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

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

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-20/21/22

Safety Statements 

22-24/25-36/37/39-26-36

RIDADR 

3276

WGK Germany 

3

RTECS 

DA0513600

F 

10-21

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29280090

MSDS

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2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile Usage And Synthesis

Chemical Properties

White to off-white microcrystalline powder

Uses

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.]

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile(58632-95-4)Related Product Information

• 4-tert-Butylcatechol
• tert-Butyllithium
• N-Carbobenzyloxyglycine
• 4-tert-Butylphenol
• tert-Butyl methyl ether
• tert-Butyldimethylsilyl chloride
• (3-Methoxyphenyl)acetonitrile
• Diphenylacetonitrile
• Methyl 4-tert-butylbenzoate
• tert-Butanol
• tert-Butyl hydroperoxide
• Benzeneacetonitrile
• Carbonyl iron powder
• Formic acid isopropyl ester
• Acetaldoxime
• 2-HYDROXYIMINO-2-PHENYLACETONITRILE
• FORMOXIME
• O-methylhydroxylamine