6627-34-5

Basic information

• Product Name: 2,5-DICHLORO-4-NITROANILINE
• Synonyms: 2,5-dichloro-4-nitro-anilin;2,5-dichloro-4-nitro-benzenamin;Benzenamine,2,5-dichloro-4-nitro-;2,5-DICHLORO-4-NITROANILINE;TIMTEC-BB SBB003478;2,5-Dichloro-4-nitrobenzenamine;2,5-DICHLO-4-NITROANILINE;2,5-Dichloro-4-nitroaniline,97%
• CAS NO: 6627-34-5
• Molecular Formula: C₆H₄Cl₂N₂O₂
• Molecular Weight: 207.01
• EINECS: 229-591-5
• Product Categories: Intermediates of Dyes and Pigments;Amines;C2 to C6;Nitrogen Compounds;Building Blocks;C6;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 6627-34-5.mol
• Article Data: 1

Chemical Properties

• Melting Point: 154-158 °C(lit.)
• Boiling Point: 360.98°C (rough estimate)
• Flash Point: 172.2°C
• Appearance: /
• Density: 1.6257 (rough estimate)
• Vapor Pressure: 2.12E-05mmHg at 25°C
• Refractive Index: 1.6100 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: pK1:-1.74(+1) (25°C)
• BRN: 2211952
• CAS DataBase Reference: 2,5-DICHLORO-4-NITROANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DICHLORO-4-NITROANILINE(6627-34-5)
• EPA Substance Registry System: 2,5-DICHLORO-4-NITROANILINE(6627-34-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• RIDADR: 2811
• WGK Germany: 3
• RTECS: BX2950000
• Hazardous Substances Data: 6627-34-5(Hazardous Substances Data)

Usage

Chemical Properties

yellow powder

Uses

2,5-Dichloro-4-nitroaniline may be employed as an indicator for the estimation of acidity of strong acids.

General Description

2,5-Dichloro-4-nitroaniline is primary aniline indicator. Its pKa in sulfonate and water are -2.12 and -1.78, respectively.

Purification Methods

Recrystallise it from EtOH, then sublime it in vacuo.[Beilstein 12 H 735, 12 II 400.]

InChI:InChI=1/C6H4Cl2N2O2/c7-3-2-6(10(11)12)4(8)1-5(3)9/h1-2H,9H2

Synthetic route

1,4-dichloro-2,5-dinitrobenzene (17488-25-4) → 2,5-dichloro-4-nitroaniline (6627-34-5)

Conditions	Yield
With ammonia

1,4-dichloro-2,5-dinitrobenzene (17488-25-4) → 2,5-dichloro-4-nitroaniline (6627-34-5) + 2,5-dinitro-p-phenylenediamine (67382-07-4)

Conditions	Yield
With ethanol; ammonia

2,5-dichloroacetanilide (2621-62-7) → 2,5-dichloro-4-nitroaniline (6627-34-5)

Conditions	Yield
With sulfuric acid; nitric acid at 5 - 10℃; folgendes Verseifen mit verd.Natronlauge;
With nitrating mixture; sulfuric acid at 45℃; das Acetylderivat entsteht;
Multi-step reaction with 2 steps 1: nitration 2: hydrolysis View Scheme

2,5-dichloroacetanilide (2621-62-7) → 2,5-dichloro-4-nitroaniline (6627-34-5) + acetic acid-(3,6-dichloro-2-nitro-anilide) (38411-18-6)

Conditions	Yield
With nitric acid man extrahiert das 2.5-Dichlor-4-nitro-acetanilid durch Auskochen mit Benzol; die Benzolloesung dampft man ein und zersetzt das asgeschiedene Acetylderivat durch Erhitzen mit waessr.Ammoniak auf 180grad;

2,5-dchloro-4-nitroacetanilide (38411-17-5) → 2,5-dichloro-4-nitroaniline (6627-34-5)

Conditions	Yield
With sulfuric acid at 100 - 110℃;
hydrolysis;

1,4-dichloro-2,5-dinitrobenzene (17488-25-4) + ammonia (7664-41-7) → 2,5-dichloro-4-nitroaniline (6627-34-5)

1,4-dichloro-2,5-dinitrobenzene (17488-25-4) + ammonia (7664-41-7) → 2,5-dichloro-4-nitroaniline (6627-34-5) + 2,5-dinitro-p-phenylenediamine (67382-07-4)

2,5-dichloroacetanilide (2621-62-7) + HNO3+H2SO4 → 2,5-dichloro-4-nitroaniline (6627-34-5)

Conditions	Yield
und Verseifen mit Natronlauge;

para-dichlorobenzene (106-46-7) → 2,5-dichloro-4-nitroaniline (6627-34-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: HNO3+H2SO4 2: alcoholic ammonia View Scheme
Multi-step reaction with 2 steps 1: HNO3+H2SO4 2: alcohol; ammonia View Scheme

2,5-dichloro-4-nitroaniline (6627-34-5) + [1,4]naphthoquinone (130-15-4) → 2,5-dichloro-1,4-phenylenediamine (20103-09-7)

Conditions	Yield
With sodium hydroxide; hydrazine hydrate In water	96%
With sodium hydroxide; hydrazine hydrate In water	91%

di-tert-butyl dicarbonate (24424-99-5) + 2,5-dichloro-4-nitroaniline (6627-34-5) → di-tert-butyl-2,5-dichloro-4-nitrophenylimidodicarbonate (1301264-10-7)

Conditions	Yield
dmap In tetrahydrofuran at 20℃;	91%

Cyasorb UV531 (1843-05-6) + 2,5-dichloro-4-nitroaniline (6627-34-5) → 1-[2-hydroxy-4-n-octyloxy-5-(2,5-dichloro-4-nitrophenylazo)phenyl]-1-phenylmethanone

Conditions	Yield
Stage #1: 2,5-dichloro-4-nitroaniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.5h; Stage #2: Cyasorb UV531 With sodium carbonate; sodium hydroxide In water at 0 - 20℃; for 2.5h; pH=2 - 3;	78%

2-thio-N,N-dimethylbenzamide (20877-02-5) + 2,5-dichloro-4-nitroaniline (6627-34-5) → 2-(5-Amino-4-chloro-2-nitro-phenylthio)-N,N-dimethyl-benzamide (474432-18-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 24h; Heating;	75%
With potassium carbonate In DMF (N,N-dimethyl-formamide) for 24h; Heating / reflux;	75%

2,5-dichloro-4-nitroaniline (6627-34-5) + acetyl chloride (75-36-5) → 2,5-dchloro-4-nitroacetanilide (38411-17-5)

Conditions	Yield
With sodium carbonate In acetone for 1h; Reflux;	75%

methanol (67-56-1) + 2-formyl oxine (14510-06-6) + 2,5-dichloro-4-nitroaniline (6627-34-5) → 2-[(2,5-dichloro-4-nitro-phenylamino)-methoxy-methyl]-quinolin-8-ol

Conditions	Yield
With piperidine for 2h; Heating;	35%

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + 2,5-dichloro-4-nitroaniline (6627-34-5) → 4-(2,5-dichloro-4-nitro-phenyl)-morpholine (1023311-12-7)

Conditions	Yield
With potassium carbonate In acetonitrile for 17h; Heating / reflux;	19.97%

morpholine (110-91-8) + 2,5-dichloro-4-nitroaniline (6627-34-5) → 2-chloro-5-morpholino-4-nitro-aniline (103505-31-3)

methanol (67-56-1) + 2,5-dichloro-4-nitroaniline (6627-34-5) → 2-chloro-5-methoxy-4-nitro-aniline (24311-36-2)

Conditions	Yield
With sodium hydroxide

2,5-dichloro-4-nitroaniline (6627-34-5) → 1,2,4,5-tetrachlorobenzene (95-94-3) + 2,4,5-Trichloronitrobenzene (89-69-0)

Conditions	Yield
Diazotieren und Behandeln mit salzsaurer Kupfer(I)-chlorid-Loesung;

2,5-dichloro-4-nitroaniline (6627-34-5) → 1,4-dichloro-2,5-dinitrobenzene (17488-25-4)

Conditions	Yield
Diazotization.Behandeln mit Natriumnitrit;
With dihydrogen peroxide; trifluoroacetic acid

2,5-dichloro-4-nitroaniline (6627-34-5) → 2,4,5-trichloroiodobenzene (7145-82-6)

Conditions	Yield
With hydrogenchloride; acetic acid Diazotization.Eintragen von KI in die Diazoniumsalz-Loesung;

2,5-dichloro-4-nitroaniline (6627-34-5) → 2,5-dichloro-4-nitrophenol (5847-57-4)

Conditions	Yield
With sulfuric acid; sodium nitrite anschliessendes Erwaermen mit Wasser;

2,5-dichloro-4-nitroaniline (6627-34-5) → 2,3,6-trichloro-4-nitro-aniline (62406-69-3)

Conditions	Yield
With hydrogenchloride; potassium chlorate at 10 - 15℃;
With sulfuryl dichloride
With hydrogenchloride; dihydrogen peroxide In water

2,5-dichloro-4-nitroaniline (6627-34-5) → 2,5-dichloro-1,4-phenylenediamine (20103-09-7)

Conditions	Yield
bei Reduktion;

2,5-dichloro-4-nitroaniline (6627-34-5) → 1,4-dichloro-2-iodo-5-nitro-benzene (71350-52-2)

Conditions	Yield
With sulfuric acid; water; acetic acid at 0℃; Diazotization.Erwaermen der Diazoniumsalz-Loesung mit KI auf 70grad;

2,5-dichloro-4-nitroaniline (6627-34-5) → 3,6-dichloro-2,4-dinitro-aniline (22636-22-2)

Conditions	Yield
With sulfuric acid; nitric acid at -15℃;
With nitric acid at -15℃; Eintragen des erhaltenen 2.5-Dichlor-4.N-dinitro-anilins in Schwefelsaeure;
With nitric acid at -15℃; Eintragen des erhaltenen 2.5-Dichlor-4.N-dinitro-anilins in Schwefelsaeure;

2,5-dichloro-4-nitroaniline (6627-34-5) → 2-amino-3,6-dichloro-5-nitro-benzenesulfonic acid

Conditions	Yield
With tetrachloromethane; chlorosulphuric acid zuletzt in 1.2-Dichlor-benzol bei 160grad;

2,5-dichloro-4-nitroaniline (6627-34-5) + benzoyl chloride (98-88-4) → benzoic acid-(2,5-dichloro-4-nitro-anilide) (99282-29-8)

Conditions	Yield
With sodium hydroxide

2,5-dichloro-4-nitroaniline (6627-34-5) + benzenesulfonyl chloride (98-09-9) → benzenesulfonic acid-(2,5-dichloro-4-nitro-anilide) (107342-09-6)

Nonanoyl chloride (764-85-2) + 2,5-dichloro-4-nitroaniline (6627-34-5) → Nonanoic acid (2,5-dichloro-4-nitro-phenyl)-amide (6043-38-5)

Conditions	Yield
In toluene

1-thiopropane (107-03-9) + 2,5-dichloro-4-nitroaniline (6627-34-5) → 2-chloro-4-nitro-5-n-propylthioaniline (69951-07-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide

diethyl phosphorisothiocyanatidate (6374-26-1) + 2,5-dichloro-4-nitroaniline (6627-34-5) → C16H26Cl2N4O6P2S2 (69950-92-1)

Conditions	Yield
(i) SnCl2, aq. HCl, (ii) /BRN= 1708449/, CHCl3; Multistep reaction;

trifluoromethylsulfonic anhydride (358-23-6) + 2,5-dichloro-4-nitroaniline (6627-34-5) → N-(2,5-Dichloro-4-nitro-phenyl)-C,C,C-trifluoro-methanesulfonamide (57946-26-6)

1-chloro-2,4-dinitro-6-trifluoromethylbenzene (392-95-0) + 2,5-dichloro-4-nitroaniline (6627-34-5) → 2,5-dichloro-2',4,4'-trinitro-6'-trifluoromethyldiphenylamine (57730-08-2)

Upstream product

• 106-46-7 para-dichlorobenzene 
• 2621-62-7 2,5-dichloroacetanilide 
• 17488-25-4 1,4-dichloro-2,5-dinitrobenzene 
• 7664-41-7 ammonia 
• 38411-17-5 2,5-dchloro-4-nitroacetanilide 

Downstream Products

• 57946-26-6 N-(2,5-Dichloro-4-nitro-phenyl)-C,C,C-trifluoro-methanesulfonamide 
• 858501-54-9 benzenesulfonic acid-(4-amino-2-chloro-5-phenylsulfanyl-anilide) 
• 858502-18-8 benzenesulfonic acid-(2-chloro-4-nitro-5-phenylsulfanyl-anilide) 
• 873993-24-9 N,N'-(2-chloro-5-phenylsulfanyl-p-phenylene)-bis-benzenesulfonamide 
• 20103-09-7 2,5-dichloro-1,4-phenylenediamine 
• 53393-30-9 2',5'-dichloro-4-trifluoromethyl-2,4',6-trinitrodiphenylamine 
• 69951-07-1 2-chloro-4-nitro-5-n-propylthioaniline 
• 69951-05-9 2-Chloro-3-methoxy-4-nitroaniline 
• 24311-36-2 2-chloro-5-methoxy-4-nitro-aniline 
• 6392-96-7 2,5-dichloro-4-aminoacetanilide 
• 38411-17-5 2,5-dchloro-4-nitroacetanilide 
• 69950-93-2 C₂₂H₃₁ClN₄O₆P₂S₃ 

Relevant articles and documents

Construction of interconnected acidity functions based on ortho substituted anilines and N-methylanilines as indicators

The log I values of 15 mainly ortho substituted derivatives of aniline and N-methylaniline have been measured spectrophotometrically in sulfuric, perchloric, and methanesulfonic acids. A new algorithm has been suggested for construction of acidity functions enabling simultaneous and independent construction of acidity functions in various media under the condition of equal values of pKa of the same indicators in the given media. The so-called interconnected acidity functions have been constructed with using this algorithm and the log I values measured in the above media, and the pKa values have been calculated. The resulting acidity functions and pKa values agree well with the corresponding literature data.