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Name	N-Vinylcaprolactam	EINECS	218-787-6
CAS No.	2235-00-9	Density	1.049 g/cm³
PSA	20.31000	LogP	1.47040
Solubility	Soluble in water (partly).	Melting Point	35-38 °C (dec.)(lit.)
Formula	C₈H₁₃NO	Boiling Point	254.7 °C at 760 mmHg
Molecular Weight	139.197	Flash Point	112.5 °C
Transport Information	N/A	Appearance	solid
Safety	26-39	Risk Codes	22-41
Molecular Structure		Hazard Symbols	Xn
Synonyms	2H-Azepin-2-one,hexahydro-1-vinyl- (6CI,7CI,8CI);1-Vinylcaprolactam;N-Vinyl-e-caprolactam;N-Vinylazepan-2-one;1-vinylhexahydro-2h-azepin-2-one;1-ethenylazepan-2-one;Vinylcaprolactam;n-vinyl-epsilon-caprolactam;	Article Data	20

N-Vinylcaprolactam Synthetic route

: 13344-00-8
1,4-diethoxybutane

: 2235-00-9
vinylcaprolactam

Conditions

Conditions	Yield
	81.9%

: 105-60-2
caprolactam

: 74-86-2
acetylene

: 2235-00-9
vinylcaprolactam

Conditions

Conditions	Yield
With dmap; [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); tributylphosphine In toluene at 100℃; for 16h; Reagent/catalyst; Autoclave; Glovebox;	80%
With dmap; tributylphosphine In toluene at 100℃; for 16h; Reagent/catalyst; Inert atmosphere; Autoclave; Glovebox;	80%
With nitrogen; pyrrolidone potassique; toluene at 120 - 130℃; under 11032.6 Torr;

: 151455-49-1
Acetic acid 2,2-dichloro-1-(2-oxo-azepan-1-yl)-ethyl ester

A: 105-60-2
caprolactam

B: 2235-00-9
vinylcaprolactam

C: 1-((Z)-2-Chloro-vinyl)-azepan-2-one

D: 1-((E)-2-Chloro-vinyl)-azepan-2-one

Conditions

Conditions	Yield
With tetraethylammonium perchlorate In acetonitrile at 20℃; electroreduction: mercury pool cathode; working potential 2.3 V (versus SCE); Yields of byproduct given;	A n/a B 10% C n/a D n/a
With tetraethylammonium perchlorate In acetonitrile at 20℃; electroreduction: mercury pool cathode; working potential 2.3 V (versus SCE); Yield given. Title compound not separated from byproducts;	A n/a B 10% C n/a D n/a

: 105-60-2
caprolactam

: 2235-00-9
vinylcaprolactam

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 50 percent / benzene / 2 h / Heating 2: 63 percent / Et3N / CH2Cl2 / 3 h / Ambient temperature 3: 10 percent / tetraethylammonium perchlorate / acetonitrile / 20 °C / electroreduction: mercury pool cathode; working potential 2.3 V (versus SCE) View Scheme

: 914226-29-2
1-(2,2-Dichloro-1-hydroxy-ethyl)-azepan-2-one

: 2235-00-9
vinylcaprolactam

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 63 percent / Et3N / CH2Cl2 / 3 h / Ambient temperature 2: 10 percent / tetraethylammonium perchlorate / acetonitrile / 20 °C / electroreduction: mercury pool cathode; working potential 2.3 V (versus SCE) View Scheme

: 2235-00-9
vinylcaprolactam

: 19797-08-1
1-ethylhexahydro-2H-azepin-2-one

Conditions

Conditions	Yield
With triethylsilane; 1% Pd on activated carbon In water at 20℃; for 2h; Reagent/catalyst; Green chemistry; chemoselective reaction;	100%
With palladium on carbon; hydrogen; C64H118O20 In water at 20℃; for 2h; Reagent/catalyst;	100%
With ammonium formate; palladium on activated charcoal In methanol for 0.5h; Heating;	97%
With ammonium hydroxide; hydrazine hydrate In ethanol at 60℃; for 33h; Catalytic behavior;
With hydrogen In water at 80℃; under 7500.75 Torr; for 20h; Autoclave;	92 %Chromat.

: 2235-00-9
vinylcaprolactam

: 106-40-1
4-bromo-aniline

: 1-(1-(4-bromophenylamino)ethyl)azepan-2-one

Conditions

Conditions	Yield
With acetic acid In hexane at 20℃; for 14h; regiospecific reaction;	100%

: 2235-00-9
vinylcaprolactam

: 62-53-3
aniline

: 1-(1-(phenylamino)ethyl)azepan-2-one

Conditions

Conditions	Yield
With acetic acid In hexane at 20℃; for 14h; regiospecific reaction;	100%

: 2235-00-9
vinylcaprolactam

: 100-01-6
4-nitro-aniline

: 1-(1-(4-nitrophenylamino)ethyl)azepan-2-one

Conditions

Conditions	Yield
With acetic acid In hexane at 20℃; for 14h; regiospecific reaction;	100%

: 2235-00-9
vinylcaprolactam

: 106-47-8
4-chloro-aniline

: 1-(1-(4-chlorophenylamino)ethyl)azepan-2-one

Conditions

Conditions	Yield
With acetic acid In hexane at 20℃; for 14h; regiospecific reaction;	100%

N-Vinylcaprolactam Chemical Properties

Molecular Structure of 2H-Azepin-2-one,1-ethenylhexahydro- (CAS NO.2235-00-9):

IUPAC Name: 1-ethenylazepan-2-one
Empirical Formula: C₈H₁₃NO
Molecular Weight: 139.1949
H bond acceptors: 2
H bond donors: 0
Freely Rotating Bonds: 1
Polar Surface Area: 20.31 Å²
Index of Refraction: 1.548
Molar Refractivity: 42.14 cm³
Molar Volume: 132.6 cm³
Surface Tension: 43.9 dyne/cm
Density: 1.049 g/cm³
Flash Point: 112.5 °C
Enthalpy of Vaporization: 49.21 kJ/mol
Boiling Point: 254.7 °C at 760 mmHg
Vapour Pressure: 0.017 mmHg at 25°C
Melting point: 35-38 °C (dec.)(lit.)
Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
InChI
InChI=1/C8H13NO/c1-2-9-7-5-3-4-6-8(9)10/h2H,1,3-7H2
Smiles
O=C1N(C=C)CCCCC1
EINECS: 218-787-6
Product Categories: Biodegradable Polymer Monomers; Monomers; Polymer Science

N-Vinylcaprolactam Safety Profile

Hazard Codes: Harmful Xn
Risk Statements: 22-41
R22:Harmful if swallowed.
R41:Risk of serious damage to the eyes.
Safety Statements: 26-39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S39:Wear eye / face protection.
WGK Germany: 3

N-Vinylcaprolactam Specification

2H-Azepin-2-one,1-ethenylhexahydro- , with CAS number of 2235-00-9, can be called 1-vinylhexahydro-2h-azepin-2-one ; 1-ethenylazepan-2-one ; 1-ethenylhexahydro-2h-azepin-2-one ; vinylcaprolactam ; n-vinyl-epsilon-caprolactam ; n-vinylcaprolactam ; 1-ethenylhexahydro-2h-azepin-2-on ; 2h-azepin-2-one, 1-ethenylhexahydro- .

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