2,2-Bis(3-amino-4-hydroxyphenyl)propane Chemical Properties

Melting point:

248-250 °C

Boiling point:

471.1±45.0 °C(Predicted)

Density 

1.265±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

soluble in Dimethylformamide

form 

powder to crystal

pka

10.62±0.10(Predicted)

color 

White to Yellow to Orange

InChI

InChI=1S/C15H18N2O2/c1-15(2,9-3-5-13(18)11(16)7-9)10-4-6-14(19)12(17)8-10/h3-8,18-19H,16-17H2,1-2H3

InChIKey

UHIDYCYNRPVZCK-UHFFFAOYSA-N

SMILES

C(C1=CC=C(O)C(N)=C1)(C1=CC=C(O)C(N)=C1)(C)C

CAS DataBase Reference

1220-78-6(CAS DataBase Reference)

Safety Information

HS Code 

29222990

2,2-Bis(3-amino-4-hydroxyphenyl)propane Usage And Synthesis

Uses

4,4'-(Propane-2,2-diyl)bis(2-aminophenol) is a useful research chemical.

Description

2,2-Bis(3-amino-4-hydroxyphenyl)propane (BAP) is a diamine organic compound that is used in the synthesis of polyimides.

Uses

2,2-bis(4-hydroxy-3-aminophenyl)propane is used as a polyimide intermediate and functional monomer.

Hazard

2, 2-bis (3-amino-4-hydroxyphenyl)propane is irritating to the eyes and skin and may cause severe eye irritation.

Synthesis

Thedinitro compound (2) (10,000 g, 0.0314 mol) was heated to reflux inabsolute ethanol (100 mL) in the presence of wet 10% Pd/C catalyst(0.650 g). Hydrazine monohydrate (20 mL) was then added dropwiseover a period of 30 min, and the reaction was maintained at reflux for24 h. The hot solution was filtered through Celite to eliminate thecatalyst and partially concentrated under reduced pressure. Afterwards,the concentrate was poured into cold distilled water. The crude productwas filtered, washed with water, dried under vacuum and recrystallizedtwice from methanol to give (3). The diamino compound was obtainedas a white powder: yield: 88%; mp. 263 ??C (DSC); Analysis: Calculatedfor C15H18N2O2: C, 69.74%; H, 7.02%; N, 10.84%. Found: C, 69.35%;H, 7.15%; N, 11.02%. 1H NMR (400 MHz, DMSO-d6): |? (ppm); 8.57 (s,1H, OH), 6.43 (d, J=8.1 Hz, 1H, Har), 6.34 (d, J=1.8 Hz, 1H, Har),6.21 (dd, J=8.1 Hz, 1.8 Hz, 1H, Har), 4.23 (s, 2H, NH) 1.37 (s, 3H, CH3f). 13C NMR (100 MHz, DMSO-d6): |? (ppm) 142.4, 141.4, 135.4, 114.4,113.5, 113.4, 40.8, 30.9.

References

[1] Reactive and Functional Polymers, 2018, vol. 127, p. 38 - 47
[2] Chem. Zentralbl., 1904, vol. 75, # II, p. 1737
[3] Journal of the Chemical Society, 1953, p. 2612

2,2-Bis(3-amino-4-hydroxyphenyl)propane(1220-78-6)Related Product Information

• Tris(hydroxymethyl)aminomethane
• Glycine
• Lithium bis(trimethylsilyl)amide
• 3,4'-DIAMINODIPHENYLMETHANE
• Acetaminophen
• EC 2.6.1.2
• 6-Aminocaproic acid
• ALTRENOGEST
• Propane
• 2,2-Bis(3-amino-4-hydroxyphenyl)hexafluoropropane
• 4,4-BIS-(4-HYDROXY-3-NITROPHENYL)-VALERIC ACID
• 9,9-BIS(3-AMINO-4-HYDROXYPHENYL)FLUORENE
• 2,2-Bis(3-amino-4-hydroxyphenyl)propane
• AMINO ACIDS
• 4,4'-(HEXAFLUOROISOPROPYLIDENE)-2,2'-DINITRO-DIPHENOL
• 2,6-DINITRO-4-(2,2,2-TRIFLUORO-1-(4-HYDROXY-3-NITRO-PHENYL)-1-TRIFLUOROMETHYL-ETHYL)-PHENOL
• 2-ALLYL-4-(1-(3-ALLYL-4-HYDROXY-5-NITROPHENYL)-1-METHYLETHYL)-6-NITROPHENOL
• Hydroxyphenyl