2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

• ChemBase编号: 110550
• 分子式: C8H5NO3
• 平均质量: 163.1302
• 单一同位素质量: 163.02694303
• SMILES: O=c1[nH]c2c(cccc2)c(=O)o1
• Canonical SMILES: O=c1oc(=O)c2c([nH]1)cccc2
• InChI: InChI=1S/C8H5NO3/c10-7-5-3-1-2-4-6(5)9-8(11)12-7/h1-4H,(H,9,11)
• InChIKey: TXJUTRJFNRYTHH-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2,4-dihydro-1H-3,1-benzoxazine-2,4-dione
• IUPAC传统名: 1H-3,1-benzoxazine-2,4-dione
• 别名: N-羧鄰胺苯甲酐; 衣托酸酐; 靛红酸酐; 3,1-Benzoxazine-2,4(1H)-dione; Anthranilic acid N-carboxylic acid anhydride; Isatoic anhydride; 1H-benzo[d][1,3]oxazine-2,4-dione; ISATOIC ANHYDRIDE; 4H-3,1-Benzoxazine-2,4(1H)-dione; 2H-3,1-Benzoxazine-2,4(1H)-dione; 1,2-Dihydro-3,1-benzoxazine-2,4-dione; 1H-Benz[d][1,3]oxazine-2,4-dione; 2,4-Dioxo-1,2-dihydro-4H-3,1-benzoxazine; 2-(Carboxyamino)benzoic Acid Cyclic Anhydride; Isatoic Acid Anhydride; NSC 104662; NSC 29555

登记号

• CAS号: 118-48-9
• EC号: 204-255-0
• MDL号: MFCD00006700
• Beilstein号: 136786
• PubChem SID: 24895927; 162096513
• PubChem CID: 8359

理论计算性质

• Acid pKa: 9.395176
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 1.4760556
• LogD (pH = 7.4): 1.4719576
• Log P: 1.4761082
• 摩尔折射率: 41.8263 cm^3
• 极化性: 15.27678 Å^3
• 极化表面积: 55.4 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: DMSO; Methanol
• 外观: Light Brown Solid
• 熔点: 233 °C (dec.)(lit.); 234-236°C (dec.); ca 237°C dec.
• 闪点: 308 °C; 308°C(586°F); 586.4 °F
• 密度: 1.520
• 蒸汽密度: 5.6 (vs air)

安全信息

• 保存条件: Refrigerator, Under Inert Atmosphere
• 保存注意事项: Moisture Sensitive
• RTECS编号: DM3100000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 1
• 危险公开号: 36-43
• 安全公开号: 24-26-37
• TSCA收录: 是
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H317-H319; H319-H317
• GHS警示性声明: P261-P280-P305+P351+P338-P302+P352-P321-P501A; P280-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

产品相关信息

• 纯度: ≥94% (HPLC); 96%; 97%
• 级别: technical
• Empirical Formula (Hill Notation): C8H5NO3

详细说明

MP Biomedicals - 05215507

MP Biomedicals Rare Chemical collection

Sigma Aldrich - I12808

包装
100, 500 g in poly bottle

Sigma Aldrich - 58279

Other Notes
综述1；用于 2-氨基苯甲酰化的试剂。2

Toronto Research Chemicals - I777600

Isatoic anhydride is a potent inactivator of α-chymotrypsin and inactivates stoichiometrically. Isatoic Anhydride is an important compound in the preparation of serine protease inhibitors.

参考文献

• Moorman, A.J. et al.: J. AM. Chem. Soc., 104, 6785 (1982)
• Shinogi, M. et al.: J. Pharmac. Sci., 74, 782 (1982)
• Khiav, B. et al.: Int. Arch. Allergy Immunol., 113, 291 (1982)
• Susceptible to nucleophilic attack, normally at the "acid" 4-carbon. More hindered nucleophiles attack at the "carbamate" 2-carbon. In the presence of DMAP, attack is directed to C-4, giving anthranilic acid derivatives: Synthesis, 266 (1982). For reviews of the chemistry of isatoic anhydrides, including reactions with a wide range of nucleophiles and the formation of a variety of heterocyclic systems, see: Synthesis, 505 (1980); Adv. Heterocycl Chem., 28, 127 (1981).