65935-40-2

Basic information

• Product Name: 3-phenylpropyl chlorocarbonate
• Synonyms: 3-phenylpropyl chlorocarbonate
• CAS NO: 65935-40-2
• Molecular Weight: 198.649
• Mol File: 65935-40-2.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 3-phenylpropyl chlorocarbonate(CAS DataBase Reference)
• NIST Chemistry Reference: 3-phenylpropyl chlorocarbonate(65935-40-2)
• EPA Substance Registry System: 3-phenylpropyl chlorocarbonate(65935-40-2)

Safety Data

• Hazardous Substances Data: 65935-40-2(Hazardous Substances Data)

Upstream product

• 32315-10-9 bis(trichloromethyl) carbonate 
• 122-97-4 3-Phenyl-1-propanol 
• 121-44-8 triethylamine 
• 503-38-8 trichloromethyl chloroformate 
• 75-44-5 phosgene 

Downstream Products

• 38593-37-2 4-(3-Phenyl-propoxycarbonylamino)-benzoic acid 
• 37626-89-4 4-(3-Phenyl-propoxycarbonyloxy)-benzoic acid 
• 525584-13-8 1-(3'-phenylpropyloxycarbonyl)-(3S)-(t-butoxycarbonyl)aminoazetidin-2-one 
• 122-97-4 3-Phenyl-1-propanol 
• 736143-92-3 ((S)-1-Hydroxymethyl-pentyl)-carbamic acid 3-phenyl-propyl ester 
• 1439366-52-5 3-phenylpropyl N-[(2S,3R)-2-methyl-4-oxooxetan-3 - yl]carbamate 
• 1439367-14-2 (2R,3S)-3-hydroxy-2-{[(3-phenylpropoxy)carbonyl]amino}butanoic acid 

Relevant articles and documents

Microelectrode Arrays, Dihydroxylation, and the Development of an Orthogonal Safety-Catch Linker

Construction of larger molecular libraries on an addressable microelectrode array requires a method for recovering and characterizing molecules from the surface of any electrode in the array. This method must be orthogonal to the synthetic strategies needed to build the array. We report here a method for achieving this goal that employs the site-selective dihydroxylation reaction of a simple olefin.

Synthesis and structure-activity relationship (SAR) of 2-methyl-4-oxo-3- oxetanylcarbamic acid esters, a class of potent N-acylethanolamine acid amidase (NAAA) inhibitors

N-Acylethanolamine acid amidase (NAAA) is a lysosomal cysteine hydrolase involved in the degradation of saturated and monounsaturated fatty acid ethanolamides (FAEs), a family of endogenous lipid agonists of peroxisome proliferator-activated receptor-α, which include oleoylethanolamide (OEA) and palmitoylethanolamide (PEA). The β-lactone derivatives (S)-N-(2-oxo-3-oxetanyl)-3-phenylpropionamide (2) and (S)-N-(2-oxo-3-oxetanyl)- biphenyl-4-carboxamide (3) inhibit NAAA, prevent FAE hydrolysis in activated inflammatory cells, and reduce tissue reactions to pro-inflammatory stimuli. Recently, our group disclosed ARN077 (4), a potent NAAA inhibitor that is active in vivo by topical administration in rodent models of hyperalgesia and allodynia. In the present study, we investigated the structure-activity relationship (SAR) of threonine-derived β-lactone analogues of compound 4. The main results of this work were an enhancement of the inhibitory potency of β-lactone carbamate derivatives for NAAA and the identification of (4-phenylphenyl)-methyl-N-[(2S,3R)-2-methyl-4-oxo-oxetan-3-yl]carbamate (14q) as the first single-digit nanomolar inhibitor of intracellular NAAA activity (IC50 = 7 nM on both rat NAAA and human NAAA).

Chlorination of aliphatic primary alcohols via triphosgene-triethylamine activation

Activation of primary aliphatic alcohols with triphosgene and triethylamine mixtures afforded either alkyl chloride or diethylcarbamate products, and the switch in selectivity appeared to be driven by sterics. The reaction conditions to achieve this highly useful transformation were unexceptionally mild and readily tolerated by a wide range of sensitive functionalities.