31599-61-8

Basic information

• Product Name: 4-Iodo-1,2-dimethylbenzene
• Synonyms: 1,2-DIMETHYL-4-IODOBENZENE, 98+%;4-Iodo-o-xylene, 98+%;3,4-Dimethjyliodobenzene;3,4-Dimethylphenyl iodide;4-Iodo-1,2-dimethylb;1-IODO-3,4-DIMETHYLBENZENE;1,2-DIMETHYL-4-IODOBENZENE;3,4-DIMETHYL-1-IODOBENZENE
• CAS NO: 31599-61-8
• Molecular Formula: C₈H₉I
• Molecular Weight: 232.06
• EINECS: 200-208-3
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Iodine Compounds;Aryl;Building Blocks;C8;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 31599-61-8.mol

Chemical Properties

• Melting Point: -2.9°C (estimate)
• Boiling Point: 106-108 °C13 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: clear yellow to red-brown liquid
• Density: 1.633 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0912mmHg at 25°C
• Refractive Index: n20/D 1.603(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive: Light Sensitive
• BRN: 1905729
• CAS DataBase Reference: 4-Iodo-1,2-dimethylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Iodo-1,2-dimethylbenzene(31599-61-8)
• EPA Substance Registry System: 4-Iodo-1,2-dimethylbenzene(31599-61-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 31599-61-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Iodo-1,2-dimethylbenzene is used as a synthetic intermediate for the development of various pharmaceutical compounds. Its unique structure allows it to be a key component in the synthesis of a wide range of drugs, including those with potential therapeutic applications.
Used in Chemical Synthesis:
In the field of organic chemistry, 4-Iodo-1,2-dimethylbenzene serves as a valuable building block for the synthesis of various organic compounds. It can be used to produce a range of products such as:
1. 3-arylacrylamide: These compounds are used in the development of pharmaceuticals and agrochemicals.
2. 3,3-diaryl substituted acrylamide: These derivatives find applications in the field of materials science, particularly in the synthesis of polymers with specific properties.
3. 3-arylpropylamine: This class of compounds is utilized in the synthesis of various pharmaceuticals, including antidepressants and antipsychotic drugs.
4. Di-tert-butyl 1-(3,4-dimethylphenyl)hydrazine-1,2-dicarboxylate: 4-Iodo-1,2-dimethylbenzene is used as a precursor in the synthesis of various organic molecules and pharmaceuticals.
5. 2,3,7,8-tetramethyldibenzofuran: 4-Iodo-1,2-dimethylbenzene is employed in the synthesis of complex organic molecules and has potential applications in the development of novel materials.
6. N-(3-(3,4-Dimethylphenyl)-2-phthalimidopropionyl)-2-methylthioaniline: 4-Iodo-1,2-dimethylbenzene is used in the synthesis of dyes and pigments, which are essential in various industries such as textiles, plastics, and printing.

InChI:InChI=1/C8H9I/c1-6-3-4-8(9)5-7(6)2/h3-5H,1-2H3

Upstream product

• 95-47-6 o-xylene 
• 7553-56-2 iodine 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 75612-61-2 (4,5-dimethylcyclohexa-1,4-dienyl)trimethylsilane 
• 95-64-7 4-amino-o-xylene 

Downstream Products

• 5182-67-2 1,2-diiodo-4,5-dimethyl-benzene 
• 96843-22-0 1-bromo-2-chloro-4,5-dimethyl-benzene 
• 63689-71-4 4-iodyl-1,2-dimethyl-benzene 
• 10355-01-8 3,4-dimethyl-1-(phenylsulphonyl)benzene 
• 4920-95-0 3,4,3',4'-Tetramethylbiphenyl 
• 106053-06-9 4',5'-dimethoxy-3,3'',4,4''-tetramethyl-1,1':2',1''-terphenyl 
• 106053-07-0 4',4'',5',5''-tetramethoxy-3,3'',4,4''-tetramethyl-1,1':1'',2'',1'''-quaterphenyl 
• 5006-39-3 2,3,3’,4’-tetramethyl-1,1‘-biphenyl 
• 39763-72-9 1-iodo-4,5-dimethyl-2-nitrobenzene 
• 5973-71-7 3,4-dimethylbenzaldehyde 
• 6301-60-6 4-iodophthalic acid 

Relevant articles and documents

Pronounced catalytic effect of micellar solution of sodium dodecyl sulfate (SDS) for regioselective iodination of aromatic compounds with a sodium iodide/cerium(IV) trihydroxide hydroperoxide system

Micellar solutions of sodium dodecyl sulfate (SDS) catalyze the regioselective iodination of a wide range of aromatic compounds with sodium iodide in the presence of the easily prepared, water-resistant and recyclable cerium(IV) trihydroxide hydroperoxide, Ce(OH)3O2H, at room temperature. By this protocol, structurally diverse aromatic compounds including benzene and naphthalene were iodinated in good to excellent yields.

A simple and efficient iodination of aromatic compounds using I2/Choline Chloride/K2S2O8

A simple and efficient method for the iodination of aromatic compounds has been achieved in the presence of molecular iodine, choline chloride and potassium peroxodisulfate at 65 °C in acetonitrile. The rate of conversion of aromatic compounds into iodoaromatic compounds was promoted by in situ formed choline peroxodisulfate. This protocol provides an efficient access to iodoarenes with operational simplicity, good functional group tolerance and a moderate to good product yield.

PURIFIED CRYSTALLINE DETOMIDINE HYDROCHLORIDE MONOHYDRATE, ANHYDRATE AND FREE BASE WITH LOW AMOUNTS OF ISO-DETOMIDINE AND OTHER IMPURITIES BY RECRYSTALLISATION IN WATER

The present disclosure relates to crystalline detomidine hydrochloride monohydrate, anhydrous detomidine hydrochloride and detomidine free base (4-[(2,3-dimethylphenyl)methyl]-1H-lmidazole ), purified by recrystallisation in water, with a low amount (total amount of impurities is not more than 0.1% area relative to detomidine based on HPLC, UV detection at 220 nm) of the impurities iso-detomidine (4-[(3,4-dimethylphenyl)methyl]-1H-lmidazole ), iso-impurity A (((RS)-(3,4-dimethylphenyl)(1H-imidazol-4-yl)methanol)), impurity A ((RS)-(2,3-dimethylphenyl)(1H-imidazol-4-yl)methanol), "ketone impurity" (2,3-dimethylphenyl)(1H-imidazol-4-yl) methanone, impurity B ((RS)-(1-benzyl-1H-imidazol-5-yl)(2, 3-dimethyl phenyl) methanol) and impurity C (4-[(2,3-dimethylcyclohexyl)methyl]-1H-imidazole). Also disclosed are processes for recrystallising detomidine hydrochloride monohydrate from commercially available anhydrous detomidine hydrochloride in water, pharmaceutical compositions comprising detomidine hydrochloride in purified form for use as an analgesic in methods of treating human subjects, a process for validating a batch of detomidine hydrochloride drug substance by determining the content of impurities iso-detomidine and iso- impurity A by HPLC, as well as XRPD, DSC and TGA data of crystalline detomidine free base.

Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds

Herein, a disulfide-catalyzed electrophilic iodination of aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) has been developed. The disulfide activates DIH as a Lewis base to promote the iodination reaction in acetonitrile under mild conditions. This system is applicable to a wide range of electron-rich aromatic compounds, including acetanilide, anisole, imidazole, and pyrazole derivatives.

Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds

Herein, a disulfide-catalyzed electrophilic iodination of aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) has been developed. The disulfide activates DIH as a Lewis base to promote the iodination reaction in acetonitrile under mild conditions. This system is applicable to a wide range of electron-rich aromatic compounds, including acetanilide, anisole, imidazole, and pyrazole derivatives.

N-Iodosuccinimide (NIS) in Direct Aromatic Iodination

N-Iodosuccinimide (NIS) in pure trifluoroacetic acid (TFA) offers a time-efficient and general method for the iodination of a wide range of mono- and disubstituted benzenes at room temperature, as demonstrated in this paper. The starting materials were generally converted into mono-iodinated products in less than 16 hours at room temperature, without byproducts. A few deactivated substrates needed addition of sulfuric acid to increase the reaction rate. Another exception was methoxybenzenes that preferentially were iodinated by NIS in acetonitrile with only catalytic amounts of TFA.

Easy Access to Difluoromethylene-Containing Arene Analogues through Palladium-Catalysed C–H Olefination

An efficient palladium-catalysed ortho-C–H olefination of α,α-difluorophenylacetic acid derivatives using 8-aminoquinoline as a bidentate directing group has been developed. A range of olefinated arenes can thus be synthesized in a concise way. This reaction provides an easy and straightforward route to a panel of difluoromethylated arene analogues in moderate to good yields, with a satisfactory tolerance of common functional groups. Transformation of the products into a variety of other difluoromethylene-containing compounds demonstrates the utility of this method.

Synthesis of polysubstituted iodobenzene derivatives from alkynylsilanes and 1,3-dienes via diels-alder/oxidation/iodination reaction sequence

The cobalt-catalyzed Diels-Alder reaction of trimethylsilyl-substituted alkynes with 1,3-dienes led to dihydroaromatic intermediates which were transformed into iodobenzene derivatives. For this transformation, the dihydroaromatic intermediates had to be oxidized and the trimethylsilyl-substituted arene had to undergo a silicon-iodine exchange reaction. For this purpose, a number of oxidizing agents and iodonium sources were tested in order to realize the desired two transformations in a single step. Eventually, the combination of tert-butyl hydroperoxide (TBHP), zinc iodide, and potassium carbonate led to the desired oxidation/iodination in good to excellent yields in a short reaction time at ambient temperatures.

Efficient and direct iodination of alkyl benzenes using polymer/HIO4 and I2 under mild condition

An efficient and rapid method has been found for the iodination of aromatic compounds using iodine and polymer-supported periodic acid (PSPIA) as an oxidant under mild aprotic conditions. The reagent after the completion of the reaction was easily removed by filtration and was regenerated for further use. This method has some advantages such as: mild reaction conditions, straight forward procedure, inexpensive method, high yields and one-pot conversion.

Mild and selective organocatalytic iodination of activated aromatic compounds

We describe an organocatalytic iodination of activated aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) as the iodine source with thiourea catalysts in acetonitrile. The protocol is applicable to a number of aromatic substrates with significantly different steric and electronic properties. The iodination is generally highly regioselective and provides high yields of isolated products. NMR kinetic investigations conducted in THF-d 8indicate the role of sulfur in the thiourea motif as a nucleophile that is assisted by H-bonding in the key steps of the reaction. Georg Thieme Verlag Stuttgart . New York.