95-82-9

Basic information

• Product Name: 2,5-Dichloroaniline
• Synonyms: LABOTEST-BB LT00032157;FAST SCARLET GG BASE;FAST SCARLET SALT 2G;FAST SCARLET BASE 2G;CI 37010;AZOIC DIAZO COMPONENT 3;AKOS BBS-00003556;2-Amino-1,4-dichlorobenzene
• CAS NO: 95-82-9
• Molecular Formula: C₆H₅Cl₂N
• Molecular Weight: 162.02
• EINECS: 202-455-2
• Product Categories: Intermediates of Dyes and Pigments;Dyes and Pigments;Amines;C2 to C6;Nitrogen Compounds;Alpha sort;AromaticsPesticides&Metabolites;Chemical Class;D;DAlphabetic;DIA - DIC
• Mol File: 95-82-9.mol
• Article Data: 40

Chemical Properties

• Melting Point: 48 °C
• Boiling Point: 251 °C(lit.)
• Flash Point: >230 °F
• Appearance: light brown solid
• Density: 1.54
• Vapor Pressure: 0.021mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: Soluble in dilute hydrochloric acid.
• PKA: 1.60±0.10(Predicted)
• Water Solubility: ca. 0.56 g/L (20 ºC)
• Sensitive: Air & Light Sensitive
• Stability: Stable. Incompatible with acids, acid chlorides, acid anhydrides, oxidizing agents.
• BRN: 1447438
• CAS DataBase Reference: 2,5-Dichloroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Dichloroaniline(95-82-9)
• EPA Substance Registry System: 2,5-Dichloroaniline(95-82-9)

Safety Data

• Hazard Codes: T,N
• Statements: 23/24/25-33-50/53
• Safety Statements: 28-36/37-45-60-61-28A
• RIDADR: UN 3442 6.1/PG 2
• WGK Germany: 3
• RTECS: BX2610000
• F: 8
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 95-82-9(Hazardous Substances Data)

Usage

Chemical Properties

light brown solid

Uses

Different sources of media describe the Uses of 95-82-9 differently. You can refer to the following data:
1. 2,5-Dichloroaniline is used as an intermediate in the synthesis of dyestuffs, pigments, and pesticides.
2. 2,5-Dichloroaniline was used in a study to develop a fast and sensitive quantitative method for the detection of some aniline derivatives by solid-phase microextraction in gas chromatography-mass spectrometry.

Definition

ChEBI: A dichloroaniline carrying chloro groups at positions 2 and 5.

Synthesis Reference(s)

Journal of the American Chemical Society, 87, p. 2767, 1965 DOI: 10.1021/ja01090a050

General Description

Brown crystalline solid.

Air & Water Reactions

2,5-Dichloroaniline is sensitive to prolonged exposure to heat, light and air. . Insoluble in water.

Reactivity Profile

2,5-Dichloroaniline is incompatible with acids, acid chlorides, acid anhydrides and oxidizing agents.

Fire Hazard

2,5-Dichloroaniline is combustible.

Synthetic route

2,5-dichloronitrobenzene (89-61-2) → 2,5 dichloroaniline (95-82-9)

Conditions	Yield
With hydrogen; zinc dibromide; palladium on activated charcoal In ethyl acetate under 760 Torr;	100%
	99%
With platinum on activated charcoal; hydrogen at 60℃; for 1h; Temperature; Inert atmosphere; Autoclave; Supercritical conditions;	99.4%

para-dichlorobenzene (106-46-7) → 2,5 dichloroaniline (95-82-9)

Conditions	Yield
Stage #1: para-dichlorobenzene With sulfuric acid; nitric acid Stage #2: With platinum on activated charcoal; hydrogen In acetic acid under 3102.97 Torr;	95%
With ammonium hydroxide; bis(acetylacetonate)oxovanadium; tetrabutylammomium bromide; dihydrogen peroxide In acetonitrile at 90℃; for 5h; Reagent/catalyst; Solvent; Time; Molecular sieve;	57%
Multi-step reaction with 2 steps 1: H2SO4; HNO3 2: 88.9 percent / aq. H2SO4 / ethanol / 48 - 50 °C / Electrochemical reaction View Scheme
Multi-step reaction with 2 steps 1: bei der Nitrierung 2: tin; hydrochloric acid View Scheme

2,5-dichlorobenzeneboronic acid (135145-90-3) → 2,5 dichloroaniline (95-82-9)

Conditions	Yield
With copper(I) oxide; ammonium hydroxide; air In methanol at 20℃; for 20h;	89%

N-(2,5-dichlorophenyl)benzamide (6626-75-1) → 2,5 dichloroaniline (95-82-9)

Conditions	Yield
With sulfuric acid for 3h; Heating;	82%

pyridine (110-86-1) + (2,5-dichlorophenyl)hydrazine (305-15-7) → 2,5 dichloroaniline (95-82-9) + para-dichlorobenzene (106-46-7) + 2-(2,5-dichlorophenyl)pyridine (4381-30-0) + 4-(2,5-Dichloro-phenyl)-pyridine (4467-14-5)

Conditions	Yield
With KO2 for 10h; Ambient temperature; Yield given. Further byproducts given;	A 6% B 59% C n/a D n/a

(2,5-dichlorophenyl)hydrazine (305-15-7) → 2,5 dichloroaniline (95-82-9) + para-dichlorobenzene (106-46-7) + 2-(2,5-dichlorophenyl)pyridine (4381-30-0) + 4-(2,5-Dichloro-phenyl)-pyridine (4467-14-5)

Conditions	Yield
With KO2 In pyridine for 10h; Ambient temperature; Further byproducts given;	A 6% B 59% C n/a D n/a

3-Chloroacetanilide (588-07-8) → 2,5 dichloroaniline (95-82-9) + m,p-dichloroaniline (95-76-1)

Conditions	Yield
With acetic acid Durch Chlorieren und Destillation des Reaktionsproduktes mit Natronlauge;
With acetic acid Durch Chlorieren;

N-chloro-m-chloroacetanilide (29551-86-8) → 2,5 dichloroaniline (95-82-9) + m,p-dichloroaniline (95-76-1)

Conditions	Yield
With acetic acid Verseifen des Reaktionsproduktes;
With acetic acid und Verseifung des Reaktionsproduktes;

1,4-dichloro-2-nitroso-benzene (67083-41-4) + sodium methylate (124-41-4) → 2,5 dichloroaniline (95-82-9) + bis-(2,5-dichloro-phenyl)-diazene-N-oxide (961-28-4)

3,6-dichloroanthranilic acid (3032-32-4) → 2,5 dichloroaniline (95-82-9)

Conditions	Yield
at 230 - 240℃;

3,6-dichloroanthranilic acid (3032-32-4) → 2,5 dichloroaniline (95-82-9) + methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5)

Conditions	Yield
at 230 - 240℃;

2,5-dichloro-4-(2,5-dichloro-phenylazo)-aniline → 2,5 dichloroaniline (95-82-9) + 2,5-dichloro-1,4-phenylenediamine (20103-09-7)

Conditions	Yield
bei der Reduktion;

N,N-diethyl-4-(2,5-dichloro-phenylazo)-2-methyl-aniline → 2,5 dichloroaniline (95-82-9) + N,N-diethyl-2-methyl-p-phenylenediamine (2628-71-9)

Conditions	Yield
bei der Reduktion;

propan-1-ol (71-23-8) + sodium n-propoxide (6819-41-6) + 2,5-dichloronitrobenzene (89-61-2) + benzene (71-43-2) → 2,5 dichloroaniline (95-82-9) + N-(2,5-dichloro-phenyl)-alanine (99586-92-2)

sodium ethanolate (141-52-6) + 2,5-dichloronitrobenzene (89-61-2) + benzene (71-43-2) → 2,5 dichloroaniline (95-82-9) + bis-(2,5-dichloro-phenyl)-diazene-N-oxide (961-28-4)

2,5-dichloronitrobenzene (89-61-2) → 2,5 dichloroaniline (95-82-9) + N-(2,5-dichloro-phenyl)-hydroxylamine (43192-05-8)

Conditions	Yield
With sodium hydrogensulfide; water; calcium chloride

8-(2,5-dichloro-phenylazo)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione + Na2S2O4 + aqueous alkali → 2,5 dichloroaniline (95-82-9) + 8-amino-theophylline

ethanol (64-17-5) + 5-methyl-2-phenyl-2H-pyrazole-3,4-dione 4-[(2,5-dichloro-phenyl)-hydrazone] (53847-61-3) + acetic acid (64-19-7) + zinc dust → 2,5 dichloroaniline (95-82-9) + rubazonic acid

Conditions	Yield
durch Oxydation an der Luft in Gegenwart von Eisenchlorid;

hydrogenchloride (7647-01-0) + nitrobenzene (98-95-3) → 2,5 dichloroaniline (95-82-9)

Conditions	Yield
at 245℃;

ethanol (64-17-5) + 2,5-dichloronitrobenzene (89-61-2) + Raney nickel → 2,5 dichloroaniline (95-82-9)

Conditions	Yield
at 50 - 100℃; Hydrogenation;

hydrogenchloride (7647-01-0) + 2,5-dichloronitrobenzene (89-61-2) + tin → 2,5 dichloroaniline (95-82-9)

hydrogenchloride (7647-01-0) + 2,5,2',5'-tetrachlorodiazoaminobenzene (893-39-0) → 2,5 dichloroaniline (95-82-9) + 2,3,5,6-tetrachlorobenzene-1,4-diol (87-87-6)

Conditions	Yield
at 130℃;

hydrogenchloride (7647-01-0) + 2,5,2',5'-tetrachlorodiazoaminobenzene (893-39-0) + tin dichloride → 2,5 dichloroaniline (95-82-9) + (2,5-dichlorophenyl)hydrazine (305-15-7)

chlorine (7782-50-5) + 3-chloro-aniline (108-42-9) → 2,5 dichloroaniline (95-82-9) + 2,3,4-trichloroaniline (634-67-3) + m,p-dichloroaniline (95-76-1) + 2,4,5-trichloroaniline (636-30-6)

2,5-dichloronitrobenzene (89-61-2) + alcoholic potash → 2,5 dichloroaniline (95-82-9) + p-chloro-o-nitrophenol (89-64-5) + bis-(2,5-dichloro-phenyl)-diazene-N-oxide (961-28-4)

para-dichlorobenzene (106-46-7) + SO2 → 2,5 dichloroaniline (95-82-9)

3-Chloroacetanilide (588-07-8) → 2,5 dichloroaniline (95-82-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: KHCO3; hypochlorous acid 2: glacial acetic acid / und Verseifung des Reaktionsproduktes View Scheme

benzene (71-43-2) → 2,5 dichloroaniline (95-82-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: iodine; chlorine 2: bei der Nitrierung 3: tin; hydrochloric acid View Scheme

3-chloro-aniline (108-42-9) + 2-Chloroaniline (95-51-2) → 2,5 dichloroaniline (95-82-9)

Conditions	Yield
With aniline

2,5 dichloroaniline (95-82-9) + edaravone (89-25-8) → pigment yellow 10 (6407-75-6)

Conditions	Yield
Stage #1: 2,5 dichloroaniline With hydrogenchloride; sodium nitrite In water at 20℃; for 0.166667h; Stage #2: 3-methyl-1-phenylpyrazolin-5-(4H)-one In water at 20℃; for 0.166667h;	99%

3-methyl-1-phenylpyrazolin-5(4H)-one (19735-89-8) + 2,5 dichloroaniline (95-82-9) → pigment yellow 10 (6407-75-6)

Conditions	Yield
Stage #1: 2,5 dichloroaniline With hydrogenchloride; sodium nitrite In water at 20℃; for 0.333333h; Green chemistry; Stage #2: 3-methyl-1-phenylpyrazolin-5(4H)-one In water at 20℃; for 0.166667h; Green chemistry;	99%

tetrafluoroboric acid + 2,5 dichloroaniline (95-82-9) → 2,5-dichloroaniline diazonium fluoroboric salt

Conditions	Yield
Stage #1: 2,5 dichloroaniline With hydrogenchloride; acetic acid; sodium nitrite In water at 0 - 50℃; Stage #2: tetrafluoroboric acid In water at 5℃;	98.7%

2,5 dichloroaniline (95-82-9) → 2,5-dichloroanilinium hydrogen sulfate (74220-11-4)

Conditions	Yield
With sulfuric acid In dichloromethane	98.56%

2,5 dichloroaniline (95-82-9) → 2,4-dibromo-3,6-dichloroaniline (27761-65-5)

Conditions	Yield
With bromine In water at 20℃; for 0.166667h;	98%
With bromine
With N-Bromosuccinimide In tetrahydrofuran at 20℃; for 2h;
With bromine at 20 - 25℃; for 0.0333333h; pH=8.5 - 9; aq. buffer;

2,5 dichloroaniline (95-82-9) + 6-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester (79607-22-0, 70271-77-1) → 6-chloro-4-oxo-N'-(2,5-dichlorophenyl)-1,4-dihydroquinoline-3-carboxamide (1636164-11-8)

Conditions	Yield
In diphenylether at 210℃; for 1h;	98%

2,5 dichloroaniline (95-82-9) + 1-hydroxy-9,9-dimethoxy-10-anthrone (81386-60-9) → 1-hydroxy-9-(2,5-dichlorophenylimino)-10-anthrone

Conditions	Yield
In toluene for 18h; Reflux;	98%

2,5 dichloroaniline (95-82-9) → 2,5-dichloronitrobenzene (89-61-2)

Conditions	Yield
With fluoro alcohol In water; ethyl acetate; acetonitrile at -20℃; for 0.0833333h;	97%

2,5 dichloroaniline (95-82-9) + potassium ethyl xanthogenate (140-89-6) → 5-chloro-2-mercaptobenzothiazole (5331-91-9)

Conditions	Yield
In dimethyl sulfoxide at 160℃;	97%
In N,N-dimethyl-formamide at 120℃; for 0.2h; microwave irradiation;	93%
for 0.0833333h; Microwave irradiation;	79%

sodium molybdate + chloro-trimethyl-silane (75-77-4) + 2,5 dichloroaniline (95-82-9) → Mo(VI)[(N-2,5-Cl3C6H2)2Cl2(dimethoxyethane)] (339550-51-5)

Conditions	Yield
With triethylamine In 1,2-dimethoxyethane byproducts: [(CH3)3Si]2O, NaCl, (C2H5)3NHCl; (Ar), mixed with suspn. of Mo complex, treated with chloromethylsilane, stirred under reflux for 18 h, cooled to room temp.; filtered, washed (DME), evapd.(vac.), cooled to 0°C, elem. anal.,NMR, MAS, XRD;	97%

2,5 dichloroaniline (95-82-9) + 1-phenylethyl 2,2,2-trichloroacetimidate (99421-72-4) → 2,5-dichloro-N-(1-phenylethyl)aniline (1036572-20-9)

Conditions	Yield
With camphor-10-sulfonic acid In dichloromethane at 20℃; for 24h; Reagent/catalyst; Inert atmosphere;	97%

2,5 dichloroaniline (95-82-9) + Benzoyl isothiocyanate (532-55-8) → N-(2,5-dichlorophenyl)-N'-benzoylthiocarbamide (6281-57-8)

Conditions	Yield
In tetrahydrofuran at 60 - 65℃; for 0.166667h; Microwave irradiation;	96%
In acetone	79%
In acetone
In acetone

2,5 dichloroaniline (95-82-9) + 3-(trimethylsilyl)propynoyl chloride (66224-70-2) → N-(2,5-dichlorophenyl)-3-(trimethylsilyl)prop-2-ynamide

Conditions	Yield
With pyridine In diethyl ether at -50℃; for 1h; Acylation;	96%
In diethyl ether at 25℃; for 1h;

formic acid (64-18-6) + 2,5 dichloroaniline (95-82-9) → N-(2,5-dichlorophenyl)formamide (6639-55-0)

Conditions	Yield
at 20℃; for 4h; Green chemistry;	95%
at 20℃; for 3.33333h; Irradiation;	95%
at 20℃; for 72h;	67%

2,5 dichloroaniline (95-82-9) → 2-bromo-1,4-dichlorobenzene (1435-50-3)

Conditions	Yield
Stage #1: 2,5 dichloroaniline With hydrogen bromide; sodium nitrite In water at -5 - 0℃; for 0.0833333h; Stage #2: With hydrogen bromide; copper(I) bromide In water at 20 - 50℃; for 0.75h;	95%
Diazotization.Behandlung der Diazoniumsalz-Loesung mit CuBr und HBr;

2,5 dichloroaniline (95-82-9) → 1,4-dichloro-2-fluorobenzene (348-59-4)

Conditions	Yield
Stage #1: 2,5 dichloroaniline With hydrogenchloride; fluoroboric acid; sodium nitrite In water at 25℃; for 0.00555556h; Balz-Schiemann Reaction; Stage #2: In 1,2-dichloro-benzene at 200℃; for 0.0166667h; Balz-Schiemann Reaction;	95%
With hydrogenchloride; tetrafluoroboric acid; sodium nitrite Erhitzen des Reaktionsprodukts;

2,5 dichloroaniline (95-82-9) → 2,5,2',5'-tetrachlorodiazoaminobenzene (893-39-0)

Conditions	Yield
With hydrogenchloride; sodium nitrite In water at 0 - 20℃; for 3h;	95%
With hydrogenchloride; sodium acetate; sodium nitrite
Stage #1: 2,5 dichloroaniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.333333h; Stage #2: 2,5 dichloroaniline In water at 0 - 5℃; for 0.0833333h;

2,5 dichloroaniline (95-82-9) + 2,5-hexanedione (110-13-4) → N-(2′,5′-dichlorophenyl)-2,5-dimethylpyrrole

Conditions	Yield
With calcium(II) chloride dihydrate In neat (no solvent) for 0.166667h; Paal-Knorr Pyrrole Synthesis; Microwave irradiation; Green chemistry;	95%
With Cl(1-)*C5H14NO(1+)*3ZnCl2 In neat (no solvent) at 20℃; for 0.166667h; Paal-Knorr Pyrrole Synthesis; Sealed tube; Sonication; Green chemistry;	86%
With MIL-53(Al) In neat (no solvent) at 80℃; for 0.5h; Paal-Knorr Pyrrole Synthesis; Sonication;	85%

2,5 dichloroaniline (95-82-9) → 1,4-dibromo-2,5-dichlorobenzene (4571-24-8) + 1,2,4-tribromo-3,6-dichlorobenzene (73557-61-6)

Conditions	Yield
With tert.-butylnitrite; bromine; copper(ll) bromide In acetonitrile at 50℃; for 0.25h;	A 2% B 95%

2,5 dichloroaniline (95-82-9) + [Bis(methylthio)methylene]malononitrile (5147-80-8) → 2-[(2,5-Dichloro-phenylamino)-methylsulfanyl-methylene]-malononitrile

Conditions	Yield
With resin D261 In acetonitrile Heating;	95%

2,5 dichloroaniline (95-82-9) + phenylacetylene (536-74-3) → 2,5-dichloro-N-(1-phenylethylidene)aniline

Conditions	Yield
With Ph3P-Au(phthalimide); C20H38N5(1+)*H(1+)*2BF4(1-) at 50℃; for 4h; Inert atmosphere;	95%
With C20H38N5(1+)*H(1+)*2BF4(1-); C16H8AuN2O4(1-)*C15H29N2(1+) at 50℃; for 4h; Inert atmosphere;	93%
With gallium(III) trichloride at 60℃; for 12h; regioselective reaction;

2,5 dichloroaniline (95-82-9) + 5-bromo-2-prop-2-ynyloxy-benzaldehyde (122835-14-7) + phosphorous acid trimethyl ester (121-45-9) → dimethyl ((5-bromo-2-(prop-2-yn-1-yloxy)phenyl)((2,5-dichlorophenyl)amino)methyl)phosphonate

Conditions	Yield
With triethylamine sulfate In neat (no solvent) at 20℃; for 0.5h; Green chemistry;	95%

2,5 dichloroaniline (95-82-9) → Potassium; 4-amino-2,5-dichloro-benzenesulfonate

Conditions	Yield
With sodium hydroxide; sulfuric acid In 1,2-dichloro-benzene at 35 - 40℃; Product distribution; var. alkaline agents;	94.1%
With potassium hydroxide; sulfuric acid In 1,2-dichloro-benzene at 35 - 40℃; Yield given;

formaldehyd (50-00-0) + 2,5 dichloroaniline (95-82-9) + 1-benzyl-3-diazo-1,3-dihydro-2H-indol-2-one (461677-71-4) → 1-benzyl-3-((2,5-dichlorophenyl)amino)-3-(hydroxymethyl)indolin-2-one (1598427-65-6)

Conditions	Yield
With dirhodium tetraacetate In water; ethyl acetate at 60℃; for 2h;	94%
With rhodium(II) acetate dimer In ethyl acetate at 60℃; for 2h;	94%

2,5 dichloroaniline (95-82-9) + carbon monoxide (201230-82-2) + o-iodo-methyl-benzoic acid (610-97-9) → 2-(2,5-dichlorophenyl)isoindoline-1,3-dione (1485-35-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 1h; Schlenk technique;	94%

2,5 dichloroaniline (95-82-9) → 5-chloro-2-mercaptobenzothiazole (5331-91-9)

Conditions	Yield
	93.5%

2,5 dichloroaniline (95-82-9) → 2,5-dichloroaniline-3-sulfonic acid

Conditions	Yield
With sulfuric acid In 1,2-dichloro-benzene at 175 - 180℃; 3-5 h;	93.2%

2,5 dichloroaniline (95-82-9) + p-benzoquinone (106-51-4) → 2-(2',5'-dichlorophenyl)-1,4-benzoquinone (79756-69-7)

Conditions	Yield
Stage #1: 2,5 dichloroaniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 1.5h; Stage #2: p-benzoquinone With sodium acetate In water	93%
Meerwein arylation;	70%

Upstream product

• 588-07-8 3-Chloroacetanilide 
• 29551-86-8 N-chloro-m-chloroacetanilide 
• 67083-41-4 1,4-dichloro-2-nitroso-benzene 
• 124-41-4 sodium methylate 
• 71-23-8 propan-1-ol 
• 6819-41-6 sodium n-propoxide 
• 89-61-2 2,5-dichloronitrobenzene 
• 71-43-2 benzene 
• 141-52-6 sodium ethanolate 
• 110-86-1 pyridine 
• 305-15-7 (2,5-dichlorophenyl)hydrazine 
• 64-17-5 ethanol 
• 53847-61-3 5-methyl-2-phenyl-2H-pyrazole-3,4-dione 4-[(2,5-dichloro-phenyl)-hydrazone] 
• 64-19-7 acetic acid 

Downstream Products

• 2044-72-6 N-(2,5-dichlorophenyl)-3-oxobutanamide 
• 61832-96-0 N-(2,5-dichloro-phenyl)-maleamic acid 
• 83551-39-7 1,3-bis-(2,5-dichloro)phenyl thiourea 
• 13201-85-9 1,3-bis(2,5-dichlorophenyl)urea 
• 5392-82-5 2,5-dichlorophenylisocyanate 
• 36053-86-8 N-(2,5-dichloro-phenyl)-β-alanine 
• 100389-22-8 α-(2,5-dichloro-anilino)-isobutyric acid ethyl ester 
• 64745-38-6 3-[1-(2,5-dichloro-phenylimino)-ethyl]-dihydro-furan-2-one 
• 140617-63-6 N²-(2,5-dichloro-phenyl)-[1,3,5]triazine-2,4,6-triyltriamine 
• 108011-91-2 benzo[b]thiophene-2-carboxylic acid-(2,5-dichloro-anilide) 
• 96460-14-9 3-[2]furyl-3-oxo-propionic acid-(2,5-dichloro-anilide) 
• 3386-42-3 (2,5-dichlorophenyl)isothiocyanate 
• 17122-58-6 N-(2,5-dichlorophenyl)-2-(hydroxyimino)acetamide 
• 54282-10-9 trans-crotonic acid-(2,5-dichloro-anilide) 

Relevant articles and documents

Method for synthesizing 2, 5-dichloroaniline by kettle-type continuous hydrogenation

The invention provides a method for synthesizing 2, 5-dichloroaniline by kettle-type continuous hydrogenation. The method involves a feeding pump, a preheater, a reactor, a gas-liquid separator and anextraction pump, the feeding pump, the preheater, the reactor, the gas-liquid separator and the extraction pump are sequentially connected in series, and a plurality of hydrogen distribution pipes are arranged in the reactor, a plurality of through holes are formed in the side surface of the hydrogen distribution pipes, and a catalyst is arranged in the hydrogen distribution pipes; the method forsynthesizing 2, 5-dichloroaniline through kettle-type continuous hydrogenation comprises the following steps of: inputting a 2, 5-dichloronitrobenzene solution into the reactor through the feeding pump, inputting hydrogen into the reactor, adsorbing the hydrogen through the catalyst, and then reacting the hydrogen with the 2, 5-dichloronitrobenzene solution to generate 2, 5-dichloroaniline; by adopting the catalyst with high nitro-reduction activity, byproducts are few, and efficient conversion of the raw materials can be realized only at a reaction temperature of 50-80DEG C. By adopting themethod to continuously react for 720 hours, the raw material conversion rate is greater than 95%, and the product selectivity is greater than 95%.

A mild and selective Cu(II) salts-catalyzed reduction of nitro, azo, azoxy, N-aryl hydroxylamine, nitroso, acid halide, ester, and azide compounds using hydrogen surrogacy of sodium borohydride

The first mild, in situ, single-pot, high-yielding well-screened copper (II) salt-based catalyst system utilizing the hydrogen surrogacy of sodium borohydride for selective hydrogenation of a broad range of nitro substrates into the corresponding amine under habitancy of water or methanol like green solvents have been described. Moreover, this catalytic system can also activate various functional groups for hydride reduction within prompted time, with low catalyst-loading, without any requirement of high pressure or molecular hydrogen supply. Notably, this system explores a great potential to substitute expensive traditional hydrogenation methodologies and thus offers a greener and simple hydrogenative strategy in the field of organic synthesis.

A new process to prepare 3,6-dichloro-2-hydroxybenzoic acid, the penultimate intermediate in the synthesis of herbicide dicamba

Glyphosate [N-(phosphonomethyl)glycine] is a broad spectrum, post-emergent herbicide that is among the most widely used agrochemicals globally. Over the past 30 years, there has been a development of glyphosate-resistant weeds, which pose a significant challenge to growers and crop scientists, resulting in lower crop yields and increased costs. 3,6-Dichloro-2-methoxybenzoic acid (dicamba) is the active ingredient in XtendiMax a standalone herbicide developed by Bayer Crop Science to control broadleaf weeds, including glyphosate-resistant species. 3,6-Dichloro-2-hydroxybenzoic acid (3,6-DCSA) is the penultimate intermediate in the synthesis of dicamba. Existing dicamba manufacturing routes utilize a high temperature, high pressure Kolbe-Schmitt carboxylation to prepare 3,6-DCSA. Described in this Letter is a new, non-Kolbe-Schmitt process to prepare 3,6-DCSA from salicylic acid in four chemical steps.