3077-13-2

Basic information

• Product Name: N,N-BIS(2-HYDROXYPROPYL)ANILINE
• Synonyms: 1,1'-(PHENYLIMINO)DI-2-PROPANOL;ANILINODI-2-PROPANOL;N,N-BIS(2-HYDROXYPROPYL)ANILINE;1,1’-(phenylimino)bis-2-propano;1,1’-(phenylimino)bis-2-Propanol;1,1’-phenyliminodipropan-2-ol;2-Propanol, 1,1-(phenylimino)bis-;1-[N-(2-hydroxypropyl)anilino]propan-2-ol
• CAS NO: 3077-13-2
• Molecular Formula: C₁₂H₁₉NO₂
• Molecular Weight: 209.28
• EINECS: 221-360-7
• Mol File: 3077-13-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 358.5 °C at 760 mmHg
• Flash Point: 180.2 °C
• Appearance: /
• Density: 1.106 g/cm³
• Refractive Index: 1.5510 to 1.5550
• PKA: 14.44±0.20(Predicted)
• CAS DataBase Reference: N,N-BIS(2-HYDROXYPROPYL)ANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-BIS(2-HYDROXYPROPYL)ANILINE(3077-13-2)
• EPA Substance Registry System: N,N-BIS(2-HYDROXYPROPYL)ANILINE(3077-13-2)

Safety Data

• Hazardous Substances Data: 3077-13-2(Hazardous Substances Data)

Usage

General Description

N,N-BIS(2-HYDROXYPROPYL)ANILINE, also known as bis(2-hydroxypropyl)aniline, is a chemical compound with the formula C15H24N2O2. It is a bifunctional amine and alcohol that is commonly used as an intermediate in the production of polyurethane and epoxy resins. N,N-BIS(2-HYDROXYPROPYL)ANILINE is often utilized as a curing agent in the production of adhesives, coatings, and sealants. It is also used as a surfactant, emulsifier, and corrosion inhibitor in various industrial applications. N,N-BIS(2-HYDROXYPROPYL)ANILINE is considered to be moderately hazardous, and proper safety precautions should be taken when handling this compound.

Synthetic route

aniline (62-53-3) + methyloxirane (75-56-9, 16033-71-9) → 1-anilino-propan-2-ol (3233-06-5) + N-phenyl-bis-(2-hydroxypropyl)amine (3077-13-2)

Conditions	Yield
With zinc(II) bis(tetrafluoroborate) hydrate at 20℃; for 0.333333h; Inert atmosphere; Neat (no solvent);	A 97% B n/a
With ferrocenium(III) tetrafluoroborate In neat (no solvent) at 0 - 25℃; for 7h; regioselective reaction;	A 74% B 19%
With water at 100℃;

1-iodopropan-2-ol (996-21-4) + aniline (62-53-3) → 1-anilino-propan-2-ol (3233-06-5) + N-phenyl-bis-(2-hydroxypropyl)amine (3077-13-2)

Conditions	Yield
With triethylamine In methanol for 4h; Reflux;	A 60% B 2.5%

aniline (62-53-3) + methyloxirane (75-56-9, 16033-71-9) → N-phenyl-bis-(2-hydroxypropyl)amine (3077-13-2)

Conditions	Yield
With 1,4-dioxane at 170℃;

2-chloro-propionic acid methyl ester (17639-93-9) + aniline (62-53-3) → N-phenyl-bis-(2-hydroxypropyl)amine (3077-13-2)

Conditions	Yield
With lithium aluminium tetrahydride Multistep reaction;

1,2-propylene cyclic carbonate (108-32-7) + aniline (62-53-3) → 2,6-dimethyl-4-phenylmorpholine (109605-09-6) + 2-anilino-1-propanol (16955-09-2) + 1-anilino-propan-2-ol (3233-06-5) + 2,5-dimethyl-4-phenylmorpholine (1258887-18-1) + N-phenyl-bis-(2-hydroxypropyl)amine (3077-13-2) + N-(2-hydroxypropyl)-N-(2-hydroxy-1-methylethyl)aniline (129118-34-9)

Conditions	Yield
With tri-n-octyl(methyl)phosphonium bromide at 170℃; for 40h; Ionic liquid; Neat (no solvent);

N-phenyl-bis-(2-hydroxypropyl)amine (3077-13-2) + diisopropoxydivinylsilane (144967-39-5) → 2,2-divinyl-4,8-dimethyl-6-phenyl-1,3-dioxa-6-aza-2-silacyclooctane (144967-47-5)

Conditions	Yield
With sodium methylate In 1,4-dioxane; methanol Heating;	50%

N-phenyl-bis-(2-hydroxypropyl)amine (3077-13-2) + acetone (67-64-1) → 2,2,4,8-Tetramethyl-6-phenyl-[1,3,6]dioxazocane

Conditions	Yield
With 3 A molecular sieve In dichloromethane Ambient temperature;	42%

phosgene (75-44-5) + N-phenyl-bis-(2-hydroxypropyl)amine (3077-13-2) → 4,8-Dimethyl-6-phenyl-5,6,7,8-tetrahydro-4H-1,3,6-dioxazocin-2-one (93371-13-2) + 4,8-Dimethyl-6-phenyl-5,6,7,8-tetrahydro-4H-1,3,6-dioxazocin-2-one (93371-13-2, 93371-14-3)

Conditions	Yield
With pyridine In ethyl acetate	A 19% B 26%

formaldehyd (50-00-0) + N-phenyl-bis-(2-hydroxypropyl)amine (3077-13-2) → bis-{4-[bis-(2-hydroxy-propyl)-amino]-phenyl}-methane (13364-26-6)

Conditions	Yield
With hydrogenchloride; ethanol

N-phenyl-bis-(2-hydroxypropyl)amine (3077-13-2) → 2,6-dimethyl-4-phenylmorpholine (109605-09-6)

Conditions	Yield
With sulfuric acid at 160℃;

N-phenyl-bis-(2-hydroxypropyl)amine (3077-13-2) → 2,6-dimethyl-4-[4-(4-nitro-phenylazo)-phenyl]-morpholine (101741-62-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2SO4 / 160 °C View Scheme

Upstream product

• 62-53-3 aniline 
• 75-56-9 methyloxirane 
• 17639-93-9 2-chloro-propionic acid methyl ester 
• 108-32-7 1,2-propylene cyclic carbonate 
• 996-21-4 1-iodopropan-2-ol 

Downstream Products

• 13364-26-6 bis-{4-[bis-(2-hydroxy-propyl)-amino]-phenyl}-methane 
• 109605-09-6 2,6-dimethyl-4-phenylmorpholine 
• 93371-13-2 4,8-Dimethyl-6-phenyl-5,6,7,8-tetrahydro-4H-1,3,6-dioxazocin-2-one 
• 93371-13-2 4,8-Dimethyl-6-phenyl-5,6,7,8-tetrahydro-4H-1,3,6-dioxazocin-2-one 
• 144967-47-5 2,2-divinyl-4,8-dimethyl-6-phenyl-1,3-dioxa-6-aza-2-silacyclooctane 

Relevant articles and documents

Fe(Cp)2BF4: An efficient lewis acid catalyst for the aminolysis of epoxides

Ferrocenium tetrafluoroborate [Fe(Cp)2BF4] is an efficient Lewis acid catalyst for the aminolysis of aromatic, aliphatic, and cyclic epoxides using aniline and substituted anilines as the nucleophile to provide regioselective β-amino alcohols in 61-97% yields under solvent-free conditions at room temperature. The ring opening of cyclohexene oxide with aliphatic amines gave 2-aminocyclohexanols in 33-98% yields at 60 °C under solvent-free conditions. Georg Thieme Verlag Stuttgart New York.

The reaction of primary aromatic amines with alkylene carbonates for the selective synthesis of bis-N-(2-hydroxy)alkylanilines: The catalytic effect of phosphonium-based ionic liquids

At T ≥ 140 °C, different primary aromatic amines (pX-C 6H4NH2; X = H, OCH3, CH3, Cl) react with both ethylene- and propylene-carbonates to yield a chemoselective N-alkylation process: bis-N-(2-hydroxyalkyl)anilines [pX-C 6H4N(CH2CH(R)OH)2; R = H, CH 3] are the major products and the competitive formation of carbamates is substantially ruled out. At 140 °C, under solventless conditions, the model reaction of aniline with ethylene carbonate goes to completion by simply mixing stoichiometric amounts of the reagents. However, a class of phosphonium ionic liquids (PILs) such as tetraalkylphosphonium halides and tosylates turn out to be active organocatalysts for both aniline and other primary aromatic amines. A kinetic analysis monitored by 13C NMR spectroscopy, shows that bromide exchanged PILs are the most efficient systems, able to impart a more than 8-fold acceleration to the reaction. The reactions of propylene carbonate take place at a higher temperature than those of ethylene carbonate, and only in the presence of PIL catalysts. A mechanism based on the Lewis acidity of tetraalkylphosphonium cations and the nucleophilicity of halide anions has been proposed to account for both the reaction chemoselectivity and the function of the catalysts.

The Stereochemical Investigation of 8-Membered 1,3,6-Dioxazocines via NMR

The stereochemical properties of 2-,4-,7-, and 8-methyl substituted 5,6,7,8-tetrahydro-1,3,6-dioxazocines have been investigated by their pmr and cmr spectroscopy.On the basis of the coupling constants and γ-effects, the stereochemical structures are discussed.