| Identification | More | [Name]
Bromopropylate | [CAS]
18181-80-1 | [Synonyms]
4-Bromo-alpha-(4-bromophenyl)-alpha-hydroxybenzeneacetic acid 1-methylethyl ester
ACAROL
ACAROL (TM)
BROMOPROPYLATE
BROMPROPYLAT
BROMPROPYLATE
ISOPROPYL-4,4'-DIBROMOBENZILATE
NEORON(R)
PHENISOBROMOLATE
1-methylethyl4-bromo-alpha-(4-bromophenyl)-alpha-hydroxybenzeneacetate
1-methylethyl4-bromo-alpha-(4-bromophenyl)-alpha-hydroxybenzeneacetate[qr]
4,4’-dibromobenzilicacidisopropylester
4,4’-dibromobenzilicacidisopropylester[qr]
4,4’-dibromo-benzilicaciisopropylester
4-bromo-alpha-(4-bromophenyl)-alpha-hydroxy-benzeneaceticaci1-methyleth
4-bromo-alpha-(4-bromophenyl)-alpha-hydroxy-benzeneaceticaci1-methylethyl
4-bromo-alpha-(4-bromophenyl)-alpha-hydroxybenzeneaceticacid1-methylethyl
4-bromo-alpha-(4-bromophenyl)-alpha-hydroxybenzeneaceticacid1-methylethyles
ascarol2e
ascarol2e[qr] | [EINECS(EC#)]
242-070-7 | [Molecular Formula]
C17H16Br2O3 | [MDL Number]
MFCD00078632 | [Molecular Weight]
428.12 | [MOL File]
18181-80-1.mol |
| Chemical Properties | Back Directory | [Melting point ]
77° | [Boiling point ]
504°C (rough estimate) | [density ]
1.5582 (rough estimate) | [refractive index ]
1.6010 (estimate) | [Fp ]
>100 °C | [storage temp. ]
0-6°C | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
neat | [pka]
11.18±0.29(Predicted) | [color ]
White to Off-White | [Water Solubility ]
<0.5mg/L(20 ºC) | [BRN ]
2152560 | [Henry's Law Constant]
2.1×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) | [Major Application]
agriculture
environmental | [InChI]
1S/C17H16Br2O3/c1-11(2)22-16(20)17(21,12-3-7-14(18)8-4-12)13-5-9-15(19)10-6-13/h3-11,21H,1-2H3 | [InChIKey]
FOANIXZHAMJWOI-UHFFFAOYSA-N | [SMILES]
CC(C)OC(=O)C(O)(c1ccc(Br)cc1)c2ccc(Br)cc2 | [CAS DataBase Reference]
18181-80-1(CAS DataBase Reference) | [NIST Chemistry Reference]
Bromopropylate(18181-80-1) | [EPA Substance Registry System]
18181-80-1(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R38:Irritating to the skin. | [WGK Germany ]
2 | [RTECS ]
DD2100000 | [HS Code ]
29181990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Aquatic Acute 1
Aquatic Chronic 1 | [Hazardous Substances Data]
18181-80-1(Hazardous Substances Data) | [Toxicity]
LD50 orally in rats: 5000 mg/kg (Kenaga, Allison) |
| Hazard Information | Back Directory | [Description]
Bromopropylate is an acaricide that is mainly used to control mites. It has a low aqueous solubility and is not considered to be highly volatile. It may be persistent in soil and water systems depending on local conditions. Bromopropylate is not expected to leach into groundwater. It tends to have a low to moderate toxicity to fauna and flora but data is scant. It also has a low mammalian toxicity if ingested but little other health related information is available. | [Chemical Properties]
White crystals. Melting point 77°C, relative density 1.59, vapor pressure 1.066×10-5 Pa (20°C), 0.7 Pa (100°C). Soluble in various organic solvents, including acetone, benzene, isopropanol, methanol, and xylene; solubility in water at 20°C <0.5 mg/kg. Stable at room temperature and in neutral media, but unstable under acidic or alkaline conditions. | [Uses]
Acaricide. | [Production Methods]
The commercial production of bromopropylate involves synthesising the compound isopropyl 2,2-bis(4-bromophenyl)-2-hydroxyacetate through a multi-step organic process. It begins with the bromination of phenyl compounds to produce 4-bromobenzene derivatives, which are then coupled to form a bis(4-bromophenyl)acetate intermediate. This is followed by esterification with isopropyl alcohol under acidic conditions to yield the final active ingredient. The process requires precise control of temperature and reaction time to ensure high purity and yield. | [Mechanism of action]
Non systemic with contact action and residual activity. It acts mainly as a neurotoxin, disrupting the normal signalling processes of the mite nervous system leading to death. It is an antagonist of octopamine receptors and may also interfere with cellular energy metabolism, specifically by acting as a weak inhibitor of mitochondrial respiration, which is essential for ATP production. | [Pesticide Type]
Insecticide; Acaricide |
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