7330-46-3

Usage

Uses

Used in Cooling Water Systems:
MBAA is used as a corrosion inhibitor for metals in cooling water systems to prevent the degradation of metal components and extend the life of the system.
Used in Industrial and Consumer Products:
MBAA is used as a stabilizer in various industrial and consumer products to enhance their durability and performance.
Used in Resin and Plastic Production:
MBAA is used as a polymerization catalyst in the production of resins and plastics, facilitating the formation of these materials and improving their properties.
Used in Environmental Management:
Proper handling and disposal of MBAA are crucial to minimize its environmental impact and potential health risks, particularly due to its moderate toxicity to aquatic organisms and its bioaccumulation potential.

Synthetic route

formaldehyd (50-00-0) + anthranilic acid (118-92-3) → 4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3)

Conditions	Yield
With hydrogenchloride In water at 70℃; for 4h;	85%
With hydrogenchloride In water at 70℃; for 4h;	33.6%
With hydrogenchloride In water at 70℃; for 40h; Product distribution / selectivity;

4,4'-methylenebisanthranilic acid dimethyl ester (31383-81-0) → 4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3)

Conditions	Yield
With sodium hydroxide

N,N'-methylene bis(anthranilic acid) (61098-02-0) → 4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3)

Conditions	Yield
With hydrogenchloride

hydrogenchloride (7647-01-0) + N,N'-methylene bis(anthranilic acid) (61098-02-0) → 4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3)

anthranilic acid (118-92-3) → 4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: water; alcohol / 20 °C 2: diluted hydrochloric acid View Scheme

4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3) + propargyl bromide (106-96-7) → C21H18N2O4

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 20℃; for 48h;	96%

4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3) + acetic anhydride (108-24-7) → 6,6'-Methylenebis<2-methyl-4H-3,1-benzoxazin-4-one> (20006-47-7)

Conditions	Yield
for 5h; Heating;	95%
for 6h; Heating;	90%
for 10h; Condensation; Heating;

4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3) + C15H11ClN2 → C45H30N6O2

Conditions	Yield
With N,N-dimethyl-formamide for 0.075h; Microwave irradiation;	95%

4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3) + 2-chloro-3-(4-chlorophenyl)-1,8-naphthyridine (439277-55-1) → C43H24Cl2N6O2

Conditions	Yield
With N,N-dimethyl-formamide for 0.1h; Microwave irradiation;	95%

2-chloro-3-(4-fluorophenyl)-1,8-naphthyridine (1082429-86-4) + 4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3) → C43H24F2N6O2

Conditions	Yield
With N,N-dimethyl-formamide for 0.0916667h; Microwave irradiation;	94%

C15H8ClF3N2 (1191445-84-7) + 4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3) → C45H24F6N6O2

Conditions	Yield
With N,N-dimethyl-formamide for 0.1h; Microwave irradiation;	94%

2-chloro-3-(2-(trifluoromethyl)phenyl)-1,8-naphthyridine (1191445-85-8) + 4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3) → C45H24F6N6O2

Conditions	Yield
With N,N-dimethyl-formamide for 0.0916667h; Microwave irradiation;	93%

4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3) + 2-chloro-3-(4-methoxyphenyl)-1,8-naphthyridine (474266-27-8) → C45H30N6O4

Conditions	Yield
With N,N-dimethyl-formamide for 0.0833333h; Microwave irradiation;	93%

4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3) + 2-chloro-3-phenyl-1,8-naphthyridine (33760-73-5) → C43H26N6O2

Conditions	Yield
With N,N-dimethyl-formamide for 0.075h; Microwave irradiation;	93%

2-chloro-3-[3-(trifluoromethyl)phenyl][1,8]naphthyridine (1082349-69-6) + 4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3) → C45H24F6N6O2

Conditions	Yield
With N,N-dimethyl-formamide for 0.0833333h; Microwave irradiation;	92%

4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3) + 2-chloro-3-2-(2-chlorophenyl)-1,8-naphthyridine (845533-62-2) → C43H24Cl2N6O2

Conditions	Yield
With N,N-dimethyl-formamide for 0.0916667h; Microwave irradiation;	92%

2-chloro-3-(2-fluorophenyl)-1,8-naphthyridine (1082475-88-4) + 4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3) → C43H24F2N6O2

Conditions	Yield
With N,N-dimethyl-formamide for 0.0833333h; Microwave irradiation;	92%

4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3) + 2-chloro-3-(3-methoxyphenyl)[1,8]naphthyridine → 6-(3-methoxyphenyl)-10-{[6-(3-methoxyphenyl)-12-oxo-12H-[1,8]naphthyridino[2,1-b]quinazolin-10-yl]methyl}-12H-[1,8]naphthyridino[2,1-b]quinazolin-12-one

Conditions	Yield
With N,N-dimethyl-formamide for 0.0833333h; Microwave irradiation;	92%

4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3) + 2-bromomethyl-1,4,6-trioxaspiro<4.4>nonane (84298-07-7) → C29H34N2O10

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 70℃; for 12h;	91%

4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3) + 2-chloro-3-(3-chlorophenyl)-1,8-naphthyridine (756500-65-9) → C43H24Cl2N6O2

Conditions	Yield
With N,N-dimethyl-formamide for 0.0833333h; Microwave irradiation;	91%

2-chloro-3-(3-fluorophenyl)-1,8-naphthyridine (1082349-60-7) + 4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3) → C43H24F2N6O2

Conditions	Yield
With N,N-dimethyl-formamide for 0.0833333h; Microwave irradiation;	91%

bis(trichloromethyl) carbonate (32315-10-9) + 4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3) → 6,6'-methylenebis-2H-[3,1]benzoxazine-2,4(1H)-dione (30354-57-5)

Conditions	Yield
In 1,4-dioxane for 6h; Heating;	90%

4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3) + 2-chloroetyl vinyl ether (110-75-8) → C23H26N2O6

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 70℃; for 48h;	88%

4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3) + acetic anhydride (108-24-7) → 4,4'-Bis(acetylamino)diphenylmethane-3,3'-dicarboxylic Acid (47548-81-2)

Conditions	Yield
In acetic acid for 4h; Heating;	80%

4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3) + 4-Nitrophenyl isocyanate (100-28-7) → 2-amino-5-(3-carboxy-4-(3(4-nitrophenyl)ureido)benzyl)benzoic acid (1056452-05-1)

Conditions	Yield
In tetrahydrofuran at 20℃; Product distribution / selectivity;	67%

4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3) + m-chlorophenyl isocyanate (2909-38-8) → 5,5'-methylenebis(2-(3-(3-chlorophenyl)ureido)benzoic acid) (1056451-92-3)

Conditions	Yield
In tetrahydrofuran at 20℃;	67%

2,5-dimethylfuran (625-86-5) + 4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3) → 6,6'-methylenebis(1,4-dihydro-1,4-dimethyl-1,4-epoxynaphthalene) (92958-40-2)

Conditions	Yield
With isopentyl nitrite In 1,4-dioxane; 1,2-dichloro-ethane for 1h; Heating;	61%

4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3) + 2,3,4,5-tetraphenylcyclopenta-2,4-dienone (479-33-4) → 6,6'-methylenebis(1,2,3,4-tetraphenylnaphthalene) (92958-38-8)

Conditions	Yield
With isopentyl nitrite In 1,4-dioxane; 1,2-dichloro-ethane for 0.5h; Heating;	51%

anthracene (120-12-7) + 4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3) → 2,2'-methylenebis(triptycene) (92958-39-9)

Conditions	Yield
With isopentyl nitrite In 1,4-dioxane; 1,2-dichloro-ethane for 1h; Heating;	46%

4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3) + 4-acetamido-3-chlorobenzenesulphonyl chloride (16761-18-5) → 5,5'-methylenebis(2-(4-acetamido-3-chlorophenylsulfonamido)benzoic acid) (1056452-12-0)

Conditions	Yield
Stage #1: 4,4'-diamino-3,3'-dicarboxydiphenylmethane; 4-acetamido-3-chlorobenzenesulphonyl chloride With sodium carbonate In water at 50 - 85℃; for 1h; Stage #2: With hydrogenchloride In water at 20℃;	45%

4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3) → 4,4'-methylenebis(1,2-diiodobenzene) (92958-43-5)

Conditions	Yield
With iodine; isopentyl nitrite In 1,4-dioxane; 1,2-dichloro-ethane for 1h; Heating;	29%

methanol (67-56-1) + 4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3) → 4,4'-methylenebisanthranilic acid dimethyl ester (31383-81-0)

Conditions	Yield
With hydrogenchloride for 5h; Heating;	27.5%
With hydrogenchloride

4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3) + p-toluenesulfonyl chloride (98-59-9) → 2-(4-methylphenylsulfonylamino)-5-[4-(4-methylphenylsulfonylamino)-benzyl]-benzoic acid (951665-71-7)

Conditions	Yield
Stage #1: 4,4'-diamino-3,3'-dicarboxydiphenylmethane; p-toluenesulfonyl chloride With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 0.5h; Stage #2: With hydrogenchloride In water	25.77%

4,4'-diamino-3,3'-dicarboxydiphenylmethane (7330-46-3) + benzoyl chloride (98-88-4) → 6,6'-bis-benzamido-3,3'-methanediyldibenzoic acid (47793-13-5)

Conditions	Yield
With pyridine at 0℃; for 5h;	20%

Upstream product

• 50-00-0 formaldehyd 
• 118-92-3 anthranilic acid 
• 7647-01-0 hydrogenchloride 
• 61098-02-0 N,N'-methylene bis(anthranilic acid) 
• 31383-81-0 4,4'-methylenebisanthranilic acid dimethyl ester 

Downstream Products

• 15403-44-8 6,6'-diamino-3,3'-methanediyl-di-benzoic acid diethyl ester 
• 47793-13-5 6,6'-bis-benzamido-3,3'-methanediyldibenzoic acid 
• 101-77-9 4,4'-diamino diphenyl methane 
• 47548-81-2 4,4'-Bis(acetylamino)diphenylmethane-3,3'-dicarboxylic Acid 
• 92958-43-5 4,4'-methylenebis(1,2-diiodobenzene) 
• 92958-38-8 6,6'-methylenebis(1,2,3,4-tetraphenylnaphthalene) 
• 20006-47-7 6,6'-Methylenebis<2-methyl-4H-3,1-benzoxazin-4-one> 
• 883524-12-7 6,6'-bis-benzylamino-3,3'-methanediyldibenzoic acid dimethyl ester 
• 507485-09-8 5,5'-methylenebis-2-amino-N-methylbenzamide 

Relevant academic research and scientific papers

HOMOGENEOUS TIME RESOLVED FLUORESCENCE BASED TEST SYSTEM

The present invention concerns a fluorescence resonance energy transfer based high throughput test system to measure the formation of the HIV gp41 six-helix bundle. In a first embodiment the current invention relates to a homogeneous time resolved fluorescence-based test system comprising a first helical polypeptide consisting essentially of the sequence of IQN36 (SEQ ID NO:1); a second helical polypeptide consisting essentially of the sequence of C34 (SEQ ID NO: 2) wherein said IQN36 is labeled with a light emitting fluorophore and said C34 is labeled with an ultra-violet excitable fluorophore.

Discovering novel chemical inhibitors of human cyclophilin A: Virtual screening, synthesis, and bioassay

Cyclophilin A (CypA) is a member of cyclophilins, a family of the highly homologous peptidyl prolyl cis-trans isomerases (PPIases), which can bind to cyclosporin A (CsA). CypA plays critical roles in various biological processes, including protein folding, assembly, transportation, regulation of neuron growth, and HIV replication. The discovery of CypA inhibitor is now of a great special interest in the treatment of immunological disorders. In this study, a series of novel small molecular CypA inhibitors have been discovered by using structure-based virtual screening in conjunction with chemical synthesis and bioassay. The SPECS_1 database containing 85,000 small molecular compounds was searched by virtual screening against the crystal structure of human CypA. After SPR-based binding affinity assay, 15 compounds were found to show binding affinities to CypA at submicro-molar or micro-molar level (compounds 1-15). Seven compounds were selected as the starting point for the further structure modification in considering binding activity, synthesis difficulty, and structure similarity. We thus synthesized 40 new small molecular compounds (1-6, 15, 16a-q, 17a-d, and 18a-l), and four of which (compounds 16b, 16h, 16k, and 18g) showed high CypA PPIase inhibition activities with IC50s of 2.5-6.2 μM. Pharmacological assay indicated that these four compounds demonstrated somewhat inhibition activities against the proliferation of spleen cells.

Synthesis of 6,6′-methylenebisquinazolinones and 7,7′-methylenebis-1,4-benzodiazepine-2,5-diones

New C-C linked bisquinazolinones, 6,6′-methylenebis-2-aryl-3-methyl-1,2,3,4-tetrahydroquinazolin-4(3H)- one 4, 6,6′-methylene-bis-2-alkyl-3-methyl-3,4-dihydroquinazolin-4(3H)-one 6, 6,6′-methylenebis-4-oxo-2-thio-3-aryl-1,2,3,4-tetrahydro quinazoline 7 and C-C linked 7,7′-methylenebis [1,4]benzodiazepine-2,5-diones 8 have been synthesised starting from bisisatoic anhydride 1.