38064-07-2

Basic information

• Product Name: Hydroxycarbamic acid phenyl ester
• Synonyms: Hydroxycarbamic acid phenyl ester;N-Hydroxycarbamic acid phenyl ester;PhenylN-hydroxycarbamate
• CAS NO: 38064-07-2
• Molecular Formula: C₇H₇NO₃
• Molecular Weight: 153.14
• Mol File: 38064-07-2.mol

Chemical Properties

• Melting Point: 105-107 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.31g/cm³
• Refractive Index: 1.565
• PKA: 8.40±0.23(Predicted)
• CAS DataBase Reference: Hydroxycarbamic acid phenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Hydroxycarbamic acid phenyl ester(38064-07-2)
• EPA Substance Registry System: Hydroxycarbamic acid phenyl ester(38064-07-2)

Safety Data

• Hazardous Substances Data: 38064-07-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H7NO3/c9-7(8-10)11-6-4-2-1-3-5-6/h1-5,10H,(H,8,9)

Upstream product

• 1885-14-9 phenyl chloroformate 
• 102-09-0 bis(phenyl) carbonate 

Downstream Products

• 96212-74-7 5-acetyl-3-(phenoxycarbonyl)-6-phenyl-2,3,5-oxadiazabicyclo<2.2.2>oct-7-ene 
• 96212-75-8 6-acetyl-3-(phenoxycarbonyl)-5-phenyl-2,3,6-oxadiazabicyclo<2.2.2>oct-7-ene 
• 96212-73-6 5-(methoxycarbonyl)-3-(phenoxycarbonyl)-2,3,5-oxadiazabicyclo<2.2.2>oct-7-ene 
• 128252-46-0 (2S)-(-)-2-(methoxymethyl)pyrrolidine-N-carbohydroxamic acid 
• 133378-82-2 (2R,5R)-2,5-dimethylpyrrolidine N-carbohydroxamic acid 
• 133378-83-3 (2R,4aS,5aS,8R,9aR,9bR)-Perhydro-2,8-diphenyl-2H,5H,8H-bis<1,3>dioxino<5,4-b:4',5'-d>pyrrole-5-carbohydroxamic acid 
• 139391-76-7 (2R)-(+)-2-(methoxymethyl)pyrrolidine-N-carbohydroxamic acid 
• 78613-58-8 C₁₅H₁₄N₂O₄ 
• 78613-84-0 3,5-Dioxo-4-o-tolyl-[1,2,4]oxadiazolidine-2-carboxylic acid o-tolylamide 
• 78613-79-3 C₂₃H₂₁N₃O₅ 
• 128252-45-9 (-)-(S)-2-(hydroxymethyl)pyrrolidine-N-carbohydroxamic acid 
• 1010408-63-5 C₁₇H₂₂FN₅O₅ 
• 1352786-34-5 phenyl 4-chlorobenzoyloxycarbamate 
• 1446888-27-2 phenyl acetoxycarbamate 

Relevant articles and documents

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An Experimental and Computational Approach to Understanding the Reactions of Acyl Nitroso Compounds in [4 + 2] Cycloadditions

Catalytic aerobic oxidation of phenyl hydroxycarbamate 1 and 1-hydroxy-3-phenylurea 2 using CuCl2 and 2-ethyl-2-oxazoline in methanol gave acyl nitroso species in situ, which were trapped in nitroso-Diels-Alder (NDA) reactions with various dienes to afford the corresponding cycloadducts in high yields (90-98%). Competing ene products were also present for dienes containing both alkene π-bonds and allylic σ-bonds, and the ene yields are higher with 1 than with 2. The use of the chiral hydroxamic acid, (R)-1-hydroxy-3-(1-phenylethylurea) 3 (same conditions) gave NDA cycloadducts in high yields (97-99%) with no ene product from 2,3-dimethyl-1,3-butadiene. NDA cycloadducts were not obtained from other hydroxamic acid analogues [RCONHOH (R = PhCH2 4; Ph(CH2)2 5; Ph(CH2)3 6; Ph(CH2)4 7; Ph 8; 2-pyridyl 9; 3-pyridyl 10] with various dienes using copper-oxidation but rather were obtained using sodium periodate, resulting in variable NDA yields (13-51%) from hydroxamic acids 1-10 with cyclohexa-1,3-diene and 2,3-dimethyl-1,3-butadiene (several cycloadducts characterized by X-ray crystallography). The NDA and nitroso-ene reaction pathways of nitroso intermediates with dienes were mapped by DFT computations (B3LYP/6-31G), which showed that the acyl nitroso species are super-reactive and that activation energies in the NDA processes are lower than the isomerization barriers between some cis- and trans-butadienes.

Stereoselective total synthesis of the potent anti-asthmatic compound CMI-977 (LDP-977)

A short and efficient stereoselective total synthesis of CMI-977 (LDP-977), a potent and orally active anti-asthmatic compound, was developed. The key steps involve a highly diastereoselective Mukaiyama oxidative cyclization, which provides the trans-THF (tetrahydrofuran) unit and a Seyferth-Gilbert homologation to construct the triple bond in the target molecule. The synthesis of the key chiral building block was performed using Jacobsen hydrolytic kinetic resolution.

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IMPROVED PROCESS FOR THE PREPARATION OF (±)-1-(1-BENZO[B]THIEN-2-YLETHYL)-1-HYDROXYUREA

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Chemical scaffolds with structural similarities to siderophores of nonribosomal peptide-polyketide origin as novel antimicrobials against Mycobacterium tuberculosis and Yersinia pestis

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The kinetics and mechanism of the degradation reactions of substituted phenyl N-hydroxycarbamates and their N-methyl and N-phenyl analogues have been studied at pseudo-first-order reaction conditions in aqueous buffers and sodium hydroxide solutions at 20°C and 60°C and at I = 1 mol·1 -1. The dependence of log kobs on pH for phenyl N-hydroxycarbamates at pH 13 is linear with the unit slope; at pH 10-12 log kobs is pH independent. The Bronsted coefficient βlg is about -1 (pH 7-13) and -1.53 (pH > 13) indicating that the degradation reaction of phenyl N-hydroxycarbamates follows an ElcB mechanism giving the corresponding phenol/phenolate and HO-N=C=O. The latter species undergoes further decomposition to give carbonate, nitrogen and ammonia as final products. In contrast to the phenyl N-hydroxycarbamates the N-methyl derivatives at pH 7-9 undergo degradation to the corresponding phenol/phenolate, carbonate and methylamine via a concerted mechanism (βlg is about - 0.75). The only exception is 4-nitrophenyl N-hydroxy-N-methylcarbamate in which the predominant break down pathway proceeds via the Smiles rearrangement to give sodium N-methyl-(4-nitrophenoxy)carbamate. At pH > 9 the reaction of N-hydroxy-N-methylcarbamates is kinetically complex: the dependence of absorbance on time is not exponential and it proceeds as a consecutive two-step reaction. N-Hydroxy-N-phenylcarbamate under the same conditions undergoes degradation to phenol, carbonate, aniline and azoxybenzene.

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