85363-04-8

Basic information

• Product Name: N-(tert-Butoxycarbonyl)-2-aminoacetonitrile
• Synonyms: N-(TERT-BUTOXYCARBONYL)-2-AMINOACETONITRILE;BOC-2-AMINOACETONITRILE;BOC-GLY-NITRILE;AKOS 91568;Carbamic acid, (cyanomethyl)-, 1,1-dimethylethyl ester (9CI);N-BOC-2-Aminoacetonitrile;2-(Boc-aMino)acetonitrile;N-(tert-Butoxycarbonyl)-2-aminoacetonitrile 97%
• CAS NO: 85363-04-8
• Molecular Formula: C₇H₁₂N₂O₂
• Molecular Weight: 156.18
• Product Categories: N-BOC;C6 to C7;Cyanides/Nitriles;Nitrogen Compounds
• Mol File: 85363-04-8.mol
• Article Data: 22

Chemical Properties

• Melting Point: 53-57 °C(lit.)
• Boiling Point: 186 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.1832 (rough estimate)
• Refractive Index: 1.4880 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 9.96±0.46(Predicted)
• CAS DataBase Reference: N-(tert-Butoxycarbonyl)-2-aminoacetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: N-(tert-Butoxycarbonyl)-2-aminoacetonitrile(85363-04-8)
• EPA Substance Registry System: N-(tert-Butoxycarbonyl)-2-aminoacetonitrile(85363-04-8)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36
• WGK Germany: 3
• Hazardous Substances Data: 85363-04-8(Hazardous Substances Data)

Usage

Description

N-(tert-Butoxycarbonyl)-2-aminoacetonitrile is an organic building block that serves as a key intermediate in the synthesis of various organic compounds.

Uses

Used in Pharmaceutical Industry:
N-(tert-Butoxycarbonyl)-2-aminoacetonitrile is used as a synthetic intermediate for the preparation of N-(tert-butoxycarbonyl)-2-aminoacetamidoxime, which is an important compound in the pharmaceutical industry. N-(tert-Butoxycarbonyl)-2-aminoacetonitrile can be synthesized by reacting N-(tert-Butoxycarbonyl)-2-aminoacetonitrile with hydroxylamine hydrochloride.
Used in Organic Synthesis:
N-(tert-Butoxycarbonyl)-2-aminoacetonitrile is used as a versatile building block in organic synthesis for the preparation of a wide range of organic compounds. Its unique structure allows for various chemical reactions, making it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.

Upstream product

• 4530-20-5 BOC-glycine 
• 22821-76-7 4-(methylsulfonyl)benzonitrile 
• 172876-96-9 3-oxo-1λ³-benzo[d][1,2]iodaoxole-1(3H)-carbonitrile 
• 24424-99-5 di-tert-butyl dicarbonate 
• 151-63-3 cyanomethylamine sulfate 
• 51779-32-9 iminodicarboxylic acid di-tert-butyl ester 
• 35150-09-5 N-(tert-butoxycarbonyl)glycine 
• 6011-14-9 2-aminoacetonitrile hydrochloride 

Downstream Products

• 479079-15-7 tert-butyl [2-amino-2-(hydroxyimino)ethyl]carbamate 
• 540-61-4 2-aminoacetonitrile 
• 930272-56-3 2-(tert-butoxycarbonyl-aminomethyl)-5-methylpyrimidine 
• 115894-70-7 tert-butyl ((2H-tetrazol-5-yl)methyl)carbamate 
• 1373278-78-4 methyl 5-(7-(5-((tert-butoxycarbonylamino)methyl)isoxazol-3-yl)-3-(4-fluorophenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)pentanoate 
• 1360686-98-1 tert-butyl ((3-tert-butyl-1-(3-chlorophenyl)-1H-1,2,4-triazol-5-yl)methyl)carbamate 
• 479079-15-7 tert-butyl 2-(hydroxyamino)-2-iminoethylcarbamate 
• 479079-15-7 tert-butyl [(2Z)-2-amino-2-(hydroxyimino)ethyl]carbamate 
• 71904-80-8 2-((tert-butoxycarbonylamino)methyl)thiazole-4-carboxylic acid 
• 85363-08-2 4-{(S)-2-[(6-{[Benzyloxycarbonyl-(2-tert-butoxycarbonylamino-ethyl)-amino]-methyl}-pyridine-2-carbonyl)-amino]-2-methoxycarbonyl-ethyl}-imidazole-1-carboxylic acid benzyl ester 
• 486402-88-4 (1-benzyl-1H-tetrazol-5-ylmethyl)-carbamic acid tert-butyl ester 
• 218164-28-4 Boc-Aca-OH 

Relevant articles and documents

A convenient large scale synthesis of N-BOC-ethylenediamine

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Design, synthesis and cytotoxic evaluation of a library of oxadiazole-containing hybrids

The development of hybrid compounds led to the discovery of new pharmacologically active agents for some of the most critical diseases, including cancer. Herein, we describe a new series of oxadiazole-containing structures designed by a molecular hybridiz

Decarboxylative Cyanation of Aliphatic Carboxylic Acids via Visible-Light Flavin Photocatalysis

An operationally simple method is disclosed for the decarboxylative cyanation of aliphatic carboxylic acids at room temperature. Riboflavin tetraacetate, which is an inexpensive organic photocatalyst, promotes the oxidation of carboxylic acids upon visible-light activation. After decarboxylation, the generated radicals are trapped by TsCN, yielding the desired nitriles without any further additive, in a redox-neutral process. Importantly, this protocol can be adapted to flow conditions.

Room temperature decarboxylative cyanation of carboxylic acids using photoredox catalysis and cyanobenziodoxolones: a divergent mechanism compared to alkynylation

The one-step conversion of aliphatic carboxylic acids to the corresponding nitriles has been accomplished via the merger of visible light mediated photoredox and cyanobenziodoxolones (CBX) reagents. The reaction proceeded in high yields with natural and non-natural α-amino and α-oxy acids, affording a broad scope of nitriles with excellent tolerance of the substituents in the α position. The direct cyanation of dipeptides and drug precursors was also achieved. The mechanism of the decarboxylative cyanation was investigated both computationally and experimentally and compared with the previously developed alkynylation reaction. Alkynylation was found to favor direct radical addition, whereas further oxidation by CBX to a carbocation and cyanide addition appeared more favorable for cyanation. A concerted mechanism is proposed for the reaction of radicals with EBX reagents, in contrast to the usually assumed addition elimination process.