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1-Benzyl-2-methylimidazole
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Name

1-Benzyl-2-methylimidazole

 EINECS 237-333-8
CAS No. 13750-62-4 Density 1.03 g/cm3
PSA 17.82000 LogP 2.23980
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 N/A Appearance clear light yellow to amber liquid
Safety 26-36-24/25 Risk Codes 22-36/37/38
Molecular Structure Molecular Structure of 13750-62-4 (1-Benzyl-2-methyl-1H-imidazole) Hazard Symbols HarmfulXn, IrritantXi
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;

Article Data 20

1-Benzyl-2-methylimidazole Synthetic route

693-98-1

2-methylimidazole

100-39-0

benzyl bromide

13750-62-4

N-benzyl-2-methylimidazole

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With phosphorus; hydrogen iodide at 160℃;
4238-71-5

1-benzylimidazole

74-88-4

methyl iodide

13750-62-4

N-benzyl-2-methylimidazole

Conditions
ConditionsYield
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
ConditionsYield
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;
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
ConditionsYield
With sodium hydroxide 1) EtOH, reflux, 1 h; 2) reflux, 24 h; Yield given. Multistep reaction;
13750-62-4

N-benzyl-2-methylimidazole

693-98-1

2-methylimidazole

Conditions
ConditionsYield
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
ConditionsYield
With dodecacarbonyl-triangulo-triruthenium In toluene at 160℃; under 15201 Torr; for 20h; Carbonylation;96%
13750-62-4

N-benzyl-2-methylimidazole

74-88-4

methyl iodide

15095-63-3

1,2-Dimethyl-3-benzyl-imidazoliumiodid

Conditions
ConditionsYield
at 60℃;95%

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: HarmfulXn,IrritantXiXi
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. 

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