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Diphenolic acid

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Name

Diphenolic acid

EINECS 204-763-2
CAS No. 126-00-1 Density 1.26 g/cm3
PSA 77.76000 LogP 3.26860
Solubility Soluble in acetic acid, acetone, ethanol, insoluble in benzene, carbon tetrachloride and dimethyl benzene, slightly soluble in water Melting Point 167-170 °C(lit.)
Formula C17H18O4 Boiling Point 507 °C at 760 mmHg
Molecular Weight 286.328 Flash Point 274.5 °C
Transport Information N/A Appearance Light brown particles
Safety 26-37/39-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 126-00-1 (Diphenolic acid) Hazard Symbols IrritantXi
Synonyms

Valericacid, 4,4-bis(p-hydroxyphenyl)- (6CI,8CI);4,4-Bis(4-hydroxyphenyl)pentanicacid;4,4-Bis(4-hydroxyphenyl)pentanoic acid;4,4-Bis(4-hydroxyphenyl)valericacid;4,4-Bis(p-hydroxyphenyl)pentanoic acid;4,4-Bis(p-hydroxyphenyl)valericacid;4,4'-Bis(4-hydroxyphenyl)valeric acid;Bisphenol acid;DPA;NSC 3371;NSC 55069;γ,γ-Bis(p-hydroxyphenyl)valeric acid;

Article Data 13

Diphenolic acid Synthetic route

123-76-2

levulinic acid

108-95-2

phenol

126-00-1

4,4-bis(4-hydroxyphenyl)valeric acid

Conditions
ConditionsYield
With sulfuric acid
With hydrogenchloride
With C16H28N4O6S2(2+)*2CF3O3S(1-); C16H28N4O6S2(2+)*2C3H7O3S2(1-) at 60℃; for 48h; Reagent/catalyst; Sealed tube; Inert atmosphere; Schlenk technique;91 mol
7297-85-0

4-hydroxy-γ-(4-hydroxyphenyl)-γ-methyl-benzenebutanoic acid methyl ester

74-88-4

methyl iodide

A

126-00-1

4,4-bis(4-hydroxyphenyl)valeric acid

B

111161-78-5

4,4-bis(4'-methoxyphenyl)pentanoic acid

C

(4'-hydroxyphenyl)-4-(4''-methoxyphenyl)pentanoic acid

Conditions
ConditionsYield
With potassium hydroxide; cobalt(II) acetate; silver(l) oxide Product distribution; multistepreaction, degradative method for the determination of the degree of branching for hyperbranched macromolecules;
123-76-2

levulinic acid

108-95-2

phenol

mineral acid

mineral acid

126-00-1

4,4-bis(4-hydroxyphenyl)valeric acid

539-88-8

4-oxopentanoic acid ethyl ester

108-95-2

phenol

126-00-1

4,4-bis(4-hydroxyphenyl)valeric acid

Conditions
ConditionsYield
With sulfuric acid In water at 0 - 20℃; for 18h; Condensation;
123-76-2

levulinic acid

108-95-2

phenol

A

126-00-1

4,4-bis(4-hydroxyphenyl)valeric acid

B

1033556-25-0

C17H18O4

Conditions
ConditionsYield
With ethanethiol at 99.84℃; for 16h; Inert atmosphere;
With C16H28N4O6S2(2+)*2C3H7O3S2(1-) at 60℃; for 48h; Reagent/catalyst; Temperature; Time; Concentration; Sealed tube; Inert atmosphere; Schlenk technique; Overall yield = 75 mol;
539-88-8

4-oxopentanoic acid ethyl ester

108-95-2

phenol

A

126-00-1

4,4-bis(4-hydroxyphenyl)valeric acid

B

7297-86-1

ethyl diphenolate

Conditions
ConditionsYield
With C16H28N4O6S2(2+)*2CF3O3S(1-); C16H28N4O6S2(2+)*2C3H7O3S2(1-) at 60℃; for 48h; Reagent/catalyst; Sealed tube; Inert atmosphere; Schlenk technique; Overall yield = 80 mol;A 22 mol
B 58 mol
624-45-3

levulinic acid methyl ester

108-95-2

phenol

A

126-00-1

4,4-bis(4-hydroxyphenyl)valeric acid

B

7297-85-0

4-hydroxy-γ-(4-hydroxyphenyl)-γ-methyl-benzenebutanoic acid methyl ester

Conditions
ConditionsYield
With C16H28N4O6S2(2+)*2CF3O3S(1-); C16H28N4O6S2(2+)*2C3H7O3S2(1-) at 60℃; for 48h; Sealed tube; Inert atmosphere; Schlenk technique; Overall yield = 79 mol;A 22 mol
B 57 mol
2052-15-5

butyl levulinate

108-95-2

phenol

A

126-00-1

4,4-bis(4-hydroxyphenyl)valeric acid

B

7297-88-3

butyl diphenolate

Conditions
ConditionsYield
With C16H28N4O6S2(2+)*2CF3O3S(1-); C16H28N4O6S2(2+)*2C3H7O3S2(1-) at 60℃; for 48h; Sealed tube; Inert atmosphere; Schlenk technique; Overall yield = 81 mol;A 16 mol
B 65 mol
67-56-1

methanol

126-00-1

4,4-bis(4-hydroxyphenyl)valeric acid

7297-85-0

4-hydroxy-γ-(4-hydroxyphenyl)-γ-methyl-benzenebutanoic acid methyl ester

Conditions
ConditionsYield
With sulfuric acid for 8h; Fischer-Speier Esterification; Reflux;99%
With sulfuric acid for 3h; Esterification; Heating;97%
for 2h; Reflux;96%
67-56-1

methanol

126-00-1

4,4-bis(4-hydroxyphenyl)valeric acid

149-73-5

trimethyl orthoformate

7297-85-0

4-hydroxy-γ-(4-hydroxyphenyl)-γ-methyl-benzenebutanoic acid methyl ester

Conditions
ConditionsYield
With p-toluenesulfonic acid monohydrate for 16h; Reflux;98%

Diphenolic acid Specification

The Benzenebutanoic acid, 4-hydroxy-γ-(4-hydroxyphenyl)-γ-methyl-, with the CAS registry number 126-00-1, is also known as 4,4-Bis(p-hydroxyphenyl)valericacid. Its EINECS number is 204-763-2. This chemical's molecular formula is C17H18O4 and molecular weight is 286.32. What's more, its systematic name is 4,4-bis(4-hydroxyphenyl)pentanoic acid. It is used as a pharmaceutical intermediate and widely used in food, medicine, chemical industry, light industry and other industries.

Physical properties of Benzenebutanoic acid, 4-hydroxy-γ-(4-hydroxyphenyl)-γ-methyl- are: (1)ACD/LogP: 2.89; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.97; (4)ACD/LogD (pH 7.4): 0.17; (5)ACD/BCF (pH 5.5): 11.25; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 108.06; (8)ACD/KOC (pH 7.4): 1.69; (9)#H bond acceptors: 4; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 44.76 Å2; (13)Index of Refraction: 1.612; (14)Molar Refractivity: 78.99 cm3; (15)Molar Volume: 227.2 cm3; (16)Polarizability: 31.31×10-24cm3; (17)Surface Tension: 55.8 dyne/cm; (18)Density: 1.26 g/cm3; (19)Flash Point: 274.5 °C; (20)Enthalpy of Vaporization: 81.82 kJ/mol; (21)Boiling Point: 507 °C at 760 mmHg; (22)Vapour Pressure: 4.21E-11 mmHg at 25°C.

Preparation: the crude product can be prepared by levulinic acid and phenol in the presence of catalyst, in acid medium reaction system, then refinined to the finished product.

Uses of Benzenebutanoic acid, 4-hydroxy-γ-(4-hydroxyphenyl)-γ-methyl-: it can be used to produce 4,4-bis-(4-hydroxy-phenyl)-valeric acid methyl ester by heating. It will need reagent conc. H2SO4 with the reaction time of 3 hours. The yield is about 97%.

Benzenebutanoic acid, 4-hydroxy-γ-(4-hydroxyphenyl)-γ-methyl- can be used to produce 4,4-bis-(4-hydroxy-phenyl)-valeric acid methyl ester by heating

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)CCC(c1ccc(O)cc1)(c2ccc(O)cc2)C
(2)Std. InChI: InChI=1S/C17H18O4/c1-17(11-10-16(20)21,12-2-6-14(18)7-3-12)13-4-8-15(19)9-5-13/h2-9,18-19H,10-11H2,1H3,(H,20,21)
(3)Std. InChIKey: VKOUCJUTMGHNOR-UHFFFAOYSA-N

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