Di-tert-butyl azodicarboxylate
di-tert-butyl (E)-diazene-1,2-dicarboxylate · Di-tert-butyl diazene-1,2-dicarboxylate · DI-T-BUTYL AZODICARBOXYLATE · Di-tert-Butyl azodic · Di-tert-butyl azodiformate · SKL270 · NSC 109889 · DI-TERT-BUTYL AZODICARBOXYALTE
식별자 및 물리적 특성
| CAS No. | 870-50-8 |
|---|---|
| 분자식 | C10H18N2O4 |
| 평균 분자량 | 230.26 g/mol |
| 단동위원소 질량 | 230.12665706 g/mol |
| SMILES | CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C |
| InChIKey | QKSQWQOAUQFORH-UHFFFAOYSA-N |
| PubChem CID | 97268 |
| EC No. | 212-796-9 |
| DTXSID | DTXSID201306310 |
화학 및 물리적 성질
| XLogP | 2.9 |
|---|---|
| 극성 표면적 | 77.3 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 4 |
| 회전 가능 결합 수 | 4 |
| 무거운 원자 수 | 16 |
| 형식 전하 | 0 |
| 복잡도 | 267 |
| 녹는점 | 89-92 °C(lit.) |
| 끓는 점 | 287.1±9.0 °C(Predicted) |
| 밀도 | 1.06±0.1 g/cm3(Predicted) |
| 저장 조건 | 2-8°C |
| 용해도 | 클로로포름(소량으로 용해), 메탄올(약간 용해됨) |
| 물리적 상태 | 결정 또는 결정성 분말 |
| 색상 | 노란색 |
| 용해도 | 불용성 |
| BRN | 1911434 |
| InChI | InChI=1S/C10H18N2O4/c1-9(2,3)15-7(13)11-12-8(14)16-10(4,5)6/h1-6H3 |
| InChIKey | QKSQWQOAUQFORH-VAWYXSNFSA-N |
| SMILES | N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O |
화학적 성질
yellow crystals or crystalline powder
안전 및 규제
| GHS 분류 | This chemical does not meet GHS hazard criteria for 10.7% (6 of 56) of reports.WarningH315 (89.3%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (89.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (87.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 56 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 6 of 56 reports by companies.There are 7 notifications provided by 50 of 56 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Hazard Classes and Categories | Skin Irrit. 2 (89.3%)Eye Irrit. 2 (89.3%)STOT SE 3 (87.5%) |
| 수질 위해 등급(WGK) | 3 |
| 운송 번호(UN) | 1325 |
| 관세 코드 | 29270000 |
| 위험 문구(R) | 36/37/38-11 |
| 위험 표시 | Xi,F |
| 안전 문구(S) | 26-36-37/39-16 |
| 포장분류 | II |
| 위험 등급 | 3 |
| 위험 참고 사항 | Irritant |
| 저장 분류 | 11 - Combustible Solids |
용도
용도
Di-tert-butyl azodicarboxylate is a reagent used in the preparation of acyl hydrazinedicarboxylates. It is also used in the electrophilic amination of beta-keto esters catalyzed by an axially chiral guanidine. It serves as a precursor in an enantioselective synthesis of 3,6-dihyropyridazines employing organocatalysts such as L-proline or (S)-2-pyrrolidinyl tetrazole. It is also utilized in the asymmetric Friedel-Crafts amination through a chiral organocatalyst. Further, it acts as a reactant for preparation of hexapeptide key fragments through stereo selective selenocyclization/oxidative deselenylation reactions. In addition to this, it is employed as a starting material in the synthesis of pyrroloisoquinoline template through stereoselective N-acyliminium-mediated cyclization and enolate amination for preparation of peptidomimetic compounds and Barbier-type propargylation reactions.
일반 설명
Di-tert-butyl azodicarboxylate is a an acid labile reagent for Mitsunobu reactions allowing facile isolation of products and for the electrophilic amination and hydrazination of enolates and lithium alkyls.