CAS No.7300-91-6,4-Maleimidophenol Suppliers

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Basic Information

Molecular Structure:
CAS No.:	7300-91-6
Name:	4-Maleimidophenol
Article Data:	42

Formula:	C₁₀H₇NO₃
Molecular Weight:	189.17
Synonyms:	Maleimide,N-(p-hydroxyphenyl)- (6CI,7CI,8CI);4-Maleimidophenol;N-(4-Hydroxyphenyl)maleimide;N-(p-Hydroxyphenyl)maleimide;NSC 148152;NSC39735;p-Hydroxyphenylmaleimide;p-Maleimidophenol;
EINECS:	230-750-6
Density:	1.47 g/cm³
Boiling Point:	397 °C at 760 mmHg
Flash Point:	193.9 °C
PSA:	57.61000
LogP:	0.88660

Synthetic route

: 108-31-6
maleic anhydride

: 123-30-8
4-amino-phenol

: 7300-91-6
N-(4-hydroxyphenyl)maleimide

Conditions

Conditions	Yield
Stage #1: maleic anhydride; 4-amino-phenol In acetone at 20℃; for 1h; Stage #2: With sodium acetate; triethylamine; hydroquinone In toluene at 115℃; for 2.5h;	88.5%
Stage #1: maleic anhydride; 4-amino-phenol In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: With phosphorus pentoxide; sulfuric acid In N,N-dimethyl-formamide at 70℃; for 2h;	84%
With sulfuric acid; phosphorus pentoxide In N,N-dimethyl-formamide at 70℃; for 2h;	56.8%

: 143629-26-9, 28173-23-1
4'-hydroxymaleanilic acid

: 7300-91-6
N-(4-hydroxyphenyl)maleimide

Conditions

Conditions	Yield
With 1,1,1,3,3,3-hexamethyl-disilazane; zinc dibromide In toluene for 6h; Heating;	85%
With sodium acetate; acetic anhydride In tetrahydrofuran at 60℃; for 8h;	83.3%
With toluene-4-sulfonic acid; N,N-dimethyl-formamide In toluene at 110℃;	64%

: C11H11NO3

: 7300-91-6
N-(4-hydroxyphenyl)maleimide

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane Reflux;	72%

: 6637-46-3
4-(acetoxyphenyl)maleimide

: 7300-91-6
N-(4-hydroxyphenyl)maleimide

Conditions

Conditions	Yield
In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; sulfuric acid; water	63%

: 28173-23-1, 143629-26-9
N-(4-hydroxy-phenyl)-maleamic acid

: 7300-91-6
N-(4-hydroxyphenyl)maleimide

Conditions

Conditions	Yield
With acetyl chloride; acetone
With toluene-4-sulfonic acid In N,N-dimethyl-formamide; toluene at 110℃;
With toluene-4-sulfonic acid In N,N-dimethyl-formamide; toluene at 110℃;

: exo-4-dodecyl-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxy-N-(4-hydroxyphenyl)imide

A: 7300-91-6
N-(4-hydroxyphenyl)maleimide

B: 75308-12-2
2-(n-dodecyl)furan

Conditions

Conditions	Yield
In dimethylsulfoxide-d6 at 50 - 105℃; Reactivity;

: 123-30-8
4-amino-phenol

: 7300-91-6
N-(4-hydroxyphenyl)maleimide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: acetone / 2 h / 20 °C 2: toluene-4-sulfonic acid / N,N-dimethyl-formamide; toluene / 110 °C View Scheme
Multi-step reaction with 2 steps 1: acetone / 2 h / 20 °C 2: toluene-4-sulfonic acid; N,N-dimethyl-formamide / toluene / 110 °C View Scheme
Multi-step reaction with 2 steps 1: acetone / 2 h / 20 °C 2: toluene-4-sulfonic acid / N,N-dimethyl-formamide; toluene / 110 °C View Scheme

: 108-31-6
maleic anhydride

: C21H26N2O2

: 123-30-8
4-amino-phenol

A: 7300-91-6
N-(4-hydroxyphenyl)maleimide

B: C29H26N2O6

Conditions

Conditions	Yield
In N,N-dimethyl-formamide; toluene at 20℃; for 2h; Dean-Stark; Cooling with ice;

...Expand

: 7300-91-6
N-(4-hydroxyphenyl)maleimide

: 1885-14-9
phenyl chloroformate

: C17H11NO5

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3h;	97%

: 7300-91-6
N-(4-hydroxyphenyl)maleimide

: 75308-12-2
2-(n-dodecyl)furan

: exo-4-dodecyl-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxy-N-(4-hydroxyphenyl)imide

Conditions

Conditions	Yield
In acetone at 55℃;	96%

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Specification

The 4-Maleimidophenol is an organic compound with the formula C₁₀H₇NO₃. The IUPAC name of this chemical is 1-(4-hydroxyphenyl)pyrrole-2,5-dione. With the CAS registry number 7300-91-6, it is also named as 1-(4-Hydroxyphenyl)-1H-pyrrole-2,5-dione. The product's category is Miscellaneous.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.35; (2)ACD/LogD (pH 5.5): 0.35 A; (3)CD/LogD (pH 7.4): 0.34; (4)ACD/BCF (pH 5.5): 1.09; (5)ACD/BCF (pH 7.4): 1.06; (6)ACD/KOC (pH 5.5): 37.09; (7)ACD/KOC (pH 7.4): 35.83; (8)#H bond acceptors: 4; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 2; (11)Polar Surface Area: 46.61Å²; (12)Index of Refraction: 1.672; (13)Molar Refractivity: 48.2 cm³; (14)Molar Volume: 128.6 cm³; (15)Polarizability: 19.1×10^-24cm³; (16)Surface Tension: 71.2 dyne/cm; (17)Enthalpy of Vaporization: 67.26 kJ/mol; (18)Vapour Pressure: 7.15E-07 mmHg at 25°C.

Preparation of 4-Maleimidophenol: It can be obtained by maleic acid anhydride and 4-amino-phenol. This reaction will need reagents P₂O₅, H₂SO₄ and solvent dimethylformamide at the temperature of 70°C. The reaction time is 2 hour(s). The yield is about 56.8 %.

Uses of 4-Maleimidophenol: it can react with 3-phenyl-acryloyl chlorideto get 3-phenylacrylic acid 4-(2,5-dioxo-2,5-dihydropyrrole-1-yl)-phenyl ester. This reaction will need reagent Et₃N and solvent dimethylformamide. The yield is about 95.1 %.

People can use the following data to convert to the molecule structure.
1. Canonical SMILES: C1=CC(=CC=C1N2C(=O)C=CC2=O)O
2. InChI: InChI=1S/C10H7NO3/c12-8-3-1-7(2-4-8)11-9(13)5-6-10(11)14/h1-6,12H
3. InChIKey: BLLFPKZTBLMEFG-UHFFFAOYSA-N