4-톨루엔술포닐 시안
4-톨루엔술포닐시안 · TsCN · 4-Methylbenzenesulfonyl cyanide · P-TOLUENESULFONYL CYANIDE · 4-Toluenesulfonyl Cyanide · Benzenesulfonylcyanide, 4-Methyl- · 4-Methylbenzene-1-sulfonyl cyanide · Tos-CN
식별자 및 물리적 특성
| CAS No. | 19158-51-1 |
|---|---|
| 분자식 | C8H7NO2S |
| 평균 분자량 | 181.21 g/mol |
| 단동위원소 질량 | 181.01974946 g/mol |
| SMILES | Cc1ccc(S(=O)(=O)C#N)cc1 |
| InChIKey | JONIMGVUGJVFQD-UHFFFAOYSA-N |
| PubChem CID | 87946 |
| EC No. | 242-849-1 |
| DTXSID | DTXSID50172685 |
| 현지명 | 4-톨루엔술포닐 시안 |
화학 및 물리적 성질
| XLogP | 2.3 |
|---|---|
| 극성 표면적 | 66.3 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 3 |
| 회전 가능 결합 수 | 1 |
| 무거운 원자 수 | 12 |
| 형식 전하 | 0 |
| 복잡도 | 285 |
| 녹는점 | 47-50 °C (lit.) |
| 끓는 점 | 105-106 °C/1 mmHg (lit.) |
| 밀도 | 1.3055 (rough estimate) |
| 굴절률 | 1.5650 (estimate) |
| 인화점 | >230 °F |
| 저장 조건 | 2-8°C |
| 용해도 | Acetonitrile (Slightly), Chloroform (Slightly), DMSO (Sparingly), Ethyl Acetate |
| 물리적 상태 | 결정질 고체 |
| 색상 | 하얀색 |
| BRN | 2048159 |
| 안정성 | 흡습성, 수분 민감성 |
| InChI | InChI=1S/C8H7NO2S/c1-7-2-4-8(5-3-7)12(10,11)6-9/h2-5H,1H3 |
| InChIKey | JONIMGVUGJVFQD-UHFFFAOYSA-N |
| SMILES | C1(S(C#N)(=O)=O)=CC=C(C)C=C1 |
화학적 성질
White powder
안전 및 규제
| GHS 분류 | DangerH312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]P260, P261, P264, P264+P265, P271, P280, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P362+P364, P363, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 44 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| 수질 위해 등급(WGK) | 3 |
| 운송 번호(UN) | UN 3261 8/PG 2 |
| 관세 코드 | 2930909899 |
| 위험 문구(R) | 20/21-34 |
| 위험 표시 | C |
| 안전 문구(S) | 26-27-28-36/37/39-45 |
| 포장분류 | III |
| 위험 등급 | 8Acute Tox. 4 DermalAcute Tox. 4 InhalationEye Dam. 1Skin Corr. 1B |
| 기존화학 물질 | KE-24847 |
| F 고인화성물질 | 10-21 |
| 저장 분류 | 8A - Combustible corrosive hazardous materials |
용도
용도
Tosyl cyanide is used in a free-radical cyanation of B-alkylcatecholboranes. Also used as a component in a hetero-Diels-Alder reaction with 1,3-bis-silyl enol ethers leading to 4-hyroxypyridines.
일반 설명
p-Toluenesulfonyl cyanide is an electron-deficient nitrile. It undergoes hetero-Diels-Alder reaction with silyl enol ether of cyclohexenone to yield hydrolytically sensitive [4+2] adduct. It also undergoes facile [2+3] cycloaddition reaction with azides to form 5-sulfonyl tetrazoles. p-Toluenesulfonyl cyanide also reacts with alcohols in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1,4-diazabicyclo[2.2.2]octane (DABCO) to yield sulfinates.