4-Di-t-butyl-2,5-dimethoxybenzene;
Classification / Family	Redox Shuttle, Battery materials, Energy materials, Lithium ion batteries (LLIBs)

Chemical Structure

Product Details

Purity	>99% (GC)
Melting Point	103-104 °C
Appearance	White to off-white powder

MSDS Documentation

1,4-Di-tert-butyl-2,5-dimethoxybenzene MSDS Sheet

Literature and Reviews

High-Rate Overcharge Protection of LiFePO4-Based Li-Ion Cells Using the Redox Shuttle Additive 2,5-Ditertbutyl-1,4-dimethoxybenzene, J. Dahn et al., J. Electrochem. Soc., 152 (6), A1283 (2005); DOI 10.1149/1.1906025.
Asymmetric Form of Redox Shuttle Based on 1,4-Di-tert-butyl-2,5-dimethoxybenzene, W. Weng et al., J. Electrochem. Soc., 160 (10), A1711 (2013); DOI: 10.1149/2.044310jes.
Smart Polymeric Cathode Material with Intrinsic Overcharge Protection Based on a 2,5-Di-tert-butyl- 1,4-dimethoxybenzene Core Structure, Adv. Funct. Mater., 22 (21), 4485-4492 (2012); DOI: 10.1002/adfm.201200458.

Understanding the redox shuttle stability of 3,5-di-tert-butyl-1,2-dimethoxybenzene for overcharge protection of lithium-ion batteries, J. Power Source, 195 (15), 4957-4962 (2010); DOI: 10.1016/j.jpowsour.2010.02.075.
A redox-active organic salt for safer Na-ion batteries, W. Ji et al., Nano Energy, 72, 104705 (2020); DOI: 10.1016/j.nanoen.2020.104705.
An Extremely Durable Redox Shuttle Additive for Overcharge Protection of Lithium-ion Batteries, J. Zhang et al., Mater. Today Energy, 13, 308-311 (2019); DOI: 10.1016/j.mtener.2019.06.003..