94-48-4

Basic information

• Product Name: 2,4,5-TRIMETHYLANILINE
• Synonyms: trans-3,7-dimethyl-2,6-octadien-1-ylbenzoate;1-AMINO-2,4,5-TRIMETHYLBENZENE;2,4,5-TRIMETHYLAMINOBENZENE;GERANYL BENZOATE;FEMA 2511;PSEUDOCUMIDINE;PSI-CUMIDINE;TIMTEC-BB SBB008592
• CAS NO: 94-48-4
• Molecular Formula: C₁₇H₂₂O₂
• Molecular Weight: 258.36
• EINECS: 202-337-0
• Product Categories: Amines and Anilines;Alphabetical Listings;Flavors and Fragrances;G-H
• Mol File: 94-48-4.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 305 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.996 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.76E-05mmHg at 25°C
• Refractive Index: n20/D 1.517(lit.)
• CAS DataBase Reference: 2,4,5-TRIMETHYLANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,5-TRIMETHYLANILINE(94-48-4)
• EPA Substance Registry System: 2,4,5-TRIMETHYLANILINE(94-48-4)

Safety Data

• Hazard Codes: C
• WGK Germany: 2
• RTECS: RG5925300
• HazardClass: AIR SENSITIVE, CORROSIVE
• Hazardous Substances Data: 94-48-4(Hazardous Substances Data)

Usage

Description

2,4,5-Trimethylaniline is an organic compound with the chemical formula C9H13N. It is a derivative of aniline, where three methyl groups are attached to the benzene ring at the 2nd, 4th, and 5th positions. 2,4,5-TRIMETHYLANILINE is characterized by its amine functional group, which gives it basic properties and the ability to form salts with acids.

Uses

Used in Chemical Synthesis:
2,4,5-Trimethylaniline is used as a chemical intermediate in the synthesis of various organic compounds, including dyes, pharmaceuticals, and agrochemicals. Its reactivity and the presence of the amine group make it a versatile building block for the creation of a wide range of products.
Used in Dye Production:
In the dye industry, 2,4,5-trimethylaniline is used as a precursor for the production of certain dyes. Its ability to form complexes with metal ions and its compatibility with various substrates make it suitable for creating dyes with specific color properties and applications.
Used in Pharmaceutical Industry:
2,4,5-Trimethylaniline is used as a starting material in the synthesis of certain pharmaceutical compounds. Its basic nature and the presence of the amine group allow it to be easily modified and incorporated into drug molecules, potentially leading to the development of new therapeutic agents.
Used in Agrochemicals:
In the agrochemical industry, 2,4,5-trimethylaniline is used as a building block for the development of various agrochemical products, such as pesticides and herbicides. Its chemical properties make it suitable for the creation of compounds that can effectively control pests and weeds in agricultural settings.

Preparation

From geraniol and benzoyl chloride in anhydrous pyridine; also from geraniol and benzoyl chloride using the Schotten– Baumman reaction.

InChI:InChI=1/C17H22O2/c1-14(2)8-7-9-15(3)12-13-19-17(18)16-10-5-4-6-11-16/h4-6,8,10-12H,7,9,13H2,1-3H3/b15-12+

Upstream product

• 106-24-1 Geraniol 
• 65-85-0 benzoic acid 
• 612058-51-2 (E)-(3,7-dimethyl-2,6-octadienyloxy)(diphenyl)phosphine 
• 85909-02-0 N-benzyl-N-(tert-butoxycarbonyl)-benzamide 
• 98-88-4 benzoyl chloride 
• 93-98-1 N-phenyl benzoyl amide 
• 135364-97-5 tert-butyl benzoyl(tert-butoxycarbonyl)carbamate 
• 101137-69-3 tert-butyl benzoyl(phenyl)carbamate 
• 55-21-0 benzamide 
• 74542-54-4 N,N-phenyl-p-toluenesulfonylbenzamide 
• 100-53-8 phenylmethanethiol 
• 2902-69-4 2,2,2-trichloroacetophenone 
• 93-58-3 benzoic acid methyl ester 
• 769-78-8 vinyl benzoate 

Downstream Products

• 89637-67-2 Benzoic acid (E)-5-(3,3-dimethyl-oxiranyl)-3-methyl-pent-2-enyl ester 
• 139034-04-1 Benzoic acid 3-[2-(3,3-dimethyl-oxiranyl)-ethyl]-3-methyl-oxiranylmethyl ester 
• 88218-65-9 (2E,6E)-8-hydroxy-3,7-dimethylocta-2,6-dien-1-yl benzoate 
• 88218-66-0 (E,E)-3,7-dimethyl-8-oxo-2,6-octadienyl benzoate 
• 89637-71-8 (E)-3-methyl-6-oxohex-2-en-1-yl benzoate 
• 103784-72-1 1,7-dichloro-3,7-dimethyloct-2(E)-ene 
• 106-24-1 Geraniol 
• 100-51-6 benzyl alcohol 
• 93-58-3 benzoic acid methyl ester 
• 93998-08-4 3,7-dimethyl-1-phenyl-3-vinyloct-6-en-1-one 
• 99-86-5 1-methyl-4-isopropyl-1,3-cyclohexadiene 
• 71648-34-5 α-terpinyl benzoate 

Relevant articles and documents

Biomimetic Syntheses of Analogs of Hongoquercin A and B by Late-Stage Derivatization

The hongoquercins are tetracyclic meroterpenoid natural products with the trans-transoid decalin-dihydrobenzopyran ring system, which display a range of different bioactivities. In this study, the syntheses of a range of hongoquercins using gold-catalyzed enyne cyclization reactions and further derivatization are described. The parent enyne resorcylate precursors were synthesized biomimetically from the corresponding dioxinone keto ester via regioselective acylation, Tsuji-Trost allylic decarboxylative rearrangement, and aromatization. The dioxinone keto ester 12 was prepared in 6 steps from geraniol using allylic functionalization and alkyne synthesis.

Cesium Carbonate Catalyzed Esterification of N-Benzyl- N-Boc-amides under Ambient Conditions

We report a general activated amide to ester transformation catalyzed by Cs2CO3. Using this approach, esterification proceeds under relatively mild conditions and without the need for a transition metal catalyst. This method exhibits broad substrate scope and represents a practical alternative to existing esterification strategies. The synthetic utility of this protocol is demonstrated via the facile synthesis of crown ether derivatives and the late-stage modification of a representative natural product and several sugars in reasonable yields.

Systematic Evaluation of Sulfoxides as Catalysts in Nucleophilic Substitutions of Alcohols

Herein, a method for the nucleophilic substitution (SN) of benzyl alcohols yielding chloro alkanes is introduced that relies on aromatic sulfoxides as Lewis base catalysts (down to 1.5 mol-%) and benzoyl chloride (BzCl) as reagent. A systematic screening of various sulfoxides and other sulfinyl containing Lewis bases afforded (2-methoxyphenyl)methyl sulfoxide as optimal catalyst. In contrast to reported formamide catalysts, sulfoxides also enable the application of plain acetyl chloride (AcCl) as reagent. In addition, it was demonstrated that weakly electrophilic carboxylic acid chlorides like BzCl promote Pummerer rearrangement of sulfoxides already at room temperature. This side-reaction also provided the explanation, why sulfoxide catalyzed SN-reactions of alcohols do not allow the effective production of aliphatic and electron deficient chloro alkanes. Comparison experiments provided further insight into the reaction mechanism.