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Naled

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Identification
Molecular formula
C4H7Br2Cl2O4P
CAS number
300-76-5
IUPAC name
(1,2-dibromo-2,2-dichloro-ethyl) dimethyl phosphate
State
State

At room temperature, Naled is a solid, but it is often handled as a liquid since it is commercially supplied as a solution in organic solvents.

Melting point (Celsius)
27.00
Melting point (Kelvin)
300.15
Boiling point (Celsius)
220.00
Boiling point (Kelvin)
493.15
General information
Molecular weight
380.89g/mol
Molar mass
380.9000g/mol
Density
1.9613g/cm3
Appearence

Naled appears as a white solid at room temperature with a slight pungent odor. In commercial form, it may also appear as an amber liquid due to the solvents it is dissolved in. It is usually supplied as an emulsifiable concentrate.

Comment on solubility

Solubility of (1,2-dibromo-2,2-dichloro-ethyl) dimethyl phosphate

The solubility of (1,2-dibromo-2,2-dichloro-ethyl) dimethyl phosphate, with the chemical formula C4H7Br2Cl2O4P, can be influenced by several factors. Here are some key points to consider:

  • Polarity: The presence of electronegative atoms, such as Br, Cl, and O, contributes to the compound's polarity, affecting how well it dissolves in polar solvents like water.
  • Hydrophobic groups: The dimethyl phosphate portion of the molecule may provide some hydrophobic characteristics, potentially reducing its solubility in water.
  • Solvent selections: This compound is likely to have better solubility in organic solvents such as methanol or acetone, due to similar polarities.

In general, compounds containing multiple halogens, like Br and Cl, tend to have lower water solubility due to increased hydrophobic interactions. However, solubility can also depend on temperature and the specific solvent environment.

As with many organophosphate esters, understanding the solubility characteristics is crucial for applications in agriculture and environmental chemistry where dispersion and bioavailability play vital roles.


Interesting facts

Interesting Facts about (1,2-Dibromo-2,2-Dichloro-Ethyl) Dimethyl Phosphate

(1,2-Dibromo-2,2-dichloro-ethyl) dimethyl phosphate is a fascinating compound with a range of applications and significant properties that have drawn the attention of scientists and researchers alike. Here are some captivating details:

  • Pesticide use: This compound has garnered interest due to its role as an organophosphate pesticide. It acts effectively in controlling various pests, making it valuable in agricultural practices.
  • Environmental persistence: It is noteworthy for its stability and potential to persist in the environment, which prompts discussions about ecological impacts and the balance between agricultural benefits and environmental health.
  • Toxicological studies: Research surrounding this compound frequently involves toxicological studies, highlighting its potential effects on human health and non-target species. The study of its impact necessitates rigorous safety protocols in its application.
  • Chemical Synthesis: The compound is synthesized through sophisticated chemical methods, which often involve reactions between various halogenated agents and phosphorus-containing compounds. This process not only emphasizes the complexity of organic chemistry but also showcases the innovative techniques employed in modern laboratories.
  • Structure-activity relationship (SAR): Its unique structure, featuring both bromine and chlorine atoms, provides an intriguing case for studying the structure-activity relationships in similar compounds, facilitating the design of more effective agricultural chemicals.

In summary, the compound (1,2-dibromo-2,2-dichloro-ethyl) dimethyl phosphate stands at the intersection of agricultural science and environmental chemistry. Its dual role as both a useful pesticide and a subject of environmental scrutiny underscores its complexity and significance in contemporary chemical research.

Synonyms
naled
Dibrom
300-76-5
Bromchlophos
Dibromfos
Alvora
Ortho-Dibrom
Flibol Ex
Arthodibrom
Fosbrom
Hibrom
Bromex (insecticide)
1,2-Dibromo-2,2-dichloroethyl dimethyl phosphate
(1,2-Dibromo-2,2-dichloroethyl) dimethyl phosphate
Naledu [Polish]
Bromex 50
Naledu
ENT 24988
Ortho 4355
Phosphoric acid, 1,2-dibromo-2,2-dichloroethyl dimethyl ester
OMS 75
UNII-PAM1AI9KU1
(+/-)-Naled
PAM1AI9KU1
RE-4355
Dimethyl-1,2-dibromo-2,2-dichloroethyl phosphate
DTXSID1024209
CHEBI:38729
Ethanol, 1,2-dibromo-2,2-dichloro-, dimethyl phosphate
NALED [HSDB]
NALED [ISO]
NALED [MI]
NALED [MART.]
Dimethyl 1,2-dibromo-2,2-dichloroethyl phosphate
O,O-Dimethyl O-2,2-dichloro-1,2-dibromoethyl phosphate
DTXCID404209
BRP
Naledu (Polish)
O-(1,2-Dibromo-2,2-dicloro-etil)-O,O-dimetil-fosfato [Italian]
Fosforan O-1,2-dwubromo-2,2-dwuchloroetylo-O,O-dwumetylowy [Polish]
O-(1,2-Dibroom-2,2-dichloor-ethyl)-O,O-dimethyl-fosfaat [Dutch]
Phosphate de O,O-dimethyle et de O-(1,2-dibromo-2,2-dichlorethyle) [French]
O-(1,2-Dibromo-2,2-dicloro-etil)-O,O-dimetil-fosfato
RE 4355
O-(1,2-Dibroom-2,2-dichloor-ethyl)-O,O-dimethyl-fosfaat
Orthodibromo
Fosforan O-1,2-dwubromo-2,2-dwuchloroetylo-O,O-dwumetylowy
Nikabrom
NALED (MART.)
Phosphate de O,O-dimethyle et de O-(1,2-dibromo-2,2-dichlorethyle)
Caswell No. 586
o-(1,2-Dibromo-2,2-dichloroethyl)-o,o-dimethyl phosphate
Naled 1000 microg/mL in Acetonitrile
Naled [ANSI:BSI:ISO]
CAS-300-76-5
HSDB 1148
EINECS 206-098-3
EPA Pesticide Chemical Code 034401
BRN 2049930
Orthodibrom
Lucanal
AI3-24988
O-(1,2-Dibromo-2,2-dicloro-etil)-O,O-dimetil-fosfato (Italian)
O-(1,2-Dibroom-2,2-dichloor-ethyl)-O,O-dimethyl-fosfaat (Dutch)
Fosforan O-1,2-dwubromo-2,2-dwuchloroetylo-O,O-dwumetylowy (Polish)
Phosphate de O,O-dimethyle et de O-(1,2-dibromo-2,2-dichlorethyle) (French)
o-Dibrom 8E
Naled (ACGIH)
O,O-Dimethyl-O-(1,2-dibromo-2,2-dichloroethyl)phosphate
Spectrum_001775
SpecPlus_000358
O,O-Dimethyl-O-(1,2-dibrom-2,2-dichlor-aethyl)-phosphat [German]
O-(1,2-Dibrom-2,2-dichlor-aethyl)-O,O-dimethyl-phosphat [German]
Spectrum2_001858
Spectrum3_000809
Spectrum4_000649
Spectrum5_001928
BSPBio_002277
KBioGR_000997
KBioSS_002256
DivK1c_006454
SCHEMBL117764
SPBio_001676
CHEMBL1887067
BUYMVQAILCEWRR-UHFFFAOYSA-
KBio1_001398
KBio2_002255
KBio2_004823
KBio2_007391
KBio3_001777
O,O-Dimethyl-O-(1,2-dibrom-2,2-dichlor-aethyl)-phosphat
O-(1,2-Dibrom-2,2-dichlor-aethyl)-O,O-dimethyl-phosphat
Tox21_201641
Tox21_300845
CCG-39396
RE4355
AKOS015903004
ENT 24,988
USEPA/OPP Pesticide Code: 034401
NCGC00163711-01
NCGC00163711-02
NCGC00163711-03
NCGC00163711-04
NCGC00163711-05
NCGC00163711-06
NCGC00254748-01
NCGC00259190-01
AI3-24989
A7855
NS00009646
1,2Dibromo2,2dichloroethyl dimethyl phosphate
Dimethyl 1,2dibromo2,2dichloroethyl phosphate
O(1,2Dibromo2,2dicloroetil)O,Odimetilfosfato
C18749
Dibrom(R), PESTANAL(R), analytical standard
Naled (Dibrom) 100 microg/mL in Acetonitrile
O(1,2Dibrom2,2dichloraethyl)O,Odimethylphosphat
O(1,2Dibroom2,2dichloorethyl)O,Odimethylfosfaat
O,ODimethylO(1,2dibrom2,2dichloraethyl)phosphat
O,ODimethyl O2,2dichloro1,2dibromoethyl phosphate
O,ODimethylO(1,2dibromo2,2dichloroethyl)phosphate
Q424822
Ethanol, 1,2dibromo2,2dichloro, dimethyl phosphate
Fosforan O1,2dwubromo2,2dwuchloroetyloO,Odwumetylowy
1,2-Dibromo-2,2-dichloroethyl dimethyl phosphatic acid
O,O-dimethyl-O-2,2-dichloro-1,2-dibromoethyl phosphate
Dimethyl-1,2-dibromo-2,2-dichloroethyl phosphate (OSHA)
O-(1,2-dibrom-2,2-dichloraethyl)-O,O-dimethyl-phosphat
(RS)-1,2-DIBROMO-2,2-DICHLOROETHYL DIMETHYL PHOSPHATE
Phosphate de O,Odimethyle et de O(1,2dibromo2,2dichlorethyle)
O-(1,2-dibrom-2,2-dichloraethyl)-O,O-dimethyl-phosphat (German)
Phosphoric acid, 1,2dibromo2,2dichloroethyl dimethyl ester (8CI)
Phosphoric acid, 1,2dibromo2,2dichloroethyl dimethyl ester (8CI)(9CI)
InChI=1/C4H7Br2Cl2O4P/c1-10-13(9,11-2)12-3(5)4(6,7)8/h3H,1-2H3
206-098-3