2,2'-Bis(trifluoromethyl)benzidine
[CAS# 341-58-2]

Identification

• Classification: Organic raw materials >> Amino compound >> Cycloalkylamines, aromatic monoamines, aromatic polyamines and derivatives and salts
• Name: 2,2'-Bis(trifluoromethyl)benzidine
• Synonyms: 2,2'-Bis(trifluoromethyl)-4,4'-biphenyldiamine
• Molecular Formula: C₁₄H₁₀F₆N₂
• Molecular Weight: 320.23
• CAS Registry Number: 341-58-2
• EC Number: 671-105-2
• SMILES: C1=CC(=C(C=C1N)C(F)(F)F)C2=C(C=C(C=C2)N)C(F)(F)F

Properties

• Melting point: 183 °C

Safety Data

• Hazard Symbols: GHS06;GHS07 Danger
• Risk Statements: H301-H319
• Safety Statements: P264-P264+P265-P270-P280-P301+P316-P305+P351+P338-P321-P330-P337+P317-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	3	H311

Discovery and Applications

2,2'-Bis(trifluoromethyl)benzidine, also known as TFMB, was discovered in the mid-20th century as part of the ongoing efforts to develop advanced aromatic diamines for high-performance polymers. TFMB, with the molecular formula C14H10F6N2, features two trifluoromethyl groups attached to a benzidine backbone. These trifluoromethyl groups impart unique properties such as enhanced thermal stability, chemical resistance, and improved solubility. The discovery of TFMB represented a significant advancement in polymer chemistry, providing a key building block for the synthesis of materials designed to withstand extreme conditions and rigorous performance requirements.

TFMB is primarily used as a monomer in the synthesis of polyimides. Polyimides derived from TFMB exhibit excellent thermal stability, mechanical strength, and chemical resistance. The trifluoromethyl groups enhance these properties, making the resulting polyimides suitable for applications that demand high performance under extreme conditions.

The aerospace industry leverages TFMB-based polyimides for their lightweight, durable, and heat-resistant properties. These materials are critical in manufacturing components for aircraft, spacecraft, and satellites. The exceptional thermal stability and mechanical strength of TFMB-based polyimides ensure that aerospace components maintain their integrity and performance in the harsh environments of space and high-altitude operations.

In the electronics sector, TFMB-based polyimides are used as insulating films, flexible circuit substrates, and protective coatings for electronic components. Their superior electrical insulation properties and thermal stability make them ideal for high-performance electronic devices. These polyimides are essential in producing flexible printed circuit boards (PCBs) and various semiconductor components, contributing to the miniaturization and enhanced performance of advanced electronic devices.

TFMB-based polyimides are also used in the development of advanced membranes for gas separation and filtration. The unique structure of TFMB imparts high selectivity and permeability to these membranes, making them effective in industrial applications such as natural gas processing, air separation, and carbon capture.

The chemical resistance and thermal stability of TFMB-based polyimides make them suitable for high-performance coatings and adhesives. These materials are used in protective coatings for equipment exposed to harsh chemicals and high temperatures. Additionally, TFMB-based adhesives provide strong and durable bonds in applications where conventional adhesives would fail.

References

2024. Crosslinked Colorless Polyimide Films via Oxazole Groups as Crosslinking Agent: Preparation and Properties. Chinese Journal of Polymer Science, 42(7).
DOI: 10.1007/s10118-024-3235-0

2024. Lightweight and strong toughness of polyimide/SiO2 composite aerogels with super-high working temperature for high-performance thermal insulation and flame-resistant application. Journal of Materials Science, 59(6).
DOI: 10.1007/s10853-024-10087-8

2024. Synthesis of optically transparent copolyimides based on alicyclic and fluorine-containing diamine. Russian Chemical Bulletin, 73(3).
DOI: 10.1007/s11172-024-4322-7