17614-10-7

Basic information

• Product Name: (1-Methylethyl)carbaMic Acid Phenyl Ester
• Synonyms: (1-Methylethyl)carbaMic Acid Phenyl Ester;N-(1-Methylethyl)carbaMic Acid Phenyl Ester;NSC 190576;PhenylN-(propan-2-yl)carbamate
• CAS NO: 17614-10-7
• Molecular Formula: C₁₀H₁₃NO₂
• Molecular Weight: 179
• Product Categories: Aromatics;Intermediates
• Mol File: 17614-10-7.mol

Chemical Properties

• Boiling Point: 246.1°Cat760mmHg
• Flash Point: 102.7°C
• Appearance: /
• Density: 1.058g/cm³
• Vapor Pressure: 0.0276mmHg at 25°C
• Refractive Index: 1.507
• CAS DataBase Reference: (1-Methylethyl)carbaMic Acid Phenyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: (1-Methylethyl)carbaMic Acid Phenyl Ester(17614-10-7)
• EPA Substance Registry System: (1-Methylethyl)carbaMic Acid Phenyl Ester(17614-10-7)

Safety Data

• Hazardous Substances Data: 17614-10-7(Hazardous Substances Data)

Usage

Uses

Intermediate in the preparation of Torsemide metabolites.

InChI:InChI=1/C10H13NO2/c1-8(2)11-10(12)13-9-6-4-3-5-7-9/h3-8H,1-2H3,(H,11,12)

Upstream product

• 75-31-0 isopropylamine 
• 1885-14-9 phenyl chloroformate 
• 1795-48-8 Isopropyl isocyanate 
• 108-95-2 phenol 
• 102-09-0 bis(phenyl) carbonate 
• 35180-03-1 chloromethyl phenyl carbonate 
• 118-55-8 phenyl Salicylate 

Downstream Products

• 84942-51-8 O-phenyl N-isopropyl-N-isocyanato-carbonyl-carbamate 
• 864908-76-9 2-iodophenyl isopropylcarbamate 
• 81787-62-4 o-((trimethylsilyl)ethynyl)phenol 
• 2281-78-9 4-chloro-N-(isopropylcarbamoyl)benzenesulfonamide 
• 5673-38-1 N-(isopropylcarbamoyl)-4-methylbenzenesulfonamide 
• 56211-40-6 torasemide 
• 28177-54-0 2,6-diiodo-phenol 
• 899427-44-2 2,6-bis(trimethylsilyl)phenyl isopropylcarbamate 
• 899427-38-4 2-hydroxyphenylmethyl-6-iodophenyl isopropylcarbamate 
• 899427-47-5 2,6-diiodophenyl isopropylcarbamate 

Relevant articles and documents

Discovery of Novel UDP- N-Acetylglucosamine Acyltransferase (LpxA) Inhibitors with Activity against Pseudomonas aeruginosa

This study describes a novel series of UDP-N-acetylglucosamine acyltransferase (LpxA) inhibitors that was identified through affinity-mediated selection from a DNA-encoded compound library. The original hit was a selective inhibitor of Pseudomonas aeruginosa LpxA with no activity against Escherichia coli LpxA. The biochemical potency of the series was optimized through an X-ray crystallography-supported medicinal chemistry program, resulting in compounds with nanomolar activity against P. aeruginosa LpxA (best half-maximal inhibitory concentration (IC50) 20 μM and MIC > 128 μg/mL). The mode of action of analogues was confirmed through genetic analyses. As expected, compounds were active against multidrug-resistant isolates. Further optimization of pharmacokinetics is needed before efficacy studies in mouse infection models can be attempted. To our knowledge, this is the first reported LpxA inhibitor series with selective activity against P. aeruginosa.

A facile synthesis of sulfonylureas: Via water assisted preparation of carbamates

A novel and simple approach to the synthesis of sulfonylureas has been reported. It involved the reaction of various amines with diphenyl carbonate to yield the corresponding carbamates, which subsequently reacted with different sulphonamides to produce different sulfonylureas in excellent yields. The first reaction of diphenyl carbonate with amines was carried out in aqueous:organic (H2O:THF, 90:10) medium at room temperature to produce carbamates that paved a straightforward route to sulfonylureas after reaction with sulfonamides. The above process avoided traditional multistep protocols and the use of hazardous, irritant, toxic and moisture sensitive reagents such as phosgene, isocyanates and/or chloroformates.

Efficient synthesis of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate: A versatile precursor to o-benzyne

(Chemical Equation Presented) An efficient procedure for the gram-scale preparation of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate, a versatile precursor to o-benzyne, is presented. The three-step sequence utilizes phenol as the starting material, requires only one chromatographic purification, and ultimately delivers the desired silyltriflate in 66% overall yield. 2009 American Chemical Society.

Facile preparation of 2-iodophenyl trifluoromethanesulfonates: Superior aryne precursors

A comparative study of 3-methoxyaryne precursors revealed 2-iodo-3-methoxyphenyl triflate as the most effective in nonpolar solvent. Use of Hoppe's N-isopropyl carbamate allows for the systematic preparation of a variety of 2-iodophenyl triflates via a directed ortho-lithiation-iodination- decarbamation sequence. These steps are possible without isolation of the intermediate iodophenyl carbamates. Georg Thieme Verlag Stuttgart.

PROCESS FOR THE PREPARATION OF HIGHLY PURE TORSEMIDE

The present invention provides a novel process for the preparation of highly pure torsemide [1] by reacting of 4-m-tolylamino-3-pyridinesulfonamide [2] with phenyl isopropylcarbamate in the presence of lithium base (F I, II). The present invention also provides a novel intermediate - torsemide lithium, also in hydrate or solvate form - which is a stable, solid compound, and may be simply isolated from the reaction mixture to give after acidification practically pure torsemide [1] without further purification steps.

Synthesis of substituted phenols by directed ortho-lithiation of in situ N-silyl-protected O-aryl N-monoalkylcarbamates

A simple, high-yield procedure has been developed for the ortho-lithiation and subsequent ortho-substitution of phenols by a manifold of electrophiles. N,C-Dilithiation of O-aryl N-monoalkylcarbamates proved to be impossible due to a cleavage reaction of

A highly-efficient synthesis of benzoxazine-2,4-diones

Base-promoted reaction of salicylate esters with isocyanates provides a highly efficient route to benzoxazine-2,4-diones.

α-Haloalkyl Haloformates and Related Compounds 1. A Convenient Synthesis of Carbamates via Chloromethyl Carbamates

The preparation of carbamates under mild conditions utilizing a new class of activated carbonates (containing chloromethyl function) is described.

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