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Isopropalin

HCID 36606
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Basic information

CAS
33820-53-0
Standard SMILES
CCCN(CCC)c1c([N+](=O)[O-])cc(C(C)C)cc1[N+](=O)[O-]
InChIKey
NEKOXWSIMFDGMA-UHFFFAOYSA-N
Molecular formula
C15H23N3O4
Average molar mass
309.36 g/mol
Monoisotopic mass
309.16885622

Overview

Isopropalin is a C-nitro compound.

Names & identifiers

Preferred name
Isopropalin
IUPAC
2,6-dinitro-4-propan-2-yl-N,N-dipropylaniline
English name
ISOPROPALIN
Molecular formula
C15H23N3O4
Molecular weight
309.36

Names & synonyms

ISOPROPALIN33820-53-0PaarlanIsopropaline4-Isopropyl-2,6-dinitro-N,N-dipropylanilineEL-179Cumidine, 2,6-dinitro-N,N-dipropyl-2,6-Dinitro-N,N-dipropylcumidineDTXSID8024157Benzenamine, 4-(1-methylethyl)-2,6-dinitro-N,N-dipropyl-52GZD1I41N4-(1-Methylethyl)-2,6-dinitro-N,N-dipropylbenzenamine
Show more names
PAARLAN(R)Isopropalin 0Isopropalin 97%ISOPROPALIN STANDARDISOPROPALIN, 1GM, NEATEthiofencarb Impurity 9
DTXCID904157RefChem:149785251-690-72,6-dinitro-4-propan-2-yl-N,N-dipropylaniline4-isopropyl-2,6-dinitro-N,N-dipropyl-anilineCaswell No. 506AIsopropaline [ISO-French]CAS-33820-53-0

Database identifiers

CAS
33820-53-0
PubChem CID
36606
DTXSID
DTXSID8024157
ChEMBL
CHEMBL1256728
ChEBI
CHEBI:82189
UNII
52GZD1I41N
EC Number
251-690-7
Nikkaji
J19.922B

Properties

Computed structural properties

XLogP
5.6
Topological polar surface area
94.9 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
5
Rotatable bonds
6
Heavy atoms
22
Formal charge
0
Complexity
348

Experimental & physicochemical properties

Pesticides · 5 items

Pesticide -> EPA IRIS

Herbicides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Herbicides, Nitroaromatic

Pesticide (Isopropalin) -> USDA PDB

Color/FormRed-orange liquid
Solubility · 2 items

In water at 25 °C, 0.1 mg/l. In acetone, hexane, benzene, chloroform, diethyl ether, acetonitrile, and methanol, all > 1 kg/l at 25 °C.

Readily soluble in organic solvents

CorrosivityNon-corrosive
DecompositionToxic fumes are emitted when heated to decomposition.
Vapor Pressure · 2 items

0.00003 [mmHg]

1.9 mPa at 30 °C

Physical DescriptionRed-orange; liquid; [HSDB]
Stability/Shelf LifeSusceptible to decomposition by UV irradiation.

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P273, P280, P303+P361+P353, P370+P378, P391, P403+P235, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationReg. (EC) No 2076/2002
Fire PotentialTechnical material is not flammable. /Technical grade/
Hazards SummaryNOEL (rat) = 15 mg/kg/day for 90 days; Effects included decreased hemoglobin levels in animals receiving higher doses; [IRIS] May be irritating to skin and eyes; [HSDB]
FIFRA Requirements · 2 items

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Isopropalin is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0005; Pesticide type: herbicide; Registration Standard Date: 08/01/81; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): Isopropalin; Data Call-in (DCI) Date(s): 08/20/90; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Chemistry & industry

Pharmacology

Metabolism/MetabolitesSelective herbicide, which affects physiological growth processes associated with seed germination.

Uses & manufacturing

Uses · 5 items

Used as selective pre-emergence herbicide to control grasses and broad-leaved weeds in transplant tobacco; [HSDB]

Cancelled--no longer registered as a pesticide for use in the US; [HSDB]

Farming (Pesticides) [Category: Industry]

The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Selective herbicide. Soil incorporated, preemergence for grasses, broadleaf weeds in transplant tobacco (flue/air cured).

Methods of ManufacturingMade by the reaction of dipropylamine with 1-chloro-4-isopropyl-2,6-dinitrobenzene.
Formulations/PreparationsEmulsifiable concentrate

Applications

UsesHerbicide.

Additional notes

DefinitionChEBI: Isopropalin is a C-nitro compound.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Collision Cross Section
172.4 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID8024157]
Other Experimental PropertiesDecomposed by UV light.

Physicochemical properties

Boiling point
449.64 °C · 449.64°C (rough estimate)
Density
1.122 · 1.1220 (rough estimate)
refractive index
1.56 · 1.5600 (estimate)
Flash point
40 °C · 40 °C
storage temp.
0 · 0-6°C
form
Liquid
pka
1.27 · 1.27±0.50(Predicted)
Water Solubility
0.1 mg/L · 0.1mg/L(25 ºC)
BRN
2762577 · 2762577
Henry's Law Constant
1.9 · 1.9×10-1 mol/(m3Pa) at 25℃, Mackay et al. (2006)
InChI
1S/C15H23N3O4/c1-5-7-16(8-6-2)15-13(17(19)20)9-12(11(3)4)10-14(15)18(21)22/h9-11H,5-8H2,1-4H3
InChIKey
NEKOXWSIMFDGMA-UHFFFAOYSA-N
SMILES
CCCN(CCC)c1c(cc(cc1[N+]([O-])=O)C(C)C)[N+]([O-])=O
FDA UNII
52 GZD1I41N · 52GZD1I41N
EPA Substance Registry System
Isopropalin (33820-53-0)
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
2 · GHS02,GHS09
Signal word
Warning
Hazard statements
226 · H226-H410
Precautionary statements
210 · P210-P233-P240-P241-P242-P273
Hazard Codes
N
Risk Statements
10 · 10-50/53
Safety Statements
60 · 60-61
RIDADR
1993 · 1993
WGK Germany
3 · 3
RTECS
9286000 · BX9286000
HazardClass
3.2 · 3.2
PackingGroup
III
HS Code
29214990 · 29214990
Storage Class
3 · 3 - Flammable liquids
Hazard Classifications
1 Aquatic · Aquatic Acute 1Aquatic Chronic 1Flam. Liq. 3
Hazardous Substances Data
33820 · 33820-53-0(Hazardous Substances Data)

Notice revokes the tolerances for the residues of the herbicide isopropalin in or on the raw agricultural commodities peppers and tomatoes, removing section 180.313 from the CFR. Related food uses were voluntarily cancelled by the registrant before 1982.

Hazard Classes and CategoriesFlam. Liq. 3 (100%)
State Drinking Water Guidelines(FL) FLORIDA 105 ug/l
Explosive Limits and PotentialDo not store near heat or flame as closed containers may explode due to pressure build-up.
Skin, Eye, and Respiratory IrritationsBenefin and related compounds /including isopropalin/ may cause skin and eye irritation. ...

Safety & protection

Storage ConditionsAvoid freezing. Do not store near heat or flame.
Disposal Methods · 2 items

Group I Containers: Combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) should be disposed of in pesticide incinerators or in specified landfill sites. /Organic or metallo-organic pesticides/

Group II Containers: Non-combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) must first be triple-rinsed. Containers that are in good condition may be returned to the manufacturer or formulator of the pesticide product, or to a drum reconditioner for reuse with the same type of pesticide product, if such reuse is legal under Department of Transportation regulations (eg 49 CFR 173.28). Containers that are not to be reused should be punctured ... and transported to a scrap metal facility for recycling, disposal or burial in a designated landfill. /Organic or metallo-organic pesticides/

Preventive Measures · 3 items

Avoid breathing spray mist or eye, skin, clothing contact. Keep away from children.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Allowable Tolerances · 1 item

Notice revokes the tolerances for the residues of the herbicide isopropalin in or on the raw agricultural commodities peppers and tomatoes, removing section 180.313 from tne CFR. Related food uses were voluntarily cancelled by the registrant before 1982.

Personal Protective Equipment (PPE)Coveralls, long sleeved shirt, impermeable gloves for handling.

Toxicology

Target OrgansHematologic
Ecotoxicity ValuesLC50 Fathead minnow >0.1 mg/l/96 hr /Conditions of bioassay not specified/
EPA IRIS Information · 3 items

Isopropalin

Hematologic

1.5 x 10 ^-2 mg/kg-day

Soil Adsorption/Mobility · 1 item

Isopropalin was incorporated in soil, and tomato and pepper seeds were planted in some of the plots. Tobacco transplants were placed in other plots. After all were harvested, wheat was sown and harvested the following year. Analyses of soil and plants involved TLC, column chromatography, GC-MS and thin-layer radioautography. In soil, in addition to bound and unidentified compounds, nine metabolites were identified in addition to unchanged isopropalin: 2,6-dinitro-N-propylcumidine, 2,6-dinitro-cumidine, 2-amino-N,N-dipropylamino-6-nitrocumidine, 2-amino-6-nitro-N-propylcumidine, 2-ethyl-5-isopropyl-7-nitro-1-propylbenzimidazole, 4'-isopropyl-2',6'-dinitro-N-propylpropionanilide, 4'-isopropyl-2',6'-dinitropropionanilide, and alpha, alpha-dimethyl-3,5-dinitro-4-dipropylaminobenzyl alcohol. Negligible amounts of isopropalin or its degradation products were found in the plants grown on treated soil.

Non-Human Toxicity ExcerptsChickens, dogs, mallard duck and rabbits receiving oral doses of 2000 mg/kg (highest tested) or bobwhite quail and Japanese quail receiving 1000 mg/kg suffered no fatality.
RAIS Toxicity Values · 4 items

0.015

IRIS Current

0.15

HEAST Current

Acceptable Daily IntakesEPA RfD= 0.015 mg/kg
Non-Human Toxicity Values · 2 items

LD50 Rabbit percutaneous >2000 mg/kg

LD50 Rat oral >5000 mg/kg

Hazard Quotient Level 0.1 or Cancer Risk Level 1E-06 · 6 items

1.20e+03

1.80e+04

4.00e+01

5.00e+01

9.20e-01

1.50e-02

Hazard Quotient Level 3 or Cancer Risk Level 1E-04 · 6 items

3.50e+03

5.30e+04

1.20e+02

5.00e+01

1.50e-02

Volatile

Regulatory information

FIFRA Requirements · 2 items

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Isopropalin is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0005; Pesticide type: herbicide; Registration Standard Date: 08/01/81; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): Isopropalin; Data Call-in (DCI) Date(s): 08/20/90; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Notice revokes the tolerances for the residues of the herbicide isopropalin in or on the raw agricultural commodities peppers and tomatoes, removing section 180.313 from the CFR. Related food uses were voluntarily cancelled by the registrant before 1982.

State Drinking Water Guidelines(FL) FLORIDA 105 ug/l

Safety data

wgk
3
rtecs
BX9286000
ridadr
1993
hs_code
29214990
risk_code
10-50/53
Signal word
Warning
Symbol(GHS)
GHS02,GHS09
hazard_code
N
safety_code
60-61
hazard_class
3.2
Storage Class
3 - Flammable liquids
packing_group
III
Hazard statements
H226-H410
Hazard Classifications
Aquatic Acute 1Aquatic Chronic 1Flam. Liq. 3
Precautionary statements
P210-P233-P240-P241-P242-P273
Hazardous Substances Data
33820-53-0(Hazardous Substances Data)