2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

CAS No.：58632-95-4

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2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile Basic information

Product Name:	2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile
Synonyms:	alpha-[[[(1,1-dimethylethoxy)carbonyl]oxy]imino]-benzeneacetonitril;N-TERT-BUTOXYCARBONYLOXYIMINO-2-PHENYLACETONITRILE;2-(tert-Butoxycarbon;Boc-ON 2-(tert-ButoxycarbonyloxyiMino)-2-phenylacetonitrile;N-((tert-Butoxycarbonyl)oxy)benziMidoyl cyanide;BOC-ON, 99% 25GR;BOC-ON, 99% 5GR;2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile
CAS:	58632-95-4
MF:	C13H14N2O3
MW:	246.26
EINECS:	261-370-9
Product Categories:	Biochemistry;Peptide Synthesis;Protection & Derivatization Reagents (for Synthesis);Protective Reagents (Peptide Synthesis);Synthetic Organic Chemistry;Boc-Amino acid series;Pharmaceutical Raw Materials
Mol File:	58632-95-4.mol

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
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 Information

Provider	Language
2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile	English
ACROS	English
SigmaAldrich	English
ALFA	English

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, 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.]

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile Preparation Products And Raw materials

Preparation Products

tert-Butyl 2-(methylamino)ethylcarbamate-->N-Boc-L-Histidine-->Boc-Aib-OH-->BOC-D-Phenylalanine-->1-(Boc-amino)cyclopropanecarboxylic acid-->(R)-4-Boc-2-methylpiperazine-->Boc-L-Threonine-->1,9-BIS-BOC-1,5,9-TRIAZANONANE-->BIS- BOC-SPERMIDINE-->1-N-BOC-1,2-CIS-CYCLOHEXYLDIAMINE-->1-Boc-3,3-dimethylpiperazine-->BOC-GLY-GLY-GLY-OH-->N-BOC-ALPHA-METHYL-L-PROLINE-->(1S,2S)-Boc-1,2-diaminocyclohexane-->METHYL 4-BOC-PIPERAZINE-2-CARBOXYLATE-->2-HYDROXYMETHYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER

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