CAS 932-90-1|CAS 622-31-1|CAS 622-32-2|Benzaldoxime|N-(phenylmethylidene)hydroxylamine|Benzaldehyde oxime|benzaldoxime|(E)-N-(phenylmethylidene)hydroxylamine|syn-Benzaldoxime|(E)-Benzaldehyde oxime|...

General Information

Structure

Molecular Formula

C₇H₇NO

Molecular Mass

121.13658

Exact Mass

121.05276385

Charge

InChI

InChI=1S/C7H7NO/c9-8-6-7-4-2-1-3-5-7/h1-6,9H

InChIKey

VTWKXBJHBHYJBI-UHFFFAOYSA-N

Canonic Smiles

O/N=C/c1ccccc1

Isomeric Smiles

N(=C\c1ccccc1)/O

Calculated Properties

JChem

Acid pKa

8.73708

H Acceptors

H Donor

LogD (pH = 5.5)

1.6939479

LogD (pH = 7.4)

1.6757065

Log P

1.695228

Molar Refractivity

36.4637

Polarizability

13.57526

Polar Surface Area

32.59

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC Traditional name

benzaldoxime benzaldoxime,syn

Synonyms

Benzaldehyde oximeBenzaldoximesyn-Benzaldoxime(E)-苯甲醛肟(E)-Benzaldehyde oxime(E)-Benzaldehyde oxime(E)-Benzaldoximetrans-BenzaldoximeBenzaldoxime, predominantly (E)-isomer苯甲醛肟, 主要为 E式异构体BENZALDEHYDE OXIME

IUPAC name

N-(phenylmethylidene)hydroxylamine (E)-N-(phenylmethylidene)hydroxylamine

Names and Identifiers

Registration numbers

CAS Number

932-90-1622-31-1622-32-2

MDL Number

MFCD00002119

Beilstein Number

774138

EC Number

213-261-2

PubChem SID

2485474924847415162075762

PubChem CID

5324611

Registration numbers

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Sigma Aldrich

245674

Packaging
10, 50 g in glass bottle

TRC

B183750

An antioxidant

Molecule Details

References

PubChem Literature

From Data Sources

• Jeong, H., et al.: Bioorg. Med. Chem. Lett., 16, 5576 (2006)

• Andresen Bergstroem, M., et al.: J. Med. Chem., 51, 2541 (2006)

• 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).

• 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.

• 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):

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

benzaldoxime benzaldoxime,syn

Synonyms

IUPAC name

N-(phenylmethylidene)hydroxylamine (E)-N-(phenylmethylidene)hydroxylamine

Registration numbers

CAS Number

932-90-1622-31-1622-32-2

MDL Number

MFCD00002119

Beilstein Number

774138

EC Number

213-261-2

PubChem SID

2485474924847415162075762

PubChem CID

5324611

Molecule Details

Sigma Aldrich

245674

Packaging
10, 50 g in glass bottle

TRC

B183750

An antioxidant

References

PubChem Literature

From Data Sources

• Jeong, H., et al.: Bioorg. Med. Chem. Lett., 16, 5576 (2006)

• Andresen Bergstroem, M., et al.: J. Med. Chem., 51, 2541 (2006)

• 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).

• For conversion to the isothiocyanate, see Thiourea, A12828.

Bioactivity

PubChem BioAssay

Properties

Molecule

ID:88864