535-87-5

Basic information

• Product Name: 3,5-Diaminobenzoic acid
• Synonyms: 3,5-DIAMINOBENZOIC ACID;DiaMinobenzoic aci;5-Carboxybenzene-1,3-diamine, 5-Carboxyphenylene-1,3-diamine;3,5- twoaMinobenzoic acid;3, 5-2 aMino acid;3,5-DiaMinoben;3,5-Diaminobenzoic acid Vetec(TM) reagent grade, 98%;BENZOIC ACID,3,5-DIAMINO MFC7 H8 N2 O2
• CAS NO: 535-87-5
• Molecular Formula: C₇H₈N₂O₂
• Molecular Weight: 152.15
• EINECS: 208-621-0
• Product Categories: Organic acids;Aromatic Amino AcidsFluorescent Probes, Labels, Particles and Stains;Fluorescent Labels;Other Fluorescent Labels;Peptide Synthesis;Unnatural Amino Acid Derivatives
• Mol File: 535-87-5.mol
• Article Data: 20

Chemical Properties

• Melting Point: 235-238 °C (dec.)(lit.)
• Boiling Point: 274.61°C (rough estimate)
• Flash Point: 235-240°C
• Appearance: White to gray/Powder
• Density: 1.2804 (rough estimate)
• Vapor Pressure: 3.17E-09mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• Storage Temp.: 2-8°C
• Solubility: DMSO (Sparingly), Methanol (Slightly)
• PKA: pK1:5.30 (25°C)
• Water Solubility: Very soluble in water.
• Merck: 14,2978
• BRN: 2086484
• CAS DataBase Reference: 3,5-Diaminobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Diaminobenzoic acid(535-87-5)
• EPA Substance Registry System: 3,5-Diaminobenzoic acid(535-87-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: DG6186000
• TSCA: Yes
• Hazardous Substances Data: 535-87-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 535-87-5 differently. You can refer to the following data:
1. 3,5-diaminobenzoic acid be used as organic intermediates.
2. 3,5-Diaminobenzoic acid is an analog of diatriazoate, which has been shown to have antigenicity properties towards the monoclonal antibodies. It is used as pharmaceutical intermediate.

Purification Methods

Crystallise the acid from water. The dihydrochloride has m 226-228o(dec). [Beilstein 14 H 453, 14 III 1179, 14 IV 1304.]

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

Synthetic route

3,5-dinitrobenzoic acid (99-34-3) → 3.5-diaminobenzoic acid (535-87-5)

Conditions	Yield
With palladium 10% on activated carbon; ammonium formate; silica gel In methanol for 1.5h; Milling;	99%
With sodium hydroxide In water at 25 - 30℃; under 1500.15 Torr; pH=7 - 8; Reagent/catalyst; Pressure;	98.8%
With hydrazine hydrate In neat (no solvent) at 20℃; for 0.5h; chemoselective reaction;	96%

3,5-dibromobenzoic acid (618-58-6) → 3.5-diaminobenzoic acid (535-87-5)

Conditions	Yield
With ammonium hydroxide In water at 20℃; for 9h; Green chemistry;	92%

3,5-dinitrophthalic acid (4277-02-5) → 3.5-diaminobenzoic acid (535-87-5)

Conditions	Yield
With hydrogenchloride; tin

3,5-dinitrobenzoic acid (99-34-3) + ammonium sulfide → 3.5-diaminobenzoic acid (535-87-5)

3,5-dinitrobenzoic acid (99-34-3) + water (7732-18-5) + ammonium sulfide → 3.5-diaminobenzoic acid (535-87-5)

hydrogenchloride (7647-01-0) + 3,5-dinitrobenzoic acid (99-34-3) + tin → 3.5-diaminobenzoic acid (535-87-5)

hydrogenchloride (7647-01-0) + 3,5-dinitrophthalic acid (4277-02-5) + tin → 3.5-diaminobenzoic acid (535-87-5)

5-(trifluoromethyl)benzene-1,3-diamine (368-53-6) → C14H13F3N4O + C14H14N4O3 + C21H19F3N6O2 + 3.5-diaminobenzoic acid (535-87-5)

Conditions	Yield
In water for 8h; UV-irradiation; Title compound not separated from byproducts.;

3,5-dinitrobenzotrifluoride (401-99-0) → 3.5-diaminobenzoic acid (535-87-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / hydrogen / Pd/C / methanol / 20 °C 2: H2O / 8 h / UV-irradiation View Scheme

benzoic acid (65-85-0) → 3.5-diaminobenzoic acid (535-87-5)

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

2.4.5.7-Tetranitro-1-oxy-naphthalin (81417-03-0) → 3.5-diaminobenzoic acid (535-87-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid / 100 °C 2: tin; hydrochloric acid View Scheme

3,5-dinitrobenzoic acid (99-34-3) → 3-amino-5-nitro-benzoic acid (618-84-8) + 3.5-diaminobenzoic acid (535-87-5)

Conditions	Yield
With hydrogen In methanol at 20℃; under 750.075 Torr; for 2h; chemoselective reaction;

C22H22N2O4 → 3.5-diaminobenzoic acid (535-87-5)

Conditions	Yield
In ethanol; dichloromethane at 25℃; Kinetics;

3-chlorosalicylaldehyde (1927-94-2) + 3.5-diaminobenzoic acid (535-87-5) → 3,5-bis{[(E)-3-chloro-2-hydroxybenzylidene]amino}benzoic acid

Conditions	Yield
In methanol for 3h; Reflux;	99%

3.5-diaminobenzoic acid (535-87-5) + benzoyl chloride (98-88-4) → 3,5-bis(benzoylamino)benzoic acid (194731-58-3)

Conditions	Yield
In 1-methyl-pyrrolidin-2-one at 0℃; for 3h;	98.6%

3.5-diaminobenzoic acid (535-87-5) + 3,4-dihydroxybenzaldehyde (139-85-5) → C21H16N2O6

Conditions	Yield
In methanol at 85℃; for 3h;	98%

3.5-diaminobenzoic acid (535-87-5) + 4,4'-(1,1,1,3,3,3-hexafluoroisopropylidene)diphthalic anhydride (1107-00-2) → polymer, inherent viscosity 0.76 dl/g; monomer(s): 3,5-diaminobenzoic acid; 4,4\-(hexafluoroisopropylidene)diphthalic anhydride

Conditions	Yield
In various solvent(s) at 200℃;	97.3%

3.5-diaminobenzoic acid (535-87-5) + 4,4'-(1,1,1,3,3,3-hexafluoroisopropylidene)diphthalic anhydride (1107-00-2) → Reaxys ID: 11558590

Conditions	Yield
In 3-methyl-phenol at 60 - 200℃;	97%

5-iodosalicyclaldehyde (1761-62-2) + 3.5-diaminobenzoic acid (535-87-5) → 3,5-bis{[(E)-2-hydroxy-5-iodobenzylidene]amino}benzoic acid

Conditions	Yield
In methanol for 3h; Reflux;	97%

3,5-diodosalicylaldehyde (2631-77-8) + 3.5-diaminobenzoic acid (535-87-5) → 3,5-bis{[(E)-2-hydroxy-3,5-diiodobenzylidene]amino}benzoic acid

Conditions	Yield
In methanol for 3h; Reflux;	97%

methanol (67-56-1) + 3.5-diaminobenzoic acid (535-87-5) → methyl 3,5-diaminobenzoate (1949-55-9)

Conditions	Yield
With hydrogenchloride	96%
With thionyl chloride ice-NaCl cold bath, 45 min, 40 deg C, 4 h;	94%
With sulfuric acid at 90℃; for 6h; Cooling with ice; Reflux;	89%

di-tert-butyl dicarbonate (24424-99-5) + 3.5-diaminobenzoic acid (535-87-5) → 3,5-di-(tert-butyloxycarbonylamino)benzoic acid (133887-83-9)

Conditions	Yield
With triethylamine In methanol	96%
In 1-methyl-pyrrolidin-2-one at 0 - 20℃; Inert atmosphere;	94%
With sodium hydroxide In tert-butyl alcohol at 20℃; for 16h;	87%

maleic anhydride (108-31-6) + 3.5-diaminobenzoic acid (535-87-5) → C15H12N2O8

Conditions	Yield
In chloroform for 20h; Reflux;	96%

3.5-diaminobenzoic acid (535-87-5) + 2,3,4-trihydroxybenzylaldehyde (2144-08-3) → C21H16N2O8

Conditions	Yield
In methanol at 85℃; for 3h;	96%

maleic anhydride (108-31-6) + 3.5-diaminobenzoic acid (535-87-5) → 3,5-bis(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)benzoic acid (98704-22-4)

Conditions	Yield
With sodium hydroxide In methanol for 1h;	94%
Stage #1: maleic anhydride; 3.5-diaminobenzoic acid In chloroform for 20h; Heating; Stage #2: With sodium acetate; acetic anhydride at 100℃; for 1.5h; Further stages.;	72%
Stage #1: maleic anhydride; 3.5-diaminobenzoic acid In chloroform for 20h; Reflux; Stage #2: With sodium acetate; acetic anhydride at 100℃; for 2h;	69%

ethanol (64-17-5) + 3.5-diaminobenzoic acid (535-87-5) → 3,5-diaminobenzoic acid ethyl ester (1949-51-5)

Conditions	Yield
With sulfuric acid at 20℃; for 72h; Reflux;	94%
With thionyl chloride for 24h; Heating;	93%
With thionyl chloride In ethanol at 0℃; Inert atmosphere; Reflux;	91%
With sulfuric acid for 18h; Heating;	90%

9-Chloroacridine (1207-69-8) + 3.5-diaminobenzoic acid (535-87-5) → 3-(9-acridinylamino)-5-aminobenzoic acid (655238-61-2)

Conditions	Yield
With 4-methyl-morpholine In ethanol; chloroform	94%

3.5-diaminobenzoic acid (535-87-5) + trifluoroacetic anhydride (407-25-0) → 3,5-bis(trifluoroacetamido)benzoic acid

Conditions	Yield
In tetrahydrofuran at 25℃; for 3h;	94%
In tetrahydrofuran at 0 - 30℃; for 6h; Inert atmosphere;	94%

3.5-diaminobenzoic acid (535-87-5) + 4-nitrobenzaldehdye (555-16-8) → 3,5-bis(4-nitrobenzylideneamino)benzoic acid

Conditions	Yield
In methanol at 20℃;	93%

citraconic acid anhydride (616-02-4) + 3.5-diaminobenzoic acid (535-87-5) → 3,5-bis(3-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoic acid (143659-09-0)

Conditions	Yield
Stage #1: citraconic acid anhydride; 3.5-diaminobenzoic acid In acetone at 25℃; for 2h; Stage #2: With 1,1,1,3,3,3-hexamethyl-disilazane; zinc(II) chloride In N,N-dimethyl-formamide; toluene for 5h; Reflux;	92%

3.5-diaminobenzoic acid (535-87-5) + salicylaldehyde (90-02-8) → 3,5-bis{[(E)-2-hydroxybenzylidene]amino}benzoic acid

Conditions	Yield
In methanol for 3h; Reflux;	92%

3.5-diaminobenzoic acid (535-87-5) + 5-chloro-3-iodosalicylaldehyde (215124-03-1) → 3,5-bis{[(E)-5-chloro-2-hydroxy-3-iodobenzylidene]amino}benzoic acid

Conditions	Yield
In methanol for 3h; Reflux;	92%

3.5-diaminobenzoic acid (535-87-5) + acetic anhydride (108-24-7) → 3,5-bis(acetamido)benzoic acid (7743-39-7)

Conditions	Yield
With potassium carbonate In water at 20℃;	91%

4-chlorosalicylaldehyde (2420-26-0) + 3.5-diaminobenzoic acid (535-87-5) → 3,5-bis{[(E)-4-chloro-2-hydroxybenzylidene]amino}benzoic acid

Conditions	Yield
In methanol for 3h; Reflux;	91%

3.5-diaminobenzoic acid (535-87-5) + 3-bromo-5-chlorosalicylaldehyde (19652-32-5) → 3,5-bis{[(E)-3-bromo-5-chloro-2-hydroxybenzylidene]amino}benzoic acid

Conditions	Yield
In methanol for 3h; Reflux;	91%

maleic anhydride (108-31-6) + 3.5-diaminobenzoic acid (535-87-5) → C11H10N2O5

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 6h;	90.7%

3.5-diaminobenzoic acid (535-87-5) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → 3,5-bis((((9H-fluoren-9-yl)methoxy)carbonyl)amino)benzoic acid (248602-44-0)

Conditions	Yield
With sodium carbonate In tetrahydrofuran; water at 20℃;	90%
With sodium hydrogencarbonate In 1,4-dioxane at 0 - 20℃; for 9h;	72%
With sodium hydrogencarbonate In water

3.5-diaminobenzoic acid (535-87-5) + N,N'-hexamethylenedi(trimellitimidic acid) dichloride (37710-66-0) → polymer; monomer(s): N,N\-hexamethylenedi(trimellitimidic acid) dichloride; 3,5-diaminobenzoic acid

Conditions	Yield
Stage #1: 3.5-diaminobenzoic acid; N,N'-hexamethylenedi(trimellitimidic acid) dichloride In 1-methyl-pyrrolidin-2-one at -10℃; for 0.5h; Stage #2: With methyloxirane In 1-methyl-pyrrolidin-2-one at 20℃; for 4h;	90%

3.5-diaminobenzoic acid (535-87-5) + chloroacetyl chloride (79-04-9) → 3,5-bis(2-chloroacetamido)benzoic acid

Conditions	Yield
In tetrahydrofuran at 20℃; for 2h; Cooling;	90%

3.5-diaminobenzoic acid (535-87-5) + 5-chlorosalicyclaldehyde (635-93-8) → 3,5-bis{[(E)-5-chloro-2-hydroxybenzylidene]amino}benzoic acid

Conditions	Yield
In methanol for 3h; Reflux;	90%

3.5-diaminobenzoic acid (535-87-5) → methyl 3,5-diaminobenzoate (1949-55-9)

Conditions	Yield
With sulfuric acid In methanol at 90℃; for 6h;	89%
With thionyl chloride In methanol	60%

Upstream product

• 99-34-3 3,5-dinitrobenzoic acid 
• 65-85-0 benzoic acid 
• 81417-03-0 2.4.5.7-Tetranitro-1-oxy-naphthalin 
• 618-58-6 3,5-dibromobenzoic acid 
• 401-99-0 3,5-dinitrobenzotrifluoride 
• 368-53-6 5-(trifluoromethyl)benzene-1,3-diamine 
• 7647-01-0 hydrogenchloride 
• 4277-02-5 3,5-dinitrophthalic acid 
• 7732-18-5 water 

Downstream Products

• 5505-16-8 3,5-diamino-2,4,6-triiodobenzoic acid 
• 51-36-5 3,5-dichlorobenzoic acid 
• 403695-89-6 3,5-diamino-2,4,6-tribromo-benzoic acid 
• 108-45-2 m-phenylenediamine 
• 98704-22-4 3,5-bis(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)benzoic acid 
• 53882-07-8 diethyl N,N'-[5-carboxy-1,3-phenylene]-dioxamate 
• 1949-55-9 methyl 3,5-diaminobenzoate 
• 146669-27-4 3,5-bis{[(2Z)-3-carboxyprop-2-enoyl]amino}benzoic acid 
• 1949-51-5 3,5-diaminobenzoic acid ethyl ester 
• 248602-44-0 3,5-bis((((9H-fluoren-9-yl)methoxy)carbonyl)amino)benzoic acid 
• 848483-60-3 3,5-di(tetraethyl ethylamino-2,2-bisphosphonate)benzoic acid 
• 192636-26-3 3,5-Bis[4-(benzyloxycarbonyl)-2-oxo-1,4-diazabutyl]-benzoic acid 
• 77898-32-9 (C₄H₉)3SnOOCC₆H₃(NH₂)2-3,5 
• 162993-50-2 3,5-diazido-benzoic acid 

Relevant articles and documents

Synthesis of CoFe2O4@Pd/Activated carbon nanocomposite as a recoverable catalyst for the reduction of nitroarenes in water

Efficient reduction of nitro compounds into amines is an important industrial transformation. So, it is a great deal to design new catalysts for efficient reduction of the nitro compounds especially in water. In this work, a new magnetic Pd/activated carbon nanocomposite (CoFe2O4@Pd/AC) was synthesized via metal-impregnation-pyrolysis method. The CoFe2O4@Pd/AC was fully characterized by FT-IR, PXRD, FESEM, TEM, VSM, EDX-mapping and BET techniques. The results showed that CoFe2O4@Pd/AC is a highly reactive and easily recoverable magnetic catalyst for the reduction of the nitro compounds by using NaBH4 in water. For instance, aniline was obtained in high yield (99%) after 75 ?min at 25 ?C by using just 6 ?mg of the catalyst. In addition, CoFe2O4@Pd/AC was recovered by a simple magnetic decantation and it exhibits stable activity and remains intact during the catalytic process with no significant loss in activity (8 cycles).

A polyamine dendritic polymer-copper complex: A reusable catalyst for the additive-free amination of aryl bromides, and iodides

A porphyrin-initiated amine-functionalized polyepichlorohydrin dendritic polymer (PPECH-Amine) was effectively synthesized, and its water-soluble copper complex (PPECH-Amine-Cu) was developed by treating it with copper acetate. PPECH-Amine and PPECH-Amine-Cu were characterised by different spectroscopic and microscopic techniques. PPECH-Amine-Cu was identified as a reusable catalyst for the amination of bromo- and iodo-benzene derivatives in aqueous media. Due to the presence of residual amino groups in the PPECH-Amine-Cu catalyst, the protocol does not need any additional base additive, as ammonia itself acts as a base and a coupling partner. Due to the good water-soluble nature of this catalyst, it can be easily separated and reused up to six reaction cycles without any loss in its activity.

Preparation method of 3,5-diaminobenzoic acid

The invention discloses a preparation method of 3,5-diaminobenzoic acid. The preparation method comprises steps as follows: m-dinitrobenzoic acid and hydrogen are subjected to a reduction reaction in a solvent under the action of a hydrogenation catalyst, and after the reaction, 3,5-diaminobenzoic acid is obtained through treatment, wherein the hydrogenation catalyst is an Ni-M-Al three-way catalyst, and M is La, Yb or Ce. According to the preparation method of 3,5-diaminobenzoic acid, the new three-way catalyst is adopted as the hydrogenation catalyst, the pressure of hydrogenation is effectively reduced, meanwhile, the usage quantity of the catalyst is reduced, and accordingly, 3,5-diaminobenzoic acid prepared through catalytic hydrogenation has higher industrial application value.