4-hydroxy-3,5-diiodobenzonitrile

• ChemBase ID: 86429
• Molecular Formular: C7H3I2NO
• Molecular Mass: 370.91376
• Monoisotopic Mass: 370.83040972
• SMILES: N#Cc1cc(c(c(c1)I)O)I
• Canonical SMILES: N#Cc1cc(I)c(c(c1)I)O
• InChI: InChI=1S/C7H3I2NO/c8-5-1-4(3-10)2-6(9)7(5)11/h1-2,11H
• InChIKey: NRXQIUSYPAHGNM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy-3,5-diiodobenzonitrile
• IUPAC Traditional name: ioxynil
• Synonyms: 2,6-Diiodo-4-cyanophenol; 3,5-Diiodo-4-hydroxybenzonitrile; 4-Cyano-2,6-diiodophenol; Actril; Bentrol; CA 69-15; Certrol; Cipotril; Exp 30004A; Ioksynil; Ioxynil; Joxynil; MB 8873; Toxynil; Trevespan; 3,5-Diiodo-4-hydroxybenzonitrile; 4-hydroxy-3,5-diiodobenzonitrile; 4-Hydroxy-3,5-diiodobenzonitrile; Ioxynil; 4-Hydroxy-3,5-diiodobenzonitrile; 4-羟基-3,5-二碘苄腈; 碘苯腈; 3,5-二碘-4-羟基苯甲腈

Database IDs

• CAS Number: 1689-83-4
• EC Number: 216-881-1
• MDL Number: MFCD00016422
• Beilstein Number: 2364041
• PubChem SID: 162073545; 24862183
• PubChem CID: 15530

CALCULATED PROPERTIES

• Acid pKa: 5.6092486
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.1365912
• LogD (pH = 7.4): 1.7637402
• Log P: 3.3836656
• Molar Refractivity: 60.4855 cm^3
• Polarizability: 23.569996 Å^3
• Polar Surface Area: 44.02 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 200-207°C

Safety Information

• Storage Warning: Light Sensitive
• RTECS: DI4025000
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 2811; UN3439
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; III
• Risk Statements: 21-23/25-36-48/22-50/53-63; 63-21-23/25-36-48/22-50/53
• Safety Statements: 36/37-45-60-61-63
• TSCA Listed: 否
• GHS Pictograms: GHS06; GHS08; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H312-H319-H331-H361d-H373-H410; H301-H331-H312-H319-H361-H373-H400-H410
• GHS Precautionary statements: P260-P301+P310-P305+P351+P338-P302+P352-P405-P501A; P261-P273-P280-P301 + P310-P305 + P351 + P338-P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2

Product Information

• Purity: 97%
• Grade: PESTANAL®, analytical standard
• Empirical Formula (Hill Notation): C7H3I2NO

DETAILS

Sigma Aldrich - 36131

Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

Toronto Research Chemicals - D455160

3,5-Diiodo-4-hydroxybenzonitrile is used in the preparation of herbicides Bromoxynil and Ioxynil.

REFERENCES

• Andreasen, C., et al.: Weed Res., 46, 503 (2006)
• Mithila, J., et al.: Weed Sci., 56, 12 (2006)