N-(phenylmethylidene)hydroxylamine

• ChemBase ID: 88864
• Molecular Formular: C7H7NO
• Molecular Mass: 121.13658
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(phenylmethylidene)hydroxylamine; (E)-N-(phenylmethylidene)hydroxylamine
• IUPAC Traditional name: benzaldoxime; benzaldoxime,syn
• Synonyms: (E)-Benzaldoxime; trans-Benzaldoxime; Benzaldehyde oxime; Benzaldoxime; (E)-Benzaldehyde oxime; Benzaldoxime, predominantly (E)-isomer; BENZALDEHYDE OXIME; (E)-Benzaldehyde oxime; syn-Benzaldoxime; (E)-苯甲醛肟; 苯甲醛肟, 主要为 E式异构体

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 8.73708
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.6939479
• LogD (pH = 7.4): 1.6757065
• Log P: 1.695228
• Molar Refractivity: 36.4637 cm^3
• Polarizability: 13.57526 Å^3
• Polar Surface Area: 32.59 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Dichloromethane; Methanol
• Apperance: White Solid
• Melting Point: 126-128°C; 33-35°C; 34-36 °C(lit.)
• Boiling Point: 104 °C/6 mmHg(lit.); 118-120°C/10mm; 118-120°C/10mm
• Flash Point: 108°C; 108°C(226°F); 109 °C; 228.2 °F
• Density: 1.110
• Refractive Index: 1.5900; n20/D 1.591(lit.)

Safety Information

• Storage Warning: Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37; 26-37/39
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥97.0% (GC); 97% (mixture of cis and trans); 98%
• Grade: purum
• Linear Formula: C6H5CH=NOH

DETAILS

Sigma Aldrich - 245674

Packaging
10, 50 g in glass bottle

Toronto Research Chemicals - B183750

An antioxidant

REFERENCES

• 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).