66907-71-9

Basic information

• Product Name: N-cyclohexyl-1-phenyl-1H-tetraazol-5-amine
• Synonyms: N-cyclohexyl-1-phenyl-1H-tetraazol-5-amine
• CAS NO: 66907-71-9
• Molecular Formula: C₁₃H₁₇N₅
• Molecular Weight: 243.30758
• Mol File: 66907-71-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-cyclohexyl-1-phenyl-1H-tetraazol-5-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-cyclohexyl-1-phenyl-1H-tetraazol-5-amine(66907-71-9)
• EPA Substance Registry System: N-cyclohexyl-1-phenyl-1H-tetraazol-5-amine(66907-71-9)

Safety Data

• Hazardous Substances Data: 66907-71-9(Hazardous Substances Data)

Upstream product

• 3878-67-9 N-phenyl-N'-cyclohexyl carbodiimide 
• 1516888-45-1 1-cyclohexyl-3-phenylselenourea 
• 722-03-2 N-cyclohexyl-N'-phenylthiourea 
• 103-72-0 phenyl isothiocyanate 
• 108-91-8 cyclohexylamine 

Downstream Products

• 66907-72-0 (1-cyclohexyl-1H-tetrazol-5-yl)-phenyl-amine 

Relevant articles and documents

Method for preparing 5-aminotetrazole compound

The invention discloses a method for preparing a 5-aminotetrazole compound. The method comprises the following steps: adding bis-substituted selenourea shown in the formula II in the description, ionic liquid loaded iodobenzene diacetate shown in the formula III in the description, sodium azide and alkali A into a solvent B, stirring at -10 to -80 DEG C and conducting cyclization reaction, and after the reaction is finished, conducting aftertreatment on the reaction liquid to prepare the 5-aminotetrazole compound shown in the formula I in the description. Compared with the conventional method, a green reagent, namely, ionic liquid loaded iodobenzene diacetate, is adopted, so that the use of heavy metal is avoided, the operation is simple and convenient, and the reaction yield is high.

An expedient route to the azoles through oxidative desulfurization using iodine reagent

A novel and expedient regioselective method for the synthesis of 5-aminotetrazoles and 3-amino-1,2,4-triazoles through oxidative desulfurization of corresponding 1,3-disubstituted thioureas has been discovered and optimized for the process conditions. The process is broadly applicable to structurally diverse 1,3-disubstituted thioureas.

O -iodoxybenzoic acid mediated oxidative desulfurization initiated domino reactions for synthesis of azoles

A systematic exploration of thiophilic ability of o-iodoxybenzoic acid (IBX) for oxidative desulfurization to trigger domino reactions leading to new methodologies for synthesis of different azoles is described. A variety of highly substituted oxadiazoles, thiadiazoles, triazoles, and tetrazoles have been successfully synthesized in good to excellent yields, starting from readily accessible thiosemicarbazides, bis-diarylthiourea, 1,3-disubtituted thiourea, and thioamides.

Tandem regioselective synthesis of tetrazoles and related heterocycles using iodine

A one-pot, tandem process has been developed for the synthesis of a library of tetrazoles from aryl isothiocyanates. Condensation of aryl isothiocyanates with ammonia, and aryl amines (R-NH2) provided mono, 1,3-disubstituted symmetrical and unsymmetrical thioureas, which on desulfurization with molecular iodine (I2) led to formation of the corresponding heterocumulene (cyanamides or carbodiimides). The in situ generated heterocumulene on subsequent treatment with sodium azide at room temperature gave corresponding tetrazoles. The product regioselectivity for unsymmetrical 1,3-disubstituted thioureas was found to be correlated with the basicities (pKa's) of the parent amines attached to the thiourea. Aryl-sec-alkyl unsymmetrical thioureas gave thioamido guanidino products rather than the 5-aminotetrazoles produced by HgCl2 mediation of the reaction. Bis-thioureas derived from aryl isothiocyanates and hydrazine gave thiadiazoles exclusively.

Reactions of Trimethylsilyl Azide with Heterocumulenes

Trimethylsilyl azide (TMSA) reacted with aryl isocyanates to give arylcarbamoyl azides, 1-aryl-5(4H)-tetrazolinones, and / or 1-aryl-4-(arylcarbamoyl)-5(4H)-tetrazolinones, whose yields were dependent on the reaction conditions.The reaction between TMSA and benzoyl or thiobenzoyl isocyanates provides a facile method for the preparation of 5-aryl-3-hydroxy-1,2,4-oxadiazoles or -1,2,4-thiadiazoles, respectively.However, with phenyl or benzoyl isothiocyanate, 1-anilino-1,2,3,4-thiatriazole or benzoylcyanamide was obtained in low yield, respectively.TMSA reacted with carbodiimides to afford the corresponding 5-aminotetrazoles.Tetraphenylsuccinimide, N-(diphenylacetyl)tetraphenylsuccinimide, 1,3-bis(diphenylmethyl)urea, and / or benziloylamide were obtained from the reaction of TMSA with diphenyl ketene.The pathways for the formation of the above products are also described.