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N-(2-Hydroxyethyl)acetamide

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Name

N-(2-Hydroxyethyl)acetamide

EINECS 205-530-8
CAS No. 142-26-7 Density 1.052 g/cm3
PSA 49.33000 LogP -0.49430
Solubility Soluble in water, 1e+006 mg/L @ 25°C (est), soluble in alcohol and ether. Melting Point 15.8 °C
Formula C4H9NO2 Boiling Point 291.471 °C at 760 mmHg
Molecular Weight 103.121 Flash Point 151.037 °C
Transport Information N/A Appearance clear viscous white to yellow liquid
Safety 26-36 Risk Codes 36/37/38-41-37/38
Molecular Structure Molecular Structure of 142-26-7 (N-(2-Hydroxyethyl)acetamide) Hazard Symbols IrritantXi
Synonyms

2-Acetamidoethanol;2-Acetylaminoethanol;2-N-Acetylaminoethanol;Acetylcolamine;N-(b-Hydroxyethyl)acetamide;N-Acetyl-2-aminoethanol;N-Acetylethanolamine;N-Ethanolacetamide;b-Hydroxyethylacetamide;

Article Data 73

N-(2-Hydroxyethyl)acetamide Synthetic route

108-21-4

Isopropyl acetate

141-43-5

ethanolamine

142-26-7

2-acetylaminoethanol

Conditions
ConditionsYield
With 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine In acetonitrile at 20℃; for 15h; Schlenk technique; Inert atmosphere;100%
With N,N'-Mes2imidazol-2-ylidene In tetrahydrofuran at 23℃; for 24h;34%
108-24-7

acetic anhydride

141-43-5

ethanolamine

142-26-7

2-acetylaminoethanol

Conditions
ConditionsYield
With Cp2Ti(OSO2C8F17)2 at 20℃; for 0.0166667h; Neat (no solvent);99%
yttria-stabilized zirconia In acetonitrile at 20℃; for 4h;98%
With Methylenediphosphonic acid at 20℃; for 1h; neat (no solvent); chemoselective reaction;96%
79-20-9

acetic acid methyl ester

141-43-5

ethanolamine

142-26-7

2-acetylaminoethanol

Conditions
ConditionsYield
With N,N'-Mes2imidazol-2-ylidene In tetrahydrofuran at 23℃; for 24h;99%
With 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine In acetonitrile at 20℃; for 15h; Schlenk technique; Inert atmosphere;97%
With Merrifield resin-supported N3=P(MeNCH2CH2)3N In tetrahydrofuran at 23 - 25℃; Inert atmosphere;66%
for 6h; Acylation; Heating;
13483-16-4

2,4,6-triacetyloxy-1,3,5-triazine

141-43-5

ethanolamine

142-26-7

2-acetylaminoethanol

Conditions
ConditionsYield
at 25℃; for 0.0833333h; neat (no solvent); chemoselective reaction;99%
19220-93-0

pentafluorophenyl acetate

141-43-5

ethanolamine

142-26-7

2-acetylaminoethanol

Conditions
ConditionsYield
In N,N-dimethyl-formamide98%
In N,N-dimethyl-formamide
141-43-5

ethanolamine

64-19-7

acetic acid

142-26-7

2-acetylaminoethanol

Conditions
ConditionsYield
tetraphosphorus decasulfide; triphenyl antimony oxide at 50℃; for 1h;95%
With zinc(II) oxide for 3h; Reflux; chemoselective reaction;95%
at 180℃;93%
at 160 - 200℃;
141-43-5

ethanolamine

141-78-6

ethyl acetate

142-26-7

2-acetylaminoethanol

Conditions
ConditionsYield
With sodium carbonate In methanol at 60℃; for 24h; Product distribution / selectivity; Reflux;95%
With indium; iodine for 15h; Heating;82%
140-11-4

Benzyl acetate

141-43-5

ethanolamine

142-26-7

2-acetylaminoethanol

Conditions
ConditionsYield
With N,N'-Mes2imidazol-2-ylidene In tetrahydrofuran at 23℃; for 24h;95%
30074-98-7

1-Acetyl-4(1H)-pyridinon

141-43-5

ethanolamine

142-26-7

2-acetylaminoethanol

Conditions
ConditionsYield
In dichloromethane for 0.0833333h; Ambient temperature;85%
76397-53-0

3-acetylthiazolidine-2-thione

141-43-5

ethanolamine

142-26-7

2-acetylaminoethanol

Conditions
ConditionsYield
In dichloromethane at 25℃; for 0.0166667h;83%

N-(2-Hydroxyethyl)acetamide Consensus Reports

Reported in EPA TSCA Inventory.

N-(2-Hydroxyethyl)acetamide Specification

The N-(2-Hydroxyethyl)acetamide, with the CAS registry number 142-26-7, is also known as N-Acetylethanolamine. It belongs to the classification code of Skin / Eye Irritant. Its EINECS registry number is 205-530-8. This chemical's molecular formula is C4H9NO2 and molecular weight is 103.12. What's more, its IUPAC name is the same with its product name. This chemical can be prepared by ethanolamine with methyl acetate. It is mainly used in dye and pharmaceutical synthesis.

Physical properties about N-(2-Hydroxyethyl)acetamide are: (1)ACD/LogP: -1.336; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.34; (4)ACD/LogD (pH 7.4): -1.34; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 4.47; (8)ACD/KOC (pH 7.4): 4.47; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 49.33 Å2; (13)Index of Refraction: 1.438; (14)Molar Refractivity: 25.74 cm3; (15)Molar Volume: 98.004 cm3; (16)Polarizability: 10.204×10-24cm3; (17)Surface Tension: 36.596 dyne/cm; (18)Density: 1.052 g/cm3; (19)Flash Point: 151.037 °C; (20)Enthalpy of Vaporization: 61.601 kJ/mol; (21)Boiling Point: 291.471 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

Preparation of N-(2-Hydroxyethyl)acetamide: this chemical can be prepared by acetic acid anhydride with 2-amino-ethanol. This reaction needs reagent NaOH and solvents propan-2-ol, H2O at ambient temperature. The reaction time is 30 min. The yield is 74 %.

N-(2-Hydroxyethyl)acetamide can be prepared by acetic acid anhydride with 2-amino-ethanol.

Uses of N-(2-Hydroxyethyl)acetamide: it is used to produce other chemicals. For example, it can react with carbon monoxide to get 3-acetyl-oxazolidin-2-one. This reaction needs reagents PdCl2, NaOAc and solvents 1,2-dimethoxy-ethane at ambient temperature. The reaction pressure is 2280.0002 Pa. The yield is 91 %.

N-(2-Hydroxyethyl)acetamide can react with carbon monoxide to get 3-acetyl-oxazolidin-2-one.

When you are dealing with this chemical, you should be very careful. This chemical may cause inflammation to the skin or other mucous membranes and it has serious damage to eyes. It is irritating to eyes, respiratory system and skin. Therefore, you should wear suitable protective clothing. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(NCCO)C
(2) InChI: InChI=1S/C4H9NO2/c1-4(7)5-2-3-6/h6H,2-3H2,1H3,(H,5,7)
(3) InChIKey: PVCJKHHOXFKFRP-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rabbit LD50 skin > 20mL/kg (20mL/kg)   Union Carbide Data Sheet. Vol. 4/21/1967,
rat LD50 oral 26950mg/kg (26950mg/kg)   Journal of the American College of Toxicology. Vol. 12(3), Pg. 225, 1993.

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