Compound: BINAPACRYL
SMILES: O=[N+]([O-])c1c(OC(=O)C=C(C)C)c(cc(c1)[N+](=O)[O-])C(CC)C
InChIKey: ZRDUSMYWDRPZRM-UHFFFAOYSA-N
Synonyms: BINAPACRYL, 485-31-4, Morocide, Acricid, Ambox, Dapacryl, Dinapacryl, Morrocid, Dinoseb methacrylate, Niagara 9044, HOE 2784 OA, Dinoseb, 3,3-dimethylacryl ester, FMC 9044, HOE 2784, NIA 9044, 2-(1-Methylpropyl)-4,6-dinitrophenyl 3-methyl-2-butenoate, ENT 25,793, 2-sec-Butyl-4,6-dinitrophenyl senecioate, 3-Methylcrotonic acid 2-sec-butyl-4,6-dinitrophenyl ester, 2,4-Dinitro-6-sec-butylphenyl 2-methylcrotonate, 2-sec-Butyl-4,6-dinitrophenyl 3-methylcrotonate, 3,3-Dimethylacrylic acid 2-sec-butyl-4,6-dinitrophenyl ester, 3-Methyl-2-butenoic acid 2-sec-butyl-4,6-dinitrophenyl ester, DTXSID9040269, 2-sec-Butyl-4,6-dinitrophenyl-3,3-dimethylacrylate, 2-sec-Butyl-4,6-dinitrophenyl 3-methyl-2-butenoate, 4,6-Dinitrophenyl-2-sec-butyl-3-methyl-2-butenonate, Phenol, 2-sec-butyl-4,6-dinitro-, 3-methylcrotonate, 4X685BB13A, Crotonic acid, 3-methyl-, 2-sec-butyl-4,6-dinitrophenyl ester, 3-Methyl-2-butenoic acid 2-(1-methylpropyl)-4,6-dinitrophenyl ester, Senecioic acid 2-sec-butyl-4,6-dinitrophenyl ester, 2-sec-Butyl-4,6-dinitrophenyl beta,beta-dimethylacrylate, 4,6-Dinitro-2-sec-butylphenyl beta,beta-dimethylacrylate, 2-(1-Methylpropyl)-4,6-dinitrophenyl 3,3-dimethylacrylate, DTXCID7020269, 2-(1-Methylpropyl)-4,6-dinitrophenyl beta,beta-dimethacrylate, (6-(1-Methyl-propyl)-2,4-dinitro-fenyl)-3,3-dimethyl-acrylaat, (6-(1-Methyl-propyl)-2,4-dinitro-phenyl)-3,3-dimethyl-acrylat, (6-(1-Metil-propil)-2,4-dinitro-fenil)-3,3-dimetil-acrilato, 3,3 Dimethyl-acrylate de 2,4-dinitro-6-(1-methylpropyle) phenyle, 3,3 dimethyl-acrylate de 2,4-dinitro-6-(1-methylpropyle)phenyl, (rs)-2-sec-butyl-4,6-dinitrophenyl 3-methylcrotonate, binapacrile, binapakril, RefChem:568353, CHEBI:82153, 207-612-9, Endosan, (2-butan-2-yl-4,6-dinitrophenyl) 3-methylbut-2-enoate, 2-Butenoic acid, 3-methyl-, 2-(1-methylpropyl)-4,6-dinitrophenyl ester, 2-(butan-2-yl)-4,6-dinitrophenyl 3-methylbut-2-enoate, 2-sek.Butyl-4,6-dinitrofenylester kyseliny 3-methylkrotonove, Caswell No. 086, Binapacryl [ANSI:BSI:ISO], HSDB 1518, EINECS 207-612-9, EPA Pesticide Chemical Code 012201, BRN 2013712, UNII-4X685BB13A, AI3-25793, Senecioic acid 2-sec butyl-4,6-dinitrophenyl ester, BINAPACRYL [MI], BINAPACRYL [ISO], BINAPACRYL [HSDB], (6-(1-Methyl-propyl)-2,4-dinitro-fenyl)-3,3-dimethyl-acrylaat [Dutch], (6-(1-Metil-propil)-2,4-dinitro-fenil)-3,3-dimetil-acrilato [Italian], 2-sek.Butyl-4,6-dinitrofenylester kyseliny 3-methylkrotonove [Czech], (6-(1-Methyl-propyl)-2,4-dinitro-phenyl)-3,3-dimethyl-acrylat [German], 3,3 Dimethyl-acrylate de 2,4-dinitro-6-(1-methylpropyle) phenyle [French], 3,3 dimethyl-acrylate de 2,4-dinitro-6-(1-methylpropyle)phenyl [French], 3,3 dimethyl-acrylate de 2,4-dinitro-6-(1-methylpropyle)phenyle [French], SCHEMBL54301, CHEMBL3182974, SCHEMBL29609584, CHEBI:83366, ZRDUSMYWDRPZRM-UHFFFAOYSA-, 3,3 dimethyl-acrylate de 2,4-dinitro-6-(1-methylpropyle)phenyle, AAA48531, MSK25029, Tox21_301554, AKOS015888368, MSK25029-1000A, 2-Butenoic acid, 3-methyl-, 2-(1-methylpropyl)-4,6-dinitrophenyl ester (9CI), Binapacryl 10 microg/mL in Cyclohexane, NCGC00255512-01, CAS-485-31-4, DB-051558, NS00021171, Binapacryl, PESTANAL(R), analytical standard, C19022, Binapacryl Solution in Acetonitrile, 1000ug/mL, 2-sec-butyl-4,6-dinitrophenyl 3-methylbut-2-enoate, Q3468507, 4,6-Dinitrophenyl-2-(1-methylpropyl) 3-methylbut-2-enoate, 2-sec-Butyl-4,6-dinitrophenyl 3-methylcrotonate (binapacryl), 4,6-Dinitro-2-sec-butylphenyl .beta.,.beta.-dimethylacrylate, 2-(1-Methylpropyl)-4,6-dinitrophenyl .beta.,.beta.-dimethacrylate, InChI=1/C15H18N2O6/c1-5-10(4)12-7-11(16(19)20)8-13(17(21)22)15(12)23-14(18)6-9(2)3/h6-8,10H,5H2,1-4H3
Theoretical properties:
molecular_formula: C15H18N2O6
molecular_weight: 322.31 g/mol
exact_mass: 322.11648630 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 5
heavy_atom_count: 23
topological_polar_surface_area: 118 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: COLORLESS CRYSTALLINE POWDER
color: COLORLESS CRYSTALLINE POWDER
odor: Faint aromatic odor
melting_point: 66-67 °C
density: 1.2307 @ 20 °C/4 °C
solubility: Insoluble in water but soluble in organic solvents as follows: acetone 78%; ethanol 11%; isophorone 57%; kerosene 10%; xylene 70%
vapor_pressure: 0.00000032 [mmHg]
Descriptions:
pubchem: 2-sec-butyl-4,6-dinitrophenyl 3-methylbut-2-enoate is an enoate ester obtained by formal condensation of the carboxy group of 3,3-dimethylacrylic acid with the phenolic hydroxy group of dinoseb. It is a C-nitro compound and an enoate ester. It is functionally related to a dinoseb.
chebi: An enoate ester obtained by formal condensation of the carboxy group of 3,3-dimethylacrylic acid with the phenolic hydroxy group of dinoseb.
chembl: BINAPACRYL is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Binapacryl was used as a miticide and fungicide. Chemically, it is an ester derivative of dinoseb.  Although binapacryl has low toxicity itself, it is readily metabolized to form dinoseb, which is highly toxic.
International trade in binapacryl is regulated by the Rotterdam Convention; it has been withdrawn as a pesticide, since products were highly toxic to mammals, fish and aquatic invertebrates.