119-58-4

Basic information

• Product Name: 4,4'-Bis(dimethylamino)benzhydrol
• Synonyms: 4,4'-BIS(DIMETHYLAMINO)DIPHENYL CARBINOL;4,4'-BIS(DIMETHYLAMINO)BENZHYDROL;BDC-OH;BENZENEMETHANOL, 4-(DIMETHYLAMINO)-ALPHA-[4-(DIMETHYLAMINO)PHENYL]-;BIS(4-DIMETHYLAMINOPHENYL)METHANOL;N,N,N',N'-TETRAMETHYL-4,4'-DIAMINODIPHENYLCARBINOL;MICHLER'S HYDROL;4-(dimethylamino)-alpha-[4-(dimethylamino)phenyl]-benzenemethano
• CAS NO: 119-58-4
• Molecular Formula: C₁₇H₂₂N₂O
• Molecular Weight: 270.37
• EINECS: 204-335-5
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 119-58-4.mol
• Article Data: 15

Chemical Properties

• Melting Point: 100-102 °C(lit.)
• Boiling Point: 413.48°C (rough estimate)
• Flash Point: 228.743 °C
• Appearance: Slightly yellow to brownish crystalline powder
• Density: 1.0023 (rough estimate)
• Refractive Index: 1.5486 (estimate)
• Solubility: soluble in Toluene
• Water Solubility: Soluble
• CAS DataBase Reference: 4,4'-Bis(dimethylamino)benzhydrol(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Bis(dimethylamino)benzhydrol(119-58-4)
• EPA Substance Registry System: 4,4'-Bis(dimethylamino)benzhydrol(119-58-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: DC7525000
• F: 8-10-23
• Hazardous Substances Data: 119-58-4(Hazardous Substances Data)

Usage

Description

4,4'-Bis(dimethylamino)benzhydrol is an organic compound with the chemical formula C15H19N2O. It is a slightly yellow to brownish crystalline powder that serves as a crucial intermediate in the synthesis of various dyes and organic compounds. Its unique chemical structure, featuring two dimethylamino groups attached to a benzhydrol core, endows it with specific properties that make it valuable in different applications across various industries.

Uses

Used in Dye Industry:
4,4'-Bis(dimethylamino)benzhydrol is used as a dye intermediate for the production of various types of dyes. Its chemical structure allows for the creation of a wide range of colors, making it a versatile component in the dye manufacturing process. The compound's ability to form stable complexes with other molecules contributes to the development of dyes with improved properties, such as enhanced colorfastness and brightness.
Used in Organic Synthesis:
4,4'-Bis(dimethylamino)benzhydrol is also utilized as a key building block in organic synthesis, particularly for the synthesis of complex organic molecules with diverse applications. Its unique structure facilitates the formation of new chemical bonds and the creation of novel compounds with potential uses in pharmaceuticals, agrochemicals, and other specialty chemicals. The compound's reactivity and functional groups make it an essential component in the development of new molecules with specific properties and applications.

Synthesis Reference(s)

Tetrahedron Letters, 30, p. 957, 1989 DOI: 10.1016/S0040-4039(00)95289-4

Upstream product

• 101-61-1 4,4'-methylene-bis(N,N-dimethylaniline) 
• 64-19-7 acetic acid 
• 64-17-5 ethanol 
• 90-94-8 bis(p-dimethylaminophenyl)methanone 
• 71-41-0 pentan-1-ol 
• 108-88-3 toluene 
• 19422-49-2 1,1,2,2-tetrakis<4-(dimethylamino)phenyl>-1,2-ethanediol 
• 2785-29-7 benzyl potassium 
• 100-51-6 benzyl alcohol 
• 57752-15-5 3-[bis-(4-dimethylamino-phenyl)-methyl]-pentane-2,4-dione 
• 3908-72-3 bis-(4,4'-bis-dimethylamino-benzhydryl)-sulfide 
• 2123-34-4 4,4'-(aminomethylene)bis(N,N-dimethylaniline) 
• 67-56-1 methanol 
• 49742-78-1 (dma)2CH-SO₂Ph 

Downstream Products

• 43001-40-7 N-(4,4'-bis-dimethylamino-benzhydryl)-phthalimide 
• 43001-70-3 N-(4,4'-bis-dimethylamino-benzhydryl)-p-toluidine 
• 101152-72-1 (2-amino-5-methyl-phenyl)-bis-(4-dimethylamino-phenyl)-methane 
• 2491-74-9 N,N-dimethyl-4-(4-nitrophenylazo)aniline 
• 145494-07-1 N-(4,4'-bis-dimethylamino-benzhydryl)-4-phenylazo-aniline 
• 13394-58-6 bis-(4-dimethylamino-phenyl)-(2,4-dimethyl-phenyl)-methane 
• 71173-71-2 N,N'-bis-(4,4'-bis-dimethylamino-benzhydryl)-urea 
• 6310-65-2 1-{bis(4-[dimethylamino]phenyl)methyl}naphthalen-2-ol 
• 91023-16-4 (4-diethylamino-phenyl)-bis-(4-dimethylamino-phenyl)-methane 
• 95748-22-4 2-(bis(4-dimethylaminophenyl)methyl)malonic acid diethyl ester 
• 120105-03-5 bis<4-dimethylaminophenyl>(3-methylindol-1-yl)methane 
• 120105-04-6 bis<4-dimethylaminophenyl>(3-methylindol-2-yl)methane 
• 132870-24-7 N-2-benzotriazole 
• 19759-89-8 4,4'-((1H-benzo[d][1,2,3]triazol-1-yl)-methylene)-bis(N,N-di-methylaniline) 

Relevant articles and documents

4,4'-TETRAMETHYLDIAMINODIPHENYLMETHANOL FROM TETRABASE WITH HEMIN IN ACETIC ACID

4,4'-Tetramethyldiaminodiphenylmethanol was formed in 90 percent yield by oxidizing Tetrabase with hemin and hydrogen peroxide at 4 deg C in acetic acid (80 percent).

New ferrocenyl-containing organic hole-transporting materials for perovskite solar cells in regular (n-i-p) and inverted (p-i-n) architectures

Three triphenylamine derivatives containing ferrocenyl groups (JW6, JW7 and JW8) were synthesized by facile syntheses. Their HOMO levels match the valence band energy of CH3NH3PbI3. The introduction of ferrocenyl was aimed to obtain hole transporting materials with high mobility for perovskite solar cells. JW7 shows higher hole mobility (4.2 × 10?4 cm2 V?1 s?1) than JW6 (1.3 × 10?4 cm2 V?1 s?1) and JW8 (1.5 × 10?4 cm2 V?1 s?1). Their film-forming properties are affected by their molecule structures. The methoxyl and N,N-dimethyl terminal substituents of JW7 and JW8 are beneficial for having better solubility than JW6. The regular mesoporous TiO2-based perovskite solar cells (n-i-p) and the inverted planar heterojunction perovskite solar cells (p-i-n) fabricated using JW7 show the highest power conversion efficiency of 9.36% and 11.43% under 100 mW cm?2 AM1.5G solar illumination. For p-i-n cells, the standard HTM PEDOT-based cell reaches an efficiency of 12.86% under the same conditions.

FLUOROGENIC AMINO ACIDS

Provided herein are compounds (i.e., fluorogenic amino acids (FgAAs), e.g., compounds of Formulae (I), (II), (III), and (IV)) that can be used in fluorescent labeling of biomolecules (e.g., proteins) and/or cells. Also described herein are methods of labeling and detecting biomolecules and/or cells by incorporating the FgAA compounds described herein into the biomolecules and/or cells (e.g., by enzymatic incorporation). Also provided herein are biomolecules, cells, compositions, and kits comprising the FgAA compounds described herein.

Hydrogenation of Carbonyl Derivatives with a Well-Defined Rhenium Precatalyst

The first efficient and general rhenium-catalyzed hydrogenation of carbonyl derivatives was developed. The key to the success of the reaction was the use of a well-defined rhenium complex bearing a tridentate diphosphinoamino ligand as the catalyst (0.5 mol %) at 70 °C in the presence of H2 (30 bar). The mechanism of the reaction was investigated by DFT(PBE0-D3) calculations.