58632-95-4 Usage
Description
2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile is an organic compound that serves as a valuable intermediate in the synthesis of various pharmaceuticals and organic molecules. It is characterized by its ability to protect amino groups during peptide synthesis and multi-step organic synthesis, ensuring the selective protection and deprotection of functional groups in complex molecular structures.
Uses
Used in Pharmaceutical Synthesis:
2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile is used as a protecting group for amino groups in the pharmaceutical industry. Its application is crucial for the synthesis of complex peptides and small molecules, as it allows chemists to selectively protect and deprotect functional groups, facilitating the assembly of intricate molecular structures without unwanted side reactions.
Used in Organic Synthesis:
In the field of organic synthesis, 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile is employed as a versatile intermediate for the preparation of a wide range of organic molecules. Its use enables the protection of amino groups during multi-step synthesis processes, ensuring the successful construction of target molecules with high purity and yield.
Overall, 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile plays a significant role in both the pharmaceutical and organic synthesis industries, providing a reliable method for protecting amino groups and facilitating the synthesis of complex molecules with potential applications in various fields.
Synthesis Reference(s)
Organic Syntheses, Coll. Vol. 6, p. 199, 1988Tetrahedron Letters, 16, p. 4393, 1975 DOI: 10.1016/S0040-4039(00)91133-X
Purification Methods
Triturate the solid with 90% aqueous MeOH, filter, wash with 90% aqueous MeOH and dry it in a vacuum. Recrystallise it from MeOH (needles or plates), but use warm MeOH and cool to crystallise; do not boil as it decomposes slowly. IR has max 1785 (C=O) cm-1 and NMR (CDCl3) usually shows two tert-butyl singlets for syn and anti isomers. Store it in a brown bottle (fridge). It evolves CO2 at room temperature (stoppered bottle can explode!), but can be stored over silica gel which may extend its useful life to more than a year. [Itoh et al. Org Synth 59 95 1980.]
Check Digit Verification of cas no
The CAS Registry Mumber 58632-95-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,8,6,3 and 2 respectively; the second part has 2 digits, 9 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 58632-95:
(7*5)+(6*8)+(5*6)+(4*3)+(3*2)+(2*9)+(1*5)=154
154 % 10 = 4
So 58632-95-4 is a valid CAS Registry Number.
InChI:InChI=1/C13H14N2O3/c1-13(2,3)17-12(16)18-15-11(9-14)10-7-5-4-6-8-10/h4-8H,1-3H3/b15-11-
58632-95-4Relevant articles and documents
Carbonic acid esters, and the preparation thereof and their use
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, (2008/06/13)
Carbonic acid esters of the formula substituent(s) substituents(s) wherein R'1 is lower alkyl which may have substituent)s) selected from the group of halogen, lower alkoxy and aryloxy, or ar(lower)-alkyl which may have substituents)s) selected from the group of lower alkoxy, halogen, nitro and cyano, and R'2 is benzotriazolyl which may have halogen; or a group represented by the formula: STR1 wherein Y' and Z' are each cyano, nitro, carbamoyl, esterified carboxy, lower alkanoyl, aroyl or disubstituted carbamoyl; provided that when R'2 is a group represented by the formula: STR2 wherein Y' and Z' are each cyano, nitro, carbamoyl or esterified carboxy, R'1 is ar(lower) alkyl having substituent(s) selected from the group of lower alkoxy, halogen, nitro and cyano. A process for the protection of amino and/or imino groups in compounds containing them by reacting them with the aforementioned esters is also disclosed.
