2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

Synonym(s):2-(tert-Butoxycarbonyloxyimino)-2-phenyl-acetonitrile;Boc-ON

CAS NO.：58632-95-4
Empirical Formula: C13H14N2O3
Molecular Weight: 246.26
MDL number: MFCD00001863
EINECS: 261-370-9
SAFETY DATA SHEET (SDS)
Update Date: 2023-04-23 13:52:06

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile Structural

What is 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile?

Chemical properties

White to off-white microcrystalline powder

The Uses of 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

Widely used for protection of amino groups in peptide synthesis and multi-step organic synthesis of small molecules.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 6, p. 199, 1988
Tetrahedron 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.]

Properties of 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

Melting point:	85-88 °C (lit.)
Boiling point:	389.26°C (rough estimate)
Density	1.1855 (rough estimate)
refractive index	1.6450 (estimate)
storage temp.	-20°C
solubility	Soluble in water or 1% acetic acid
form	Fine Crystalline Powder
color	White to slightly beige
Water Solubility	insoluble
Sensitive	Moisture Sensitive
BRN	2217296
CAS DataBase Reference	58632-95-4(CAS DataBase Reference)
EPA Substance Registry System	Benzeneacetonitrile, .alpha.-[[[(1,1-dimethylethoxy)carbonyl]oxy]imino]- (58632-95-4)

Safety information for 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

Signal word	Danger
Pictogram(s)	Skull and Crossbones Acute Toxicity GHS06 Exclamation Mark Irritant GHS07
GHS Hazard Statements	H301:Acute toxicity,oral H302:Acute toxicity,oral H312:Acute toxicity,dermal H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H332:Acute toxicity,inhalation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P280:Wear protective gloves/protective clothing/eye protection/face protection. P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P405:Store locked up. P501:Dispose of contents/container to..…