120-07-0

Basic information

• Product Name: 2,2'-(Phenylimino)diethanol
• Synonyms: (bis(2-hydroxyethyl)amino)benzene;2,2’-(phenylamino)diethanol;2,2’-(phenylimino)bis(ethanol);2,2’-(phenylimino)bis-ethano;2,2’-(phenylimino)bis-Ethanol;2,2’-(phenylimino)di-ethano;2-[(2-Hydroxy-ethyl)-phenyl-amino]-ethanol;diethanolaniline
• CAS NO: 120-07-0
• Molecular Formula: C₁₀H₁₅NO₂
• Molecular Weight: 181.23
• EINECS: 204-368-5
• Product Categories: Intermediates of Dyes and Pigments;organic chemical
• Mol File: 120-07-0.mol

Chemical Properties

• Melting Point: 56-58 °C(lit.)
• Boiling Point: 270 °C
• Flash Point: 200 °C
• Appearance: White to brown/Crystalline Mass, Crystals or Chunks
• Density: 1.1
• Vapor Density: >1 (vs air)
• Vapor Pressure: <0.01 mm Hg ( 20 °C)
• Refractive Index: 1.5464 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 3g/l
• PKA: 14.31±0.10(Predicted)
• Water Solubility: 45 g/L (20 ºC)
• Sensitive: Air Sensitive & Hygroscopic
• Stability: Hygroscopic, Light Sensitive
• BRN: 2096832
• CAS DataBase Reference: 2,2'-(Phenylimino)diethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-(Phenylimino)diethanol(120-07-0)
• EPA Substance Registry System: 2,2'-(Phenylimino)diethanol(120-07-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-41-48/20/21/22-37/38
• Safety Statements: 26-39-36/37/39
• WGK Germany: 2
• RTECS: KM2100000
• TSCA: Yes
• Hazardous Substances Data: 120-07-0(Hazardous Substances Data)

Usage

Uses

Used in Hair Coloring Agents:
2,2'-(Phenylimino)diethanol is used as an active ingredient in the hair coloring industry for its ability to effectively impart color to hair while maintaining its health and integrity. Its chemical structure allows for better interaction with hair proteins, ensuring a longer-lasting and more vibrant color result.
Used in Resin Compositions:
In the field of polymer chemistry, 2,2'-(Phenylimino)diethanol is utilized as a key component in the formulation of resin compositions. Its inclusion enhances the resin's properties, such as adhesion, flexibility, and durability, making it suitable for a wide range of applications, including coatings, adhesives, and composite materials.
Used in Cured Film Production:
2,2'-(Phenylimino)diethanol plays a crucial role in the production of cured films, where it acts as a cross-linking agent. This enhances the film's mechanical strength, thermal stability, and resistance to environmental factors, making it ideal for applications in the automotive, electronics, and packaging industries.
Used in Semiconductor Device Manufacturing:
The compound is also employed in the semiconductor industry, where it serves as a critical material in the fabrication of various semiconductor devices. Its unique properties contribute to the improvement of device performance, reliability, and overall efficiency.

Preparation

N-Phenyldiethanolamine is obtained by the addition of aniline and ethylene oxide.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C10H15NO2/c12-8-6-11(7-9-13)10-4-2-1-3-5-10/h1-5,12-13H,6-9H2/p+1

Synthetic route

iodobenzene (591-50-4) + 2,2'-iminobis[ethanol] (111-42-2) → 2,2'-(phenylimino)bis[ethanol] (120-07-0)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 100℃; for 3h;	95%

aniline (62-53-3) + 2-chloro-ethanol (107-07-3) → 2,2'-(phenylimino)bis[ethanol] (120-07-0)

Conditions	Yield
With sodium hydroxide at 100℃; for 72h;	87%
With calcium carbonate; potassium iodide In water for 8h; Reflux;	86%
With calcium carbonate; potassium iodide In water for 8h; Reflux; Inert atmosphere; Schlenk technique;	86%

oxirane (75-21-8) + aniline (62-53-3) → 2,2'-(phenylimino)bis[ethanol] (120-07-0)

Conditions	Yield
With water; propionic acid at 0 - 10℃;	85%
at 80 - 90℃; im Rohr;
at 80 - 90℃;

[1,3]-dioxolan-2-one (96-49-1) + aniline (62-53-3) → 2,2'-(phenylimino)bis[ethanol] (120-07-0) + 2-Anilinoethanol (122-98-5)

Conditions	Yield
With tri-i-butyl(methyl)phosphonium tosylate at 170℃; for 8h; Ionic liquid; Neat (no solvent);	A 74% B n/a
With Na-Y zeolite In Triethylene glycol dimethyl ether at 160℃; for 2h;	A 19% B 63%
In neat (no solvent) at 140℃; for 14h;

methanol (67-56-1) + formaldehyd (50-00-0) + aniline (62-53-3) → 2,2'-(phenylimino)bis[ethanol] (120-07-0) + 2-Anilinoethanol (122-98-5)

Conditions	Yield
With tert.-butylhydroperoxide; titanium(III) chloride at 20℃; for 0.5h; Acidic aq. solution; Inert atmosphere;	A 15% B 30%

phenyliminodiacetic acid diethyl ester (55932-12-2) → 2,2'-(phenylimino)bis[ethanol] (120-07-0)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran Ambient temperature;	26%
With lithium aluminium tetrahydride In tetrahydrofuran at 80℃; for 2h;

2-Amino-6-bromopyridine (19798-81-3) + pyridine-2-boronic acid N-phenyldiethanolamine ester (882521-96-2) → 6-amino-2-2’-pyridylbipyridine (178039-84-4) + 2,2'-(phenylimino)bis[ethanol] (120-07-0)

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran for 24h; Suzuki-Miyaura cross-coupling; Reflux; Inert atmosphere;

6-bromopyridine-3-amine (13534-97-9) + pyridine-2-boronic acid N-phenyldiethanolamine ester (882521-96-2) → 2,2'-(phenylimino)bis[ethanol] (120-07-0) + [2,2’-bipyridin]-5-amine (160539-04-8)

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran for 24h; Suzuki-Miyaura cross-coupling; Reflux; Inert atmosphere;

[1,3]-dioxolan-2-one (96-49-1) + 2-Anilinoethanol (122-98-5) → carbon dioxide (124-38-9) + 2,2'-(phenylimino)bis[ethanol] (120-07-0)

Conditions	Yield
at 140℃; Kinetics; Neat (no solvent); chemospecific reaction;

methanol (67-56-1) + acetone (67-64-1) + N-methylaniline (100-61-8) → 2,2'-(phenylimino)bis[ethanol] (120-07-0) + C11H17NO (1413925-42-4) + N-(2-hydroxyethyl)-N-methylaminobenzene (93-90-3) + 2-Anilinoethanol (122-98-5)

Conditions	Yield
With tert.-butylhydroperoxide; titanium tetrachloride; zinc In water at 20℃; Inert atmosphere;	A n/a B 20 %Spectr. C n/a D n/a

2,2'-(phenylimino)bis[ethanol] (120-07-0) + tert-butyldimethylsilyl chloride (18162-48-6) → N,N-bis[2-[(1-tert-butyl-1,1-diemthylsilyl)oxy]ethyl]-N-phenylamine (148717-08-2)

Conditions	Yield
With 1H-imidazole In dichloromethane for 5h;	100%

2,2'-(phenylimino)bis[ethanol] (120-07-0) + propargyl bromide (106-96-7) → N,N-bis(2-(prop-2-ynyloxy)ethyl)aniline (1202493-52-4)

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In water; toluene at 20℃; for 24h;	100%
With tetrabutylammomium bromide; sodium hydroxide In water; toluene at 20℃; for 3h;	96%
With sodium hydride In N,N-dimethyl-formamide; toluene; mineral oil at 0 - 20℃; for 1h; Inert atmosphere;	72%
With tetrabutylammomium bromide; potassium hydroxide In dimethyl sulfoxide at 60℃; for 24h;	55%
With potassium hydroxide In dimethyl sulfoxide at 50℃; for 120h;

2,2'-(phenylimino)bis[ethanol] (120-07-0) + methanesulfonyl chloride (124-63-0) → N,N-bis<2-<(methylsulfonyl)oxy>ethyl>aniline (22964-38-1)

Conditions	Yield
With triethylamine In chloroform at 0℃; for 1h;	99.6%
With triethylamine In dichloromethane at 20℃; for 1h;	96.4%
With triethylamine In ethyl acetate at 20℃; for 1h;	89%

2,2'-(phenylimino)bis[ethanol] (120-07-0) → 1-bromo-4-benzene (13165-33-8)

Conditions	Yield
With methanol; tetraethylammonium chloride; bromine In dichloromethane at 35℃;	99%
With periodic acid; sodium bromide In water at 20℃; for 0.166667h; regioselective reaction;	93%
With N-Bromosuccinimide In dichloromethane at 20℃; for 24h; Darkness;	89%

2,2'-(phenylimino)bis[ethanol] (120-07-0) + t-butyldimethylsiyl triflate (69739-34-0) → N,N-bis[2-[(1-tert-butyl-1,1-diemthylsilyl)oxy]ethyl]-N-phenylamine (148717-08-2)

Conditions	Yield
With 2,6-dimethylpyridine In dichloromethane at -80 - 20℃; for 1h; silylation;	99%

2,2'-(phenylimino)bis[ethanol] (120-07-0) + acetyl chloride (75-36-5) → bis(2-acetoxyethyl)aniline (19249-34-4)

Conditions	Yield
With triethylamine In tetrahydrofuran at 35℃; for 15h;	99%
With triethylamine In tetrahydrofuran	98%
With triethylamine In dichloromethane at 20 - 25℃; for 2h; Cooling with ice;	96%

2,2'-(phenylimino)bis[ethanol] (120-07-0) + tin(II) n-butoxide (14254-05-8, 26306-46-7, 130287-64-8) → 5-phenyl-(2,8-dioxa-5-aza-1-stanna)bicyclo[3.3.01.5]octane

Conditions	Yield
In toluene Inert atmosphere; Schlenk technique;	99%

4-iodobenzoic acid (619-58-9) + 2,2'-(phenylimino)bis[ethanol] (120-07-0) → C24H21I2NO4 (1436920-32-9)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 3h;	98.8%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 72h;	98.8%

4-iodobenzoic acid (619-58-9) + 2,2'-(phenylimino)bis[ethanol] (120-07-0) → C25H23I2NO3

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 72h;	98.8%

2,2'-(phenylimino)bis[ethanol] (120-07-0) + 5-amino-3-methyl-thiophene-2,4-dicarbonitrile (52603-48-2) → C17H17N5O2S (162245-60-5)

Conditions	Yield
Stage #1: 5-amino-3-methyl-thiophene-2,4-dicarbonitrile With nitrosylsulfuric acid; sulfuric acid; acetic acid; propionic acid at 0 - 5℃; for 1h; Stage #2: 2,2'-(phenylimino)bis[ethanol] With acetic acid In water Cooling with ice; Stage #3: With ammonia In water pH=4;	98%

2,2'-(phenylimino)bis[ethanol] (120-07-0) + benzoyl chloride (98-88-4) → 2-[phenyl(2-benzoyloxyethyl)amino]ethyl benzoate (24867-51-4)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 24h; Acylation;	97%
With triethylamine In dichloromethane at 0℃; for 3h; Acylation;	86%

2,2'-(phenylimino)bis[ethanol] (120-07-0) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 4-(bis(2-chloroethyl)amino)benzaldehyde (1208-03-3)

Conditions	Yield
Stage #1: 2,2'-(phenylimino)bis[ethanol]; N,N-dimethyl-formamide With trichlorophosphate at 0 - 40℃; for 8h; Vilsmeier-Haack formylation; Inert atmosphere; Stage #2: With potassium carbonate In water Cooling with ice;	97%
Stage #1: N,N-dimethyl-formamide With trichlorophosphate In water; N,N-dimethyl-formamide at 0℃; for 0.75h; Stage #2: 2,2'-(phenylimino)bis[ethanol] In water; N,N-dimethyl-formamide at 0 - 110℃; for 2h;	96%
With trichlorophosphate at 90℃; for 2h;	95%

Upstream product

• 75-21-8 oxirane 
• 62-53-3 aniline 
• 107-21-1 ethylene glycol 
• 107-07-3 2-chloro-ethanol 
• 122-98-5 2-Anilinoethanol 
• 55932-12-2 phenyliminodiacetic acid diethyl ester 
• 96-49-1 [1,3]-dioxolan-2-one 
• 626-61-9 4-Chloropyridine 
• 111-42-2 2,2'-iminobis[ethanol] 
• 67-56-1 methanol 
• 50-00-0 formaldehyd 
• 19798-81-3 2-Amino-6-bromopyridine 
• 882521-96-2 pyridine-2-boronic acid N-phenyldiethanolamine ester 
• 13534-97-9 6-bromopyridine-3-amine 

Downstream Products

• 54628-37-4 N'-{4-[bis-(2-hydroxy-ethyl)-amino]-benzylidene}-N,N-bis-(2-hydroxy-ethyl)-p-phenylenediamine 
• 6926-86-9 Di--methan 
• 19249-34-4 bis(2-acetoxyethyl)aniline 
• 24867-51-4 2-[phenyl(2-benzoyloxyethyl)amino]ethyl benzoate 
• 51919-94-9 N,N-bis-(2-propionyloxy-ethyl)-aniline 
• 112578-34-4 N,N-bis-[2-(4-nitro-benzenesulfonyloxy)-ethyl]-aniline 
• 86147-30-0 N,N-bis-(2-vinyloxy-ethyl)-aniline 
• 83090-71-5 N,N-bis-(2-butyryloxy-ethyl)-aniline 
• 52202-97-8 2-methyl-2-oxo-6-phenylperhydro-1,3,6,2-dioxaazaphosphocin 
• 92653-76-4 2,2'-[4-(3,5-dimethyl-isoxazol-4-ylazo)-phenylazanediyl]-bis-ethanol 
• 7178-41-8 N,N-Divinyl-anilin 
• 13105-77-6 2-(N-prop-2-ynyl-anilino)-ethanol 
• 121599-29-9 N-Phenyl-bis-<2-hydroxy-aethyl>-amin-bis- 
• 56152-47-7 2-methyl-6-phenyl-1,3,6,2λ⁵-dioxazaphosphocine 2-sulfide 

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