1-Benzyl-2-methylimidazole supplier

Name
1-Benzyl-2-methyl-1H-imidazole
EINECS 237-333-8
CAS No. 13750-62-4
Article Data20
CAS DataBase
Density 1.03 g/cm³
Solubility Insoluble in water
Melting Point 120 - 127oC
Formula C₁₁H₁₂N₂
Boiling Point 296.8 °C at 760 mmHg
Molecular Weight 172.23
Flash Point 136.3 °C
Transport Information
Appearance clear light yellow to amber liquid
Safety 26-36-24/25
Risk Codes 22-36/37/38
Molecular Structure
Hazard Symbols Xn, Xi
Synonyms Imidazole,1-benzyl-2-methyl- (8CI);1-Benzyl-2-methyl-1H-imidazole;1B2MZ;2-Methyl-N-benzylimidazole;Curezol 1B2MZ;Epicure BMI 12;JER Cure BMI 12;N-Benzyl-2-methylimidazole;
PSA 17.82000
LogP 2.23980

Synthetic route

: 693-98-1
2-methylimidazole

: 100-39-0
benzyl bromide

: 13750-62-4
N-benzyl-2-methylimidazole

Conditions

Conditions	Yield
Stage #1: 2-methylimidazole With sodium hydride at -0.16℃; Schlenk technique; Inert atmosphere; Stage #2: benzyl bromide In tetrahydrofuran Inert atmosphere; Schlenk technique; Reflux;	99%
With sodium hydroxide In water at 20℃; for 0.333333h; Temperature; Micellar solution;	93%
With N,N,N',N'',N'''-pentamethyldiethylenetriamine; potassium tert-butylate; copper(I) bromide In toluene at 20℃; for 9.5h; Inert atmosphere;	90%
With potassium carbonate In acetonitrile at 70℃;

: 693-98-1
2-methylimidazole

: 13750-62-4
N-benzyl-2-methylimidazole

Conditions

Conditions	Yield
With ammonium formate; palladium on activated charcoal In methanol for 1h; Heating;	97%

: 693-98-1
2-methylimidazole

: 100-44-7
benzyl chloride

: 13750-62-4
N-benzyl-2-methylimidazole

Conditions

Conditions	Yield
With N,N,N',N'',N'''-pentamethyldiethylenetriamine; potassium tert-butylate; copper(I) bromide In toluene at 20℃; for 9.5h; Inert atmosphere;	89%
With potassium carbonate In acetonitrile Reflux;	80%
With potassium carbonate In chloroform for 6h; Reflux;	75.56%

: 5272-57-1
1-benzyl-2-(hydroxymethyl)imidazole hydrochloride

: 13750-62-4
N-benzyl-2-methylimidazole

Conditions

Conditions	Yield
With phosphorus; hydrogen iodide at 160℃;

: 4238-71-5
1-benzylimidazole

: 74-88-4
methyl iodide

: 13750-62-4
N-benzyl-2-methylimidazole

Conditions

Conditions	Yield
With n-butyllithium 1.) Et2O, -78 deg C, 2.5 h; 20 deg C, 1 h, 2.) -78 deg C -> room temperature; room temperature, 15 min; Yield given. Multistep reaction;

: 4238-71-5
1-benzylimidazole

: 74-88-4
methyl iodide

A: 13750-62-4
N-benzyl-2-methylimidazole

B: 90408-21-2
2-methyl-1-(1-phenylethyl)-1H-imidazole

Conditions

Conditions	Yield
With n-butyllithium Product distribution; multistep reaction: 1.) Et2O, -78 deg C, 0.5 h; other temperatures, times; reactions of lithiated N-protected imidazoles with various electrophiles;	A 46 % Spectr. B 25 % Spectr.
With n-butyllithium 1) dimethoxyethane, -60 deg C, 10 min, 2) -60 deg C, 1.5 h, warm to r.t.; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 693-98-1
2-methylimidazole

: 100-39-0
benzyl bromide

A: 13750-62-4
N-benzyl-2-methylimidazole

B: 91473-32-4
2-Methyl-4-phenylmethyl-1H-imidazole

Conditions

Conditions	Yield
With sodium hydroxide 1) EtOH, reflux, 1 h; 2) reflux, 24 h; Yield given. Multistep reaction;

...Expand

: 13750-62-4
N-benzyl-2-methylimidazole

: 693-98-1
2-methylimidazole

Conditions

Conditions	Yield
With triethylsilane; palladium 10% on activated carbon In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;	97%
With potassium tert-butylate; oxygen; dimethyl sulfoxide at 0℃; for 0.25h;	85%
With ammonia; sodium

: 13750-62-4
N-benzyl-2-methylimidazole

: 558-37-2
tert-butylethylene

: 201230-82-2
carbon monoxide

: 4,4-dimethyl-1-(2-methyl-1-phenylmethyl-1H-imidazol-4-yl)-1-pentanone

Conditions

Conditions	Yield
With dodecacarbonyl-triangulo-triruthenium In toluene at 160℃; under 15201 Torr; for 20h; Carbonylation;	96%

...Expand

: 13750-62-4
N-benzyl-2-methylimidazole

: 74-88-4
methyl iodide

: 15095-63-3
1,2-Dimethyl-3-benzyl-imidazoliumiodid

Conditions

Conditions	Yield
at 60℃;	95%

: 13750-62-4
N-benzyl-2-methylimidazole

: ammonium thiocyanate

: palladium dichloride

: 1421070-24-7
Pd(SCN)2(1-benzyl-2-methylimidazole)2

Conditions

Conditions	Yield
In acetonitrile for 2h; Reflux;	92%

...Expand

: 13750-62-4
N-benzyl-2-methylimidazole

: 78-95-5
chloroacetone

: 14872-20-9, 15227-47-1, 14052-12-1
trans dichlorobispyridine palladium (II)

B: C14H17N2O(1+)*Cl(1-)

Conditions

Conditions	Yield
In tetrahydrofuran for 48h; Inert atmosphere; Schlenk technique; Reflux;	A n/a B 90%

...Expand

: 13750-62-4
N-benzyl-2-methylimidazole

: palladium dichloride

: 1421070-23-6
PdCl2(1-benzyl-2-methylimidazole)2

Conditions

Conditions	Yield
In acetonitrile for 2h; Reflux;	88%

: 83-34-1
3-Methylindole

: 13750-62-4
N-benzyl-2-methylimidazole

: 1419209-72-5
1-benzyl-2-methyl-3-(3-methyl-1H-indol-2-yl)imidazolium bromide

Conditions

Conditions	Yield
With N-Bromosuccinimide In 1,4-dioxane at 12 - 15℃; for 0.5h;	88%

: 108-86-1
bromobenzene

: 13750-62-4
N-benzyl-2-methylimidazole

: 1-benzyl-2-methyl-5-phenyl-1H-imidazole

Conditions

Conditions	Yield
With potassium carbonate; triphenylphosphine; palladium diacetate In N,N-dimethyl-formamide at 140℃; for 24h; Phenylation;	85%

: 13750-62-4
N-benzyl-2-methylimidazole

: cobalt(II) chloride hexahydrate

: {Co(1-benzyl-2-methyl-1H-imidazole)2Cl2}

Conditions

Conditions	Yield
In methanol at 25℃;	85%
In methanol at 25℃; for 24h;	85%

: 13750-62-4
N-benzyl-2-methylimidazole

: [Pd(μ-Br)Br(1-butyl-3-methylimidazol-2-ylidene)]2

: [PdBr2(1-butyl-3-methylimidazol-2-ylidene)(1-benzyl-2-methylimidazole)]

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 1h;	85%

: 13750-62-4
N-benzyl-2-methylimidazole

: di(1-butyl-1,3-dihydro-3-methyl-2H-imidazol-2-ylidene)di-μ-iododiiododipalladium

: [PdI2(1-butyl-3-methylimidazol-2-ylidene)(1-benzyl-2-methylimidazole)]

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 1h;	82%

: 13750-62-4
N-benzyl-2-methylimidazole

: mercury dichloride

: {Hgo(1-benzyl-2-methyl-1H-imidazole)2Cl2}

Conditions

Conditions	Yield
In methanol at 25℃;	81%

: 13750-62-4
N-benzyl-2-methylimidazole

: 2,4,6-trimethoxybenzyl chloride

: 1-benzyl-3-(2,4,6-trimethoxybenzyl)-2-methylimidazolium chloride

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 90 - 110℃; for 24h; Inert atmosphere; Schlenk technique;	81%

: 13750-62-4
N-benzyl-2-methylimidazole

: 35606-00-9
(4Z)-5-(bromo-methyl)-2,2,6,6-tetramethylhept-4-en-3-one

: 1387639-68-0
1-benzyl-3-[(2Z)-2-tert-butyl-5,5-dimethyl-4-oxohex-2-en-1-yl]-2-methyl-1H-imidazol-3-ium bromide

Conditions

Conditions	Yield
In benzene at 20℃;	79%

: 13750-62-4
N-benzyl-2-methylimidazole

: 7462-71-7, 15295-67-7, 59310-37-1
(2Z)-4-bromo-1,3-diphenylbut-2-en-1-one

: 1349778-51-3
Br(1-)*C27H25N2O(1+)

Conditions

Conditions	Yield
In benzene at 20℃;	78%

: 13750-62-4
N-benzyl-2-methylimidazole

: C18H15BrN2O3

: C29H27N4O3(1+)*Br(1-)

Conditions

Conditions	Yield
In tetrahydrofuran at 5 - 20℃; for 12h; Inert atmosphere; Cooling with ice;	78%

: 13750-62-4
N-benzyl-2-methylimidazole

: 83160-36-5
5-(bromomethyl)-4,5-dihydro-3,3-diphenyl-2(3H)-furanone

: 1-Benzyl-2-methyl-3-(5-oxo-4,4-diphenyl-tetrahydro-furan-2-ylmethyl)-3H-imidazol-1-ium; bromide

Conditions

Conditions	Yield
In diethyl ether at 100℃; for 16h;	75%

: 13750-62-4
N-benzyl-2-methylimidazole

: 14140-15-9
4-(2-bromoethyl)phenol

: 1-benzyl-3-[2-(4-hydroxyphenyl)ethyl]-2-methylimidazolium bromide

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 90 - 110℃; for 24h; Inert atmosphere; Schlenk technique;	75%

: 13750-62-4
N-benzyl-2-methylimidazole

: 141-32-2
acrylic acid n-butyl ester

A: (E)-butyl 3-(1-benzyl-2-methyl-1H-imidazol-5-yl)acrylate

B: (2E,2’E)-dibutyl 3,3’-(1-benzyl-2-methyl-1H-imidazol-4,5-diyl)diacrylate

Conditions

Conditions	Yield
With copper diacetate; palladium diacetate In 1,4-dioxane at 100℃; for 15h; Reagent/catalyst; regioselective reaction;	A 74% B 12 %Spectr.

...Expand

: 13750-62-4
N-benzyl-2-methylimidazole

: 1663-39-4
tert-Butyl acrylate

: (E)-tert-butyl 3-(1-benzyl-2-methyl-1H-imidazol-5-yl)acrylate

Conditions

Conditions	Yield
With copper diacetate; palladium diacetate In 1,4-dioxane at 100℃; for 15h; regioselective reaction;	74%

: 20449-21-2
2-(but-3-en-1-yl)-2-methyl-1,3-dioxolane

: 13750-62-4
N-benzyl-2-methylimidazole

: 201230-82-2
carbon monoxide

: 1-(1-Benzyl-2-methyl-1H-imidazol-4-yl)-5-(2-methyl-[1,3]dioxolan-2-yl)-pentan-1-one

Conditions

Conditions	Yield
With dodecacarbonyl-triangulo-triruthenium In toluene at 160℃; under 15200 Torr; for 20h;	72%

...Expand

: 13750-62-4
N-benzyl-2-methylimidazole

: 1592-20-7
4-Vinylbenzyl chloride

: 1-benzyl-3-(4-vinylbenzyl)-2-methylimidazolium chloride

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 90 - 110℃; for 24h; Inert atmosphere; Schlenk technique;	72%

: 13750-62-4
N-benzyl-2-methylimidazole

: 5332-26-3
N-(bromomethyl)phtalimide

: 1-benzyl-3-(N-methylphthalimide)-2-methylimidazolium bromide

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 90 - 110℃; for 24h; Inert atmosphere; Schlenk technique;	71%

: hydroxygallium naphthalocyaninetetrasulfonic acid

: 13750-62-4
N-benzyl-2-methylimidazole

: 4C11H13N2(1+)*C48H21GaN8O13S4(4-)

Conditions

Conditions	Yield
In methanol; water	70%

: 13750-62-4
N-benzyl-2-methylimidazole

: cobalt(II) chloride hexahydrate

: 1934-75-4
sodium dicyanamide

: [Co(dicyanamide)2(1-benzyl-2-methylimidazole)2]n

Conditions

Conditions	Yield
In methanol for 0.25h;	70%

...Expand

: 13750-62-4
N-benzyl-2-methylimidazole

: 140-88-5
ethyl acrylate

: (E)-ethyl 3-(1-benzyl-2-methyl-1H-imidazol-5-yl)acrylate

Conditions

Conditions	Yield
With copper diacetate; palladium diacetate In 1,4-dioxane at 100℃; for 15h; regioselective reaction;	70%

: 13750-62-4
N-benzyl-2-methylimidazole

: 540-51-2
2-bromoethanol

: 1-benzyl-3-(2-hydroxyethyl)-2-methylimidazolium bromide

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 90 - 110℃; for 24h; Inert atmosphere; Schlenk technique;	68%

1-Benzyl-2-methylimidazole Chemical Properties

IUPAC Name: 1-Benzyl-2-methylimidazole
Following is the structure of 1H-Imidazole,2-methyl-1-(phenylmethyl)- (CAS NO.13750-62-4):

Empirical Formula: C₁₁H₁₂N₂
Molecular Weight: 172.2264 g/mol
EINECS: 237-333-8
Index of Refraction: 1.571
Molar Refractivity: 54.96 cm³
Molar Volume: 167.2 cm³
Density: 1.03 g/cm³
Flash Point: 136.3 °C
Surface Tension: 38.2 dyne/cm
Enthalpy of Vaporization: 51.52 kJ/mol
Boiling Point: 296.8 °C at 760 mmHg
Vapour Pressure: 0.00247 mmHg at 25 °C
Product Categories: Imidazol & Benzimidazole; Building Blocks; Heterocyclic Building Blocks; Imidazoles
Appearance of 1H-Imidazole,2-methyl-1-(phenylmethyl)- (CAS NO.13750-62-4): clear light yellow to amber liquid
Water Solubility of 1H-Imidazole,2-methyl-1-(phenylmethyl)- (CAS NO.13750-62-4): insoluble
Canonical SMILES: CC1=NC=CN1CC2=CC=CC=C2
InChI: InChI=1S/C11H12N2/c1-10-12-7-8-13(10)9-11-5-3-2-4-6-11/h2-8H,9H2,1H3
InChIKey: FBHPRUXJQNWTEW-UHFFFAOYSA

1-Benzyl-2-methylimidazole Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rabbit	LDLo	skin	200mg/kg (200mg/kg)		National Technical Information Service. Vol. OTS0539680,
rat	LD50	oral	1gm/kg (1000mg/kg)		National Technical Information Service. Vol. OTS0539680,

1H-Imidazole,2-methyl-1-(phenylmethyl)- (CAS NO.13750-62-4) hasn't been listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65. And the toxicological properties have not been fully investigated.

1-Benzyl-2-methylimidazole Safety Profile

Hazard Codes: Harmful Xn, Irritant XiXi
Risk Statements: 22-36/37/38
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-24/25
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
RTECS: NI7722500

1-Benzyl-2-methylimidazole Specification

1H-Imidazole,2-methyl-1-(phenylmethyl)- , its cas register number is 13750-62-4. It also can be called 1-Benzyl-2-methylimidazole ; and 1-Benzyl-2-methyl-1H-imidazole .
1H-Imidazole,2-methyl-1-(phenylmethyl)- (CAS NO.13750-62-4) is hazardous, so the first aid measures and others should be known. Such as: When on the skin: Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's inhaled: Remove from exposure and move to fresh air immediately. Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product : Wash mouth out with water, and get medical aid immediately.
1H-Imidazole,2-methyl-1-(phenylmethyl)- (CAS NO.13750-62-4) should avoid the condition like incompatible materials. It is not compatible with strong oxidizing agents. And also prevent it to broken down into hazardous decomposition products: nitrogen oxides, carbon monoxide, carbon dioxide. However, its hazardous polymerization has not been reported. In addition, it should be stored in a cool, dry place, or stored in a tightly closed container.

Product Name

1-Benzyl-2-methyl-1H-imidazole

Synthetic route

1-Benzyl-2-methylimidazole Chemical Properties

1-Benzyl-2-methylimidazole Toxicity Data With Reference

1-Benzyl-2-methylimidazole Safety Profile

1-Benzyl-2-methylimidazole Specification

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