2210-25-5

Basic information

• Product Name: N-Isopropylacrylamide
• Synonyms: Acrylamide, N-isopropyl.;N-Isopropylacrylamide, stabilized, pure, 99%;N-Isopropylacrylamide ,99% [pure,stabilized];N-ISOPROPYLACRYLAMIDE, 99%, STABILIZED, PURE;NIPAAm;n-isopropylacrylamide ,98% [pure,stabilized];N-isopropylacrylamide ,99%;N-Isopropylacrylamide ,99% [stabilized]
• CAS NO: 2210-25-5
• Molecular Formula: C₆H₁₁NO
• Molecular Weight: 113.16
• EINECS: 218-638-5
• Product Categories: Acrylamide and Methacrylamide;Acrylic Monomers;Monomers
• Mol File: 2210-25-5.mol
• Article Data: 15

Chemical Properties

• Melting Point: 60-63 °C(lit.)
• Boiling Point: 89-92 °C2 mm Hg(lit.)
• Flash Point: 119.664 °C
• Appearance: White to light yellow/Crystalline Powder or Crystals
• Density: 1.0223 (rough estimate)
• Vapor Pressure: 0.076mmHg at 25°C
• Refractive Index: 1.4210 (estimate)
• Storage Temp.: 0-6°C
• PKA: 14.83±0.46(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: N-Isopropylacrylamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Isopropylacrylamide(2210-25-5)
• EPA Substance Registry System: N-Isopropylacrylamide(2210-25-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36-36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• RTECS: AS3675000
• TSCA: Yes
• Hazardous Substances Data: 2210-25-5(Hazardous Substances Data)

Usage

Description

N-Isopropylacrylamide (NIPAM) is a biocompatible monomeric unit that can be used in the formation of stimuli responsive polymers due to its temperature sensitive properties, which include temperature-based volumetric and phase changes. These properties change when the temperature of the solution reaches a lower critical solution temperature (LCST).

Chemical Properties

white to light yellow crystalline powder or

Uses

Different sources of media describe the Uses of 2210-25-5 differently. You can refer to the following data:
1. NIPAM can be used to prepare poly(NIPAM) for a variety of applications such as tissue engineering, cell culture, biomedical coating, drug delivery, and muscle regeneration.
2. Binders in textiles, paper, adhesives, detergents, cosmetics.N-Isopropylacrylamide is used to produce poly(N-isopropylacrylamide) (pNIPA, pNIPAAm, pNIPAA or pNIPAm) thermo sensitive polymer- or copolymer-based hydrogels. Polymers that contain NIPAM shrink dramatically above 33°C. Monomer used in the preparation of thermally sensitive, water-swellable hydrogels.

Application

N-Isopropylacrylamide (NIPAM) can be used to prepare poly(NIPAM) based thermosetting polymers, which can be used for a variety of applications such as tissue engineering, cell culture, biomedical coating, drug delivery, and muscle regeneration.Monomer used in the preparation of thermally sensitive, water-swellable hydrogels.

General Description

N-Isopropylacrylamide (NIPAM) is a biocompatible monomeric unit that can be used in the formation of stimuli responsive polymers due to its temperature sensitive properties. These properties include temperature based volumetric and phase changes, which change when the temperature of the solution reaches a lower critical solution temperature (LCST).

Flammability and Explosibility

Notclassified

Purification Methods

Fractionate the amide under reduced pressure, and recrystallise the solid distillate from hexane (m 59o), *C6H6 (m 62o) or *C6H6/hexane (m 62-63o). Store it with 0.05% of 4-tert-butylcatechol. It is used for making water soluble swellable hydrogels. [Beilstein 4 IV 517.]

InChI:InChI=1/C6H11NO/c1-4(2)5(3)6(7)8/h4H,3H2,1-2H3,(H2,7,8)

Synthetic route

β-methoxy-N-isopropylpropionic acid amide → N-Isopropylacrylamide (2210-25-5)

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

acrylonitrile (107-13-1) + isopropyl alcohol (67-63-0) → N-Isopropylacrylamide (2210-25-5)

Conditions	Yield
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 → N-Isopropylacrylamide (2210-25-5)

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

β-isopropylamino-N-isopropylpropionic acid amide → N-Isopropylacrylamide (2210-25-5)

Conditions	Yield
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;

isopropylamine (75-31-0) + acrylic acid (79-10-7) → N-Isopropylacrylamide (2210-25-5)

Conditions	Yield
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;

isopropylamine (75-31-0) + 3-hydroxypropionic acid (503-66-2) → N-Isopropylacrylamide (2210-25-5) + acrylic acid (79-10-7)

Conditions	Yield
silica gel at 250℃; Gas phase;	A 24.1% B 36.4%

isopropylamine (75-31-0) + acrylic acid methyl ester (292638-85-8) → N-Isopropylacrylamide (2210-25-5)

Conditions	Yield
With aluminum oxide; phosphoric acid at 400℃;

3-chloro-propionic acid isopropylamide (22813-48-5) + triethylamine (121-44-8) → N-Isopropylacrylamide (2210-25-5)

Conditions	Yield
With copper at 140℃;

propene (187737-37-7) + acrylonitrile (107-13-1) → N-Isopropylacrylamide (2210-25-5)

Conditions	Yield
With sulfuric acid

N-allyl-N-isopropyl-acrylamide (57934-24-4) → N-Isopropylacrylamide (2210-25-5)

Conditions	Yield
With palladium dichloride Heating;

3-isopropylamino-propionic acid isopropylamide → N-Isopropylacrylamide (2210-25-5)

Conditions	Yield
With aluminum oxide; vanadia at 350℃;

isopropylamine (75-31-0) + acryloyl chloride (814-68-6) → N-Isopropylacrylamide (2210-25-5)

Conditions	Yield
In dichloromethane

acrylic acid (79-10-7) → N-Isopropylacrylamide (2210-25-5)

C11H17NO → N-Isopropylacrylamide (2210-25-5)

Conditions	Yield
With 4-methoxy-phenol at 400 - 440℃; under 30.003 - 60.006 Torr; Pyrolysis;

C20H21NO → N-Isopropylacrylamide (2210-25-5)

Conditions	Yield
With iron(III) chloride; 10H-phenothiazine at 170 - 180℃;	6.6 g

N-Isopropylacrylamide (2210-25-5) → poly(N-isopropylacrylamide)

Conditions	Yield
With 2-dimethylbismuthanyl-2-methyl-propionitrile; 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide at 60℃; for 2h; Product distribution / selectivity;	100%
With methyl 2-dimethylbismuthanyl-2-methylpropanoate In N,N-dimethyl-formamide at 60℃; for 6h; Product distribution / selectivity;	99%
With methyl 2-dimethylbismuthanyl-2-methylpropanoate In N,N-dimethyl-formamide at 100℃; for 8h; Product distribution / selectivity;	94%

N-Isopropylacrylamide (2210-25-5) → poly(N-isopropylacrylamide), number-average molecular weight 2.95E4, polydispersity 1.82, tacticity m/r 81/19, reversible addition-fragmentation chain transfer polymerization; monomer(s): N-isopropylacrylamide

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); 1-Phenylethyl phenyldithioacetate; yttrium(III) trifluoromethanesulfonate In methanol; toluene at 60℃; for 4h; Kinetics; Product distribution; Further Variations:; Reagents; Solvents;	100%

N-Isopropylacrylamide (2210-25-5) + 5-chloro-1H-indole (17422-32-1) → 3-(5-chloro-1H-indol-1-yl)-N-isopropylpropanamide

Conditions	Yield
With potassium hydroxide In 1,4-dioxane at 50℃;	100%

6-chloroindole (17422-33-2) + N-Isopropylacrylamide (2210-25-5) → 3-(6-chloro-1H-indol-1-yl)-N-isopropylpropanamide

Conditions	Yield
With potassium hydroxide In 1,4-dioxane at 50℃;	100%

N-Isopropylacrylamide (2210-25-5) → N-(isopropyl)propionamide (10601-63-5)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 2585.81 Torr; for 15h; Autoclave;	99%
With (1+)*OTf(1-); Gantrez 149; bis[(2-diphenylphosphino)ethyl]amine hydrochloride; hydrogen at 25℃; 1.) CH3CN, 10 h; 2.) H2O;	94%
With 1-methyl-pyrrolidin-2-one; hydrogen; polymer-bound Pd(0) phosphine catalyst at 20℃;
With Pd*apo-ferritin; hydrogen In water-d2 at 7℃; for 1h; pH=7.5;
With hydrogen In water; toluene for 2.5h; pH=3 - 7;	>= 99 %Chromat.

N-Isopropylacrylamide (2210-25-5) → poly(N-isopropylacrylamide); monomer(s): N-isopropylacrylamide

Conditions	Yield
With 2-methyl-2-methyltellanyl-propionitrile; 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide at 60℃; for 3h;	99%
With ammonium persulfate; N,N'-Methylenebisacrylamide; N,N,N,N,-tetramethylethylenediamine at 4℃; for 8h; polymerization;	82%
With 2,2'-azobis(isobutyronitrile) In benzene at 60℃; for 1h;

N-Isopropylacrylamide (2210-25-5) → poly(N-isopropylacrylamide), Mn=13400, PDI=1.06; monomer(s): N-isopropylacrylamide

Conditions	Yield
With 2-dimethylstibanyl-2-methylpropionic acid ethyl ester; 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide at 60℃; for 12h;	99%

N-Isopropylacrylamide (2210-25-5) → poly(N-isopropylacrylamide), Mn=26700, PDI=1.09; monomer(s): N-isopropylacrylamide

Conditions	Yield
With 2-dimethylstibanyl-2-methylpropionic acid ethyl ester; 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide at 60℃; for 12h;	99%

N-Isopropylacrylamide (2210-25-5) → Reaxys ID: 11387996

Conditions	Yield
With ethyl 2-methyl-2-methyl tellurium propionate; 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide at 60℃; for 6h; Product distribution / selectivity;	99%
With 2,2'-azobis(isobutyronitrile); 2-dimethylstibanyl-2-methylpropionic acid ethyl ester at 60℃; for 12h; Product distribution / selectivity; Neat (no solvent);	99%
With 2,2'-azobis(isobutyronitrile); 2-dimethylstibanyl-2-methylpropionic acid ethyl ester at 60℃; for 12h; Product distribution / selectivity; Neat (no solvent);	99%
With 2,2'-azobis(isobutyronitrile) In methanol at 65℃;

poly(vinyl pyrrolidone) + N-Isopropylacrylamide (2210-25-5) → Reaxys ID: 15741930

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) at 60℃; for 6h; Neat (no solvent);	99%

poly(styrene) + N-Isopropylacrylamide (2210-25-5) → Reaxys ID: 15741865

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide at 60℃; for 6h;	99%

N-Isopropylacrylamide (2210-25-5) + phenylacetylene (536-74-3) → N-isopropyl-5-phenyl-4-pentynamide (1453502-79-8)

Conditions	Yield
With C29H26N2O5Ru; sodium acetate In 1,4-dioxane at 100℃; for 96h; Inert atmosphere;	99%

N-Isopropylacrylamide (2210-25-5) + toluene-4-sulfonic acid hydrazide (1576-35-8) → N-isopropyl-3-tosylpropanamide

Conditions	Yield
In water at 65℃; for 24h; Green chemistry;	99%

N-Isopropylacrylamide (2210-25-5) + Diphenylphosphine oxide (4559-70-0) → C18H22NO2P

Conditions	Yield
With (1S,2S)-1,2-Cy[NC(Me)CHC(Me)N(2,6-Et2C6H3)]2YN(SiMe3)2 In toluene at 20℃; for 1h; Schlenk technique; Inert atmosphere; regioselective reaction;	99%

N-Isopropylacrylamide (2210-25-5) → poly(N-isopropylacrylamide), tacticity - meso diad 71 percent, racemo diad 29 percent, radical polymerization, hot water insoluble; monomer(s): N-isopropylacrylamide

Conditions	Yield
With air; tributyl borane; yttrium(III) trifluoromethanesulfonate In methanol at -78℃; for 24h;	98%

N-Isopropylacrylamide (2210-25-5) → poly(N-isopropylacrylamidde), obtained by radical polymerization; monomer(s): N-isopropylacrylamide

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); ytterbium(III) triflate In methanol at 60℃;	98%

N-Isopropylacrylamide (2210-25-5) → poly(N-isopropylacrylamide), tacticity - meso diad 84 percent, racemo diad 16 percent, radical polymerization, hot water insoluble; monomer(s): N-isopropylacrylamide

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); lutetium triflate In methanol at 60℃; for 3h;	97%

N-Isopropylacrylamide (2210-25-5) → poly(N-isopropylacrylamide), number-average molecular weight 1.83E4, polydispersity 1.76, tacticity m/r 87/13, reversible addition-fragmentation chain transfer polymerization; monomer(s): N-isopropylacrylamide

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); 1-phenylethynyl phenyldithioacetate; ytterbium(III) triflate In methanol; toluene at 30℃; for 24h; Irradiation;	97%

N-Isopropylacrylamide (2210-25-5) + 2-phenylprop-2-yl phenyldithioacetate (377725-60-5) → polymer, Mn = 5.98E4, Mw/Mn = 1.85; monomer(s): N-isopropylacrylamide; cumyl phenyldithioacetate

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); yttrium(III) trifluoromethanesulfonate In methanol; toluene for 6h; Heating;	97%

N-Isopropylacrylamide (2210-25-5) + vinyl azlactone (29513-26-6) → poly[(N-isopropyl acrylamide)-co-(vinyl azalactone)], Mw 5.1E5 Da by viscosimetry; monomer(s): N-isopropyl acrylamide, ca. 80 percent; 2-vinyl-4,4-dimethyl-2-oxazoline-5-one, ca. 20 percent

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In tert-butyl alcohol at 70℃; for 20h;	96%

N-Isopropylacrylamide (2210-25-5) + vinyl azlactone (29513-26-6) → poly[(N-isopropyl acrylamide)-co-(vinyl azlactone)], Mw 5.1E5 Da by viscosimetry in THF at 30 deg C; monomer(s): N-isopropyl acrylamide, ca. 80 mol percent; 2-vinyl-4,4-dimethyl-2-oxazolin-5-one, ca. 20 mol percent

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In tert-butyl alcohol at 70℃; for 20h;	96%

N-Isopropylacrylamide (2210-25-5) + t-butyl diazoacetate (35059-50-8) → tert-butyl 2-isopropylaminocarbonyl-cyclopropanecarboxylate

Conditions	Yield
dmap In chlorobenzene at 20℃; for 20h;	96%
dmap; CoII(3,5-DitBu-ChenPhyrin) In chlorobenzene at 20℃; for 20h; Product distribution / selectivity; Inert atmosphere;	96%

poly(methyl methacrylate) + N-Isopropylacrylamide (2210-25-5) → Reaxys ID: 15741850

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide at 60℃; for 3h;	96%

N-Isopropylacrylamide (2210-25-5) + C31H56NS3(1+)*Cl(1-) (1219699-13-4) → C181H331N26O25S3(1+)*Cl(1-)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide at 65℃; for 5h; Inert atmosphere;	96%

N-Isopropylacrylamide (2210-25-5) + Cyclopentamine (1003-03-8) → C11H22N2O (1001346-58-2)

Conditions	Yield
In methanol at 140℃; for 0.5h; Microwave irradiation;	96%

N-Isopropylacrylamide (2210-25-5) + phosphonic acid diethyl ester (762-04-9) → diethyl 3-(isopropylamino)-3-oxopropylphosphonate (1446473-49-9)

Conditions	Yield
With C26H53N4NdSi4 at 20℃; for 0.333333h; Inert atmosphere;	96%

N-Isopropylacrylamide (2210-25-5) + para-iodoanisole (696-62-8) → N-(1-methylethyl)-3-(4-methoxyphenyl)-(E)-propenamide (132638-37-0)

Conditions	Yield
With sodium carbonate In N,N-dimethyl acetamide; water at 130℃; for 2h; Heck Reaction;	96%
With sodium carbonate In N,N-dimethyl acetamide; water at 125℃; for 4h; Heck Reaction; Sealed tube;	92%

iodobenzene (591-50-4) + N-Isopropylacrylamide (2210-25-5) → N-isopropylcinnamamide (23784-47-6)

Conditions	Yield
With tetrabutylammomium bromide; triethylamine In water at 100℃; for 17h; Heck Reaction;	96%
With triethylamine In N,N-dimethyl-formamide at 130℃; for 5h; Heck Reaction;	95%
With sodium carbonate In N,N-dimethyl acetamide; water at 130℃; for 5h; Heck Reaction; Inert atmosphere;	94%
With triethylamine In N,N-dimethyl-formamide at 120℃; for 2h; Heck Reaction;	70%

N-Isopropylacrylamide (2210-25-5) → poly(N-isopropylacrylamide), tacticity - meso diad 67 percent, racemo diad 33 percent, radical polymerization, hot water insoluble; monomer(s): N-isopropylacrylamide

Conditions	Yield
With ytterbium(III) chloride; 2,2'-azobis(isobutyronitrile) In methanol at 60℃; for 3h;	95%

N-Isopropylacrylamide (2210-25-5) + acrylic acid (79-10-7) + 2-methyl-butyl acrylate (97-88-1) → polymer, linear, MW ca. 49000; monomers: N-isopropylacrylamide, 85 mol percent; butyl-methacrylate, 5 mol percent; acrylic acid, 10 mol percent

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In tetrahydrofuran at 60℃; for 24h;	95%

Upstream product

• 75-31-0 isopropylamine 
• 292638-85-8 acrylic acid methyl ester 
• 79-10-7 acrylic acid 
• 22813-48-5 3-chloro-propionic acid isopropylamide 
• 121-44-8 triethylamine 
• 187737-37-7 propene 
• 107-13-1 acrylonitrile 
• 503-66-2 3-hydroxypropionic acid 
• 814-68-6 acryloyl chloride 
• 57934-24-4 N-allyl-N-isopropyl-acrylamide 
• 67-63-0 isopropyl alcohol 

Downstream Products

• 23784-47-6 (2E)-N-isopropyl-3-phenylacrylamide 
• 159534-85-7 N-isopropyl 2-nitrocinnamide 
• 75-31-0 isopropylamine 
• 79-10-7 acrylic acid 
• 1638610-63-5 2-(2-benzoylbenzofuran-3-yl)-N-isopropylpropanamide 
• 23784-47-6 N-isopropylcinnamamide 
• 23784-75-0 C₁₃H₁₇NO₂ 

Relevant articles and documents

A ritter-type reaction over H-ZSM-5: Synthesis of N-isopropylacrylamide from acrylonitrile and isopropyl alcohol

Catalytic synthesis of N-isopropylacrylamide from acrylonitrile and isopropyl alcohol has been studied using a variety of solid acids in a solid-liquid reaction system at 423 K. Among typical solid and liquid acids, H-ZSM-5 exhibited an exceptionally high catalytic activity. The activity (per gram) of H-ZSM-5 increased as the Al-content (100Al/(Si + Al)%) increased and then decreased through a maximum at an Al content of 2.63%. The specific activity per one acid site, which was estimated from the initial rate and the acid amount, increased greatly as the Al content decreased, which resembles those of the hydrophobicity and the acid strength. The superiority of H-ZSM-5 activity over other strong and hydrophobic solid acids suggests the importance of the unique pore structure. While H-ZSM-5 deactivated severely during the reaction, the catalytic activities were mostly recovered by calcination at 773 K in air. IR spectroscopy and adsorption measurements revealed that the deactivation of H-ZSM-5 was mainly caused by the formation of a polymer of acrylonitrile on the catalyst surface blocking the micropores, but not limiting desorption of the product from the micropores.

Iridium-Catalyzed Asymmetric Hydroalkenylation of Norbornene Derivatives

Transition-metal-catalyzed asymmetric hydroalkenylation of alkenes provides an atom-economical method to build molecular complexity from easily available materials. Herein we report an iridium-catalyzed asymmetric hydroalkenylation of unconjugated alkenes with acrylamides and acrylates. The catalytic hydroalkenylation of norbornene derivatives occurred to form products with allylic stereocenters with high chemo-, regio-, and stereoselectivities. DFT calculations revealed that the migratory insertion is irreversible and the enantiodetermination step.

MANUFACTURING METHOD OF β-SUBSTITUTED PROPIONIC ACID AMIDE AND N-SUBSTITUTED (METH)ACRYLAMIDE

PROBLEM TO BE SOLVED: To provide a method for industrially manufacturing β-alkoxy propionic acid amide, β-amino propionic acid amide and N-substituted (meth)acryl amide using (meth)acrylic acid ester as starting material at high yield and high purity. SOLUTION: There is provided a method for obtaining N-substituted (meth)acryl amide represented by target compound formula (7) by conducting an amidation reaction with amine using β-substituted propionic acid ester represented by the formula (1) of a product of a Michael addition reaction of (meth)acrylic acid ester and alcohol or amine in presence of a metal complex as a catalyst to obtain β-substituted propionic acid amide represented by the formula (3) and conducting a thermal decomposition reaction of β-substituted propionic acid amide in presence of the metal complex as the catalyst to eliminate alcohol or amine. A-CH2-C(R1)H-C(=O)-OR2 (1), A-CH2-C(R1)H-C(=O)-N(R3)R4 (3), CH2=C(R1)-C(=O)-N(R3)R4 (7) SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT