Bis(4-amino-3-carboxyphenyl)methane supplier

Name
MBAA
EINECS 230-830-0
CAS No. 7330-46-3
Article Data7
CAS DataBase
Density 1.442 g/cm³
Solubility
Melting Point 262℃ (water acetic acid )
Formula C₁₅H₁₄N₂O₄
Boiling Point 576.4 °C at 760 mmHg
Molecular Weight 286.287
Flash Point 302.4 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Anthranilicacid, 5,5'-methylenedi- (6CI,7CI,8CI);3,3'-Dicarboxy-4,4'-diaminodiphenylmethane;4,4'-Diamino-3,3'-dicarboxydiphenylmethane;4,4'-Diaminodiphenylmethane-3,3'-dicarboxylic acid;5,5'-Methylenebis[2-aminobenzoic acid];5,5'-Methylenedianthranilic acid;Benzoic acid, 5,5'-methylenebis[2-amino-;CB 37136;NCI 37136;
PSA 126.64000
LogP 3.00060

Synthetic route

: 50-00-0
formaldehyd

: 118-92-3
anthranilic acid

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

Conditions

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;

: 31383-81-0
4,4'-methylenebisanthranilic acid dimethyl ester

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

Conditions

Conditions	Yield
With sodium hydroxide

: 61098-02-0
N,N'-methylene bis(anthranilic acid)

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

Conditions

Conditions	Yield
With hydrogenchloride

: 7647-01-0
hydrogenchloride

: 61098-02-0
N,N'-methylene bis(anthranilic acid)

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: 118-92-3
anthranilic acid

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

Conditions

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

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: 106-96-7
propargyl bromide

: C21H18N2O4

Conditions

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

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: 108-24-7
acetic anhydride

: 20006-47-7
6,6'-Methylenebis<2-methyl-4H-3,1-benzoxazin-4-one>

Conditions

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

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: C15H11ClN2

: C45H30N6O2

Conditions

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

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: 439277-55-1
2-chloro-3-(4-chlorophenyl)-1,8-naphthyridine

: C43H24Cl2N6O2

Conditions

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

: 1082429-86-4
2-chloro-3-(4-fluorophenyl)-1,8-naphthyridine

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: C43H24F2N6O2

Conditions

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

: 1191445-84-7
C15H8ClF3N2

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: C45H24F6N6O2

Conditions

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

: 1191445-85-8
2-chloro-3-(2-(trifluoromethyl)phenyl)-1,8-naphthyridine

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: C45H24F6N6O2

Conditions

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

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: 474266-27-8
2-chloro-3-(4-methoxyphenyl)-1,8-naphthyridine

: C45H30N6O4

Conditions

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

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: 33760-73-5
2-chloro-3-phenyl-1,8-naphthyridine

: C43H26N6O2

Conditions

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

: 1082349-69-6
2-chloro-3-[3-(trifluoromethyl)phenyl][1,8]naphthyridine

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: C45H24F6N6O2

Conditions

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

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: 845533-62-2
2-chloro-3-2-(2-chlorophenyl)-1,8-naphthyridine

: C43H24Cl2N6O2

Conditions

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

: 1082475-88-4
2-chloro-3-(2-fluorophenyl)-1,8-naphthyridine

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: C43H24F2N6O2

Conditions

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

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: 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

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

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: 84298-07-7
2-bromomethyl-1,4,6-trioxaspiro<4.4>nonane

: C29H34N2O10

Conditions

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

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: 756500-65-9
2-chloro-3-(3-chlorophenyl)-1,8-naphthyridine

: C43H24Cl2N6O2

Conditions

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

: 1082349-60-7
2-chloro-3-(3-fluorophenyl)-1,8-naphthyridine

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: C43H24F2N6O2

Conditions

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

: 32315-10-9
bis(trichloromethyl) carbonate

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: 30354-57-5
6,6'-methylenebis-2H-[3,1]benzoxazine-2,4(1H)-dione

Conditions

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

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: 110-75-8
2-chloroetyl vinyl ether

: C23H26N2O6

Conditions

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

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: 108-24-7
acetic anhydride

: 47548-81-2
4,4'-Bis(acetylamino)diphenylmethane-3,3'-dicarboxylic Acid

Conditions

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

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: 100-28-7
4-Nitrophenyl isocyanate

: 1056452-05-1
2-amino-5-(3-carboxy-4-(3(4-nitrophenyl)ureido)benzyl)benzoic acid

Conditions

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

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: 2909-38-8
m-chlorophenyl isocyanate

: 1056451-92-3
5,5'-methylenebis(2-(3-(3-chlorophenyl)ureido)benzoic acid)

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃;	67%

: 625-86-5
2,5-dimethylfuran

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: 92958-40-2
6,6'-methylenebis(1,4-dihydro-1,4-dimethyl-1,4-epoxynaphthalene)

Conditions

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

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: 479-33-4
2,3,4,5-tetraphenylcyclopenta-2,4-dienone

: 92958-38-8
6,6'-methylenebis(1,2,3,4-tetraphenylnaphthalene)

Conditions

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

: 120-12-7
anthracene

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: 92958-39-9
2,2'-methylenebis(triptycene)

Conditions

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

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: 16761-18-5
4-acetamido-3-chlorobenzenesulphonyl chloride

: 1056452-12-0
5,5'-methylenebis(2-(4-acetamido-3-chlorophenylsulfonamido)benzoic acid)

Conditions

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%

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: 92958-43-5
4,4'-methylenebis(1,2-diiodobenzene)

Conditions

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

: 67-56-1
methanol

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: 31383-81-0
4,4'-methylenebisanthranilic acid dimethyl ester

Conditions

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

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: 98-59-9
p-toluenesulfonyl chloride

: 951665-71-7
2-(4-methylphenylsulfonylamino)-5-[4-(4-methylphenylsulfonylamino)-benzyl]-benzoic acid

Conditions

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%

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: 98-88-4
benzoyl chloride

: 47793-13-5
6,6'-bis-benzamido-3,3'-methanediyldibenzoic acid

Conditions

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

Bis(4-amino-3-carboxyphenyl)methane Specification

The Bis(4-amino-3-carboxyphenyl)methane, with the CAS registry number 7330-46-3, is also known as 5,5'-Methylenedianthranilic acid. Its EINECS number is 230-830-0. This chemical's molecular formula is C₁₅H₁₄N₂O₄ and molecular weight is 286.28. What's more, its systematic name is 3,3'-methanediylbis(6-aminobenzoic acid).

Physical properties of Bis(4-amino-3-carboxyphenyl)methane are: (1)ACD/LogP: 2.19; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 0.41; (4)ACD/LogD (pH 7.4): -1.92; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 6.16; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 6; (10)#H bond donors: 6; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 59.08 Å²; (13)Index of Refraction: 1.714; (14)Molar Refractivity: 77.89 cm³; (15)Molar Volume: 198.4 cm³; (16)Polarizability: 30.88×10^-24 cm³; (17)Surface Tension: 80.3 dyne/cm; (18)Density: 1.442 g/cm³; (19)Flash Point: 302.4 °C; (20)Enthalpy of Vaporization: 90.8 kJ/mol; (21)Boiling Point: 576.4 °C at 760 mmHg; (22)Vapour Pressure: 3.96E-14 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: O=C(O)c1cc(ccc1N)Cc2cc(C(=O)O)c(N)cc2
(2)InChI: InChI=1/C15H14N2O4/c16-12-3-1-8(6-10(12)14(18)19)5-9-2-4-13(17)11(7-9)15(20)21/h1-4,6-7H,5,16-17H2,(H,18,19)(H,20,21)
(3)InChIKey: QRUWUSOUUMPANJ-UHFFFAOYAT

Product Name

MBAA

Synthetic route

Bis(4-amino-3-carboxyphenyl)methane Specification

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