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Cas Database

120-82-1

120-82-1

Identification

  • Product Name:Benzene,1,2,4-trichloro-

  • CAS Number: 120-82-1

  • EINECS:204-428-0

  • Molecular Weight:181.449

  • Molecular Formula: C6H3Cl3

  • HS Code:2903.69 Oral, rat, LD50: 756 mg/kg

  • Mol File:120-82-1.mol

Synonyms:1,2,4-Trichlorobenzol;1,2,5-Trichlorobenzene;1,3,4-Trichlorobenzene;HostetexL-PEC;NSC 406697;unsym-Trichlorobenzene;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn, DangerousN, IrritantXi, ToxicT, FlammableF

  • Hazard Codes: Xn:Harmful;

  • Signal Word:Warning

  • Hazard Statement:H302 Harmful if swallowedH315 Causes skin irritation H410 Very toxic to aquatic life with long lasting effects

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Refer for medical attention. In case of skin contact Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention . In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention . Exposures to high concentrations via inhalation are potentially hazardous to the lungs, kidneys and liver. Prolonged or repeated exposures or short exposure to high concentrations via inhalation are potentially hazardous to the lungs, kidneys and liver. Prolonged or repeated exposure to the eyes is likely to result in moderate pain and transient irritation. Prolonged or repeated contact with the skin may result in moderate irritation and possible systemic effects. Ingestion: May cause kidney and liver damage. (USCG, 1999) Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Aromatic hydrocarbons and related compounds/

  • Fire-fighting measures: Suitable extinguishing media Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. Special Hazards of Combustion Products: May contain toxic hydrogen chloride and phosgene. Behavior in Fire: Decomposes to form hydrogen chloride and phosgene. (USCG, 1999) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. If solid: sweep spilled substance into sealable containers. Then store and dispose of according to local regulations. SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a POTW is acceptable only after review by the governing authority. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must meet Hazardous Material Criteria for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Separated from strong oxidants, acids and food and feedstuffs.1,2,4-Trichlorobenzenes are liquids at room temperature and are shipped in bulk in aluminum tank trucks and steel or stainless steel tank cars.

  • Exposure controls/personal protection:Occupational Exposure limit valuesRecommended Exposure Limit: Ceiling value: 5 ppm (40 mg/cu m).Biological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 64 Articles be found

Catalytic Dehalogenation of Highly Chlorinated Benzenes and Aroclors Using PdCl2(dppf) and NaBH4: Efficiency, Selectivity, and Base Support

Lassová, Luisa,Lee, Hian Kee,Hor, T.S. Andy

, p. 3538 - 3543 (1998)

Reported herein is a convenient one-pot system that can dehalogenate highly chlorinated benzenes at room temperature with reasonable conversion rates using PdCl2(dppf) (dppf = 1,1′-bis-(diphenylphosphino)ferrocene) as catalyst, NaBH4 as reducing agent, TMEDA (N,N,N',N'-tetra-methyl-1,2-ethylenediamine) as supporting base, and THF as solvent. Total conversion of substrate to less chlorinated isomers is achieved within 200 h when hexachloro-, pentachloro-, and tetrachlorobenzenes are used. Degradation to benzene is not achievable, but the efficiency shown in the partial dechlorination is encouraging. A pronounced selectivity is accomplished with removal of meta-substituted chlorines being preferred over ortho- or para-substituted Cl atoms. The sequence in which reagents are added is also critical, thus indicating a protective role of the base. The effectiveness of the method was tested on the PCB mixtures Aroclor 1242, 1248, and 1254. Dechlorination efficiency at 67 °C is satisfactory.

Antagonism/agonism modulation to build novel antihypertensives selectively triggering I1-imidazoline receptor activation

Del Bello, Fabio,Bargelli, Valentina,Cifani, Carlo,Gratteri, Paola,Bazzicalupi, Carla,Diamanti, Eleonora,Giannella, Mario,Mammoli, Valerio,Matucci, Rosanna,Micioni Di Bonaventura, Maria Vittoria,Piergentili, Alessandro,Quaglia, Wilma,Pigini, Maria

, p. 496 - 501 (2015)

Pharmacological studies have suggested that I1-imidazoline receptors are involved in the regulation of cardiovascular function and that selective I1-agonists, devoid of the side effects associated with the common hypotensive α2

Photoreductive dehalogenation of halogenated benzene derivatives using ZnS or CdS nanocrystallites as photocatalysts

Yin, Hengbo,Wada, Yuji,Kitamura, Takayuki,Yanagida, Shozo

, p. 227 - 231 (2001)

ZnS nanocrystallites (nc-ZnS) prepared in N,N-dimethylformamide (DMF) photocatalyze dehalogenation of halogenated benzenes to benzene as the final product from chlorinated benzenes and to difluorobenzenes from fluorinated benzenes in the presence of triethylamine (TEA) as an electron donor under UV light irradiation (λ > 300 nm). When CdS nanocrystallites (nc-CdS) are used as a photocatalyst (λ > 400 nm), halogenated benzenes are photoreductively dehalogenated, yielding trichlorobenzene from hexachlorobenzene and tetrafluorobenzene isomers from hexafluorobenzene as the final products. Photoformed electrons on nc-ZnS and nc-CdS have such negative reduction potentials that these electrons reduce polyhalogenated benzenes, leading to the successive dehalogenation. nc-ZnS exhibits higher photocatalytic activity than nc-CdS due to the more negative potential of the electrons on nc-ZnS than that on nc-CdS. The higher activities of nc-ZnS and nc-CdS compared to their bulk forms are explained as being due to their quantum size effects and the adsorptive interaction between the substrates and the nanosized photocatalysts. ZnS nanocrystallites (nc-ZnS) prepared in N,N-dimethylformamide (DMF) photocatalyze dehalogenation of halogenated benzenes to benzene as the final product from chlorinated benzenes and to difluorobenzenes from fluorinated benzenes in the presence of triethylamine (TEA) as an electron donor under UV light irradiation (λ>300 nm). When CdS nanocrystallites (nc-CdS) are used as a photocatalyst (λ>400 nm), halogenated benzenes are photoreductively dehalogenated, yielding trichlorobenzene from hexachlorobenzene and tetrafluorobenzene isomers from hexafluorobenzene as the final products. Photoformed electrons on nc-ZnS and nc-CdS have such negative reduction potentials that these electrons reduce polyhalogenated benzenes, leading to the successive dehalogenation. nc-ZnS exhibits higher photocatalytic activity than nc-CdS due to the more negative potential of the electrons on nc-ZnS than that on nc-CdS. The higher activities of nc-ZnS and nc-CdS compared to their bulk forms are explained as being due to their quantum size effects and the adsorptive interaction between the substrates and the nanosized photocatalysts.

Dehalogenation of o-dihalogen substituted arenes and α,α′-dihalogen substituted o-xylenes with lanthanum metal

Nishiyama, Yutaka,Kawabata, Hiroshi,Nishino, Toshiki,Hashimoto, Kouji,Sonoda, Noboru

, p. 6609 - 6614 (2003)

It was found that lanthanum metal caused the dehalogenation of o-dihalogen substituted arenes and α,α′-dihalogen substituted o-xylenes to generate the corresponding benzynes and o-quinodimethanes. When o-dihalogen substituted arenes were allowed to react with lanthanum metal in the presence of dienes, the Diels-Alder products between benzyne and dienes were formed in moderate to good yields. Similarly, the Diels-Alder adducts of o-quinodimethane with dienophiles were obtained, in the reaction of α,α′-dibromo-o-xylenes with lanthanum metal in the presence of dienophiles.

-

Kauer,DuVall,Alquist

, p. 1335,1336 (1947)

-

Iron(iii)porphyrin electrocatalyzed enantioselective carbon-chloride bond cleavage of hexachlorocyclohexanes (HCHs): Combined experimental investigation and theoretical calculations

Liang, Xu,Li, Minzhi,Mack, John,Lobb, Kevin,Zhu, Weihua

, p. 11470 - 11476 (2018/08/28)

Enantioselective electrocatalysis of α-, β-, γ- and δ-hexachlorocyclohexanes (HCHs) by tetrakis-pentafluorophenyl-Fe(iii)porphyrin is described. The first example of the combined use of electrochemical measurements and theoretical calculations to determine the mechanism of the enantioselective C-Cl bond cleavage of the electrocatalysis is reported. The electrochemical measurements demonstrate that the reactivity of the HCHs follows the order γ-HCH > α-HCH > δ-HCH > β-HCH. Steric considerations and a molecular orbital theory approach can be used to rationalize the enantioselective nature of the catalysis based on the ease of approach of each Cl atom to the central Fe(i) ion and a consideration of the nodes on the C-Cl bonds that weaken these bonds in a manner that results in bond cleavage and the formation of an Fe-Cl bond.

PROCESS FOR THE PREPARATION OF ORGANIC HALIDES

-

Paragraph 00143, (2017/08/01)

The present invention provides a halo-de-carboxylation process for the preparation of organic chlorides, organic bromides and mixtures thereof, from their corresponding carboxylic acids, using a chlorinating agent selected from trichloroisocyanuric acid (TCCA), dichloroisocyanuric acid (DCCA), or combination thereof, and a brominating agent.

Dicamba preparation process

-

Paragraph 0051; 0052; 0053, (2017/04/03)

The invention belongs to the technical field of herbicide dicamba preparation and relates to a dicamba preparation process. The dicamba preparation process includes steps: taking benzene as a raw material to generate 1,2,4-trichlorobenzene through directional chlorination, catalysis, re-chlorination and rectification; hydrolyzing the 1,2,4-trichlorobenzene to generate a mixture of 2,5-dichlorophenol and 2,4-dichlorophenol, and separating and purifying to obtain 2,5-dichlorophenol; using the 2,5-dichlorophenol to prepare 3,6-dichlorosalicylic acid; subjecting the 3,6-dichlorosalicylic acid to methylation, saponification, acidification and the like to obtain dicamba. By optimization of technical steps and parameters, the whole dicamba preparation process has advantages of simplicity, low cost, high yield, high selectivity, remarkable reduction of wastewater and increase of equipment utilization rate.

A method for the synthesis of 2, 5 - dichlorophenol (by machine translation)

-

Paragraph 0068; 0069, (2016/10/09)

The invention relates to a 2, 5?Dichiorophenol synthetic method, which belongs to the technical field of the synthesis of the key intermediate chamber. The invention is composed of a pure chlorization generated 1, 2, 4?Trichlorobenzene and santochlor is easy to separate, thereby avoiding the difficulties caused by the separating of the high production cost and low production efficiency; because the 1, 2, 4?Trichlorobenzene and to two chiorophenoxy can be obtained respectively 2, 5?Dichiorophenol, utilization rate of raw materials is high, thereby avoiding the waste of the by-product, so that the production cost is greatly reduced. In addition, the two paradichlorbenzene through two different method to obtain 2, 5?Dichiorophenol. The synthesis technique of this invention is simple, the production cost is low, the utilization rate of raw materials is high, and the craft there are few by-products, less generation of three wastes, is more suitable for large-scale industrial production. (by machine translation)

Substd. photoisomerization arom. compd. method

-

Paragraph 0064, (2017/01/02)

Isomerizing substituted aromatic compounds (I), comprises carrying out isomerization in the presence of a salt melt, which contains a metal compound (II) and at least one metal compound (III). Isomerizing substituted aromatic compounds of formula (Ar1-R n) (I) or their mixtures, comprises carrying out isomerization in the presence of a salt melt, which contains a metal compound of formula ([M1][X1] m 1) (II) and at least one metal compound of formula ([M2][X2] m 2) (III). Ar1 : n-valent aryl radical; R : halo, alkyl, fluoroalkyl, aryl, alkyl-aryl or amino; M1 : Al, Ga, In, Cu, Fe, Co or Ni; X1, X2 : halo, preferably Cl or Br; M2, m2 : alkaline earth metal or alkali metal, where M2 is preferably Li, Na, or K; m1 : Al, Ga, In, Fe(III), Co, Ni or Cu(II); and n : >= 2, preferably 2.

Process route upstream and downstream products

Process route

2,4,6-Trichlorophenol
88-06-2,67471-29-8

2,4,6-Trichlorophenol

Pentachlorophenol
87-86-5,67471-28-7

Pentachlorophenol

1,3,5-trichlorobenzene
108-70-3,63697-19-8

1,3,5-trichlorobenzene

1,2,4-Trichlorobenzene
120-82-1,63697-18-7

1,2,4-Trichlorobenzene

1,2,3-trichlorobenzene
87-61-6

1,2,3-trichlorobenzene

Conditions
Conditions Yield
With oxygen; fly ash; at 400 ℃; Further byproducts given. Title compound not separated from byproducts; Formation of xenobiotics;
1,2,3,4,5,6-hexachlorocyclohexane
608-73-1,119911-70-5,6108-11-8,8073-23-2

1,2,3,4,5,6-hexachlorocyclohexane

water
7732-18-5

water

hydrogenchloride
7647-01-0,15364-23-5

hydrogenchloride

2,4-dichlorophenol
120-83-2,40477-79-0

2,4-dichlorophenol

2,4,6-Trichlorophenol
88-06-2,67471-29-8

2,4,6-Trichlorophenol

1,2,4-Trichlorobenzene
120-82-1,63697-18-7

1,2,4-Trichlorobenzene

Conditions
Conditions Yield
at 200 ℃; α-benzene hexachloride; im geschlossenen Rohr;
para-dichlorobenzene
106-46-7,84348-21-0

para-dichlorobenzene

4-chlorobenzotrifluoride
98-56-6

4-chlorobenzotrifluoride

3-chlorotrifluoromethylbenzene
98-15-7

3-chlorotrifluoromethylbenzene

1-chloro-2-(trifluoromethyl)benzene
88-16-4

1-chloro-2-(trifluoromethyl)benzene

1,2,4-Trichlorobenzene
120-82-1,63697-18-7

1,2,4-Trichlorobenzene

Conditions
Conditions Yield
With α,α,α-trifluorotoluene; chlorine; iron(III) chloride; In tetrachloromethane; Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;
With α,α,α-trifluorotoluene; chlorine; iron(III) chloride; In tetrachloromethane; Product distribution; Rate constant;
α,α,α-trifluorotoluene
98-08-8

α,α,α-trifluorotoluene

4-chlorobenzotrifluoride
98-56-6

4-chlorobenzotrifluoride

3-chlorotrifluoromethylbenzene
98-15-7

3-chlorotrifluoromethylbenzene

1-chloro-2-(trifluoromethyl)benzene
88-16-4

1-chloro-2-(trifluoromethyl)benzene

1,2,4-Trichlorobenzene
120-82-1,63697-18-7

1,2,4-Trichlorobenzene

Conditions
Conditions Yield
With para-dichlorobenzene; chlorine; iron(III) chloride; In tetrachloromethane; Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;
With para-dichlorobenzene; chlorine; iron(III) chloride; In tetrachloromethane; Product distribution; Rate constant;
1,2,4,5-tetrachlorobenzene
95-94-3

1,2,4,5-tetrachlorobenzene

para-dichlorobenzene
106-46-7,84348-21-0

para-dichlorobenzene

chlorobenzene
108-90-7

chlorobenzene

1,2-dichloro-benzene
95-50-1

1,2-dichloro-benzene

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

1,2,4-Trichlorobenzene
120-82-1,63697-18-7

1,2,4-Trichlorobenzene

Conditions
Conditions Yield
With potassium hydroxide; hydrogen; palladium on activated charcoal; In water; at 50 ℃; for 0.5h; Product distribution; Aliquat 336 and other phase-transfer catalysts, different multiphase systems, different time and solvents;
73%
4%
4%
With potassium hydroxide; sodium hypophosphite; cetyltributylphosphonium bromide; isobutyric Acid; palladium on activated charcoal; In 2,2,4-trimethylpentane; at 50 ℃; for 2h; Product distribution; varying conditions (solvent, aqueous phase, hydrogen source, phase-transfer agent, time), other aromatic halides, competitive hydrodehalogenations;
With potassium hydroxide; hydrogen; palladium on activated charcoal; In 2,2,4-trimethylpentane; at 50 ℃; for 0.5h; Product distribution; add. of Aliquat 336, var. phase-transfer cat.; var. base: Ca(OH)2; add. of polyethylene glycol monomethyl ether; add of NaBO3*H2O or KF; var. solv. and time;
73 % Chromat.
4 % Chromat.
4 % Chromat.
1,2,4,5-tetrachlorobenzene
95-94-3

1,2,4,5-tetrachlorobenzene

para-dichlorobenzene
106-46-7,84348-21-0

para-dichlorobenzene

1,2-dichloro-benzene
95-50-1

1,2-dichloro-benzene

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

1,2,4-Trichlorobenzene
120-82-1,63697-18-7

1,2,4-Trichlorobenzene

Conditions
Conditions Yield
With carbon dioxide; tetrabutylammomium bromide; In N,N-dimethyl-formamide; at -5 - 0 ℃; Further byproducts given; Electrochemical reaction;
9%
8%
1%
2%
With [2,2]bipyridinyl; nickel dichloride; zinc; In water; N,N-dimethyl-formamide; at 80 ℃; for 6h; Title compound not separated from byproducts;
66.0 % Spectr.
5.8 % Spectr.
3.9 % Spectr.
15.2 % Spectr.
1,2,3,4,-tetrachlorobenzene
634-66-2

1,2,3,4,-tetrachlorobenzene

para-dichlorobenzene
106-46-7,84348-21-0

para-dichlorobenzene

chlorobenzene
108-90-7

chlorobenzene

1,2-dichloro-benzene
95-50-1

1,2-dichloro-benzene

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

1,2,4-Trichlorobenzene
120-82-1,63697-18-7

1,2,4-Trichlorobenzene

1,2,3-trichlorobenzene
87-61-6

1,2,3-trichlorobenzene

Conditions
Conditions Yield
With sodium tetrahydroborate; In ethanol; acetonitrile; at 40 ℃; for 1.3h; Product distribution; tetrahydro derivative of (2,12-dimethyl-3,7,11,17-tetraazabicyclo<11.3.1>heptadeca-1(17),2,11,13,15-pentaene)nickel(II) bis(tetrafluoroborate); other catalysts and solvents; other tetra-, tri- and dichlorobenzenes; with cumene; NH2OH*H2O used a reductor;
1,2,3,4,-tetrachlorobenzene
634-66-2

1,2,3,4,-tetrachlorobenzene

para-dichlorobenzene
106-46-7,84348-21-0

para-dichlorobenzene

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

1,2,4-Trichlorobenzene
120-82-1,63697-18-7

1,2,4-Trichlorobenzene

Conditions
Conditions Yield
With lithium perchlorate; In tetrahydrofuran; methanol; at 25 ℃; for 6h; Product distribution; Electrochemical reaction;
chlorobenzene
108-90-7

chlorobenzene

1,3,5-trichlorobenzene
108-70-3,63697-19-8

1,3,5-trichlorobenzene

para-dichlorobenzene
106-46-7,84348-21-0

para-dichlorobenzene

1,2-dichloro-benzene
95-50-1

1,2-dichloro-benzene

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

1,2,4-Trichlorobenzene
120-82-1,63697-18-7

1,2,4-Trichlorobenzene

Conditions
Conditions Yield
With chlorine; In gaseous matrix; at 329.9 ℃; for 0.0416667h; Product distribution; Rate constant;
1,2-dichloro-benzene
95-50-1

1,2-dichloro-benzene

para-dichlorobenzene
106-46-7,84348-21-0

para-dichlorobenzene

chlorobenzene
108-90-7

chlorobenzene

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

1,2,4-Trichlorobenzene
120-82-1,63697-18-7

1,2,4-Trichlorobenzene

1,2,3-trichlorobenzene
87-61-6

1,2,3-trichlorobenzene

Conditions
Conditions Yield
PdCl2/C; at 400 ℃; Mechanism; Product distribution; effect of different metal chloride catalyst supported on activated charcoal; effect of other carriers;

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