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
• Article Data: 14

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

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

Downstream Products

• 99981-31-4 diethoxyphosphoryloxy-carbamic acid phenyl ester 
• 100799-81-3 diisopropoxyphosphoryloxy-carbamic acid phenyl ester 
• 96212-73-6 5-(methoxycarbonyl)-3-(phenoxycarbonyl)-2,3,5-oxadiazabicyclo<2.2.2>oct-7-ene 
• 78613-56-6 C₁₃H₁₆N₂O₅ 
• 78613-77-1 C₁₉H₂₅N₃O₇ 
• 1010408-63-5 C₁₇H₂₂FN₅O₅ 

Relevant articles and documents

Iron-Catalyzed Intramolecular C—H Amidation of N-Benzoyloxyureas

A redox-neutral Fe-catalyzed intramolecular C—H amidation of N-benzoyloxyureas is described. This methodology employs a simple iron complex in situ generated from Fe(OTf)2 and bipyridine as the catalyst and N-benzoyloxyureas as the nitrene prec

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.

IMPROVED AMINOHYDROXYLATION OF ALKENES

The invention relates to a process for the aminohydroxylation of alkenes using N-oxycarbamate reagents, e.g. N-acyloxycarbamate, N-alkyloxycarbonyloxycarbamate and N-aralkoxycarbonyloxycarbamate reagents. The invention particularly relates to an intermolecular aminohydroxylation reaction that can be carried out in the absence of added base. The invention also relates to novel N-oxycarbamate reagents that are stable crystalline materials. The process of the invention is useful in the synthesis of compounds having a vicinal amino alcohol moiety, such as biologically active compounds.