491616-55-8

Basic information

• Product Name: 1,2-Ethenediol, 1-amino-2-phenyl-
• Synonyms: 1,2-Ethenediol, 1-amino-2-phenyl-
• CAS NO: 491616-55-8
• Molecular Formula: C₈H₉NO₂
• Molecular Weight: 151.16
• Mol File: 491616-55-8.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,2-Ethenediol, 1-amino-2-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Ethenediol, 1-amino-2-phenyl-(491616-55-8)
• EPA Substance Registry System: 1,2-Ethenediol, 1-amino-2-phenyl-(491616-55-8)

Safety Data

• Hazardous Substances Data: 491616-55-8(Hazardous Substances Data)

Usage

Functional groups

Amino and hydroxyl groups

Versatility

Building block for organic synthesis

Applications

Intermediate in pharmaceutical and agrochemical production

Therapeutic potential

Anti-inflammatory and antioxidant agent

Synthesis method

Reaction of 1,2-ethanediol with phenethylamine in the presence of a catalyst

Industrial and therapeutic applications

Wide range of uses in both fields

Upstream product

• 4410-31-5 (RS)-mandelamide 

Downstream Products

• 4410-31-5 (RS)-mandelamide 

Relevant articles and documents

The mandelamide keto-enol system in aqueous solution. Generation of the enol by hydration of phenylcarbamoylcarbene

Flash photolysis of diazophenylacetamide in aqueous solution produced phenylcarbamoylcarbene, whose hydration generated a transient species that was identified as the enol isomer of mandelamide. This assignment is based on product identification and the shape of the rate profile for decay of the enol transient, through ketonization to its carbonyl isomer, as well as by the form of acid - base catalysis of and solvent isotope effects on the decay reaction. Rates of enolization of mandelamide were also determined, by monitoring hydrogen exchange at its benzylic position, and these, in combination with the ketonization rate measurements, gave the keto - enol equilibrium constant pKE = 15.88, the acidity constant of the enol ionizing as an oxygen acid, pQaE = 8.40, and the acidity constant of the amide ionizing as a carbon acid pQaK = 24.29. (These acidity constants are concentration quotients applicable at ionic strength = 0.10 M.) These results show the enol content and carbon acid strength of mandelamide, like those of mandelic acid and methyl mandelate, to be orders of magnitude less than those of simple aldehydes and ketones; this difference can be attributed to resonance stabilization of the keto isomers of mandelic acid and its ester and amide derivatives, through electron delocalization into their carbonyl groups from the oxygen and nitrogen substituents adjacent to these groups. The enol of mandelamide, on the other hand, again like the enols of mandelic acid and methyl mandelate, is a substantially stronger acid than the enols of simple aldehydes and ketones. This difference can be attributed to the electronegative nature of the oxygen and nitrogen substituents geminal to the enol hydroxyl group in the enols of mandelic acid and its derivatives; in support of this, the acidity constants of these enols correlate well with field substituent constants of these geminal groups.