Tert-Butyl isocyanide
2-ISOCYANO-2-METHYL-PROPANE · T-BUTYLISOCYANIDE · TBIN · TERT-BUTYL ISONITRILE · Propane, 2-isocyano-2-methyl- · 2-methylpropyl isocyanide · (CH3)3CNC · tert-Butyl isocyanide
식별자 및 물리적 특성
| CAS No. | 7188-38-7 |
|---|---|
| 분자식 | C5H9N |
| 평균 분자량 | 83.13 g/mol |
| 단동위원소 질량 | 83.07349929 g/mol |
| SMILES | [C-]#[N+]C(C)(C)C |
| InChIKey | FAGLEPBREOXSAC-UHFFFAOYSA-N |
| PubChem CID | 23577 |
| ChEBI | CHEBI:235305 |
| EC No. | 230-553-5 |
| DTXSID | DTXSID60222145 |
화학 및 물리적 성질
| XLogP | 0.9 |
|---|---|
| 극성 표면적 | 4.4 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 1 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 6 |
| 형식 전하 | 0 |
| 복잡도 | 77 |
| 녹는점 | 148-150 °C |
| 끓는 점 | 91 °C(lit.) |
| 밀도 | 0.735 g/mL at 25 °C(lit.) |
| 굴절률 | n20/D 1.376(lit.) |
| 인화점 | -2 °C |
| 저장 조건 | Inert atmosphere,2-8°C |
| 용해도 | 에탄올, 메탄올, 에테르, 톨루엔, 디클로로메탄과 같은 유기용매에 용해됩니다. |
| 물리적 상태 | 액체 |
| 비중 | 0.735 |
| 색상 | 무색의 |
| BRN | 1903156 |
| 안정성 | 냉각 |
| InChI | InChI=1S/C5H9N/c1-5(2,3)6-4/h1-3H3 |
| InChIKey | FAGLEPBREOXSAC-UHFFFAOYSA-N |
| SMILES | C(C)(C)(C)[N+]#[C-] |
화학적 성질
clear colorless liquid
안전 및 규제
| 수질 위해 등급(WGK) | 3 |
|---|---|
| RTECS 번호 | EQ7102500 |
| 운송 번호(UN) | UN 1993 3/PG 2 |
| 관세 코드 | 29299090 |
| 위험 문구(R) | 11-23-2017/11/23 |
| 위험 표시 | F,T |
| 안전 문구(S) | 16-45 |
| 포장분류 | II |
| 위험 등급 | 3Acute Tox. 2 InhalationFlam. Liq. 2 |
| 저장 분류 | 3 - Flammable liquids |
용도
개요
tert-Butyl isocyanide is a key regent for synthesizing many heterocycles and can undergo many cyclization reactions1. It is a colorless liquid, with a strong smell, bench-stable, and soluble in most organic solvents, including methanol, ethanol, ether, toluene, and dichloromethane. Many combinations of 5-member heterocycles with C, N, S, and O atoms, and even boron-containing cycles can be done via [4+1] cycloaddition. Except for heterocyclization, the reagent can be used as a mild esterification reagent, especially in the chemistry of β-lactam antibiotics, penicillins, and cephalosporins. The Passerini reaction with α-geminal polyhalogenated aldehydes allows easy esterification of such intricate substrates.
용도
tert-Butyl isocyanide is used in a tin-free procedure for alkyl radical reactions in the presence of a free-radical initiator. It is a useful intermediate in multicomponent reactions. It is also used in the synthesis of coumarines, 4H-chromenes, isoxazolines and to trap 2-cyclopropylidene-1,3-diones.
일반 설명
Carbon dative bond formation by tert-butyl isocyanide on the germanium (100) surface has been reported. It also forms complexes with metals and inserts into metal-carbon bonds to form iminoacyls.
제조 및 합성 방법
제조 방법
CAUTION: Use a well-ventilated hood and observe all precautions when using hydrogen cyanide.To a 1-1, stainless steel Hoke pressure cylinder in a well-ventilated hood is added 196 gm (3.5 moles) of isobutene, 95 gm (3.5 moles) of hydrogen cyanide, and 100 gm (0.7 mole) or cuprous bromide. The cylinder is closed, shaken for 15 hr at 70°C, cooled to room temperature, and vented cautiously in the hood, and the viscous residue is poured slowly into aqueous potassium cyanide (260 gm in 100 ml of water) to decompose the cuprous complex, liberating an organic layer. The organic layer is separated, dried, and distilled under reduced pressure to afford 97 g tert-Butyl isocyanide, b.p. 60-63°C (314 mm Hg), ng 1.3749, IR 2143 s, 1472 m, 1368 m, 1230 m, 1208 m, 855 w c m - 1; yield, 33% based on starting isobutylene; 16% based on CuBr.