N-(phenylmethylidene)hydroxylamine

• ChemBase编号: 88864
• 分子式: C7H7NO
• 平均质量: 121.13658
• 单一同位素质量: 121.05276385
• SMILES: N(=C\c1ccccc1)/O
• Canonical SMILES: O/N=C/c1ccccc1
• InChI: InChI=1S/C7H7NO/c9-8-6-7-4-2-1-3-5-7/h1-6,9H
• InChIKey: VTWKXBJHBHYJBI-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: N-(phenylmethylidene)hydroxylamine; (E)-N-(phenylmethylidene)hydroxylamine
• IUPAC传统名: benzaldoxime; benzaldoxime,syn
• 别名: (E)-苯甲醛肟; 苯甲醛肟, 主要为 E式异构体; (E)-Benzaldoxime; trans-Benzaldoxime; Benzaldehyde oxime; Benzaldoxime; (E)-Benzaldehyde oxime; Benzaldoxime, predominantly (E)-isomer; BENZALDEHYDE OXIME; (E)-Benzaldehyde oxime; syn-Benzaldoxime

登记号

• CAS号: 622-32-2; 622-31-1; 932-90-1
• EC号: 213-261-2
• MDL号: MFCD00002119
• Beilstein号: 774138
• PubChem SID: 24854749; 24847415; 162075762
• PubChem CID: 5324611

理论计算性质

• Acid pKa: 8.73708
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 1.6939479
• LogD (pH = 7.4): 1.6757065
• Log P: 1.695228
• 摩尔折射率: 36.4637 cm^3
• 极化性: 13.57526 Å^3
• 极化表面积: 32.59 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Acetone; Dichloromethane; Methanol
• 外观: White Solid
• 熔点: 126-128°C; 33-35°C; 34-36 °C(lit.)
• 沸点: 104 °C/6 mmHg(lit.); 118-120°C/10mm; 118-120°C/10mm
• 闪点: 108°C; 108°C(226°F); 109 °C; 228.2 °F
• 密度: 1.110
• 折射率: 1.5900; n20/D 1.591(lit.)

安全信息

• 保存注意事项: Irritant
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26-37; 26-37/39
• TSCA收录: 是
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

产品相关信息

• 纯度: ≥97.0% (GC); 97% (mixture of cis and trans); 98%
• 级别: purum
• 线性分子式: C6H5CH=NOH

详细说明

Sigma Aldrich - 245674

包装
10, 50 g in glass bottle

Toronto Research Chemicals - B183750

An antioxidant

参考文献

• Jeong, H., et al.: Bioorg. Med. Chem. Lett., 16, 5576 (2006)
• Andresen Bergstroem, M., et al.: J. Med. Chem., 51, 2541 (2006)
• For conversion to the isothiocyanate, see Thiourea, A12828.
• The oximate anion displaces activated aromatic nitro (or halogen) substituents. A second mole of oximate functions as base with elimination of benzonitrile and overall conversion of the nitro-compound to a phenol: J. Org. Chem., 39, 3343 (1974):
  
• Conjugate addition of the oximate anion to ɑ?-unsaturated acetylenic carbonyl compounds gives ?-dicarbonyl compounds: J. Org. Chem., 59, 1219 (1994). For example with reaction scheme, see Methyl phenylpropiolate, B24587.
• Aldoximes are conventionally dehydrated to nitriles with acetic anhydride; see, e.g.: Org. Synth. Coll., 2, 622 (1943). Many other dehydration methods have been described, including: Triethyl orthoformate and acid: J. Org. Chem., 39, 3424 (1974). DMF - SOCl₂: Tetrahedron Lett., 25, 3365 (1984). SOCl₂ - DMAP: Synthesis, 472 (1983). DCC: Synth. Commun., 3, 101 (1973); Chem. Ber., 107, 1221 (1974). PPh₃ - CBr₄: Synth. Commun., 20, 2785 (1990). Trichloromethyl chloroformate (diphosgene): Synthesis, 129 (1990). For a further example, see Trichloroacetonitrile, A10565. See also Hydroxylamine hydrochloride, A15398 for one-pot conversion of aldehydes to nitriles.
• Chlorination followed by elimination of HCl from the benzohydroxamoyl chloride leads, in situ, to the 1,3-dipole benzonitrile oxide. See, e.g.: Org. Synth. Coll., 5, 504 (1973).