56961-25-2

Basic information

• Product Name: 4-AMINO-3,5-DICHLOROBENZOIC ACID
• Synonyms: 4-Carboxy-2,6-dichloroaniline;Benzoic acid, 4-amino-3,5-dichloro-;TIMTEC-BB SBB003491;RARECHEM AL BO 0318;4-AMINO-3,5-DICHLOROBENZOIC ACID;3,5-DICHLORO-4-AMINOBENZOIC ACID;BUTTPARK 35\03-08;LABOTEST-BB LT00455638
• CAS NO: 56961-25-2
• Molecular Formula: C₇H₅Cl₂NO₂
• Molecular Weight: 206.03
• EINECS: 260-468-9
• Product Categories: AMINOACID;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Aromatic Amino Acids;Peptide Synthesis;Unnatural Amino Acid Derivatives
• Mol File: 56961-25-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 290-293 °C(lit.)
• Boiling Point: 344.2 °C at 760 mmHg
• Flash Point: 162 °C
• Appearance: Cream/Powder
• Density: 1.607 g/cm³
• Vapor Pressure: 2.56E-05mmHg at 25°C
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 4.12±0.10(Predicted)
• BRN: 2805751
• CAS DataBase Reference: 4-AMINO-3,5-DICHLOROBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-3,5-DICHLOROBENZOIC ACID(56961-25-2)
• EPA Substance Registry System: 4-AMINO-3,5-DICHLOROBENZOIC ACID(56961-25-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-37
• WGK Germany: 2
• RTECS: DG1930000
• TSCA: Yes
• Hazardous Substances Data: 56961-25-2(Hazardous Substances Data)

Usage

Chemical Properties

Cream powder

InChI:InChI=1/C7H5Cl2NO2/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2H,10H2,(H,11,12)/p-1

Synthetic route

4-amino-benzoic acid (150-13-0) → 4-amino-3,5-dichlorobenzoic acid (56961-25-2)

Conditions	Yield
With hydrogenchloride; dihydrogen peroxide; acetic acid In water at 60℃; for 4h; Solvent;	60%
With sulfuryl dichloride In acetic acid at 60℃; for 1.41667h;	45%
With sulfuryl dichloride; acetic acid
With sulfuryl dichloride; chloroform
With hydrogenchloride; potassium chlorate; sodium acetate; acetic acid

N-(3.5-dichloro-4-amino-benzoyl)-L-glutamic acid (881180-72-9) → 4-amino-3,5-dichlorobenzoic acid (56961-25-2) + Pyroglutamic acid (149-87-1)

Conditions	Yield
at 240℃;

3,5-dichloro-4-acetamidobenzoic acid (98588-83-1) → 4-amino-3,5-dichlorobenzoic acid (56961-25-2)

Conditions	Yield
With sodium hydroxide

4-amino-benzoic acid (150-13-0) → 4-amino-3,5-dichlorobenzoic acid (56961-25-2) + 2,4,6-trichloroaniline (634-93-5)

Conditions	Yield
With chlorine; acetic acid

4-nitro-benzoic acid (62-23-7) → 4-amino-3,5-dichlorobenzoic acid (56961-25-2)

Conditions	Yield
With aluminium trichloride; sodium chloride; tin(ll) chloride

p-(acetylamino)benzoic acid (556-08-1) → 4-amino-3,5-dichlorobenzoic acid (56961-25-2) + 4-amino-3-chlorobenzoic acid (2486-71-7)

Conditions	Yield
With hydrogenchloride; chlorine; acetic acid 1.) RT, overnight, 2) reflux, 30 min; Multistep reaction. Title compound not separated from byproducts;	A n/a B 85 % Spectr.
With hydrogenchloride; chlorine; acetic acid 1.) RT, overnight, 2.) reflux, 30 min; Yield given. Multistep reaction;

p-aminoethylbenzoate (94-09-7) → 4-amino-3,5-dichlorobenzoic acid (56961-25-2)

Conditions	Yield
(i) aq. H2O2, aq. HCl, (ii) aq. NaOH; Multistep reaction;

chlorine (7782-50-5) + 4-amino-benzoic acid (150-13-0) + acetic acid (64-19-7) → 4-amino-3,5-dichlorobenzoic acid (56961-25-2) + 2,4,6-trichloroaniline (634-93-5)

Conditions	Yield
at 20℃;

hydrogenchloride (7647-01-0) + 4-amino-benzoic acid (150-13-0) + potassium chlorate → 4-amino-3,5-dichlorobenzoic acid (56961-25-2) + 2,4,6-trichloroaniline (634-93-5)

p-(acetylamino)benzoic acid (556-08-1) → 4-amino-3,5-dichlorobenzoic acid (56961-25-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; chlorine 2: aqueous NaOH View Scheme

4-amino-benzoic acid (150-13-0) + 4-methoxycarbonyl aniline (619-45-4) → 4-amino-3,5-dichlorobenzoic acid (56961-25-2)

2,6-dichloro-1-nitrobenzoic acid (69708-32-3) → 4-amino-3,5-dichlorobenzoic acid (56961-25-2)

Conditions	Yield
With sodium azide; sulfuric acid In chloroform at 45℃; for 5h; Temperature; Cooling with ice;

3,5-dichlorobenzoic acid (51-36-5) → 4-amino-3,5-dichlorobenzoic acid (56961-25-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid; nitric acid / 5 h / 100 °C / Cooling with ice 2: sulfuric acid; sodium azide / chloroform / 5 h / 45 °C / Cooling with ice View Scheme

ethanol (64-17-5) + 4-amino-3,5-dichlorobenzoic acid (56961-25-2) → 4-amino-3,5-dichlorobenzoic acid ethyl ester (74878-31-2)

Conditions	Yield
With thionyl chloride at 60℃; for 18h;	100%
With thionyl chloride at 60℃; for 18h;	100%

methanol (67-56-1) + 4-amino-3,5-dichlorobenzoic acid (56961-25-2) → methyl 4-amino-3,5-dichlorobenzoate (41727-48-4)

Conditions	Yield
Stage #1: methanol With thionyl chloride at -4 - 0℃; for 1.58333h; Stage #2: 4-amino-3,5-dichlorobenzoic acid at 15 - 30℃; for 72h;	100%
With thionyl chloride at 0 - 20℃; for 16h;	9.4 g

4-amino-3,5-dichlorobenzoic acid (56961-25-2) + adamantan-2-amine hydrochloride (10523-68-9) → N-(2-adamantyl)-4-amino-3,5-dichlorobenzamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In ethyl acetate at 20℃; for 22h;	100%

4-amino-3,5-dichlorobenzoic acid (56961-25-2) + benzyl bromide (100-39-0) → 3,5-dichloro-4-dibenzylaminobenzoic acid

Conditions	Yield
Stage #1: 4-amino-3,5-dichlorobenzoic acid; benzyl bromide With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃; for 16.166h; Stage #2: With hydrogenchloride In tetrahydrofuran; water; N,N-dimethyl-formamide at 0℃;	88%

4-amino-3,5-dichlorobenzoic acid (56961-25-2) → 2,6-Dichloroaniline (608-31-1)

Conditions	Yield
With copper(I) oxide In quinoline at 220℃; for 6h; Autoclave;	85%
In water	80%

4-amino-3,5-dichlorobenzoic acid (56961-25-2) + amantadine hydrochloride (665-66-7) → N-(1-adamantyl)-4-amino-3,5-dichlorobenzamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In ethyl acetate at 20℃; for 22h;	84%

4-amino-3,5-dichlorobenzoic acid (56961-25-2) + phenol (108-95-2) → 2',6'-dichloro-4-hydroxyazobenzene-4'-carboxylic acid

Conditions	Yield
Stage #1: 4-amino-3,5-dichlorobenzoic acid With sulfuric acid; sodium nitrite In water; acetic acid at 5℃; for 0.5h; Stage #2: phenol With sodium hydroxide In water at 5℃; Stage #3: With hydrogenchloride In water	82%

4-Azatricyclo[4.3.1.1(3,8)]undecane (22776-74-5) + 4-amino-3,5-dichlorobenzoic acid (56961-25-2) → (4-amino-3,5-dichloro-phenyl)-(4-aza-tricyclo[4.3.1.13,8]undec-4-yl)-methanone

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide at 100℃; for 12h;	70%

1,3,3-trimethyl-6-azabicyclo[3.2.1]octane (53460-46-1) + 4-amino-3,5-dichlorobenzoic acid (56961-25-2) → (4-amino-3,5-dichloro-phenyl)-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]oct-6-yl)-methanone

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide at 100℃; for 12h;	70%

1-adamantane-methylamine (3717-38-2) + 4-amino-3,5-dichlorobenzoic acid (56961-25-2) → N-adamantan-1-yl-4-amino-3,5-dichloro-N-methyl-benzamide

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide at 100℃; for 12h;	70%

N-cyclopropylcyclohexylamine (824-82-8) + 4-amino-3,5-dichlorobenzoic acid (56961-25-2) → 4-amino-3,5-dichloro-N-cyclohexyl-N-cyclopropyl-benzamide

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide at 100℃; for 12h;	70%

3-benzyl-3,6-diazabicyclo[3.2.1]octane (286947-23-7) + 4-amino-3,5-dichlorobenzoic acid (56961-25-2) → (4-amino-3,5-dichloro-phenyl)-(3-benzyl-3,6-diaza-bicyclo[3.2.1]oct-6-yl)-methanone

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide at 100℃; for 12h;	70%

4-cyclopropylamino-cyclohexanecarboxylic acid ethyl ester + 4-amino-3,5-dichlorobenzoic acid (56961-25-2) → 4-[(4-amino-3,5-dichloro-benzoyl)-cyclopropyl-amino]-cyclohexanecarboxylic acid ethyl ester (918648-98-3)

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide at 100℃; for 12h;	70%

4-amino-3,5-dichlorobenzoic acid (56961-25-2) + 1-(phenylmethyl)octahydro-1,5-diazocine (96097-97-1) → (4-amino-3,5-dichloro-phenyl)-(5-benzyl-[1,5]diazocan-1-yl)-methanone

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide at 100℃; for 12h;	70%

{2-[2-(2-Benzyloxy-5-oxo-tetrahydro-furan-3-ylcarbamoyl)-pyrrolidin-1-yl]-1-methyl-2-oxo-ethyl}-carbamic Acid tert-Butyl Ester + 4-amino-3,5-dichlorobenzoic acid (56961-25-2) → [1-[2-(4-Amino-3,5-dichloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic Acid (2-Benzyloxy-5-oxo-tetrahydro-furan-3-yl)-amide]

Conditions	Yield
	70%

4-amino-3,5-dichlorobenzoic acid (56961-25-2) → 3,5-dichloro-4-aminobenzoylchloride (58991-40-5)

Conditions	Yield
With phosphorus pentachloride In chlorobenzene at 90℃; Substitution; chlorination;	68.8%
With phosphorus pentachloride; chlorobenzene

4-amino-3,5-dichlorobenzoic acid (56961-25-2) + 2-amino-benzenethiol (137-07-5) → 4-Benzothiazol-2-yl-2,6-dichloro-phenylamine

Conditions	Yield
With PPA at 220℃; for 4h;	64%

4-amino-3,5-dichlorobenzoic acid (56961-25-2) + 2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethylamine (134179-38-7) → 4-amino-N-(11-azido-3,6,9-trioxaundecyl)-3,5-dichlorobenzamide

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 1.5h; Inert atmosphere;	61.4%

4-amino-3,5-dichlorobenzoic acid (56961-25-2) + 3-amino-9-methyl-1-phenyl-6,7-dihydro-3H-[1,4]diazepino[6,7,1-hi]indol-4-one (179024-54-5) → 4-amino-3,5-dichloro-N-(9-methyl-4-oxo-1-phenyl-3,4,6,7-tetrahydro-[1,4]diazepino[6,7,1-hi]indol-3-yl)-benzamide

Conditions	Yield
With O-[(ethoxycarbonyl)cyanomethyleneamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;	56.3%
With O-[(ethoxycarbonyl)cyanomethyleneamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane Condensation;

4-amino-3,5-dichlorobenzoic acid (56961-25-2) + N-(m-chlorophenyl)piperazine (6640-24-0) → C17H16Cl3N3O

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In N,N-dimethyl-formamide at 50℃;	47%

4-amino-3,5-dichlorobenzoic acid (56961-25-2) + C14H15N*ClH → (4-amino-3,5-dichlorophenyl)(3-azahexacyclo[7.6.0.01,5.05,12.06,10.011,15]pentadeca-7,13-dien-3-yl)methanone

Conditions	Yield
With benzotriazol-1-ol; 1,2-dichloro-ethane; triethylamine In ethyl acetate; N,N-dimethyl-formamide at 20℃;	47%

4-amino-3,5-dichlorobenzoic acid (56961-25-2) + (R)-3,9-diamino-1-phenyl-6,7-dihydro-3H-[1,4]diazepino[6,7,1-hi]indol-4-one (197895-08-2) → (3R)-4-amino-N-(9-amino-4-oxo-1-phenyl-3,4,6,7-tetrahydro[1,4]diazepino [6,7,1-hi]indol-3-yl)-3,5-dichlorobenzamide (197894-77-2)

Conditions	Yield
With O-[(ethoxycarbonyl)cyanomethyleneamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;	43%

2-methyl-4-oxopiperidine (71322-99-1) + 4-amino-3,5-dichlorobenzoic acid (56961-25-2) → 1-(4-amino-3,5-dichloro-benzoyl)-2-methyl-piperidin-4-one

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide at 100℃; for 12h;	40%

4-amino-3,5-dichlorobenzoic acid (56961-25-2) + (2RS,6RS)-2,6-dimethylpiperidin-4-one → (2R,6R)-1-(4-Amino-3,5-dichloro-benzoyl)-2,6-dimethyl-piperidin-4-one

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide at 100℃; for 12h;	40%

diazomethane (186581-53-3, 908094-01-9) + 4-amino-3,5-dichlorobenzoic acid (56961-25-2) → methyl 4-amino-3,5-dichlorobenzoate (41727-48-4)

Conditions	Yield
With acetone

4-amino-3,5-dichlorobenzoic acid (56961-25-2) → 3,5-dichlorobenzoic acid (51-36-5)

Conditions	Yield
With potassium disulphite; nitric acid Diazotization.Erwaermen der Diazoloesung mit Alkohol und Kupfersulfat;
With hydrogenchloride; copper(l) chloride; sodium nitrite 1) DMF 2) a) 30 min, 0-5 deg C b) 1h, r.t. c) 70 deg C; Yield given. Multistep reaction;

4-amino-3,5-dichlorobenzoic acid (56961-25-2) → 3,5-dichlorobenzoic acid (51-36-5) + 3,5-dichloro-1-nitrobenzene (618-62-2)

Conditions	Yield
With potassium disulphite; nitric acid Diazotization.Erwaermen der mit Eiswasser verduennten Diazoniumsalz-Loesung mit Alkohol in Gegenwart von Kupfersulfat;

4-amino-3,5-dichlorobenzoic acid (56961-25-2) → 2,6-dichloro-4,N-dinitro-aniline

Conditions	Yield
With nitric acid at 0℃;

Upstream product

• 7782-50-5 chlorine 
• 150-13-0 4-amino-benzoic acid 
• 64-19-7 acetic acid 
• 7647-01-0 hydrogenchloride 
• 51-36-5 3,5-dichlorobenzoic acid 
• 69708-32-3 2,6-dichloro-1-nitrobenzoic acid 
• 619-45-4 4-methoxycarbonyl aniline 
• 556-08-1 p-(acetylamino)benzoic acid 
• 94-09-7 p-aminoethylbenzoate 
• 62-23-7 4-nitro-benzoic acid 
• 98588-83-1 3,5-dichloro-4-acetamidobenzoic acid 
• 881180-72-9 N-(3.5-dichloro-4-amino-benzoyl)-L-glutamic acid 

Downstream Products

• 51-36-5 3,5-dichlorobenzoic acid 
• 618-62-2 3,5-dichloro-1-nitrobenzene 
• 58991-40-5 3,5-dichloro-4-aminobenzoylchloride 
• 882694-41-9 C₁₇H₁₆Cl₃N₃O 
• 1213235-02-9 ethyl 1-[1-(3,4,5-trichlorobenzyl)-1H-1,2,3-triazol-4-yl]-1H-pyrazole-4-carboxylate 
• 1213234-75-3 (3-{3-[1-(3,4,5-Trichlorobenzyl)-1H-1,2,3-triazol-4-yl]-1,2,4-oxadiazol-5-yl}-1H-pyrazol-1-yl)acetic acid 
• 1213235-12-1 5-(1H-pyrazol-5-yl)-3-[1-(3,4,5-trichlorobenzyl)-1H-1,2,3-triazol-4-yl]-1,2,4-oxadiazole 
• 1213235-13-2 ethyl (3-{3-[1-(3,4,5-trichlorobenzyl)-1H-1,2,3-triazol-4-yl]-1,2,4-oxadiazol-5-yl}-1H-pyrazol-1-yl)acetate 
• 1213234-76-4 5-{5-[1-(3,4,5-Trichlorobenzyl)-1H-1,2,3-triazol-4-yl]-1,3,4-thiadiazol-2-yl}nicotinic acid 
• 1213235-11-0 N'-hydroxy-1-(3,4,5-trichlorobenzyl)-1H-1,2,3-triazole-4-carboximidamide 
• 1213234-97-9 ethyl (5-{2-[1-(3,4,5-trichlorobenzyl)-1H-1,2,3-triazol-4-yl]pyrimidin-5-yl}-2H-tetrazol-2-yl)acetate 
• 1213234-71-9 (5-{2-[1-(3,4,5-trichlorobenzyl)-1H-1,2,3-triazol-4-yl]-1,3-thiazol-5-yl}-2H-tetrazolyl)acetic acid 
• 116763-58-7 3,3',5,5'-tetrachloro-2,2',4,4',6,6'-hexanitroazobenzene 
• 677709-84-1 4-(4-(N,N-dimethylamino)phenyldiazo)-3,5-bis(propylthio)benzoic acid 

Relevant articles and documents

Method for synthesizing BTAHNAB by taking 3, 5-dichlorobenzoic acid as raw material

The invention belongs to the technical field of organic energetic materials and preparation methods thereof, and provides a method for synthesizing a novel heat-resistant energetic material BTAHNAB bytaking 3, 5-dichlorobenzoic acid as a raw material. The method comprises the following steps of: adding 3, 5-dichlorobenzoic acid into nitro-sulfuric acid, and carrying out reaction to obtain 3, 5-dichloro-4-nitrobenzoic acid; adding the 3, 5-dichloro-4-nitrobenzoic acid into sulfuric acid, dropwise adding chloroform, adding sodium azide, and carrying out reaction to obtain 3, 5-dichloro-4-nitroaniline; sequentially adding sodium nitrate and 3, 5-dichloro-4-nitroaniline into sulfuric acid, and carrying out reaction to obtain 3, 3', 5, 5'-tetrachloro-2, 2', 4, 4', 6, 6'-hexanitroazobenzene; performing mixing with toluene, introducing ammonia gas at a constant speed, stopping introducing the ammonia gas at the end of the reaction, and continuously carrying out reaction to obtain the BTAHNAB. Through calculation and test analysis, the detonation velocity of the final product exceeds 8000m/s, the melting point is larger than 330DEG C, the thermal decomposition temperature is close to 400DEG C, and the final product has good stability and thermal stability, and is a novel heat-resistant explosive with wide application prospects.

SYNTHESIS AND STRUCTURE OF MONOCHLORO DERIVATIVES OF 2-(4-AMINOPHENYL)-5(6)-AMINOBENZIMIDAZOLE

Methods for the production of the monochloro derivatives of 2-(4-aminophenyl)-5(6)-aminobenzimidazole from chloronitrobenzanilides or by the condensation of 1,2,4-triaminobenzene with chloroaminobenzoic acid were investigated.It was established that the nitration of o-chlorobenzanilides takes place selectively in a mixture of acetic acid, acetic anhydride, and chloroform, while the nitration of 4(7)- or 5(6)-chlorobenzimidazoles takes place in sulfuric acid.The effect of the chlorine atoms and the nitro (amino) group on the IR and PMR spectra of the benzanilides and benzimidazoles is determined by their mutual position and by the position in relation of the amide bridge or the condensed imidazole ring.Analysis of the PMR spectra of the chlorodiaminophenylbenzimidazoles indicated that the amino group was localized at position 6 of the benzimidazole ring.

Carbamimidothioic acid phenylmethyl ester salts and their N,N'-tetramethyl derivatives as possible antimicrobial agents

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