1,3-Dihydro-1-(1-methylethenyl)-2H-benzimidazole-2-one supplier

Name
1-ISOPROPENYL-2-BENZIMIDAZOLIDINONE
EINECS 257-661-5
CAS No. 52099-72-6
Article Data26
CAS DataBase
Density 1.179g/cm³
Solubility
Melting Point 120-124 °C
Formula C10H10 N2 O
Boiling Point °Cat760mmHg
Molecular Weight 174.202
Flash Point °C
Transport Information
Appearance Off-White Crystalline Solid
Safety 140587
Risk Codes R22
Molecular Structure
Hazard Symbols Xn
Synonyms 2-Benzimidazolinone,1-isopropenyl- (6CI); 1-Isopropenyl-2-benzimidazolidinone;1-Isopropenyl-2-benzimidazolone; N-Isopropenyl-2-benzimidazolone; NSC 280600
PSA 37.79000
LogP 1.82020

Synthetic route

: 141-97-9
ethyl acetoacetate

: 95-54-5
1,2-diamino-benzene

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 0.0833333h; Microwave irradiation;	96%
With sodium hydroxide In o-xylene at 130℃; for 7h; Reagent/catalyst; Solvent; Temperature;	94%
In 5,5-dimethyl-1,3-cyclohexadiene for 6h; Reflux;	90%

: 105-45-3
acetoacetic acid methyl ester

: 95-54-5
1,2-diamino-benzene

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

Conditions

Conditions	Yield
With potassium hydroxide In water; xylene Heating;	78%
With potassium hydroxide In 5,5-dimethyl-1,3-cyclohexadiene; water

: 141-97-9
ethyl acetoacetate

: 95-54-5
1,2-diamino-benzene

A: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

B: 81128-80-5
2-methylbenzimidazole

Conditions

Conditions	Yield
at 150℃; for 0.0833333h;	A 75% B n/a

...Expand

: 56-23-5
tetrachloromethane

: 141-97-9
ethyl acetoacetate

: 95-54-5
1,2-diamino-benzene

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

...Expand

: 141-97-9
ethyl acetoacetate

: 95-54-5
1,2-diamino-benzene

A: 6276-48-8
4-methyl-2,3-dihydro-1H-1,5-benzodiazepin-2-one

B: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

Conditions

Conditions	Yield
With xylene

...Expand

: 6276-48-8
4-methyl-2,3-dihydro-1H-1,5-benzodiazepin-2-one

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

Conditions

Conditions	Yield
In xylene Heating;
In xylene for 3h; Heating; Yield given;

: 56-23-5
tetrachloromethane

: 141-97-9
ethyl acetoacetate

: 95-54-5
1,2-diamino-benzene

A: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

B 2-oxo-4-methyl-2.3-dihydro-1H-benzo<b><1.4>diazepine: 2-oxo-4-methyl-2.3-dihydro-1H-benzo<b><1.4>diazepine

...Expand

: 95-54-5
1,2-diamino-benzene

hexachloro-<1.3.5.2.4.6>triazatri-VP-phosphorin: hexachloro-<1.3.5.2.4.6>triazatri-VP-phosphorin

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: xylene / 1.5 h / Heating 2: xylene / 3 h / Heating View Scheme

: 30414-53-0
methyl propanoyl acetate

: 95-54-5
1,2-diamino-benzene

A 3-(sec-But-1-enyl)-2(3H)-benzimidazolone: 3-(sec-But-1-enyl)-2(3H)-benzimidazolone

B: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

...Expand

: 609-14-3
2-acetylpropanoic acid ethyl ester

: 95-54-5
1,2-diamino-benzene

A 3-(sec-But-2-enyl)-2(3H)-benzimidazolone: 3-(sec-But-2-enyl)-2(3H)-benzimidazolone

B: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

...Expand

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

: 96-32-2
bromoacetic acid methyl ester

: 406945-05-9
(3-isopropenyl-2-oxo-2,3-dihydro-benzoimidazol-1-yl)-acetic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile	99%

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

: 609-65-4
o-chlorobenzoyl chloride

: 1207377-35-2
1-(2-chlorobenzoyl)-3-(prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 5h; Inert atmosphere;	96.4%

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

: 100-44-7
benzyl chloride

: 77556-90-2
1-Benzyl-3-isopropenyl-1,3-dihydro-benzoimidazol-2-one

Conditions

Conditions	Yield
With sodium hydroxide; triethylbutylammonium chloride In benzene at 60℃; for 1h;	95%

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

: 106-94-5
propyl bromide

: 77556-86-6
1-Isopropenyl-3-propyl-1,3-dihydro-benzoimidazol-2-one

Conditions

Conditions	Yield
With sodium hydroxide; triethylbutylammonium chloride In benzene at 60℃; for 1h;	95%

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

: 109-70-6
1,3-chlorobromopropane

: 62780-84-1
1-(3-chloropropyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide	95%
In N,N-dimethyl-formamide	5.5 parts (44%)
In N,N-dimethyl-formamide	5.5 parts (44%)

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

: 106-95-6
allyl bromide

: 77556-85-5
1-Allyl-3-isopropenyl-1,3-dihydro-benzoimidazol-2-one

Conditions

Conditions	Yield
With sodium hydroxide; triethylbutylammonium chloride In benzene at 60℃; for 1h;	95%

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

: 111-83-1
1-bromo-octane

: 1016625-44-7
3-N-isopropenyl-1-N-octylbenzimidazol-2-one

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 12h;	95%

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

: 106-96-7
propargyl bromide

: 1,3-dihydro-1-(prop-1-en-2-yl)-3-(prop-2-yn-1-yl)-2H-benzo[d]imidazol-2-one

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 12h; Heating;	95%
With tetrabutylammomium bromide; sodium hydroxide In dichloromethane at 20℃; for 48h;	91%

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

: 3153-37-5
methyl 4-chlorobutyrate

: 3273-68-5
4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

Conditions

Conditions	Yield
Stage #1: 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one; methyl 4-chlorobutyrate With tetrabutylammomium bromide; potassium carbonate; potassium iodide In dimethyl sulfoxide at 110 - 115℃; Stage #2: With water; sodium hydroxide at 95 - 100℃; for 6h; Stage #3: With hydrogenchloride In water at 80 - 85℃;	95%

: 109-65-9
1-bromo-butane

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

: 77556-88-8
1-N-butyl-3-N-isopropenylbenzimidazol-2-one

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 12h;	94%
With sodium hydroxide; triethylbutylammonium chloride In benzene at 60℃; for 1h;	90%

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

: 1090902-91-2
2-(3-isopropenyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-3-nitro-benzoic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20 - 80℃; for 2h;	94%

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

: 79-10-7
acrylic acid

: 1207377-30-7
1-acryloyl-3-(prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one

Conditions

Conditions	Yield
With phosgene; triethylamine In dichloromethane at 20℃; Cooling with ice;	92.5%
Stage #1: 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one; acrylic acid With triethylamine In dichloromethane for 0.0833333h; Inert atmosphere; Cooling with ice; Stage #2: With bis(trichloromethyl) carbonate In dichloromethane at 20℃; Inert atmosphere;	77.1%

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

: 111-25-1
1-bromo-hexane

: 1016625-38-9
1-N-hexyl-3-N-isopropenylbenzimidazol-2-one

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 12h;	92%

: 75-21-8
oxirane

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

: 81942-81-6
1-(2-Hydroxy-ethyl)-3-isopropenyl-1,3-dihydro-benzoimidazol-2-one

Conditions

Conditions	Yield
With base	91%

: 88-09-5
2-Ethylbutanoic acid

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

: 1207377-19-2
1-(2-ethylbutanoyl)-3-(prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one

Conditions

Conditions	Yield
Stage #1: 2-Ethylbutanoic acid; 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one With triethylamine In dichloromethane for 0.0833333h; Inert atmosphere; Cooling with ice; Stage #2: With bis(trichloromethyl) carbonate In dichloromethane at 20℃; Inert atmosphere;	91%

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

: 142-62-1
hexanoic acid

: 1207377-17-0
1-hexanoyl-3-(prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one

Conditions

Conditions	Yield
Stage #1: 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one; hexanoic acid With triethylamine In dichloromethane for 0.0833333h; Inert atmosphere; Cooling with ice; Stage #2: With bis(trichloromethyl) carbonate In dichloromethane at 20℃; Inert atmosphere;	90.1%

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

: 610-14-0
2-nitrobenzyl chloride

: 1207377-33-0
1-(2-nitrobenzoyl)-3-(prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 5h; Inert atmosphere;	90.1%

: 6940-78-9
4-chlorobutyl bromide

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

: 81942-51-0
1-(4-chlorobutyl)-3-isopropenylbenzimidazolin-2-one

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide	90%

: 74-96-4
ethyl bromide

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

: 77556-84-4
1-Ethyl-3-isopropenyl-1,3-dihydro-benzoimidazol-2-one

Conditions

Conditions	Yield
With sodium hydroxide; triethylbutylammonium chloride In benzene at 60℃; for 1h;	90%

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

: 2009-83-8
6-chloro-1-hexanol

: 81942-52-1
1-(6-hydroxyhexyl)-3-isopropenylbenzimidazolin-2-one

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 8h;	90%

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

: 74-88-4
methyl iodide

: 77556-83-3
1-Isopropenyl-3-methyl-1,3-dihydro-benzoimidazol-2-one

Conditions

Conditions	Yield
With sodium hydroxide; triethylbutylammonium chloride In benzene at 60℃; for 1h;	90%

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

: 112-29-8
1-bromo dodecane

: 1016625-50-5
1-N-decyl-3-N-isopropenylbenzimidazol-2-one

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 12h;	90%

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

: 143-15-7
1-dodecylbromide

: 1016625-55-0
1-N-dodecyl-3-N-isopropenylbenzimidazol-2-one

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 12h;	90%

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

: 655-15-2
2-bromo-2'-fluoroacetophenone

: 1090902-81-0
1-[2-(2-fluoro-phenyl)-2-oxo-ethyl]-3-isopropenyl-1,3-dihydro-benzimidazol-2-one

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h;	90%

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

: 107-92-6
butyric acid

: 1207377-15-8
1-butyryl-3-(prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one

Conditions

Conditions	Yield
Stage #1: 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one; butyric acid With triethylamine In dichloromethane for 0.0833333h; Inert atmosphere; Cooling with ice; Stage #2: With bis(trichloromethyl) carbonate In dichloromethane at 20℃; Inert atmosphere;	90%

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

: 79-31-2
isobutyric Acid

: 1207377-18-1
1-isobutyryl-3-(prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one

Conditions

Conditions	Yield
Stage #1: 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one; isobutyric Acid With triethylamine In dichloromethane for 0.0833333h; Inert atmosphere; Cooling with ice; Stage #2: With bis(trichloromethyl) carbonate In dichloromethane at 20℃; Inert atmosphere;	89.7%

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

: 4780-79-4
1-naphthalene methanol

: 1090902-72-9
1-isopropenyl-3-naphthalen-1-ylmethyl-1,3-dihydro-benzimidazol-2-one

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 16h;	89%

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

: 109-52-4
valeric acid

: 1207377-16-9
1-pentanoyl-3-(prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one

Conditions

Conditions	Yield
Stage #1: 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one; valeric acid With triethylamine In dichloromethane for 0.0833333h; Inert atmosphere; Cooling with ice; Stage #2: With bis(trichloromethyl) carbonate In dichloromethane at 20℃; Inert atmosphere;	88.4%

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

: 120311-72-0
3-Chloropropyl 4-(Diphenylmethyl)-1-piperazinecarboxylate

: 120311-77-5
3-(2,3-Dihydro-3-methylethenyl-2-oxo-1H-benzimidazol-1-yl)propyl 4-(Diphenylmethyl)-1-piperazinecarboxylate

Conditions

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate In acetonitrile Heating;	87%

1,3-Dihydro-1-(1-methylethenyl)-2H-benzimidazole-2-one Chemical Properties

Molecular Structure of 2H-Benzimidazol-2-one,1,3-dihydro-1-(1-methylethenyl)- (CAS NO.52099-72-6):

Empirical Formula: C₁₀H₁₀N₂O
Molecular Weight: 174.1992
H bond acceptors: 3
H bond donors: 1
Freely Rotating Bonds: 1
Polar Surface Area: 23.55 Å²
Index of Refraction: 1.587
Molar Refractivity: 49.62 cm³
Molar Volume: 147.6 cm³
Surface Tension: 42.8 dyne/cm
Density: 1.179 g/cm³
InChI
InChI=1/C10H10N2O/c1-7(2)12-9-6-4-3-5-8(9)11-10(12)13/h3-6H,1H2,2H3,(H,11,13)
Smiles
c1(n(c2ccccc2[nH]1)C(=C)C)=O
BRN: 140587
Melting point: 120-124 °C
EINECS: 257-661-5
Product Categories: Benzimidazole; Aromatics Compounds; Imidaxoles; Aromatics

1,3-Dihydro-1-(1-methylethenyl)-2H-benzimidazole-2-one Safety Profile

Hazard Codes: Harmful Xn, Toxic T
Risk Statements: 22-25
R22:Harmful if swallowed.
R25 :Toxic if swallowed.
Safety Statements: 22-24/25-45
S22:Do not breathe dust.
S24/25:Avoid contact with skin and eyes.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 2810 6.1/PG 3

1,3-Dihydro-1-(1-methylethenyl)-2H-benzimidazole-2-one Specification

2H-Benzimidazol-2-one,1,3-dihydro-1-(1-methylethenyl)- , with CAS number of 52099-72-6, can be called 1-(2-Propenyl)-2-benzimidazolidinone ; 1,3-dihydro-1-(1-methylethenyl)-2h-benzimidazole-2-one ; 1-isopropenyl-1,3-dihydro-2h-1,3-benzimidazol-2-one ; 1-isopropenyl-2-benzimidazolidinone ; isopropenyl-benzimidazolidinone-2 ; iflab-bb f0451-0304 ; timtec-bb sbb006406 ; 1-(methylvinyl)-1h-benzimidazol-2(3h)-one .It is an off-white crystalline solid.

Product Name

1-ISOPROPENYL-2-BENZIMIDAZOLIDINONE

Synthetic route

1,3-Dihydro-1-(1-methylethenyl)-2H-benzimidazole-2-one Chemical Properties

1,3-Dihydro-1-(1-methylethenyl)-2H-benzimidazole-2-one Safety Profile

1,3-Dihydro-1-(1-methylethenyl)-2H-benzimidazole-2-one Specification

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