Basic information
- CAS
50594-66-6- Standard SMILES
O=C(O)c1cc(Oc2ccc(C(F)(F)F)cc2Cl)ccc1[N+](=O)[O-]- InChIKey
NUFNQYOELLVIPL-UHFFFAOYSA-N- Molecular formula
- C14H7ClF3NO5
- Average molar mass
- 361.65 g/mol
- Monoisotopic mass
- 360.99648466
Overview
Acifluorfen is a member of the class of benzoic acids that is 2-nitrobenzoic acid in which the hydrogen at position 5 is replaced by a 2-chloro-4-(trifluoromethyl)phenoxy group. It is a herbicide used for the post-emergence control of a variety of annual broadleaf weeds. It has a role as a herbicide, an agrochemical and an EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor. It is a member of benzoic acids, a monocarboxylic acid, an aromatic ether, a C-nitro compound, an organochlorine compound and an organofluorine compound.
Names & identifiers
- Preferred name
- Acifluorfen
- IUPAC
- 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid
- English name
- Acifluorfen
- Molecular formula
- C14H7ClF3NO5
- Molecular weight
- 361.66
Names & synonyms
Acifluorfen50594-66-6AcifluorfeneTackle5-(2-Chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoic acid5-[2-Chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid5-(2-Chloro-4-trifluoromethylphenoxy)-2-nitrobenzoic acidDTXSID00200222-Nitro-5-(2-chloro-4-(trifluoromethyl)phenoxy)benzoic acidOI60IB203ABenzoic acid, 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitro-DTXCID6022
Show more names
ppg-847RH-6201MC 10109MC 10978BLAZER(R)Aciuorfen
CHEBI:73172Benzoic acid, 5-(2-chloro-4-(trifluoromethyl)phenoxy)-2-nitro-RefChem:109258256-634-5AcifluorofenC14H7ClF3NO5BlazerAcifluorfen [BSI:ISO]
Database identifiers
- CAS
50594-66-6- PubChem CID
- 44073
- DTXSID
DTXSID0020022- ChEMBL
CHEMBL222440- ChEBI
CHEBI:73172- UNII
- OI60IB203A
- EC Number
- 256-634-5
- Nikkaji
- J10.218K
Properties
Computed structural properties
- XLogP
- 3
- Topological polar surface area
- 92.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 3
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 484
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Pesticides
Agrochemicals -> Pesticide active substances
Active substance -> EU Pesticides database: Not approved
Pesticide (Acifluorfen) -> USDA PDB
Pesticide
LogP
3.70
4.26
Solubility
0.12 mg/mL at 25 °C
>54.2 [ug/mL] (The mean of the results at pH 7.4)
Melting Point240 °C
Physical DescriptionSolid
Collision Cross Section244.1 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID0020022]
Physicochemical properties
- Melting point
- 151.5 · 151.5-157°
- Boiling point
- 422.4 · 422.4±45.0 °C(Predicted)
- Density
- 1.5676 · 1.5676 (estimate)
- storage temp.
- 0 · 0-6°C
- solubility
- 25 mg/mL · DMSO: 25 mg/mL (69.13 mM)
- pka
- 1.93 · 1.93±0.25(Predicted)
- form
- Solid
- color
- White to off-white
- Merck
- 13 · 13,111
- BRN
- 2953865 · 2953865
- Major Application
- agricultureenvironmental
- InChI
- InChI=1S/C14H7ClF3NO5/c15-10-5-7(14(16,17)18)1-4-12(10)24-8-2-3-11(19(22)23)9(6-8)13(20)21/h1-6H,(H,20,21)
- InChIKey
- NUFNQYOELLVIPL-UHFFFAOYSA-N
- SMILES
- C(O)(=O)C1=CC(OC2=CC=C(C(F)(F)F)C=C2Cl)=CC=C1[N+]([O-])=O
- CAS DataBase Reference
- 50594 · 50594-66-6(CAS DataBase Reference)
- FDA UNII
- 60 IB203A · OI60IB203A
- NIST Chemistry Reference
- 5 · Benzoic acid, 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitro-(50594-66-6)
- Pesticides Freedom of Information Act (FOIA)
- Acifluorfen
- EPA Substance Registry System
- Acifluorfen (50594-66-6)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 5 · GHS05,GHS07,GHS09
- Signal word
- Danger
- Hazard statements
- 302 · H302-H315-H318-H410
- Precautionary statements
- 264 · P264-P273-P280-P301+P312-P302+P352-P305+P351+P338
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xn;N,N,Xn
- Risk Statements
- 22 · 22-38-41-50/53
- Safety Statements
- 24 · 24-39-60-61
- RIDADR
- 3077 · UN 3077
- WGK Germany
- 3 · 3
- RTECS
- 5643070 · DG5643070
- TSCA
- TSCA listed
- HazardClass
- 9 · 9
- HS Code
- 29189900 · 29189900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 OralAquatic · Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Eye Dam. 1Skin Irrit. 2
- Limited Quantities
- 5 kg · 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
GHS classification
GHS Classification
Danger
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P264, P264+P265, P270, P273, P280, P301+P317, P302+P352, P305+P354+P338, P317, P321, P330, P332+P317, P362+P364, P391, and P501 (click each P-code to see the statement)
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P264+P265, P270, P273, P280, P301+P317, P302+P352, P305+P354+P338, P317, P321, P330, P332+P317, P362+P364, P391, and P501 (click each P-code to see the statement)
Hazard information
Regulatory Information2002/2076
Other Safety InformationIMAP assessments - Benzoic acid, 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitro-: Environment tier I assessment
Hazard Classes and Categories
Acute Tox. 4 (100%)
Acute toxicity - category 4
Acute Tox. 4 *
Toxicology
Carcinogen ClassificationNot listed by IARC.
USGS Health-Based Screening Levels for Evaluating Water-Quality
Acifluorfen
49315
Pesticide
80
Value is for acifluorfen, sodium CASRN 6247659
Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- DG5643070
- ridadr
- UN 3077
- hs_code
- 29189900
- risk_code
- 22-38-41-50/53
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07,GHS09
- hazard_code
- Xn;N,N,Xn
- safety_code
- 24-39-60-61
- hazard_class
- 9
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H318-H410
- Limited Quantities
- 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- Hazard Classifications
- Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Eye Dam. 1Skin Irrit. 2
- Precautionary statements
- P264-P273-P280-P301+P312-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE.
Cellular LocationsMembrane
Uses & manufacturing
UsesThis is a man-made compound that is used as a pesticide.
General Manufacturing InformationBenzoic acid, 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitro-: ACTIVE
Applications
DescriptionAcifluorfen is a post-emergence herbicide, usually used as the sodium salt. It is highly soluble in water, with a low vapour pressure and may be moderately persistent in soils and water depending upon conditions. Based on its chemical properties it has a high potential for leaching to groundwater. It has a low to moderate toxicity to most biodiversity. It is not highly toxic to human but is known to be a skin and eye irritant.
UsesAcifluorfen is an herbicide against broadleaf weeds. An environmental toxin relating to in vivo toxicity of nitroaromatics.Environmental toxin on US EPA Toxic Release Inventory list (TRI) list.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
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天津阿尔塔科技有限公司022-6537-8550 15522853686 · [email protected]
TargetMol中国（陶术生物）021-021-33632979 15002134094 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
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Henan Alfa Chemical Co., Ltd+8618339805032 · [email protected]
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Additional notes
DefinitionChEBI: A member of the class of benzoic acids that is 2-nitrobenzoic acid in which the hydrogen at position 5 is replaced by a 2-chloro-4-(trifluoromethyl)phenoxy group. It is a herbicide used for the post-emergence control of a variety of annual broadleaf weeds.
Related reactions
89 records
Compound notes
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