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NITROFEN, also known as 2,4-dichlorophenyl 4-nitrophenyl ether, is a chemical compound that exists as colorless crystals or a black solid. It is primarily recognized for its use as a herbicide, functioning as a preor post-emergence treatment to control the growth of unwanted plants.

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  • 1836-75-5 Structure
  • Basic information

    1. Product Name: NITROFEN
    2. Synonyms: 2,4-dechlorophenylp-nitrophenylether;2,4-dichloro-(4-nitrophenoxy)-Benzene;2,4-dichloro-1-(4-nitrophenoxy)-benzen;2,4-dichloro-4’-nitrophenylether;2,4-Dichlorophenyl 4-nitrophenyl ether;2,4-Dichlorophenyl p-nitrophenyl ether;2,4-Dichlorophenyl-4’-nitrophenylether;2,4-dichlorophenyl4-nitrophenylether
    3. CAS NO:1836-75-5
    4. Molecular Formula: C12H7Cl2NO3
    5. Molecular Weight: 284.09
    6. EINECS: 217-406-0
    7. Product Categories: HERBICIDE
    8. Mol File: 1836-75-5.mol
  • Chemical Properties

    1. Melting Point: 69-70°C
    2. Boiling Point: 368 ºC
    3. Flash Point: 205℃
    4. Appearance: /Solid
    5. Density: 1.3
    6. Vapor Pressure: 4.55E-05mmHg at 25°C
    7. Refractive Index: 1.6140 (estimate)
    8. Storage Temp.: 0-6°C
    9. Solubility: soluble in Methanol
    10. Water Solubility: 1mg/L(22 oC)
    11. Stability: Stable. Incompatible with strong oxidizing agents.
    12. Merck: 14,6598
    13. BRN: 1887356
    14. CAS DataBase Reference: NITROFEN(CAS DataBase Reference)
    15. NIST Chemistry Reference: NITROFEN(1836-75-5)
    16. EPA Substance Registry System: NITROFEN(1836-75-5)
  • Safety Data

    1. Hazard Codes: T,N
    2. Statements: 45-61-50/53-22
    3. Safety Statements: 45-53-61-60-50/53-22
    4. RIDADR: 3077
    5. WGK Germany: 3
    6. RTECS: KN8400000
    7. TSCA: Yes
    8. HazardClass: 9
    9. PackingGroup: III
    10. Hazardous Substances Data: 1836-75-5(Hazardous Substances Data)

1836-75-5 Usage

Uses

Used in Agricultural Industry:
NITROFEN is used as a herbicide for controlling the growth of unwanted plants in agricultural settings. Its application helps to improve crop yield by reducing competition from weeds and other unwanted vegetation.
Formerly, NITROFEN was also utilized in various other industries due to its chemical properties, such as being a crystalline solid. However, its primary and most well-known application remains in the agricultural sector for herbicidal purposes.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

NITROFEN is a nitrated and halogenated ether derivative.

Health Hazard

Nitrofen is moderately toxic by ingestionand inhalation of dusts. The lethal doses in cats from oral administration and inhalationof dusts are 300 mg/kg and 620 mg/m3/4h,respectively (NIOSH 1986). Bovine calvestreatedorally by 1.5 mL 25% nitrofen/kg produced toxic effects after 36–48 hours. Thesymptoms were increase in body temperature, depression, and progressive decrease inrespiration rate and pulse rate,similar to tribulin (Gupta and Singh 1985). An increase inthe activities of serum glutamic-oxaloacetictransaminase and glutamipyruvictransaminase was noted(Gupta and Singh 1984). Nitrofen has beenfound to cause cancer in animals. There issufficient evidence of its carcinogenicity inanimals (IARC). Oral administration in micecaused liver and lung cancers.

Fire Hazard

Flash point data for NITROFEN are not available; however, NITROFEN is probably combustible.

Safety Profile

Confirmed carcinogen with experimental carcinogenic data. Poison by ingestion. Moderately toxic by inhalation and possibly other routes. Experimental teratogenic and reproductive effects. A skin and severe eye irritant. Mutation data reported. A broad-spectrum herbicide. See also NITRO COMPOUNDS of AROMATIC HYDROCARBONS and ETHERS. When heated to decomposition it emits very toxic fumes of Cl and NOx.

Potential Exposure

Nitrofen is a contact herbicide used for pre-and post-emergency control of annual grasses and broadleaf weeds on a variety of food and ornamental crops. Occupational exposure to nitrofen, primarily through inhalation and dermal contact may occur among workers at production facilities. Field handlers of the herbicide are subject to inhalation exposure during application procedures.

Carcinogenicity

Nitrofen is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

Shipping

UN3345 Phenoxyacetic acid derivative pesticide, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard Class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.

Waste Disposal

Small quantities may be landfilled but large quantities should be incinerated. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.

Check Digit Verification of cas no

The CAS Registry Mumber 1836-75-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,8,3 and 6 respectively; the second part has 2 digits, 7 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 1836-75:
(6*1)+(5*8)+(4*3)+(3*6)+(2*7)+(1*5)=95
95 % 10 = 5
So 1836-75-5 is a valid CAS Registry Number.
InChI:InChI=1/C12H7Cl2NO3/c13-8-1-6-12(11(14)7-8)18-10-4-2-9(3-5-10)15(16)17/h1-7H

1836-75-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
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  • Detail
  • Alfa Aesar

  • (A19977)  2,4-Dichloro-1-(4-nitrophenoxy)benzene, 98%   

  • 1836-75-5

  • 5g

  • 452.0CNY

  • Detail
  • Alfa Aesar

  • (A19977)  2,4-Dichloro-1-(4-nitrophenoxy)benzene, 98%   

  • 1836-75-5

  • 25g

  • 1793.0CNY

  • Detail

1836-75-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name nitrofen

1.2 Other means of identification

Product number -
Other names niclofen

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Herbicide
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1836-75-5 SDS

1836-75-5Relevant articles and documents

Microwave assisted aromatic nucleophilic substitution reaction under solventless condition

Rebeiro, Geeta L.,Khadilkar, Bhushan M.

, p. 1405 - 1410 (2003)

We report here microwave assisted aromatic nucleophilic substitution reaction of 1-chloro-4-nitrobenzene with different phenoxides.

AGRICULTURAL CHEMICALS

-

Page/Page column 56; 95, (2019/08/08)

The present invention relates to picolinic acid derivatives that are useful in treating fungal diseases ofplants.

From Anilines to Aryl Ethers: A Facile, Efficient, and Versatile Synthetic Method Employing Mild Conditions

Wang, Dong-Yu,Yang, Ze-Kun,Wang, Chao,Zhang, Ao,Uchiyama, Masanobu

supporting information, p. 3641 - 3645 (2018/03/13)

We have developed a simple and direct method for the synthesis of aryl ethers by reacting alcohols/phenols (ROH) with aryl ammonium salts (ArNMe3+), which are readily prepared from anilines (ArNR′2, R′=H or Me). This reaction proceeds smoothly and rapidly (within a few hours) at room temperature in the presence of a commercially available base, such as KOtBu or KHMDS, and has a broad substrate scope with respect to both ROH and ArNR′2. It is scalable and compatible with a wide range of functional groups.

Synthesis, SAR and molecular docking study of novel non-β-lactam inhibitors of TEM type β-lactamase

Antipin, Roman L.,Beshnova, Daria A.,Petrov, Rostislav A.,Shiryaeva, Anna S.,Andreeva, Irina P.,Grigorenko, Vitaly G.,Rubtsova, Maya Yu.,Majouga, Alexander G.,Lamzin, Victor S.,Egorov, Alexey M.

supporting information, p. 1588 - 1592 (2017/03/17)

The novel classes of acylated phenoxyanilide and thiourea compounds were investigated for their ability to inhibit TEM type β-lactamase enzyme. Two compounds 4g and 5c reveal the inhibition potency in micromolar range and show their action by non-covalent binding in the vicinity of the TEM-171 active site. The structure activity relationship around carbon chain length and different substituents in ortho- and para-positions of acylated phenoxyanilide as well as molecular modelling study has been performed.

Structure-based design of N-substituted 1-hydroxy-4-sulfamoyl-2-naphthoates as selective inhibitors of the Mcl-1 oncoprotein

Lanning, Maryanna E.,Yu, Wenbo,Yap, Jeremy L.,Chauhan, Jay,Chen, Lijia,Whiting, Ellis,Pidugu, Lakshmi S.,Atkinson, Tyler,Bailey, Hala,Li, Willy,Roth, Braden M.,Hynicka, Lauren,Chesko, Kirsty,Toth, Eric A.,Shapiro, Paul,MacKerell, Alexander D.,Wilder, Paul T.,Fletcher, Steven

, p. 273 - 292 (2016/03/22)

Structure-based drug design was utilized to develop novel, 1-hydroxy-2-naphthoate-based small-molecule inhibitors of Mcl-1. Ligand design was driven by exploiting a salt bridge with R263 and interactions with the p2 pocket of the protein. Significantly, target molecules were accessed in just two synthetic steps, suggesting further optimization will require minimal synthetic effort. Molecular modeling using the Site-Identification by Ligand Competitive Saturation (SILCS) approach was used to qualitatively direct ligand design as well as develop quantitative models for inhibitor binding affinity to Mcl-1 and the Bcl-2 relative Bcl-xL as well as for the specificity of binding to the two proteins. Results indicated hydrophobic interactions in the p2 pocket dominated affinity of the most favourable binding ligand (3bl: Ki = 31 nM). Compounds were up to 19-fold selective for Mcl-1 over Bcl-xL. Selectivity of the inhibitors was driven by interactions with the deeper p2 pocket in Mcl-1 versus Bcl-xL. The SILCS-based SAR of the present compounds represents the foundation for the development of Mcl-1 specific inhibitors with the potential to treat a wide range of solid tumours and hematological cancers, including acute myeloid leukemia.

CsF/clinoptilolite: An efficient solid base in SNAr and copper-catalyzed Ullmann reactions

Keipour, Hoda,Hosseini, Abolfazl,Afsari, Amir,Oladee, Razieh,Khalilzadeh, Mohammad A.,Ollevier, Thierry

, p. 95 - 104 (2016/01/16)

CsF/clinoptilolite was found to be an efficient solid base catalyst for both SNAr and Ullmann ether reactions. A general and efficient one-step procedure was developed for the synthesis of biaryl ethers via direct coupling of electron-deficient aryl halides to phenols using CsF/clinoptilolite. The protocol was also applied to electron-rich aryl halides by addition of a catalytic amount of copper oxide nanoparticles. Both SNAr and Ullmann reactions were rapid and provided good to excellent yields.

Discovery of 1,2,4-triazole-1,3-disulfonamides as dual inhibitors of mitochondrial complex II and complex III

Cheng, Hua,Shen, Yan-Qing,Pan, Xia-Yan,Hou, Yi-Ping,Wu, Qiong-You,Yang, Guang-Fu

, p. 7281 - 7292 (2015/09/02)

Respiratory chain succinate-ubiquinone oxidoreductase (SQR or complex II) and ubihydroquinone-cytochrome (cyt) c oxidoreductase (cyt bc1 or complex III) have been demonstrated as the promising targets of numerous antibiotics and fungicides. As a continuation of our research work on the development of new fungicides, a series of 1,2,4-triazole-1,3-disulfonamide derivatives with dual functions targeting both SQR and cyt bc1 were designed and synthesized by coupling diverse diphenyl ether moieties with triazolesulfonamide units. These newly synthesized compounds were characterized by elemental analyses, 1H NMR and ESI-MS spectrometry. The in vitro assay indicated that most of the synthesized compounds displayed good inhibition against porcine succinate-cytochrome reductase (SCR) with IC50 values ranging from 3.2 to 81.8 μM, revealing much higher activity than that of the commercial control amisulbrom whose IC50 value is 93.0 μM. Further evaluation against the respective SQR and cyt bc1 indicated that most compounds exhibited SQR-inhibiting activity as well as cyt bc1-inhibiting activity, but the inhibition potency against SQR is much higher than that against cyt bc1, showing that the SCR inhibition might be contributed greatly by the SQR inhibition. The further antibacterial evaluation against Xanthomonas oryzae pv. oryzae revealed that four compounds showed excellent potency at the concentration of 20 μg mL-1. In particular, compounds 6h and 6j exhibited much better antibacterial activity than the commercial control bismerthiazol in terms of their EC50. Impressively, 6j has an EC90 of 33.62 μg mL-1, more than 10-fold higher than that of bismerthiazol.

MOLECULARLY IMPRINTED SMART POLYMERS (MISPs)

-

, (2011/07/29)

Molecularly imprinted smart polymers (MISPs) are provided herein, as well as novel monomers for preparing MISPs, and processes for preparing MISPs. The MISPs can be used applications such as, for example, detecting/absorbing or isolating biological and non-biological agents. The MISPs described herein comprise responsive monomeric units which undergo a physico-chemical change (e.g., a bond formation or cleavage) in response to an external change, such that the MISP selectively binds to a target molecule and releases a bound target molecule in response to the external change.

Potassium fluoride supported on natural nanoporous zeolite: A new solid base for the synthesis of diaryl ethers

Khalilzadeh, Mohammad A.,Hosseini, Abolfazl,Pilevar, Afsaneh

experimental part, p. 1587 - 1592 (2011/04/22)

An efficient and inexpensive synthesis of diaryl ethers has been developed. The process involves the nucleophilic aromatic substitution of electron-deficient aryl halides and phenols and is mediated by potassium fluoride/Clinoptilolite (KF/CP) in dimethyl sulfoxide (DMSO). The approach affords good to excellent yields of the arylated products without the need for additional cation capture. The solid base is also efficient in the Ullmann ether synthesis. A new, inexpensive solid base for the synthesis of diaryl ethers has been developed. Clinoptilolite, a natural zeolite with a high tendency for cation capture, combined with potassium fluoride, provides an efficientsolid base for the deprotonation of phenols in nucleophilic reactions. The same solid base acts as a reliable base for the copper-catalyzed synthesis of diaryl ethers. Copyright

Host-guest interaction of pesticide bifenox with cyclodextrin molecules. an electrochemical study

Hromadova, Magdalena,Sokolova, Romana,PospiSil, Lubomir,Lachmanova, Stipanka,Fanelli, Nicolangelo,Giannarelli, Stefania

body text, p. 1647 - 1664 (2010/08/05)

The reduction of nitroaromatic compound bifenox (methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate) was studied in aprotic solvents in the absence or presence of cyclodextrin (CD) molecules of different cavity sizes. βCD and γCD form complexes with bifenox i

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