619-05-6

Basic information

• Product Name: 3,4-Diaminobenzoic acid
• Synonyms: 3,4-DIAMINOBENZOIC ACID;4-Carboxy-o-phenylenediamine;3,4-DIAMINOBENZOIC ACID GRAY TO BROWNPOW DER;3,4-diaminebenzoic acid;3,4-Diaminobenzoesure;3,4-DIAMINOBENZOIC ACID 98%;3,4-Diaminobenzoic acid, 97%,;3,4-Diaminobenzoic acid, 95%+
• CAS NO: 619-05-6
• Molecular Formula: C₇H₈N₂O₂
• Molecular Weight: 152.15
• EINECS: 210-577-2
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Organic acids;Aromatic Amino Acids;Peptide Synthesis;Unnatural Amino Acid Derivatives
• Mol File: 619-05-6.mol
• Article Data: 16

Chemical Properties

• Melting Point: 208-210 °C (dec.)(lit.)
• Boiling Point: 274.61°C (rough estimate)
• Flash Point: 202.9 °C
• Appearance: Brown/Powder
• Density: 1.2804 (rough estimate)
• Vapor Pressure: 1.61E-07mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 5.02±0.10(Predicted)
• Water Solubility: Soluble in water (2.2 mg/ml at 20°C), DMF, and methanol (10 mg/ml).
• BRN: 775892
• CAS DataBase Reference: 3,4-Diaminobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Diaminobenzoic acid(619-05-6)
• EPA Substance Registry System: 3,4-Diaminobenzoic acid(619-05-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 1
• Hazardous Substances Data: 619-05-6(Hazardous Substances Data)

Usage

Description

3,4-Diaminobenzoic acid is an organic compound characterized by its brown powder appearance. It is known for its ability to undergo cyclocondensations, which allows it to form various chemical structures such as quinoxalines and benzimidazoles. This property, along with its role as a redox label, makes it a versatile molecule with potential applications in different industries.

Uses

Used in Chemical Synthesis:
3,4-Diaminobenzoic acid is used as a chemical intermediate for the synthesis of various compounds, including quinoxalines and benzimidazoles, due to its ability to undergo cyclocondensations. These synthesized compounds have a wide range of applications in the pharmaceutical, agrochemical, and materials science industries.
Used in Electrochemical Detection:
3,4-Diaminobenzoic acid is used as a redox label in the electrochemical detection of single base mismatches. This application is particularly relevant in the field of molecular diagnostics, where the accurate detection of genetic variations is crucial for the identification of diseases and the development of targeted therapies.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3,4-Diaminobenzoic acid can be utilized as a building block for the development of new drugs, taking advantage of its cyclocondensation properties to create novel molecular structures with potential therapeutic effects.
Used in Materials Science:
The ability of 3,4-Diaminobenzoic acid to form various chemical structures through cyclocondensation reactions can also be harnessed in the materials science field. This may lead to the development of new materials with specific properties, such as improved conductivity, stability, or biocompatibility, depending on the desired application.

Purification Methods

Crystallise it from H2O or toluene. [Beilstein 15 IV 1503.]

InChI:InChI=1/C7H8N2O2/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3H,8-9H2,(H,10,11)/p-1

Synthetic route

3,4-dinitrobenzoic acid (528-45-0) → 3,4-diaminobenzoic acid (619-05-6)

Conditions	Yield
With sodium tetrahydroborate In water at 40℃; for 2h; chemoselective reaction;	95%
With hydrazine hydrate In ethanol at 20℃; for 0.25h; Sonication;	94%
With hydrazine hydrate In ethanol at 70℃; for 0.166667h;	94%
With hydrazine hydrate In ethanol at 70℃; for 0.266667h;	89%

4-amino-3-nitrobenzoic acid (1588-83-6) → 3,4-diaminobenzoic acid (619-05-6)

Conditions	Yield
With hydrogenchloride; tin	73.5%
With ethanol; nickel Hydrogenation;
With hydrogenchloride; tin

3-amino-4-nitrobenzoic acid (6968-22-5) → 3,4-diaminobenzoic acid (619-05-6)

Conditions	Yield
With hydrogenchloride; tin
With hydrogenchloride; tin(ll) chloride

4-amino-3-(4-sulfamoyl-phenylazo)-benzoic acid → 3,4-diaminobenzoic acid (619-05-6)

Conditions	Yield
With hydrogenchloride; tin(ll) chloride

furan-2,3,5(4H)-trione pyridine (1:1) + 4-amino-3-nitrobenzoic acid (1588-83-6) + aluminium → 3,4-diaminobenzoic acid (619-05-6)

hydrogenchloride (7647-01-0) + 4-amino-3-nitrobenzoic acid (1588-83-6) + tin → 3,4-diaminobenzoic acid (619-05-6)

hydrogenchloride (7647-01-0) + 3-amino-4-nitrobenzoic acid (6968-22-5) + tin → 3,4-diaminobenzoic acid (619-05-6)

3-nitro-4-acetamidobenzoic acid (1539-06-6) → 3,4-diaminobenzoic acid (619-05-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous hydrochloric acid 2: tin; hydrochloric acid View Scheme
Multi-step reaction with 2 steps 1: alcohol; hydrochloric acid 2: aluminium; diluted NaOH-solution View Scheme

4-nitro-3-(N'-nitro-ureido)-benzoic acid (100949-13-1) → 3,4-diaminobenzoic acid (619-05-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: water 2: tin; hydrochloric acid View Scheme

4-chloro-3-nitrobenzoate (96-99-1) → 3,4-diaminobenzoic acid (619-05-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous NH3 / 170 °C 2: Raney nickel; ethanol / Hydrogenation View Scheme

4-methoxy-3-nitrobenzoic acid (89-41-8) → 3,4-diaminobenzoic acid (619-05-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonia / 140 - 170 °C / im Druckrohr 2: tin; hydrochloric acid View Scheme

3-methoxy-4-hydroxybenzoic acid (121-34-6) → 3,4-diaminobenzoic acid (619-05-6)

Conditions	Yield
With ammonia; metal catalyst

1,2-di(4-methylphenyl)-1,2-ethanedione (3457-48-5) + 3,4-diaminobenzoic acid (619-05-6) → 2,3-bis(4-methylphenyl)-6-quinoxalinecarboxylic acid (90833-49-1)

Conditions	Yield
With sodium acetate; acetic acid at 118℃; for 4h;	100%
In hydrogenchloride for 1h; heating on boiling water bath;	42.3%

1,2-bis(4-fluorophenyl)ethane-1,2-dione (579-39-5) + 3,4-diaminobenzoic acid (619-05-6) → 2,3-bis(4-fluorophenyl)quinoxaline-6-carboxylic acid (355397-64-7)

Conditions	Yield
With sodium acetate; acetic acid at 118℃; for 4h;	100%
H6P2W18O62 In acetic acid at 20℃; for 0.0833333h;	97%
In methanol; chloroform at 20℃;	95%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + 3,4-diaminobenzoic acid (619-05-6) → 3-N-[(9H-fluoren-9-yl)methoxycarbonyl]-amino-4-aminobenzoic acid (1071446-05-3)

Conditions	Yield
With sodium hydrogencarbonate In acetonitrile at 20℃; for 16.0833h;	100%
With sodium hydrogencarbonate In acetonitrile at 20℃; for 16.0833h;	100%
With sodium hydrogencarbonate In acetonitrile for 22h;	94%

2,5-dihydroxy-1,4-benzoquinone (615-94-1) + 3,4-diaminobenzoic acid (619-05-6) → 7,8-dihydroxyphenazine-2-carboxylic acid (1055878-48-2)

Conditions	Yield
In water at 95℃; for 15h;	100%
In ethanol for 24h; Reflux;	85%
With acetic acid In ethanol at 20℃; for 5h;	65%

formic acid (64-18-6) + 3,4-diaminobenzoic acid (619-05-6) → 1H-benzimidazole-6-carboxylic acid (15788-16-6)

Conditions	Yield
for 4h; Reflux;	99.06%
at 110℃; for 4h;	89%
With potassium tert-butylate at 110℃; for 4h;	88%
Stage #1: formic acid; 3,4-diaminobenzoic acid With hydrogenchloride In water at 20℃; for 24h; Cooling; Stage #2: With ammonia In water pH=2 - 3;	54%

p-benzyloxybenzaldehyde (4397-53-9) + 3,4-diaminobenzoic acid (619-05-6) → 2-(4-(benzyloxy)phenyl)-1H-benzo[d]imidazole-5-carboxylic acid (174422-18-5)

Conditions	Yield
With sodium metabisulfite In N,N-dimethyl-formamide at 80℃; for 6h;	99%
With hydrogenchloride; sodium sulfide; copper diacetate 1.) MeOH, heating, 2.) EtOH; Yield given. Multistep reaction;

(3Z)-1-ethyl-3-[(ethylcarbamoylamino)-methylsulfanyl-methylene]urea (797047-27-9) + 3,4-diaminobenzoic acid (619-05-6) → C11H12N4O3

Conditions	Yield
With sulfuric acid; sodium acetate In 1,4-dioxane for 1h; pH=3.5; Heating;	99%

trifluoroacetic acid (76-05-1) + 3,4-diaminobenzoic acid (619-05-6) → 2-(trifluoromethyl)-1H-benzo[d]imidazole-5-carboxylic acid (82791-93-3)

Conditions	Yield
at 70℃; for 16h;	99%
With hydrogenchloride In water for 24h; Inert atmosphere; Reflux;	94%
With hydrogenchloride; formic acid In water Reflux;

benzil (134-81-6) + 3,4-diaminobenzoic acid (619-05-6) → 2,3‐diphenylquinoxaline‐6‐carboxylic acid (32387-96-5)

Conditions	Yield
In hydrogenchloride for 1h; heating on boiling water bath;	98.5%
H6P2W18O62 In acetic acid at 20℃; for 0.166667h;	97%
With sodium acetate; acetic acid at 118℃; for 4h;	97%

methanol (67-56-1) + 3,4-diaminobenzoic acid (619-05-6) → Methyl 3,4-diaminobenzoate (36692-49-6)

Conditions	Yield
With sulfuric acid at 90℃; for 12h; Temperature;	98.1%
With thionyl chloride for 4h; Inert atmosphere;	95%
With thionyl chloride for 11h; Reflux;	94%

4,4'-dinitrobenzil (6067-45-4) + 3,4-diaminobenzoic acid (619-05-6) → 2,3-bis(4-nitrophenyl)quinoxaline-6-carboxylic acid (514197-15-0)

Conditions	Yield
With acetic acid for 12h; Heating;	98%
With nitrogen In acetic acid	98%

3,6-dibromo-phenanthrene-9,10-dione (53348-05-3) + 3,4-diaminobenzoic acid (619-05-6) → 2,7-dibromodibenzo[a,c]phenazine-11-carboxylic acid (1616777-39-9)

Conditions	Yield
With acetic acid In ethanol for 2h; Reflux;	98%

hexaketocyclohexane (527-31-1) + 3,4-diaminobenzoic acid (619-05-6) → 5,6,11,12,17,18-hexaazatrinaphthylene-2,8,14-tricarboxylic acid (872140-77-7)

Conditions	Yield
With acetic acid for 5h; Reflux;	98%

1,2-bis(4-methoxyphenyl)-1,2-ethanedione (1226-42-2) + 3,4-diaminobenzoic acid (619-05-6) → 2,3-bis(4-methoxyphenyl)-quinoxaline-6-carboxylic acid (40622-01-3)

Conditions	Yield
In hydrogenchloride for 1h; heating on boiling water bath;	97.8%
In deoxygenated acetic acid	97%
With acetic acid In sodium hydroxide	44%

dimethylglyoxal (431-03-8) + 3,4-diaminobenzoic acid (619-05-6) → 2,3-dimethyl-6-quinoxalinecarboxylic acid (17635-26-6)

Conditions	Yield
In neat (no solvent) at 24.84℃;	97%
Heating;	87%
In hydrogenchloride for 1h; heating on boiling water bath;	81.6%

5-fluoro-2-hydroxybenzaldehyde (347-54-6) + 3,4-diaminobenzoic acid (619-05-6) → 2‐(5‐fluoro‐2‐hydroxyphenyl)‐1H‐benzo[d]imidazole‐5‐carboxylic acid

Conditions	Yield
With sodium metabisulfite; choline chloride In glycerol at 50℃; for 0.5h;	97%
With sodium metabisulfite In glycerol at 50℃; for 0.5h;	97%

N,N-dimethyl-formamide (68-12-2, 33513-42-7) + 3,4-diaminobenzoic acid (619-05-6) → 1H-benzimidazole-6-carboxylic acid (15788-16-6)

Conditions	Yield
With carbon dioxide In water at 150℃; under 37503.8 Torr; for 5h;	96.1%

salicylaldehyde (90-02-8) + 3,4-diaminobenzoic acid (619-05-6) → N,N′-bis(salicylidene)-3-carboxyl-o-phenylenediamine (87578-89-0)

Conditions	Yield
In methanol for 3h; Reflux;	96%
In methanol for 3h; Reflux;	96%
In methanol at 20℃; for 6h; Inert atmosphere;	85%

malonic acid (141-82-2) + 3,4-diaminobenzoic acid (619-05-6) → 2-methyl-1H-benzoimidazole-5-carboxylic acid (709-19-3)

Conditions	Yield
With hydrogenchloride for 2.5h; Heating;	95%

benzaldehyde (100-52-7) + 3,4-diaminobenzoic acid (619-05-6) → 2-phenyl-1H-1,3-benzimidazole-5-carboxylic acid (66630-70-4)

Conditions	Yield
With ammonium acetate In ethanol at 75℃; for 5.5h;	95%
With air In ethanol at 20℃; for 2.25h;	94%
With vanadium(IV)-salen complex nanoparticles immobilized onto silica In ethanol at 20℃; for 1h;	94%

di-tert-butyl dicarbonate (24424-99-5) + 3,4-diaminobenzoic acid (619-05-6) → N,N'-di-(tert-butoxycarbonyl)-3,4-diaminobenzoic acid (66636-17-7)

Conditions	Yield
With amberlyst-15 In ethanol at 20℃; for 4.5h; chemoselective reaction;	95%
With guanidine hydrochloride In ethanol at 35 - 40℃; for 1.83333h;	93%
With potassium hydroxide In water; tert-butyl alcohol at 20℃; for 48h;	85%

3,4-diaminobenzoic acid (619-05-6) → benzo[c][1,2,5]selenadiazole-5-carboxylic acid (140669-75-6)

Conditions	Yield
With hydrogenchloride; selenium(IV) oxide In water at 80℃; for 2h;	95%
With hydrogenchloride; selenium(IV) oxide In water for 2h;	95%
With hydrogenchloride; selenium(IV) oxide In water at 20℃; for 2h;	93%

2,7-dibromobenzo[1,2-b:4,3-b’]dithiophene-4,5-dione (1258459-51-6) + 3,4-diaminobenzoic acid (619-05-6) → 2,5-dibromodithieno[2,3-a:3',2'-c]phenazine-9-carboxylic acid (1616777-44-6)

Conditions	Yield
With acetic acid In ethanol for 2h; Reflux;	95%

3,5-di-tert-butyl-2-hydroxybenzaldehyde (37942-07-7) + 3,4-diaminobenzoic acid (619-05-6) → N,N'-bis(3,5-di-tert-butylsalicylidene)-1-carboxy-3,4-phenylene-diamine

Conditions	Yield
Stage #1: 3,5-di-tert-butyl-2-hydroxybenzaldehyde; 3,4-diaminobenzoic acid In tetrahydrofuran for 0.333333h; Stage #2: With zinc(II) chloride In tetrahydrofuran for 0.75h; Reflux;	95%
With sulfuric acid In ethanol at 78℃; for 24h;	48.2%
With sulfuric acid In ethanol at 78℃; for 24h;	48.2%

1,10-phenanthroline-5,6-dione (27318-90-7) + 3,4-diaminobenzoic acid (619-05-6) → 4,5,9,14-tetraaza-benzo[b]triphenylene-11-carboxylic acid (259796-23-1)

Conditions	Yield
In ethanol for 0.166667h; Condensation; Heating;	94%
With sulfated titania (TiO2-SO42-) In ethanol at 20℃; for 0.5h;	92.8%
With toluene-4-sulfonic acid In neat (no solvent) for 2.5h; Milling; Green chemistry;	91%

indan-1,2,3-trione hydrate (485-47-2) + (methyloxycarbonylmethyl)triphenylphosphonium bromide (1779-58-4) + 3,4-diaminobenzoic acid (619-05-6) → methyl (8-carboxylindeno[1,2-b]quinoxalin-11-ylidene)acetate

Conditions	Yield
With sodium acetate In acetonitrile at 110℃; for 1h;	94%

1,1,1-trimethoxybutane (43083-12-1) + 3,4-diaminobenzoic acid (619-05-6) → 2-propyl-1H-benzo[d]imidazole-6-carboxylic acid (141838-50-8)

Conditions	Yield
Stage #1: 1,1,1-trimethoxybutane; 3,4-diaminobenzoic acid With hydrogenchloride In water at 20℃; Stage #2: With sodium hydrogencarbonate In water pH=8;	94%

Cyclohexyl isocyanide (931-53-3) + cyclohexanone (108-94-1) + 3,4-diaminobenzoic acid (619-05-6) → 4a'-(cyclohexylcarbamoyl)-1',2',3',4',4a',5',10',11a'-octahydrospiro[cyclohexane-1,11'-dibenzo[b,e][1,4]diazepine]-7'-carboxylic acid (1039656-72-8)

Conditions	Yield
With wool supported Fe3O4 nanoparticles In methanol at 20℃; for 18h; Reagent/catalyst;	94%
Stage #1: cyclohexanone; 3,4-diaminobenzoic acid With Fe3O4/SiO2 In ethanol at 20℃; for 1h; Stage #2: Cyclohexyl isocyanide In ethanol at 20℃; for 4h; regioselective reaction;	90%

methanol (67-56-1) + 3,4-diaminobenzoic acid (619-05-6) → methyl 3,4-diaminobenzoate dihydrochloride

Conditions	Yield
Stage #1: methanol; 3,4-diaminobenzoic acid With sulfuryl dichloride at 0℃; for 5h; Reflux; Stage #2: With hydrogenchloride In water	94%

Upstream product

• 1588-83-6 4-amino-3-nitrobenzoic acid 
• 7647-01-0 hydrogenchloride 
• 528-45-0 3,4-dinitrobenzoic acid 
• 121-34-6 3-methoxy-4-hydroxybenzoic acid 
• 89-41-8 4-methoxy-3-nitrobenzoic acid 
• 6968-22-5 3-amino-4-nitrobenzoic acid 
• 96-99-1 4-chloro-3-nitrobenzoate 
• 100949-13-1 4-nitro-3-(N'-nitro-ureido)-benzoic acid 
• 1539-06-6 3-nitro-4-acetamidobenzoic acid 

Downstream Products

• 87578-89-0 3,4-bis(((E)-2-hydroxybenzylidene)amino)benzoic acid 
• 36692-49-6 Methyl 3,4-diaminobenzoate 
• 23814-14-4 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid 
• 15788-16-6 5-benzimidazolecarboxylic acid 
• 23814-12-2 1h-benzotriazole-5-carboxylic acid 
• 40317-56-4 3,4-dibromo-acenaphtho[1,2-b]quinoxaline-9-carboxylic acid 
• 95-54-5 1,2-diamino-benzene 
• 15719-64-9 methylammonium carbonate 
• 175401-95-3 2-(4-cyanophenyl)benzimidazole-5-carboxylic acid 
• 180197-42-6 1H-2-(3-nitrophenyl)benzimidazole-5-carboxylic acid 
• 69570-99-6 2-(4-nitrophenyl)-1H-benzimidazole-5-carboxylic acid 
• 66636-17-7 N,N'-di-(tert-butoxycarbonyl)-3,4-diaminobenzoic acid 
• 186406-41-7 2-Phenyl-4,5-bis-(4-phenylethynyl-phenyl)-1H-imidazole 

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