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2210-25-5

Basic Information
CAS No.: 2210-25-5
Name: 2-Propenamide,N-(1-methylethyl)-
Article Data: 26
Cas Database
Molecular Structure:
Molecular Structure of 2210-25-5 (2-Propenamide,N-(1-methylethyl)-)
Formula: C6H11NO
Molecular Weight: 113.159
Synonyms: Acrylamide,N-isopropyl- (6CI,7CI,8CI);Isopropylacrylamide;N-(1-Methylethyl)-2-propenamide;
EINECS: 218-638-5
Density: 0.877 g/cm3
Melting Point: 60-63 °C(lit.)
Boiling Point: 225.074 °C at 760 mmHg
Flash Point: 119.664 °C
Solubility: Slightly soluble in water.
Appearance: white to light yellow crystalline powder
Hazard Symbols: HarmfulXn
Risk Codes: 22-36-36/37/38
Safety: 26-36/37/39
Transport Information: N/A
PSA: 29.10000
LogP: 1.08790
Synthetic route

β-methoxy-N-isopropylpropionic acid amide

2210-25-5

N-Isopropylacrylamide

Conditions
ConditionsYield
With 10H-phenothiazine; copper(II) bis(trifluoromethanesulfonate) at 140℃; for 8h; Inert atmosphere;94%
107-13-1

acrylonitrile

67-63-0

isopropyl alcohol

2210-25-5

N-Isopropylacrylamide

Conditions
ConditionsYield
H-ZSM-5 at 149.85℃; for 24h; Product distribution; Further Variations:; Catalysts; Addition;90.3%
With sulfuric acid; tetrabutyl-ammonium chloride; hydroquinone In water at 20 - 50℃; for 1h; Large scale; Green chemistry;82.3%
With sulfuric acid; acetic acid
With sulfuric acid at 5℃; for 20h;
With hydroquinone; H-ZSM-5 at 149.85℃; Product distribution; Further Variations:; Catalysts;

C9H19NO2

2210-25-5

N-Isopropylacrylamide

Conditions
ConditionsYield
With 4-methoxy-phenol; lithium tert-butoxide In glycerol at 230℃; Pyrolysis;90%

β-isopropylamino-N-isopropylpropionic acid amide

2210-25-5

N-Isopropylacrylamide

Conditions
ConditionsYield
With copper(II) bis(trifluoromethanesulfonate); 4-methoxy-phenol at 145℃; for 6h; Inert atmosphere;82%
With sulfuric acid; 4-methoxy-phenol at 180 - 220℃; under 450.045 Torr; for 6h; Reagent/catalyst;
With S2O3C; styrylated-N - aminobiphenyl(DDA) at 140℃; under 52.5053 Torr; for 36h; Inert atmosphere; Ionic liquid;
75-31-0

isopropylamine

79-10-7

acrylic acid

2210-25-5

N-Isopropylacrylamide

Conditions
ConditionsYield
tetraphosphorus decasulfide; triphenyl antimony oxide In benzene at 50℃; for 6h;56%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h;54%
With aluminum oxide at 260℃;
(i) 4-diethylamino-but-3-yn-2-one, THF, (ii) /BRN= 605259/; Multistep reaction;
With carbon monoxide; acetone; acetylene Reagens 4:Tetracarbonylnickel;
75-31-0

isopropylamine

503-66-2

3-hydroxypropionic acid

A

2210-25-5

N-Isopropylacrylamide

B

79-10-7

acrylic acid

Conditions
ConditionsYield
silica gel at 250℃; Gas phase;A 24.1%
B 36.4%
75-31-0

isopropylamine

292638-85-8

acrylic acid methyl ester

2210-25-5

N-Isopropylacrylamide

Conditions
ConditionsYield
With aluminum oxide; phosphoric acid at 400℃;
22813-48-5

3-chloro-propionic acid isopropylamide

121-44-8

triethylamine

2210-25-5

N-Isopropylacrylamide

Conditions
ConditionsYield
With copper at 140℃;
107-13-1

acrylonitrile

2210-25-5

N-Isopropylacrylamide

Conditions
ConditionsYield
With sulfuric acid
57934-24-4

N-allyl-N-isopropyl-acrylamide

2210-25-5

N-Isopropylacrylamide

Conditions
ConditionsYield
With palladium dichloride Heating;
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    Product Name N-Isopropylacrylamide CAS 2210-25-5 MF C6H11NO MW 113.16 EINECS 218-638-5 Mol File 2210-25-5.mol

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The N-Isopropylacrylamide, with the CAS registry number 2210-25-5, is also known as 2-Propenamide, N-(1-methylethyl)-. It belongs to the product categories of Acrylamide and Methacrylamide; Acrylic Monomers; Monomers. Its EINECS registry number is 218-638-5. This chemical's molecular formula is C6H11NO and molecular weight is 113.16. What's more, its IUPAC name is called N-Propan-2-ylprop-2-enamide. It should be stored in a cool, dry and well-ventilated place.

Physical properties about N-Isopropylacrylamide are: (1)ACD/LogP: 0.278; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.28; (4)ACD/LogD (pH 7.4): 0.28; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 33.74; (8)ACD/KOC (pH 7.4): 33.74; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 29.1 Å2; (13)Index of Refraction: 1.428; (14)Molar Refractivity: 33.155 cm3; (15)Molar Volume: 128.982 cm3; (16)Polarizability: 13.144×10-24cm3; (17)Surface Tension: 25.651 dyne/cm; (18)Density: 0.877 g/cm3; (19)Flash Point: 119.664 °C; (20)Enthalpy of Vaporization: 46.159 kJ/mol; (21)Boiling Point: 225.074 °C at 760 mmHg; (22)Vapour Pressure: 0.088 mmHg at 25 °C.

Preparation of N-Isopropylacrylamide: this chemical can be prepared by isopropylamine with acrylic acid. This reaction needs catalyzer Ph3SbO/P4S10 and solvent benzene at temperature of 50 °C. The reaction time is 6 hours. The yield is 56 %.

 N-Isopropylacrylamide can be prepared by isopropylamine with acrylic acid.

Uses of N-Isopropylacrylamide: (1) it is used for producing modified latex, special coatings, adhesive; (2) it is used to produce other chemicals. For example, it can react with vinylbenzene to get N-isopropyl-trans-cinnamamide. The reaction occurs with reagent RuCHPhCl2(PCy3)(1,3-dimesityl-4,5-dihydroimidazol-2-ylidene) and solvent CH2Cl2 at temperature of 40 °C. The reaction time is 15 hours. The yield is 62 %.

N-Isopropylacrylamide can react with vinylbenzene to get N-isopropyl-trans-cinnamamide.

When you are dealing with this chemical, you should be very careful. This chemical may cause damage to health and it is harmful if swallowed. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. 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: CC(C)NC(=O)C=C
(2) InChI: InChI=1S/C6H11NO/c1-4-6(8)7-5(2)3/h4-5H,1H2,2-3H3,(H,7,8)
(3) InChIKey: QNILTEGFHQSKFF-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 419mg/kg (419mg/kg)   Archives of Toxicology. Vol. 47, Pg. 179, 1981.
mouse LDLo intraperitoneal 500mg/kg (500mg/kg)   "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 6, Pg. 51, 1954.
rabbit LDLo skin 1580mg/kg (1580mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BLOOD: HEMORRHAGE
National Technical Information Service. Vol. OTS0545572,
rat LD50 oral 375mg/kg (375mg/kg) BLOOD: HEMORRHAGE

PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
National Technical Information Service. Vol. OTS0545572,