4430-09-5

Basic information

• Product Name: N N-DI-N-HEXYLANILINE 97
• Synonyms: N N-DI-N-HEXYLANILINE 97;N,N-dihexylaniline;BenzenaMine, N,N-dihexyl-;N,N-Di-N-hexylaniline 97%
• CAS NO: 4430-09-5
• Molecular Formula: C₁₈H₃₁N
• Molecular Weight: 261.45
• Product Categories: Amines;C11 to C38;Nitrogen Compounds
• Mol File: 4430-09-5.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 165 °C2 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.89 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.26E-05mmHg at 25°C
• Refractive Index: n20/D 1.507(lit.)
• CAS DataBase Reference: N N-DI-N-HEXYLANILINE 97(CAS DataBase Reference)
• NIST Chemistry Reference: N N-DI-N-HEXYLANILINE 97(4430-09-5)
• EPA Substance Registry System: N N-DI-N-HEXYLANILINE 97(4430-09-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 4430-09-5(Hazardous Substances Data)

Usage

Description

N,N-Di-N-hexylaniline, also known as N,N-dihexylaniline, is an organic compound belonging to the class of N,N-dialkylanilines. It is synthesized by refluxing a mixture of aniline, iodohexane, and potassium carbonate in ethanol. N N-DI-N-HEXYLANILINE 97 serves as a crucial intermediate in the synthesis of various organic dyes and other chemical compounds.

Uses

Used in Chemical Synthesis:
N,N-Di-N-hexylaniline is used as a key intermediate in the synthesis of various organic compounds, including dyes and other specialty chemicals. Its unique structure allows for further functionalization and modification, making it a versatile building block in the chemical industry.
Used in Dye Synthesis:
In the dye industry, N,N-di-N-hexylaniline is used as a starting material for the synthesis of 4-formyl-N,N-dihexylaniline, a vital precursor for the production of N,N′-bis[(4-(N,N-dihexylamino)benzylidene]diaminofumaronitrile, a bisazomethine dye. This dye finds applications in various fields, such as textiles, plastics, and printing inks, due to its coloristic properties and stability.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, N,N-di-N-hexylaniline, due to its structural similarity to other N,N-dialkylanilines, may potentially be used in the pharmaceutical industry as a building block for the synthesis of various drug candidates. Its ability to form stable complexes with other molecules could make it a valuable component in the development of new drugs with specific therapeutic properties.

InChI:InChI=1/C18H31N/c1-3-5-7-12-16-19(17-13-8-6-4-2)18-14-10-9-11-15-18/h9-11,14-15H,3-8,12-13,16-17H2,1-2H3

Upstream product

• 111-25-1 1-bromo-hexane 
• 62-53-3 aniline 
• 111-27-3 hexan-1-ol 
• 3839-35-8 4-methylbenzenesulfonic acid n-hexylester 
• 98-95-3 nitrobenzene 
• 66-25-1 hexanal 
• 928-95-0 (E)-2-Hexen-1-ol 
• 2305-21-7 2-hexen-1-ol 
• 143-16-8 dihexylamine 
• 108-90-7 chlorobenzene 
• 638-45-9 1-Iodohexane 

Downstream Products

• 90133-80-5 4-formyl-N,N-dihexylaniline 
• 125816-14-0 Dihexyl-(4-phenylazo-phenyl)-amine 
• 90134-12-6 4-(dihexylamino)cinnamaldehyde 

Relevant articles and documents

Reductive Alkylation of Azides and Nitroarenes with Alcohols: A Selective Route to Mono- And Dialkylated Amines

Herein, we demonstrated an efficient protocol for reductive alkylation of azides/nitro compounds via a borrowing hydrogen (BH) method. By following this protocol, selective mono- and dialkylated amines were obtained under mild and solvent-free conditions. A series of control experiments and deuterium-labeling experiments were performed to understand this catalytic process. Mechanistic studies suggested that the Ir(III)-H was the active intermediate in this reaction. KIE study revealed that the breaking of the C-H bond of alcohol might be the rate-limiting step. Notably, this solvent-free strategy disclosed a high TON of around 5600. Based on kinetic studies and control experiments, a metal-ligand cooperative mechanism was proposed.

Iridium-Catalyzed Alkylation of Amine and Nitrobenzene with Alcohol to Tertiary Amine under Base- and Solvent-Free Conditions

Herein, an efficient and green method for the selective synthesis of tertiary amines has been developed that involves iridium-catalyzed alkylation of various primary amines with aromatic or aliphatic alcohols. Notably, the catalytic protocol enables this transformation in the absence of additional base and solvent. Furthermore, the alkylation of nitrobenzene with primary alcohol to tertiary amine has also been achieved by the same catalytic system. Deuterium-labeling experiments and a series of control experiments were conducted, and the results suggested that an intermolecular borrowing hydrogen pathway might exist in the alkylation process.

Substituent modification of electro-optic chromophores with 4-cyano-5-dicyanomethylene-2,5-dihydro-1H-pyrrol-2-one as an acceptor

Electro-optic chromophores with 4-cyano-5-dicyanomethylene-2,5-dihydro-1H-pyrrol-2-one (CDCOP) and aniline moieties as an acceptor and a donor, respectively, were synthesized with modification of three substituents, among which two were attached to the aniline moiety (R) and one was introduced to the CDCOP ring (R′). Butyl and hexyl groups were introduced as R and R′, and higher melting points were observed when R and R′ were the same. For the chromophore fixation, thermal crosslinking based on cyanate trimerization was performed. The chromophore with cyanate moiety in R′ was combined with bisphenol A dicyanate, and the thermal chromophore fixation was confirmed with almost no chromophore degradation.