93839-14-6

Basic information

• Product Name: 2,4-dichloro-6-methoxyaniline
• Synonyms: 2,4-dichloro-6-methoxyaniline;2,4-Dichloro-6-methoxybenzenamine;2,4-Dichloro-6-methoxy-phenylamine
• CAS NO: 93839-14-6
• Molecular Formula: C₇H₇Cl₂NO
• Molecular Weight: 192.04258
• EINECS: 298-783-9
• Mol File: 93839-14-6.mol

Chemical Properties

• Boiling Point: 273.9°Cat760mmHg
• Flash Point: 119.4°C
• Appearance: /
• Density: 1.375g/cm³
• Vapor Pressure: 0.00559mmHg at 25°C
• Refractive Index: 1.587
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 1.96±0.10(Predicted)
• CAS DataBase Reference: 2,4-dichloro-6-methoxyaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-dichloro-6-methoxyaniline(93839-14-6)
• EPA Substance Registry System: 2,4-dichloro-6-methoxyaniline(93839-14-6)

Safety Data

• Hazardous Substances Data: 93839-14-6(Hazardous Substances Data)

Usage

Uses

Used in Dye and Pigment Industry:
2,4-dichloro-6-methoxyaniline is used as a chemical intermediate for the synthesis of dyes and pigments. Its unique molecular structure allows for the creation of a wide range of colored compounds that are used in various applications, including textiles, plastics, and printing inks.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 2,4-dichloro-6-methoxyaniline serves as a key intermediate in the production of various drugs. Its reactivity and functional groups make it a versatile building block for the synthesis of active pharmaceutical ingredients, contributing to the development of new medications.
Used in Agrochemical Industry:
2,4-dichloro-6-methoxyaniline is also utilized in the agrochemical industry as an intermediate for the synthesis of pesticides and other crop protection agents. Its chemical properties enable the development of compounds that can effectively control pests and diseases in agriculture, thereby enhancing crop yields and food security.
Safety Precautions:
It is important to handle 2,4-dichloro-6-methoxyaniline with care, as it may pose health risks if ingested, inhaled, or if it comes into contact with the skin. Proper safety measures, such as wearing protective clothing and using appropriate containment and ventilation systems, should be implemented during its use and storage to minimize potential hazards.

InChI:InChI=1/C7H7Cl2NO/c1-11-6-3-4(8)2-5(9)7(6)10/h2-3H,10H2,1H3

Upstream product

• 74672-01-8 3,5-dichloro-2-nitroanisole 
• 90-04-0 2-methoxy-phenylamine 
• 591-35-5 3,5-dichlorophenol 
• 77-78-1 dimethyl sulfate 
• 33719-74-3 3,5-dichloroanisole 
• 74672-02-9 3,5-dichloro-2-nitrophenol 
• 100948-83-2 3,5-dichloro-4-nitroanisole 

Downstream Products

• 158966-66-6 2-Chloro-1-(2,4-dichloro-6-methoxy-phenyl)-1H-pyrrole 
• 171058-86-9 2,3-Dichloro-1-(2,4-dichloro-6-methoxy-phenyl)-1H-pyrrole 
• 158966-74-6 1-(2,4-Dichloro-6-methoxy-phenyl)-1H-pyrrole-2-carboxylic acid 
• 158966-76-8 4,5-Dichloro-1-(2,4-dichloro-6-methoxy-phenyl)-1H-pyrrole-2-carboxylic acid 
• 115188-40-4 2-Chloro-6-methoxydiacetanilide 
• 82344-35-2 N-aceto-2-chloro-6-methoxyaniline 
• 136099-55-3 N-(2,6-dichloro-4-methoxyphenyl)acetamide 
• 141474-40-0 2,4-dichloro-6-methoxydiacetanilide 

Relevant articles and documents

Synthesis of sterically hindered polychlorinated biphenyl derivatives

A series of sterically hindered (methoxylated) polychlorinated biphenyl derivatives were synthesized using the Suzuki and the Ullmann coupling reactions. The Suzuki coupling with Pd(dba)2-dicyclohexylphosphino-2,6- dimethoxybiphenyl (DPDB) gave better yields (65-98%) compared to the classic Ullmann coupling reaction (20-38%). Despite the reactive catalyst system, no significant coupling with aromatic chlorine substituents was observed. Crystal structure analysis of four PCB derivatives revealed solid state dihedral angles ranging from 69.7 to 81.0, which indicates that these highly ortho-substituted PCB derivatives have some conformational flexibility. Georg Thieme Verlag Stuttgart.

2,2',3,3',6,6'-Hexachlorobiphenyl hydroxylation by active site mutants of cytochrome P450 2B1 and 2B11

The structural basis of species differences in cytochrome P450 2B- mediated hydroxylation of 2,2',3,3',6,6'-hexachlorobiphenyl (236HCB) was evaluated by using 14 site-directed mutants of cytochrome P450 2B1 and three point mutants of 2B11 expressed in Escherichia coli. To facilitate metabolite identification, seven possible products, including three hydroxylated and four dihydroxylated hexachlorobiphenyls, were synthesized by direct functionalization of precursors and Ullmann and crossed Ullmann reactions. HPLC and GCfMS analysis and comparison with authentic standards revealed that 2B1, 2B11, and all their mutants produced 4,5-dihydroxy-236HCB and 5-hydroxy- 236HCB, while 2B11 L363V and 2B1 I114V mutants also catalyzed hydroxylation at the 4-position. The amount of products formed by 2B1 mutants I114V, F206L, L209A, T302S, V363A, V363L, V367A, I477A, I477L, G478S, I480A, and I480L was smaller than that of the wild type. I477V exhibited unaltered 236HCB metabolism, and I480V produced twice as much dihydroxy product as the wild type. For 2B11, substitution of Val-114 or Asp-290 with Ile decreased the product yields. Replacement of Leu-363 with Val dramatically altered the profile of 236HCB metabolites. In addition to an increase in the overall level of hydroxylation, the mutant mainly catalyzed hydroxylation at the 4- position. Incubation of P450 2B1 with 5-hydroxy-236HCB produced 4,5- dihydroxy-236HCB, which indicates that 4,5-dihydroxy-236HCB may be formed by a direct hydroxylation of 5-hydroxy-236HCB. The findings from this study demonstrate the importance of residues 114, 206, 209, 302, 363, 367, 477, 478, and 480 in 2B1 and 114, 290, and 363 in 2B11 for 236HCB metabolism.

Synthesis of deuterium labelled 4'-hydroxydiclofenac

Diclofenac is a potentially useful substrate for the study of drug-drug interactions caused by modulation of the activity of specific isoforms of cytochrome P450. The synthesis of a deuterium labelled version of its principal human metabolite, 4'-hydroxydiclofenac, for use as an internal standard in LC-MS-MS studies, is described.

Synthesis of 2,6-disubstituted and 2,3,6-trisubstituted anilines

A number of 2,6-disubstituted and 2,3,6-trisubstituted anilines have been prepared via the selective para dehalogenation of the corresponding anilines. Modification of the substituents on the amino nitrogen demonstrates that the selectivity is derived from steric rather than electronic effects. The effects of the choice of formate hydrogen donor, Pd catalyst, solvent, and temperature upon the efficiency and selectivity of the dehalogenation are discussed.