84319-43-7

Basic information

• Product Name: 1,3,4-Oxadiazole, 2-methyl-5-(phenylmethyl)-
• CAS NO: 84319-43-7
• Molecular Formula: C10H10N2O
• Molecular Weight: 174.202
• Mol File: 84319-43-7.mol

Chemical Properties

• CAS DataBase Reference: 1,3,4-Oxadiazole, 2-methyl-5-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,4-Oxadiazole, 2-methyl-5-(phenylmethyl)-(84319-43-7)
• EPA Substance Registry System: 1,3,4-Oxadiazole, 2-methyl-5-(phenylmethyl)-(84319-43-7)

Safety Data

• Hazardous Substances Data: 84319-43-7(Hazardous Substances Data)

Upstream product

• 18489-25-3 5-benzyl-2H-tetrazole 
• 75-36-5 acetyl chloride 
• 26404-64-8 phenyl-acetic acid ethylidenehydrazide 
• 18489-25-3 5-benzyl-1H-tetrazole 
• 108-24-7 acetic anhydride 
• 73818-55-0 Bestmann ylide 
• 937-39-3 2-phenylacetylhydrazine 
• 1338916-77-0 1,1'-diphenylthiodiacetic acid dihydrazide 
• 78-39-7 Triethyl orthoacetate 
• 4870-65-9 2-bromophenylacetic acid 
• 1372151-69-3 N2-(1-ethoxyethylidene)-α-mercaptophenylacetic acid hydrazide 
• 90006-97-6 α-mercaptophenylacetic acid hydrazide 
• 16201-52-8 2-mercapto-2-phenylacetic acid methyl ester 
• 611-71-2 MANDELIC ACID 

Relevant articles and documents

Reactions of α-mercaptocarboxylic acid hydrazides with triethyl orthoesters: Synthesis of 1,3,4-thiadiazin-5(6H)-ones and 1,3,4-oxadiazoles

Reactions of α-mercapto-β-phenylpropionic and α-mercaptophenylacetic acid hydrazides with triethyl orthoesters were conducted under N2 in glacial acetic acid and resulted in the formation of two groups of products, derivatives of 1,3,4-thiadiazin-5(6H)-ones and 2-(1-mercaptomethyl)-1,3,4-oxadiazoles. When conducting the same transformations on α-mercaptophenylacetic acid hydrazide in the presence of air, two different products from the 1,3,4-oxadiazole family, the appropriate bis(1,3,4-oxadiazol-2-yl-phenylmethyl) disulfides and 2-benzyl-1,3,4- oxadiazoles, were formed with the liberation of free sulfur. The oxygenated bis(1,3,4-oxadiazol-2-yl-phenylmethyl) disulfides were reduced to the corresponding 2-(1-mercaptomethyl)-1,3,4-oxadiazoles with the use of zinc powder under mild conditions.

The synthesis of bis(1,3,4-oxadiazol-2-yl-phenylmethyl) sulfides and other related 1,3,4-oxadiazoles from 1,1′-diphenylthiodiacetic acid dihydrazide and triethyl orthoesters

Reactions of symmetrical 1,1′-diphenylthiodiacetic acid dihydrazide and triethyl orthoesters in the presence of catalytic amount of glacial acetic acid resulted in the formation of three heterocyclic products: the appropriate bis(1,3,4-oxadiazol-2-yl-phenylmethyl) sulfides, 2-benzyl-1,3,4-oxadiazoles and 2-benzoyl-1,3,4-oxadiazoles. The presence of the latter two compounds is connected with carbon-sulfur fission in the molecule of the starting hydrazide. The identity of the unexpected fission products was confirmed by parallel syntheses of the model 1,3,4-oxadiazoles from phenylacetic acid hydrazide and 2-hydroxymethyl-1,3,4-oxadiazole derivatives.

The application of cross-linked poly[styrene(iodoso diacetate)] to the synthesis of 1,3,4-oxadiazoles

The 2% cross-linked poly[styrene(iodosodiacetate)] has been synthesized, and has been applied effectively to the synthesis of 1,3,4-oxadiazole derivatives, and regenerated and reused for the same reaction.

Synthesis of 1,3,4-Oxadiazoles from Carboxylic Hydrazides and of 1,2-Oxazin-6-ones from α-(Hydroxyimino)carboxylic Esters with Keteneylidene Triphenylphosphorane

In a one-pot procedure 1,3,4-oxadiazoles 8 are prepared from carboxylic hydrazides 2 and keteneylidene triphenylphosphorane 1 via an untypical intermolecular Wittig olefination of a carbamate type carbonyl group. Under similar conditions, reaction of 1 an

TETRAZOLES IN THE SYNTHESES OF 1,3,4-OXADIAZOLES

Various variants of cleavage of tetrazoles to form 1,3,4-oxadiazoles are examined.The mechanisms and synthetic potentialities of these reactions are discussed.

Hypervalent Iodine Oxidation of N-Acylhydrazones and N-Phenylsemicarbazone: An Efficient Method for the Synthesis of Derivatives of 1,3,4-Oxadiazoles and Δ3-1,3,4-Oxadiazolines

The oxidation of ketone N-acylhydrazones 1 by phenyliodine(III) diacetate (PIDA) in alcohol gave 2-alkoxy-Δ3-1,3,4-oxadiazolines 4 in excellent yields, while the oxidative cyclization of aldehyde N-acylhydrazone 2 by PIDA in methanolic sodium acetate gave 2,5-disubstituted 1,3,4-oxadiazoles in good yields.The oxidation of acetone 4-phenylsemicarbazone afforded 2-(N-phenylimino)-Δ3-1,3,4-oxadiazoline in excellent yield.

Oxidation of Arylacetylhydrazones of Carbonyl Compounds with Lead Tetraacetate

Oxidation of the title compounds 8, 9 with lead tetraacetate at room temperature gives a variety of products depending on the substituents on the carbonyl carbon atom.Thus, on oxidation of the aldehyde derivatives 8 1,3,4-oxadiazolo derivatives 10 are obtained in good yields.However in some cases formation of N-acetyl-N-arylacetyl-N'-benzoylhydrazines 11 is also observed, whereas oxidation of the ketone hydrazones 9 gives in good yields the 2H,5H-1,3,4-oxadiazoles 15 or substituted monoacetoxy- 17 and diacetoxyalkanes 18.The reaction mechanisms are also discussed.