36016-39-4

Basic information

• Product Name: 1,1-dimethylethyl [[(2,4,6-trimethylphenyl)sulphonyl]oxy]carbamate
• Synonyms: 1,1-dimethylethyl [[(2,4,6-trimethylphenyl)sulphonyl]oxy]carbamate;N-[[(2,4,6-Trimethylphenyl)sulfonyl]oxy]carbamic acid tert-butyl ester;N-Tert-butoxycarbonyl-O-(mesitylsulfonyl)hydroxylamine;tert-Butyl (Mesitylsulfonyl)oxycarbaMate;Benzenesulfonic acid,2,4,6-triMethyl-, [(1,1-diMethylethoxy)carbonyl]azanyl ester;N-Mesitylsulfonyloxy-tert-butylcarbaMat;N-Boc-O-(mesitylsulfonyl)hydroxyamine;_x000D_N-Boc-O-(mesitylsulfonyl)hydroxylamine
• CAS NO: 36016-39-4
• Molecular Formula: C₁₄H₂₁NO₅S
• Molecular Weight: 315.38524
• EINECS: 252-837-8
• Mol File: 36016-39-4.mol
• Article Data: 45

Chemical Properties

• Melting Point: 104-105.5 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.191g/cm³
• Refractive Index: 1.515
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: 1,1-dimethylethyl [[(2,4,6-trimethylphenyl)sulphonyl]oxy]carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-dimethylethyl [[(2,4,6-trimethylphenyl)sulphonyl]oxy]carbamate(36016-39-4)
• EPA Substance Registry System: 1,1-dimethylethyl [[(2,4,6-trimethylphenyl)sulphonyl]oxy]carbamate(36016-39-4)

Safety Data

• Hazardous Substances Data: 36016-39-4(Hazardous Substances Data)

Usage

Uses

tert-Butyl (((mesityl)sulfonyl)oxy)carbamate is a useful reagent for the enantioselective aziridination of α,β-unsaturated aldehydes.

Synthesis

2-Mesitylenesufonylchloride (2.00 g, 9.17 mmol) was added to a flame dried and argon purged round-bottom flask and dissolved in ether (18 mL), followed by the addition of N-Boc-hydroxylamine (1.47 g, 1100 mmol) The flask was cooled to 0° C and then TEA was added dropwise (1.3 mL). The reaction stirred for 2 hours at 0° C, at which all starting material had been converted as seen by TLC. The TEA-Cl, white solid, was filtered, and washed with ether. The filtrate was concentrated in vacuo, and purified via flash chromatography in 25/75 EtOAc/hexane gradient. Yield was quantitative, 2.16 g, white solid.

Purification Methods

Separation of 1,1-Dimethylethyl (((2,4,6-trimethylphenyl)sulphonyl)oxy)carbamate on Newcrom R1 HPLC column:1,1-Dimethylethyl (((2,4,6-trimethylphenyl)sulphonyl)oxy)carbamate can be analyzed by this reverse phase (RP) HPLC method with simple conditions. The mobile phase contains an acetonitrile (MeCN), water, and phosphoric acid. For Mass-Spec (MS) compatible applications the phosphoric acid needs to be replaced with formic acid. Smaller 3 μm particles columns available for fast UPLC applications. This liquid chromatography method is scalable and can be used for isolation impurities in preparative separation. It also suitable for pharmacokinetics.

InChI:InChI=1/C14H21NO5S/c1-9-7-10(2)12(11(3)8-9)21(17,18)20-15-13(16)19-14(4,5)6/h7-8H,1-6H3,(H,15,16)

Upstream product

• 773-64-8 2-mesitylenesulphonyl chloride 
• 36016-38-3 tert-Butyl N-hydroxycarbamate 
• 108-67-8 1,3,5-trimethyl-benzene 
• 4248-19-5 tert-butyl carbazate 

Downstream Products

• 36016-40-7 mesitylenesulfonylhydroxylamine 
• 1234457-70-5 C₁₈H₂₂N₂O₂ 
• 1234457-72-7 C₁₁H₁₅ClN₂O₂ 
• 1234457-68-1 C₁₉H₂₄N₂O₂ 
• 55899-13-3 1-amino-3-bromopyridin-1-ium 2,4,6-trimethylbenzenesulfonate 
• 55899-02-0 3-methyl-N-aminopyridinium mesitylenesulfonate 
• 81211-89-4 1-amino-3-(dimethylamino)pyridin-1-ium 2,4,6-trimethylbenzenesulfonate 
• 81211-83-8 1-amino-5-methoxypyridinium 2,4,6-trimethylbenzenesulfonate 
• 39996-44-6 1-amino-3-cyanopyridin-1-ium 2,4,6-trimethylbenzenesulfonate 
• 40146-54-1 1-amino-3-(ethoxycarbonyl)pyridin-1-ium 2,4,6-trimethylbenzenesulfonate 
• 39996-49-1 3-acetyl-1-aminopyridin-1-ium 2,4,6-trimethylbenzenesulfonate 
• 1326216-43-6 1-amino-3-(trifluoromethyl)pyridin-1-ium 2,4,6-trimethylbenzenesulfonate 

Relevant articles and documents

Preparation, use, and safety of 0-mesitylenesulfonylhydroxylamine

The aminating reagent O-mesitylsulfonylhydroxylamine (MSH) has a known potential hazard since it contains high-energy functional groups in its structure. There are references in the literature that report several incidents involving the use of pure and crystalline MSH. The preparation and safe use of this reagent at kilo scale are described herein.

SUBSTITUTED 1,5-NAPHTHYRIDINES OR QUINOLINES AS ALK5 INHIBITORS

The present disclosure provides inhibitors of activin receptor-like kinase 5 (ALK5). Also disclosed are methods to modulate the activity of ALK5 and methods of treatment of disorders mediated by ALK5.

Pyrimidine-4 (3H)-ketone heterocyclic compound, preparation method thereof and application of pyrimidine-4 (3H)-ketone heterocyclic compound in medicine

The invention relates to pyrimidine-4 (3H)-ketone heterocyclic compounds suitable for inhibiting or regulating SHP2, a preparation method of the pyrimidine-4 (3H)-ketone heterocyclic compounds and application of the pyrimidine-4 (3H)-ketone heterocyclic compounds in medicine. Specifically, the invention relates to a compound as shown in a general formula (I) and a pharmaceutically acceptable salt thereof, a pharmaceutical composition containing the compound or the pharmaceutically acceptable salt thereof, a method for treating and/or preventing related diseases mediated by SHP2, especially cancers by using the compound or the pharmaceutically acceptable salt thereof, and a preparation method of the compound or the pharmaceutically acceptable salt thereof. The invention also relates to application of the compound or the pharmaceutically acceptable salt thereof or a pharmaceutical composition containing the compound or the pharmaceutically acceptable salt thereof in preparation of drugs for treating and/or preventing SHP2-mediated related diseases. Wherein each substituent in the general formula (I) is as defined in the specification.

AROMATIC RING DERIVATIVE AS IMMUNOREGULATION AND PREPARATION METHOD AND APPLICATION OF AROMATIC RING DERIVATIVE

Relating to a compound represented by formula (I) and a pharmaceutically acceptable salt of the compound, and an application of the compound as an S1P1 agonist.