7330-46-3

Basic information

• Product Name: MBAA
• Synonyms: AKOS BBS-00003100;CHEMBRDG-BB 5180504;MBAA;METHYLENE BIS (ANTHRANILIC ACID);5,5'-methylenedianthranilic acid;6,6'-Diamino-3,3'-methanediyl-di-benzoic acid;3,3'-Methylenebis(6-aminobenzoic acid);5,5'-Methylenebis(anthanilic acid)
• CAS NO: 7330-46-3
• Molecular Formula: C₁₅H₁₄N₂O₄
• Molecular Weight: 286.28
• EINECS: 230-830-0
• Mol File: 7330-46-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 262℃ (water acetic acid )
• Boiling Point: 576.4 °C at 760 mmHg
• Flash Point: 302.4 °C
• Appearance: /
• Density: 1.442 g/cm³
• PKA: 2.24±0.10(Predicted)
• CAS DataBase Reference: MBAA(CAS DataBase Reference)
• NIST Chemistry Reference: MBAA(7330-46-3)
• EPA Substance Registry System: MBAA(7330-46-3)

Safety Data

• Hazardous Substances Data: 7330-46-3(Hazardous Substances Data)

Usage

General Description

Methyl 2-benzimidazole carbamate (MBAA) is a chemical compound that is commonly used as a corrosion inhibitor for metals, particularly in cooling water systems. It is also used as a stabilizer for industrial and consumer products, as well as a polymerization catalyst in the production of resins and plastics. MBAA has been found to be moderately toxic to aquatic organisms and has the potential to bioaccumulate in the environment. It is important to handle and dispose of MBAA properly to minimize its environmental impact and potential health risks.

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

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

Downstream Products

• 101-77-9 4,4'-diamino diphenyl methane 
• 47793-13-5 6,6'-bis-benzamido-3,3'-methanediyldibenzoic acid 
• 1133710-27-6 3,21-dimesityl-1,5,19,23-tetraaza-3,21-diphospha[5.1.5.1]paracyclophane-7,15,25,33-tetracarboxylic acid 
• 1133710-27-6 3,21-dimesityl-1,5,19,23-tetraaza-3,21-diphospha[5.1.5.1]paracyclophane-7,15,25,33-tetracarboxylic acid 
• 1056452-05-1 2-amino-5-(3-carboxy-4-(3(4-nitrophenyl)ureido)benzyl)benzoic acid 
• 1056452-04-0 2-amino-5-(4-(3-(4-bromophenyl)ureido)-3-carboxybenzyl)benzoic acid 
• 1056451-92-3 5,5'-methylenebis(2-(3-(3-chlorophenyl)ureido)benzoic acid) 
• 1056452-12-0 5,5'-methylenebis(2-(4-acetamido-3-chlorophenylsulfonamido)benzoic acid) 

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