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MedKoo Cat#: 412589 | Name: Bromoxynil
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Bromoxynil is an organic compound with the formula HOBr₂C₆H₂CN. It is classified as a nitrile herbicide, and as such sold under many trade names. It is a white solid. It works by inhibiting photosynthesis. It is moderately toxic to mammals.

Chemical Structure

Bromoxynil
Bromoxynil
CAS#1689-84-5

Theoretical Analysis

MedKoo Cat#: 412589

Name: Bromoxynil

CAS#: 1689-84-5

Chemical Formula: C7H3Br2NO

Exact Mass: 274.8581

Molecular Weight: 276.92

Elemental Analysis: C, 30.36; H, 1.09; Br, 57.71; N, 5.06; O, 5.78

Price and Availability

Size Price Availability Quantity
1g USD 250.00 2 Weeks
5g USD 550.00 2 Weeks
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Related CAS #
No Data
Synonym
Bromoxynil; HSDB1523; HSDB-1523; HSDB 1523
IUPAC/Chemical Name
3,5-dibromo-4-hydroxybenzonitrile
InChi Key
UPMXNNIRAGDFEH-UHFFFAOYSA-N
InChi Code
InChI=1S/C7H3Br2NO/c8-5-1-4(3-10)2-6(9)7(5)11/h1-2,11H
SMILES Code
Oc1c(Br)cc(C#N)cc1Br
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 276.92 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: European Food Safety Authority (EFSA); Arena M, Auteri D, Barmaz S, Bellisai G, Brancato A, Brocca D, Bura L, Byers H, Chiusolo A, Court Marques D, Crivellente F, De Lentdecker C, De Maglie M, Egsmose M, Erdos Z, Fait G, Ferreira L, Goumenou M, Greco L, Ippolito A, Istace F, Jarrah S, Kardassi D, Leuschner R, Lythgo C, Magrans JO, Medina P, Miron I, Molnar T, Nougadere A, Padovani L, Parra Morte JM, Pedersen R, Reich H, Sacchi A, Santos M, Serafimova R, Sharp R, Stanek A, Streissl F, Sturma J, Szentes C, Tarazona J, Terron A, Theobald A, Vagenende B, Verani A, Villamar-Bouza L. Peer review of the pesticide risk assessment of the active substance bromoxynil (variant evaluated bromoxynil octanoate). EFSA J. 2017 Jun 14;15(6):e04790. doi: 10.2903/j.efsa.2017.4790. PMID: 32625507; PMCID: PMC7010205. 2: Halbach K, Aulhorn S, Lechtenfeld OJ, Lecluse M, Leippe S, Reemtsma T, Seiwert B, Wagner S, König J, Luckenbach T. Zebrafish Oatp1d1 Acts as a Cellular Efflux Transporter of the Anionic Herbicide Bromoxynil. Chem Res Toxicol. 2022 Feb 21;35(2):315-325. doi: 10.1021/acs.chemrestox.1c00371. Epub 2022 Jan 6. PMID: 34990119. 3: European Food Safety Authority (EFSA); Anastassiadou M, Arena M, Auteri D, Barmaz S, Brancato A, Brocca D, Bura L, Carrasco Cabrera L, Chiusolo A, Civitella C, Court Marques D, Crivellente F, Ctverackova L, De Lentdecker C, Egsmose M, Fait G, Ferreira L, Greco L, Ippolito A, Istace F, Jarrah S, Kardassi D, Leuschner R, Lostia A, Lythgo C, Magrans JO, Medina P, Mineo D, Miron I, Nave S, Molnar T, Padovani L, Parra Morte JM, Pedersen R, Reich H, Sacchi A, Santos M, Serafimova R, Sharp R, Stanek A, Streissl F, Sturma J, Szentes C, Tarazona J, Terron A, Theobald A, Vagenende B, Van Dijk J, Villamar-Bouza L. Peer review of the pesticide risk assessment for the active substance bromoxynil in light of negligible exposure data submitted. EFSA J. 2018 Dec 13;16(12):e05490. doi: 10.2903/j.efsa.2018.5490. PMID: 32625780; PMCID: PMC7009762. 4: Chen XX, Li WM, Wu Q, Zhi YN, Han LJ. Bromoxynil residues and dissipation rates in maize crops and soil. Ecotoxicol Environ Saf. 2011 Sep;74(6):1659-63. doi: 10.1016/j.ecoenv.2011.05.015. Epub 2011 Jun 15. PMID: 21680020. 5: Chan BSH, Chiew AL, Grainger S, Page CB, Gault A, Mostafa A, Roberts MS, Buckley NA, Isbister GK. Bromoxynil and 2-methyl-4-chlorophenoxyacetic acid (MCPA) poisoning could be a bad combination. Clin Toxicol (Phila). 2018 Sep;56(9):861-863. doi: 10.1080/15563650.2018.1433299. Epub 2018 Jan 30. PMID: 29382245. 6: Holtze MS, Sørensen SR, Sørensen J, Aamand J. Microbial degradation of the benzonitrile herbicides dichlobenil, bromoxynil and ioxynil in soil and subsurface environments--insights into degradation pathways, persistent metabolites and involved degrader organisms. Environ Pollut. 2008 Jul;154(2):155-68. doi: 10.1016/j.envpol.2007.09.020. Epub 2007 Nov 7. PMID: 17988770. 7: Semchuk K, McDuffie H, Senthilselvan A, Cessna A, Irvine D. Body mass index and bromoxynil exposure in a sample of rural residents during spring herbicide application. J Toxicol Environ Health A. 2004 Sep 10;67(17):1321-52. doi: 10.1080/15287390490471424. PMID: 15371235. 8: Cutulle MA, Armel GR, Brosnan JT, Best MD, Kopsell DA, Bruce BD, Bostic HE, Layton DS. Synthesis and evaluation of heterocyclic analogues of bromoxynil. J Agric Food Chem. 2014 Jan 15;62(2):329-36. doi: 10.1021/jf404209d. Epub 2013 Dec 27. PMID: 24354444. 9: Baxter J, Cummings SP. The degradation of the herbicide bromoxynil and its impact on bacterial diversity in a top soil. J Appl Microbiol. 2008 Jun;104(6):1605-16. doi: 10.1111/j.1365-2672.2007.03709.x. Epub 2008 Jan 23. PMID: 18217937. 10: Chiew AL, Page CB, Clancy D, Mostafa A, Roberts MS, Isbister GK. 2-Methyl-4-chlorophenoxyacetic acid (MCPA) and bromoxynil herbicide ingestion. Clin Toxicol (Phila). 2018 May;56(5):377-380. doi: 10.1080/15563650.2017.1385790. Epub 2017 Oct 9. PMID: 28988498. 11: Rogers JM, Francis BM, Barbee BD, Chernoff N. Developmental toxicity of bromoxynil in mice and rats. Fundam Appl Toxicol. 1991 Oct;17(3):442-7. doi: 10.1016/0272-0590(91)90195-a. PMID: 1794648. 12: Nowak KM, Telscher M, Seidel E, Miltner A. Unraveling microbial turnover and non-extractable residues of bromoxynil in soil microcosms with 13C-isotope probing. Environ Pollut. 2018 Nov;242(Pt A):769-777. doi: 10.1016/j.envpol.2018.07.049. Epub 2018 Jul 17. PMID: 30031310. 13: Hsu JC, Camper ND. Degradation of ioxynil and bromoxynil as measured by a modified spectrophotometric method. Can J Microbiol. 1975 Dec;21(12):2008-12. doi: 10.1139/m75-288. PMID: 1220864. 14: Semchuk KM, Rosenberg AM, McDuffie HH, Cessna AJ, Pahwa P, Irvine DG. Antinuclear antibodies and bromoxynil exposure in a rural sample. J Toxicol Environ Health A. 2007 Apr 1;70(7):638-57. doi: 10.1080/15287390600974593. PMID: 17365618. 15: Morimoto H, Shimmen T. Primary effect of bromoxynil to induce plant cell death may be cytosol acidification. J Plant Res. 2008 Mar;121(2):227-33. doi: 10.1007/s10265-008-0147-y. Epub 2008 Feb 7. PMID: 18256783. 16: Knossow N, Siebner H, Bernstein A. Isotope analysis method for the herbicide bromoxynil and its application to study photo-degradation processes. J Hazard Mater. 2020 Apr 15;388:122036. doi: 10.1016/j.jhazmat.2020.122036. Epub 2020 Jan 7. PMID: 31951995. 17: Farooq S, Yasmeen T, Niaz A, Rizwan M, Ali S. Rice straw biochar in combination with farmyard manure mitigates bromoxynil toxicity in wheat (Triticum aestivum L.). Chemosphere. 2022 May;295:133854. doi: 10.1016/j.chemosphere.2022.133854. Epub 2022 Feb 2. PMID: 35122820. 18: Ruan Z, Xu M, Xing Y, Jiang Q, Yang B, Jiang J, Xu X. Interspecies Metabolic Interactions in a Synergistic Consortium Drive Efficient Degradation of the Herbicide Bromoxynil Octanoate. J Agric Food Chem. 2022 Sep 21;70(37):11613-11622. doi: 10.1021/acs.jafc.2c03057. Epub 2022 Sep 11. PMID: 36089742. 19: Semchuk KM, McDuffie HH, Senthilselvan A, Dosman JA, Cessna AJ, Irvine DG. Factors associated with detection of bromoxynil in a sample of rural residents. J Toxicol Environ Health A. 2003 Jan 24;66(2):103-32. doi: 10.1080/15287390306401. PMID: 12653018. 20: Berling I, Buckley NA, Mostafa A, Downes MA, Grice J, Medley G, Roberts MS, Isbister GK. 2-Methyl-4-chlorophenoxyacetic acid and bromoxynil herbicide death. Clin Toxicol (Phila). 2015 Jun;53(5):486-8. doi: 10.3109/15563650.2015.1030025. Epub 2015 Apr 7. PMID: 25849311.