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

Product Name1-Benzyl-2-methyl-1H-imidazole
CAS13750-62-4
MFC11H12N2
MW172.23
EINECS237-333-8
MOL File13750-62-4.mol

Chemical Properties

Melting point	57°C
Boiling point	125-127 °C/3 mmHg (lit.)
Density	1.105 g/mL at 25 °C (lit.)
refractive index	n20/D 1.5645(lit.)
Flash point	>230 °F
storage temp.	2-8°C
pka	7.54±0.31(Predicted)
form	clear liquid
color	Colorless to Yellow
Water Solubility	insoluble
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-N
SMILES	Cc1nccn1Cc2ccccc2
CAS DataBase Reference	13750-62-4(CAS DataBase Reference)
NIST Chemistry Reference	1H-Imidazole, 2-methyl-1-(phenylmethyl)-(13750-62-4)
EPA Substance Registry System	1H-Imidazole, 2-methyl-1-(phenylmethyl)- (13750-62-4)

Safety Information

Hazard Codes	Xn,Xi
Risk Statements	22-36/37/38
Safety Statements	26-36-24/25
WGK Germany	3
RTECS	NI7722500
TSCA	TSCA listed
HS Code	29332900
Storage Class	10 - Combustible liquids
Hazard Classifications	Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
1-Benzyl-2-methyl-1H-imidazole	English
SigmaAldrich	English
ACROS	English

Usage And Synthesis

Chemical Properties

clear light yellow to amber liquid

Uses

1-Benzyl-2-methylimidazole may be employed as catalyst to investigate the effect of catalysts on the curing reaction of the biphenyl epoxy (4,4′-diglycidyloxy-3,3′,5,5′-tetramethyl biphenyl)dicyclopentadiene type phenolic resin system.

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 383, 1949 DOI: 10.1021/ja01170a002

General Description

1-Benzyl-2-methylimidazole is a nitrogen heterocycle and forms mixed ligand Pt(II) complexes. 1-Benzyl-2-methylimidazole on treatement with ammonia and sodium yields 2-methylimidazole. Deposition of plasma-polymerized 1-benzyl-2-methylimidazole (PPBMI) thin films onto glass substrates by glow discharge technique have been reported.

Synthesis

693-98-1

100-44-7

13750-62-4

A suspension of 10 mmol of 2-methyl-1H-imidazole was formed with 10 mmol of potassium carbonate in 10 mL of acetonitrile and stirred at room temperature for 15 minutes. Subsequently, 10 mmol of benzyl chloride was added to the reaction system and the reaction mixture was heated to 70 °C and stirred continuously for 72 hours. Upon completion of the reaction, the solvent was removed by rotary evaporation and the residue was dissolved in 20 mL of ethyl acetate and washed with deionized water (2 x 10 mL). The organic phase was concentrated under reduced pressure and purified by silica gel column chromatography (eluent: chloroform) to afford the target compound 1-benzyl-2-methylimidazole in 38% yield. The product was a yellow oil; UV-Vis (chloroform, λmax/nm): 290; IR (KBr, ν/cm-1): 2939, 1712, 1508, 1434, 1365, 1272, 1118, 983, 721; 1H NMR (250.13 MHz, CDCl3) δ: 7.43-7.32 (m, 5H). 7.17-7.14 (m, 2H), 6.99 (d, J=1.3 Hz, 1H), 6.84 (d, J=1.2 Hz, 1H), 5.11 (s, 2H), 2.27 (s, 3H); 13C NMR (62.9 MHz, CDCl3) δ: 144.3, 138.0, 129.3, 128.1, 127.5, 127.1, 120.9, 49.2, 13.4.

References

[1] Asian Journal of Chemistry, 2014, vol. 26, # 8, p. 2381 - 2388
[2] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 22, p. 6495 - 6499
[3] Journal of Structural Chemistry, 2016, vol. 57, # 4, p. 835 - 839
[4] Zh. Strukt. Kim., 2016, vol. 57, # 4, p. 873 - 876,4
[5] Patent: US4560690, 1985, A

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

Chemical Properties

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MSDS

Usage And Synthesis

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