| 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 |
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