80745-07-9

Basic information

• Product Name: 4-METHOXY-2,3,6-TRIMETHYLBENZENESULFONYL CHLORIDE
• Synonyms: MTR CHLORIDE;MTR-CL;4-METHOXY-2,3,6-TRIMETHYLBENZENESULFONYL CHLORIDE;4-METHOXY-2,3,6-TRIMETHYLBENZENESULPHONYL CHLORIDE;4-METHOXY-2,3,6-TRIMETHYLPHENYLSULFONYL CHLORIDE;4-METHOXY-2,3,6-TRIMETHYLBENZENE-;Benzenesulfonyl chloride, 4-methoxy-2,3,6-trimethyl- (9CI);4-Methoxy-2,3,6-trimethylphenylaulfomyl chloride
• CAS NO: 80745-07-9
• Molecular Formula: C₁₀H₁₃ClO₃S
• Molecular Weight: 248.73
• EINECS: -0
• Product Categories: SULFONYLHALIDE
• Mol File: 80745-07-9.mol

Chemical Properties

• Melting Point: 57-61 °C
• Boiling Point: 372.5°C at 760 mmHg
• Flash Point: 179.1°C
• Appearance: /
• Density: 1.25g/cm³
• Vapor Pressure: 2.05E-05mmHg at 25°C
• Refractive Index: 1.521
• Storage Temp.: −20°C
• Sensitive: Moisture Sensitive
• BRN: 4867665
• CAS DataBase Reference: 4-METHOXY-2,3,6-TRIMETHYLBENZENESULFONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHOXY-2,3,6-TRIMETHYLBENZENESULFONYL CHLORIDE(80745-07-9)
• EPA Substance Registry System: 4-METHOXY-2,3,6-TRIMETHYLBENZENESULFONYL CHLORIDE(80745-07-9)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 3
• WGK Germany: 3
• F: 3-10-21
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 80745-07-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-METHOXY-2,3,6-TRIMETHYLBENZENESULFONYL CHLORIDE is used as a sulfonating agent for the synthesis of various pharmaceuticals, facilitating the introduction of sulfonyl groups into organic molecules to enhance their therapeutic properties.
Used in Organic Chemistry:
In the field of organic chemistry, 4-METHOXY-2,3,6-TRIMETHYLBENZENESULFONYL CHLORIDE is used as a reagent for the synthesis of sulfonamides and other sulfur-containing compounds, contributing to the development of new chemical entities with potential applications in various industries.
Used in Research and Development:
4-METHOXY-2,3,6-TRIMETHYLBENZENESULFONYL CHLORIDE is employed as a key intermediate in research and development laboratories, where it is utilized to explore novel chemical reactions and synthesize new compounds with potential applications in medicine, agriculture, and other sectors.

InChI:InChI=1/C10H13ClO3S/c1-6-5-9(14-4)7(2)8(3)10(6)15(11,12)13/h5H,1-4H3

Upstream product

• 697-82-5 2,3,5-trimethylphenol 
• 20469-61-8 2,3,5-trimethylanisole 

Downstream Products

• 83031-11-2 Mtr-Ile-OH 
• 172267-50-4 N-(4-methoxy-2,3,5-trimethylphenylsulfonyl)-L-aspartic acid 
• 279255-87-7 2(R)-(4-methoxy-2,3,6-trimethylbenzenesulfonylamino)-3-methylbutyric acid benzyl ester 
• 279256-38-1 2(R)-(4-methoxy-2,3,6-trimethylbenzenesulfonylamino)-3(S)-hydroxybutyric acid 
• 279256-03-0 2(R)-2-(4-methoxy-2,3,6-trimethylbenzenesulfonylamino)-3-tert-butoxypropionic acid 
• 215448-49-0 (2S)-N-[1-[(1-amino-6-isoquinolinyl)methyl]-2-oxo-2-(1-piperidinyl)ethyl]-2-[[(4-methoxy-2,3,6-trimethylphenyl)sulfonyl]amino]-4-methylpentanamide hydrochloride 
• 215448-63-8 (3S)-4-[[1-[(1-amino-6-isoquinolinyl)methyl]-2-oxo-2-(4-morpholinyl)ethyl]amino]-3-[[(4-methoxy-2,3,6-trimethylphenyl)sulfonyl]amino]-4-oxo-butanoic acid 1,1-dimethylethylester hydrochloride 
• 215448-00-3 (3S)-4-[[1-[(1-amino-6-isoquinolinyl)methyl]-2-oxo-2-(1-piperidinyl)ethyl]amino]-3-[[(4-methoxy-2,3,6-trimethylphenyl)sulfonyl]amino]4-oxo-butanoic acid 1,1-dimethylethylester hydrochloride 
• 1018897-16-9 (R)-2-((1-(4-methoxy-2,3,6-trimethylphenylsulfonyl)pyrrolidin-2-yl)methoxy)-1-(4-(1-methylpiperidin-4-yl)piperazin-1-yl)ethanone 
• 1215009-01-0 4-methoxy-2,3,6-trimethyl-N-((1,3,5-trimethyl-1H-pyrazol-4-yl)methyl)benzenesulfonamide 
• 1215008-98-2 4-methoxy-2,3,6-trimethyl-N-(pyridin-3-yl)benzenesulfonamide 
• 1215008-92-6 4-methoxy-2,3,6-trimethyl-N-(2-methylpyridin-3-yl)benzenesulfonamide 
• 1215008-97-1 N-(3,5-dimethylisoxazol-4-yl)-4-methoxy-2,3,6-trimethylbenzenesulfonamide 
• 1215009-04-3 N-(3,5-dimethyl-1H-pyrazol-4-yl)-4-methoxy-2,3,6-trimethylbenzenesulfonamide 

Relevant articles and documents

Advantage of in situ generation of N-arylsulfonyl imines from α-amide sulfones in the phase-transfer-catalyzed asymmetric Strecker reaction

Highly efficient, catalytic enantioselective synthesis of N-arylsulfonyl α-amino nitriles from the corresponding α-amido sulfones has been achieved under toluene-aqueous potassium cyanide biphasic conditions using chiral quaternary ammonium iodide (R,R,R)-1 as an effective phase-transfer catalyst. This Strecker synthesis involving the in situ generation of the reactive N-sulfonyl imines is advantageous for the cyanation of the substrates having primary and secondary alkyl substituents.

Method for protecting amino group and restoring the same

An ω-amino group and/or α-amino group in an amino acid or a peptide can be protected with a 4-methoxy-2,3,6-trimethylbenzenesulfonyl group, and said group may easily be removed without affecting the amino acid or the peptide. Thus, the present invention is useful in the synthesis of peptide containing ω-amino group and/or α-amino group.

Method for protecting guanidino group and restoring the same

A guanidino group in an amino acid or a peptide can be protected with a specific group, i.e. pentamethylbenzensulfonyl, 2,4,6-trimethoxybenzenesulfonyl, 4-methoxy-2,3,5,6-tetramethylbenzenesulfonyl, 4-methoxy-2,6-dimethylbenzenesulfonyl or 4-methoxy-2,3,6-trimethylbenzenesulfonyl, and said group may easily be removed without affecting the amino acid or the peptide to be derived from the protected amino acid or peptide. Thus, the present invention is useful in the synthesis of peptides containing the guanidino group.

Further Studies on the Use of Multi-substituted Benzenesulfonyl Groups for Protection of the Guanidino Function of Arginine

Various multi-substituted benzenesulfonyl protecting groups for the guanidino function of arginine, removable under mild conditions such as with trifluoroacetic acid (TFA)-thioanisole, were studied.Among them, the 4-methoxy-2,6-dimethylbenzenesulfonyl (Mds) group, the 2,3,4,5,6-pentamethylbenzenesulfonyl (Pme) group, and the 4-methoxy-2,3,6-trimethylbenzenesulfonyl (Mtr) group were found to be useful.Both Mds and Pme show considerable resistance to TFA and, therefore, are suitable for procedures in which the intermediates are deprotected by TFA treatment, while Mtr is the most useful protecting group when TFA treatment is not necessary.Keywords---4-methoxy-2,6-dimethylbenzenesulfonyl (Mds); 2,4,6-trimethoxybenzenesulfonyl (Mtb); 2,3,4,5,6-pentamethylbenzenesulfonyl (Pme); 4-methoxy-2,3,6-trimethylbenzenesulfonyl (Mtr); trifluoroacetic acid-thioanisole deprotection