(tert-butoxy)carbohydrazide

• ChemBase编号: 69919
• 分子式: C5H12N2O2
• 平均质量: 132.16098
• 单一同位素质量: 132.08987763
• SMILES: C(=O)(NN)OC(C)(C)C
• Canonical SMILES: NNC(=O)OC(C)(C)C
• InChI: InChI=1S/C5H12N2O2/c1-5(2,3)9-4(8)7-6/h6H2,1-3H3,(H,7,8)
• InChIKey: DKACXUFSLUYRFU-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: (tert-butoxy)carbohydrazide
• IUPAC传统名: tert-butoxycarbohydrazide
• 别名: Boc-肼; 叔丁氧羰基肼; 肼基甲酸叔丁酯; tert-Butoxycarbonyl hydrazide; Boc-hydrazide; tert-Butyl carbazate; tert-butyl hydrazinecarboxylate; tert-Butyl carbazate; Boc-hydrazine; tert-Butoxycarbonylhydrazine

登记号

• CAS号: 3346-63-2; 870-46-2
• EC号: 212-795-3
• MDL号: MFCD00007593
• Beilstein号: 1756967
• PubChem SID: 162035644; 24892122; 24851826
• PubChem CID: 70091

理论计算性质

• Acid pKa: 13.11165
• 质子受体: 2
• 质子供体: 2
• LogD (pH = 5.5): 0.3457911
• LogD (pH = 7.4): 0.34647724
• Log P: 0.34648678
• 摩尔折射率: 34.3792 cm^3
• 极化性: 13.3093605 Å^3
• 极化表面积: 64.35 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: 37-41°C; 38-42 °C; 39-42 °C(lit.)
• 沸点: 63-65 °C/0.1 mmHg(lit.); 63-65°C/0.1mm
• 闪点: 197.6 °F; 91°C(195°F); 92 °C

安全信息

• 保存注意事项: IRRITANT; Moisture Sensitive
• 欧盟危险性物质标志: 易燃性(Flammable) (F)
• 联合国危险货物编号: UN1325
• 德国WGK号: 3
• 联合国危险货物等级: 4.1
• 联合国危险货物包装类别(PG): III
• 危险公开号: 11
• 安全公开号: 33
• TSCA收录: false; 是
• GHS危险品标识: GHS02
• GHS危险声明: H228
• GHS警示性声明: P210-P241-P280-P240-P370+P378A
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

• 纯度: ≥98.0% (GC); 95+%; 97%; 98%; 98+%
• 级别: purum
• 线性分子式: (CH3)3COCONHNH2

详细说明

Sigma Aldrich - B91005

包装
5, 25, 100, 500 g in poly bottle
Application
用于与乙烯基卤化物进行钯催化交叉偶联反应，生成 N-叔丁氧羰基-N-烯基肼。1 用于固相多肽合成2和 α-氨基醛的光学纯度测定的试剂。3可与醛发生缩合反应形成腙，腙可作为合成 HIV-1 蛋白酶抑制剂的中间体。4

Sigma Aldrich - 19740

Other Notes
制备 BOC-叠氮化物的原料，BOC-叠氮化物是引入 BOC 氨基保护的一种试剂；E. Wünsch in Houben-Weyl, Vol. 15/1, Synthese von grossen Peptiden, p. 112.；也可用作合成磺酰肼和羧基肼的试剂1

参考文献

• Monoalkylhydrazines can be prepared via reduction of Boc-hydrazones with borane-THF, and cleavage with HCl: J. Org. Chem., 46, 5413 (1981).
• Protected hydrazine derivative, permitting selective reaction at one N atom, followed by mild acidic cleavage of the Boc group. For preparation of, e.g. N-aminosuccinimide, free from the cyclic hydrazide, see: J. Org. Chem., 37, 2040 (1972). Similarly, reaction with carbonyl or sulfonyl halides, followed by cleavage with HCl, provides a route to monoacyl hydrazides: Synthesis, 244 (1980). It is also commonly used in the synthesis of aza-amino acids; see, for example: Synthesis, 141 (1991) and references therein.
• Precursor of the somewhat unstable tert-butyl azidoformate, useful for introduction of the Boc protecting group, see: Org. Synth. Coll., 5, 157 (1973). Caution! Possible violent decomposition of this azide on heating.