Boc-ON
Synonyms. Boc-ON; 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile; tert-Butyl alpha- cyanobenzylaminyl carbonate;   2-(tert-Butoxycarbonyloximino)-2-phenylacetonitrile; 2-(Boc-oxyimino)-2-phenylacetonitrile; alpha-((((1,1-Dimethylethoxy)carbonyl)oxy)imino) benzeneacetonitrile; Carbonic acid (cyanophenylmethylene)azanyl 1,1-dimethylethyl ester;

Boc-ON
 

PRODUCT IDENTIFICATION

CAS RN

58632-95-4

EINECS RN

 261-370-9

FORMULA

 (CH3)3COCOON=C(C6H5)CN

MOLE WEIGHT

 246.26

H.S CODE

 2928.00.2500

SMILES

 O=C(OC(C)(C)C)O\N=C(\C#N)c1ccccc1

CLASSIFICATION

 

EXTRA NOTES

 Protection of amines, alcohols in peptide synthesis
Other RN: 103919-55-7, 115721-57-8, 154920-47-5

 

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE

white to yellow crystalline powder

MELTING POINT

86 ~ 89 C

BOILING POINT

  

DENSITY

 

SOLUBILITY IN WATER

Insoluble
SOLVENT SOLUBILITY Soluble in ethyl acetate, ether, benzene

VAPOR DENSITY

 

log P(octanol-water)

  

VAPOR PRESSURE

  

AUTOIGNITION TEMP

  
pH

 

REFRACTIVE INDEX

 

FLASH POINT

> 100

 
STABILITY AND REACTIVITY
STABILITY Stable under normal conditions.

INCOMPATIBLE MATERIALS

Strong oxidizing agents, strong acids
POLYMERIZATION

Has not been reported

NFPA RATINGS

Health: 2; Flammability: 1; Instability: 0;

 

EXTERNAL LINKS & GENERAL DESCRIPTION

Wikipedia Linking - Peptide synthesis

Google Scholar Search

PubChem Compound Summary - Boc-ON

http://www.ncbi.nlm.nih.gov/ - Boc-ON

http://www.sigmaaldrich.com/
This reagent offers a distinct advantage over t-BOC azide which can require reaction temperatures of 50-60°C (t-BOC azide is thermally unstable and decomposes with apparent detonation at temperatures above 80°C). The oxime by-product can be easily and completely removed from the reaction mixture by extraction with ether, ethyl acetate or benzene. Deprotection of t-BOC amino acids is accomplished under mildly acidic conditions. The bibliography on page 2 lists references to the use of BOC-ON since its introduction in 1975 by Itoh et al. A number of patents to its use in pharmaceutical and agricultural applications have been issued but are not inlcuded in this bibliography

 

SALES SPECIFICATION

APPEARANCE

white to yellow crystalline powder

PURITY 

98.5% min

MELTING POINT

86 ~ 89 C

WATER

0.1% max

 

TRANSPORT & REGULATORY INFORMATION

UN NO.

3439

HAZARD SYMBOL

 6.1
PACKING GROUP III

 

SAFETY INFORMATION

HAZARD OVERVIEW

Harmful if swallowed, inhaled, or absorbed through the skin. Causes eye, skin, and respiratory tract irritation. Target Organs: Respiratory system, eyes, skin.

GHS

  

SIGNAL WORD

Warning

PICTOGRAMS

 

HAZARD STATEMENTS

H302-H312-H315-H319-H332

P STATEMENTS

P261-P280-P301+ P312-P304 + P340-P305 + P351 + P338-P302 + P352
EC DIRECTIVES

 
HAZARD CODES

 

RISK PHRASES

 20/21/22-36/37/38

SAFETY PHRASES

 26-36/37/39

 

PACKING

 

 

PRICE INFORMATION