AMINOCARB Chemical Properties

Melting point:

93-94℃

Boiling point:

347.46°C (rough estimate)

Density 

1.095

refractive index 

1.5000 (estimate)

Flash point:

100 °C

storage temp. 

0-6°C

pka

12.25±0.46(Predicted)

Water Solubility 

915mg/L(20 ºC)

Merck 

13,432

EPA Substance Registry System

Aminocarb (2032-59-9)

Safety Information

Hazard Codes 

T,N

Risk Statements 

24/25-50/53

Safety Statements 

28-36/37-45-60-61

RIDADR 

2757

RTECS 

FC0175000

HazardClass 

6.1(a)

PackingGroup 

II

HS Code 

29224999

Hazardous Substances Data

2032-59-9(Hazardous Substances Data)

Toxicity

LD50 orally in male, female rats: 40, 38 mg/kg (Gaines)

AMINOCARB Usage And Synthesis

Chemical Properties

Tan; crystalline; slightly water-soluble; melting point 93–94C.

Uses

Nonsystemic, broad-spectrum insecticide used to control the spruce budworm in forests; molluscicide

Uses

Aminocarb is a carbamate insecticide.

Uses

Insecticide.

Definition

ChEBI: A carbamate ester that is phenyl methylcarbamate substituted by a dimethylamino group at position 4 and a methyl group at position 3.

Hazard

Highly poisonous.

Environmental Fate

Plant/Surface Water. Several transformation products reported by Day (1991) include 4-amino-m-tolyl-N-methylcarbamate (AA), 4-amino-3-methylphenol (AC), 4-formamidom-tolyl-N-methylcarbamate (FA), N-(4-hydroxy-2-methylphenyl)-N-methylformamide (FC), 4-methylformamido-m-tolyl-N-methylcarbamate (MFA), 4-methylamino-m-tolyl-Nmethylcarbamate (MAA), 3-methyl-4-(methylamino)phenyl-N-methylcarbamate (MAC), phenol, methylamine and carbon dioxide. MAA was not detected in natural water but was detected in fish tissues following exposure to aminocarb-treated water in the laboratory. The metabolites FA, AC and MAC were detected in Canadian forests treated with aminocarb but the metabolites AA, MAA and FC were not detected (Day, 1991)
On and/or in bean plants, aminocarb degrades with the carbamate moiety remaining intact. Methylcarbamate derivatives identified include the 4-methylamino, 4-amino, 4- methylformamido and 4-formamido analogs (Abdel-Wahab et al., 1966)
Photolytic. When aminocarb in ethanol was irradiated by UV light, extensive degradation was observed. No degradation products were identified; however, two unidentified cholinesterase inhibitors were reported (Crosby et al., 1965).
Chemical/Physical. Aminocarb is hydrolyzed in purified water to 4-(dimethylamino)- 3-methylphenol which is then converted to 2-methyl-1,4-benzoquinone. This compound was then oxidized to form the following compounds: 6-(dimethylamino)-2-methyl-1,4- benzoquinone, 6-(methylamino)-2-methyl-1,4-benzoquinone, 5-(dimethylamino)-2- methyl-1,4-benzoquinone and 5-(methylamino)-2-methyl-1,4-benzoquinone (Leger and Mallet, 1988). When aminocarb was irradiated by a high pressure xenon-mercury lamp (λ = 253.7 nm) in aerated and degassed ethyl alcohol and cyclohexene solutions, 4- dimethylamino-3-methyl phenol formed as the major product. A duplicate run using an excitation wavelength of >300 nm yielded that same phenol as the major product. Sinceaminocarb absorbs radiation in the solar region (at λ >300 nm), this compound would be expected to undergo photochemical degradation in the environment (Addison et al., 1974)
Emits toxic fumes of nitrogen oxides when heated to decomposition (Sax and Lewis, 1987)

Metabolic pathway

Aminocarb in purified water is hydrolyzed to 4- (dimethylamino)-3-methylphenol which is in turn converted to 2-methyl-1,4-benzoquinone either by direct means or via 2-methyl-1,4-dihydroquinone. The benzoquinone reacts readily with methylamine and diethylamine present in solution to give four red chemicals. In addition, mono- and diepoxides of 2-methyl-1,4-benzoquinone are formed.

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