90283-01-5

Usage

Type of compound

Substituted benzene derivative

Chlorine atom positions

1 and 5

Methoxy group positions

2 and 3

Common uses

Intermediate in the synthesis of pharmaceuticals and agrochemicals, building block in organic chemistry

Physical state at room temperature

Clear, colorless liquid

Solubility

Sparingly soluble in water, soluble in many organic solvents

Safety precautions

Harmful if inhaled, ingested, or comes into contact with the skin

Upstream product

• 13673-92-2 3,5-dichlorocatechol 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 91-16-7 1,2-dimethoxybenzene 

Downstream Products

• 151143-60-1 2,6-dichloro-3,4-dimethoxynitrobenzene 

Relevant academic research and scientific papers

Halogenated volatiles from the fungus Geniculosporium and the actinomycete Streptomyces chartreusis

Two unidentified chlorinated volatiles X and Y were detected in headspace extracts of the fungus Geniculosporium. Their mass spectra pointed to the structures of a chlorodimethoxybenzene for X and a dichlorodimethoxybenzene for Y. The mass spectra of some constitutional isomers for X and Y were included in our databases and proved to be very similar, thus preventing a full structural assignment. For unambiguous structure elucidation all possible constitutional isomers for X and Y were obtained by synthesis or from commercial suppliers. Comparison of mass spectra and GC retention times rigorously established the structures of the two chlorinated volatiles. Chlorinated volatiles are not very widespread, but brominated or even iodinated volatiles are even more rare. Surprisingly, headspace extracts from Streptomyces chartreusis contained methyl 2-iodobenzoate, a new natural product that adds to the small family of iodinated natural products.

Synthesis of Oxygenated Derivatives of 2,3,7,8-Tetrachlorodibenzo-p-dioxin

Four monomethoxy, five dimethoxy and four dihydroxy derivatives of polychlorodibenzo-p-dioxin have been synthesized, and their physical and spectral properties (NMR and MS) have been reported.The general method for the synthesis of specific mono- and dime

13C and 17O NMR Study of Methoxy Groups in Chlorinated Di- and Trimethoxybenzenes

13C and 17O NMR data for the methoxy groups in isomeric 1,2-, 1,3- and 1,4-dimethoxybenzenes, 1,2,3-trimethoxybenzenes and most of their chlorinated derivatives and some related brominated compounds were measured for CDCl3 solutions.The 17O NMR chemical shifts show up to 60 ppm dispersion.Comparison between the compounds with and without adjacent chlorine atoms (2,6-di- and 2,4,6-trisubstitution) also showed a clear methoxy carbon chemical shift change.The number and position of the chlorine atoms in the aromatic ring give small but observable effects on the 17O NMR chemical shifts of the methoxy group if it is coplanar with the aromatic plane.Similarly, the degree and nature of the substitution have a minor effect (about 1 Hz) on the 1J(CH) direct coupling values.

Highly Selective Aromatic Chlorinations. Part 2. The Chlorination of Substituted Phenols, Anisoles, Anilines, and Related Compounds with N-Chloroamines in Acidic Solution

Phenols, anisoles, anilines, and related compounds are chlorinated in trifluoroacetic acid at room temperature by N-chlorodialkylamines and N-chlorotrialkylammonium salts.With monsubstituted compounds and their 2- and 3-substituted derivatives the reaction occurs efficiently and selectively at the 4-position.The reactivity of these substrates and the selectivity of their chlorinations are determined by electronic rather than steric effects of the substituent.Blocking the reaction with a substituent at the 4-position generally leads to only poor or moderate yields of the 2-chlorinated product.Evidence for radical and cation radical intermediates has been obtained in the reactions of some of the 4-substituted reactants and the mechanism of chlorination is discussed in the light of these findings.The reactions of selected substrates have been scaled up to give laboratory syntheses.

Mass Spectra of Chlorinated Veratroles (1,2-dimethoxybenzenes)

The behaviour of all nine chlorinated veratroles (1,2-dimethoxybenzenes) under electron impact has been investigated.The most common fragmentation processes are interpreted using metastable ion analysis and deuterium labelled compounds.For all compounds studied, the most common fragmentation route seems to be the primary loss of a methyl radical followed by loss of carbon monoxide.The ion formed has a well-known quinonoid structure and fragments by several routes elucidated by metastable ion analysis.In general, the spectra of the positional isomers are shown to be practically similar and it is apparent the e.g. the 3- and 4-chloro isomers can be differentiated only from the abundance ratio of the +. and + ions.