5-Chloro-1-methylimidazole

5-Chloro-1-methylimidazole Property

Melting point:

82-85°C(11 mmHg)

Boiling point:

82-85 °C/11 mmHg (lit.)

Density 

1.25 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.511(lit.)

Flash point:

205 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

Soluble in chloroform and insoluble in water

pka

5.31±0.10(Predicted)

form 

Oil

color 

Colorless to yellow to brown liquid

Water Solubility 

insoluble

BRN 

110509

InChI

InChI=1S/C4H5ClN2/c1-7-3-6-2-4(7)5/h2-3H,1H3

InChIKey

NYDGOZPYEABERA-UHFFFAOYSA-N

SMILES

C1N(C)C(Cl)=CN=1

CAS DataBase Reference

872-49-1(CAS DataBase Reference)

NIST Chemistry Reference

5-Chloro-1-methylimidazole(872-49-1)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933299090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

5-Chloro-1-methylimidazole Chemical Properties,Usage,Production

Chemical Properties

Pale Yellow Oil

Uses

A useful synthetic intermediate.

Uses

5-Chloro-1-methylimidazole is a labelled useful synthetic intermediate.

General Description

5-Chloro-1-methylimidazole is a 5-halo-1-methylimidazole. It participates in electron-rich iron(III) porphyrin complex catalyzed epoxidation of olefins.

Synthesis

The general procedure for the synthesis of 5-chloro-1-methylimidazole from N,N'-dimethyl oxalamide was as follows: phosphorus pentachloride (383.2 g, 1.8 mol) was added to N,N'-dimethyl oxalamide (116.1 g, 1.0 mol), and heated to 60 °C to form a melt with foam generation. Subsequently, the reaction mixture was stirred at 85-95 °C for 2 h, and then distilled to remove the resulting POCl3. The dark brown residue was dissolved in 700 mL of water and adjusted to pH 8 with 915 g of 12.75% KOH solution. The aqueous phase was extracted four times with 500 mL of dichloromethane (DCM), and the organic extracts were combined and dried over sodium sulfate. After concentration under reduced pressure, the resulting reddish brown liquid was vacuum distilled to give 5-chloro-1-methylimidazole (53.1 g, 46% yield) as a colorless liquid. The product properties were as follows: flash point 85-86 °C (22 mbar); 1H NMR (400 MHz, d6-DMSO) δ 7.33 (s, 1H, 4-H), 6.80 (s, 1H, 2-H), 3.47 (s, 3H, CH3); 13C NMR (100 MHz, d6-DMSO) δ 137.4 (C-2), 126.0 (C -4), 118.4 (C-5), 31.6 (CH3).

References

[1] Indian Journal of Chemistry - Section B Organic Chemistry Including Medicinal Chemistry, 1989, vol. 28, # 5, p. 391 - 396
[2] Patent: US2017/281501, 2017, A1. Location in patent: Paragraph 0272-0276
[3] Journal of Organic Chemistry, 2010, vol. 75, # 4, p. 1047 - 1060
[4] Archiv der Pharmazie, 1988, vol. 321, # 4, p. 193 - 197
[5] Journal of Medicinal Chemistry, 1996, vol. 39, # 14, p. 2690 - 2695