658-78-6

Usage

Uses

Reagent for the preparation of 4-nitrophenyl active esters from acids

Purification Methods

Recrystallise the ester from CHCl3/hexane [Margolis et al. J Biol Chem 253 7891 1978]. It sublimes in vacuo (m 36-38o). It is moisture sensitive. [Sakakibara & Inukai Bull Chem Soc Jpn 37 1231 1964.]

InChI:InChI=1/C8H4F3NO4/c9-8(10,11)7(13)16-6-3-1-5(2-4-6)12(14)15/h1-4H

Upstream product

• 100-02-7 4-nitro-phenol 
• 76-05-1 trifluoroacetic acid 
• 183266-61-7 1-(trifluoroacetyl)benzotriazole 
• 407-25-0 trifluoroacetic anhydride 
• 354-32-5 trifluoracetyl chloride 
• 108-24-7 acetic anhydride 
• 51599-76-9 N-trifluoroacetoxy succinimide 

Downstream Products

• 4849-52-9 N-Tosyl-glycin-O-p-nitrophenylester 
• 18459-13-7 (2S,3R,4E)-3-O-benzoyl-N-trifluoroacetyl-4-sphingenine 
• 103029-77-2 7-hydroxy-quinoxaline-6-carboxylic acid 
• 50617-60-2 3-oxo-2,3-dihydro-pyridazine-4-carboxylic acid 4-nitro-phenyl ester 
• 58083-06-0 N-acetyl-N-methylglycine p-nitrophenylester 
• 37987-76-1 diclofenac p-nitrophenyl ester 
• 1204586-29-7 4-nitrophenyl 4-acetylsulfanylbutyrate 
• 289472-87-3 {2-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-ethoxy}-acetic acid 4-nitro-phenyl ester 
• 366446-40-4 p-nitrophenyl 11-(1-diazocyclopenta-2,4-dien-2-ylcarbonyloxy)undecanoate 
• 216597-14-7 p-nitrophenyl 3-(6-trifluoroacetoamidopurine-9-yl)propionate 
• 70138-80-6 9-(2-carboxyethyl)adenine p-nitrophenyl ester 
• 195724-23-3 [1,2]Dithiolan-3-yl-acetic acid 4-nitro-phenyl ester 
• 71710-01-5 1-(carboxymethyl)-5-fluorouracil p-nitrophenyl ester 

Relevant academic research and scientific papers

Fluorination process

It has been found that a compound of formula (I) R-CF2-O-Ar, wherein R is a fluorinated alkyl group or an optionally substituted aromatic or heteroaromatic group and Ar is an optionally substituted aromatic or heteroaromatic group, can be produced by a process comprising a step of reacting a compound of formula (II) R-C(O)-O-Ar wherein R and Ar are as defined above with a fluorination agent at a temperature of below +100°C.

FLUORINATION PROCESS

It has been found that a compound of formula (I) R-CF2-O-Ar, wherein R is a fluorinated alkyl group or an optionally substituted aromatic or heteroaromatic group and Ar is an optionally substituted aromatic or heteroaromatic group, can be produced by a process comprising a step of reacting a compound of formula (II) R-C(O)-O-Ar wherein R and Ar are as defined above with a fluorination agent at a temperature of below +100°C.

Methods for the synthesis of activated ethylfumarates and their use as intermediates

Disclosed embodiments relate to improved methods for the synthesis of activated fumarate intermediates and their use in chemical synthesis. Disclosed embodiments describe the synthesis of activated fumarate esters including those derived from activating groups including: 4-nitrophenyl, diphenylphosphoryl azide, pivaloyl chloride, chlorosulfonyl isocyanate, p-nitrophenol, MEF, trifluoroacetyl and chlorine, for example, ethyl fumaroyl chloride and the subsequent use of the activated ester in situ. Further embodiments describe the improved synthesis of substituted aminoalkyl-diketopiperazines from unisolated and unpurified intermediates allowing for improved yields and reactor throughput.

Erbium(III) chloride: A very active acylation catalyst

Erbium(iii) chloride is a powerful catalyst for the acylation of alcohols and phenols. The reaction works well for a large variety of simple and functionalized substrates by using different kinds of acidic anhydrides (Ac 2O, (EtCO)2O, (PriCO)2O, (Bu tCO)2O, and (CF3CO)2), without isomerization of chiral centres. Moreover, the catalyst can be easily recycled and reused without significant loss of activity. CSIRO 2007.

A convenient trifluoroacetylation reagent: N- (trifluoroacetyl)succinimide

N-(Trifluoroacetyl)succinimide, easily prepared from trifluoroacetic anhydride and succinimide forms a novel, convenient trifluoroacetylating reagent. It trifluoroacetylates alcohols, phenols and mines, to generate trifluoroacetate esters, and trifluoroacetamides in excellent yields with very efficient work up procedures.

Neutral Hydrolysis of Substituted Phenyl Trifluoroacetates in Water-Acetonitrile Mixtures with Low Content of Water

The neutral hydrolysis of substituted phenyl trifluoroacetates has been studied in water-acetonitrile mixtures in the region 0.56-3.89M water.The large solvent deuterium isotope effect (kH2O/kD2O) of 2.3 and the thermodynamic activation parameters for the hydrolysis of 4-nitrophenyl and 2,4-dinitrophenyl trifluoroacetates are consistent with a reaction mechanism in which one water molecule acts as a nucleophile and one as a general base.A linear correlation with a slope of 3.4 is found between log kobs and log for the hydrolysis of 4-nitrophenyl trifluoroacetate.This indicates the incorporation of several water molecules in the transition state.The effect of the structure of the leaving group on the rate of the reaction is best explained by a rate-limiting attack on the carbonyl group.