oxolane-2,5-dione

• ChemBase编号: 88761
• 分子式: C4H4O3
• 平均质量: 100.07276
• 单一同位素质量: 100.01604399
• SMILES: O1C(=O)CCC1=O
• Canonical SMILES: O=C1CCC(=O)O1
• InChI: InChI=1S/C4H4O3/c5-3-1-2-4(6)7-3/h1-2H2
• InChIKey: RINCXYDBBGOEEQ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: oxolane-2,5-dione
• IUPAC传统名: succinic anhydride; oxolane-2,5-dione
• 别名: 二氢-2,5-呋喃二酮; 丁二酸酐; Succinic acid anhydride; Succinyl oxide; Dihydrofuran-2,5-dione; 2,5-Dioxotetrahydrofuran; Succinic anhydride; Dihydro-2,5-furandione; Succinic anhydride; Dihydrofuran-2,5-dione; 2,5-Diketotetrahydrofuran; Butanedioic Anhydride; NSC 8518; Rikacid SA; Succinyl Anhydride; Tetrahydro-2,5-dioxofuran; Tetrahydro-2,5-furandione

登记号

• CAS号: 108-30-5
• EC号: 203-570-0
• MDL号: MFCD00005525
• Beilstein号: 108441
• 默克索引号: 148870
• PubChem SID: 162075669; 24854387; 24848151
• PubChem CID: 7922
• CHEBI ID: 36595
• Chemspider ID: 7634
• KEGG ID: C19524
• 维基百科标题: Succinic_anhydride

理论计算性质

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): -0.26431096
• LogD (pH = 7.4): -0.26431096
• Log P: -0.26431096
• 摩尔折射率: 20.3316 cm^3
• 极化性: 8.355237 Å^3
• 极化表面积: 43.37 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Decomposes in water; DMSO; Soluble in chloroform
• 外观: Colorless crystalline needles; White Solid
• 熔点: 100-102°C; 117-120 °C; 118-120 °C; 118-120 °C(lit.); 118-120°C; 118-121°C; 119–120 °C
• 沸点: 261 °C(lit.); 261°C; 261 °C; 261°C
• 闪点: 147 °C; 157°C; 157°C(314°F)
• 密度: 1.23 g/cm^3; 1.572
• 蒸汽压: 1 mm Hg at 92 °C; 1 mmHg ( 92 °C)
• 蒸汽密度: 3.5 (vs air)

安全信息

• 保存条件: Refrigerator, Under Inert Atmosphere; Room Temperature (15-30°C), Desiccate
• 保存注意事项: Harmful/Irritant/Moisture Sensitive/Store under Argon; Moisture Sensitive
• RTECS编号: WN0875000
• 欧盟危险性物质标志: X; 刺激性(Irritant) (Xi); 有害性(Harmful) (Xn)
• 德国WGK号: 1
• 危险公开号: 22-36/37; 36/37; R:36/37
• 安全公开号: 2-25-46; 25; 25-46; S:25
• TSCA收录: 是
• GHS危险品标识: GHS07
• GHS警示词: Warning
• 半数致死量: 1510 mg/kg (oral, rat)
• GHS危险声明: H302-H319-H335
• GHS警示性声明: P261-P280-P305+P351+P338-P304+P340-P405-P501A; P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

产品相关信息

• 纯度: ≥97.0% (NT); ≥99% (GC); ≥99.0%; ≥99.0% (NT); 95+%; 97%; 99%
• 级别: puriss.; purum; SAJ first grade
• Empirical Formula (Hill Notation): C4H4O3

详细说明

MP Biomedicals - 05218902

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02102970

Crystalline
Purity: 99%

Sigma Aldrich - S7626

Application
该试剂用于蛋白质中赖氨酸的琥珀酰化。

Sigma Aldrich - 134414

包装
500 g in poly bottle

Sigma Aldrich - 239690

包装
50, 250 g in poly bottle

参考文献

• Friedel-Crafts reaction with arenes gives 3-aroylpropionic acids: Org. Synth. Coll., 2, 81 (1943). For a review of the Friedel-Crafts reactions of the anhydrides of dibasic acids, see: Org. React., 5, 229 (1949).
• For reaction with phosphoranes, in a route to 2,2-disubstituted cyclopentane-1,3-diones, see (1-Ethoxycarbonylethylidene)triphenylphosphorane, A15619.
• A method for protecting both H atoms of a primary amine consists of formation of the succinimide, followed by enolsilylation with Triisopropylsilyl trifluoromethanesulfonate, B21127, to form the 2,5-bis(triisopropylsiloxy)pyrroles. Deprotection can be effected by desilylation with dilute HCl, followed by hydrazinolysis: Tetrahedron Lett., 38, 2617 (1997).