| Identification | More | [Name]
5-Chloro-1-methylimidazole | [CAS]
872-49-1 | [Synonyms]
1-METHYL-5-CHLOROIMIDAZOLE
5-CHLORO-1-METHYL-1H-IMIDAZOLE
5-CHLORO-1-METHYLIMIDAZOLE
TIMTEC-BB SBB004296
1H-Imidazole, 5-chloro-1-methyl-
5-Chloro-1-methylimidazde
5-Chloro-1-MethylImidazole(ForAzathiopurine)
5-Chloro-1-methylimidazole,98% | [EINECS(EC#)]
212-827-6 | [Molecular Formula]
C4H5ClN2 | [MDL Number]
MFCD00014505 | [Molecular Weight]
116.55 | [MOL File]
872-49-1.mol |
| Chemical Properties | Back Directory | [Appearance]
Pale Yellow Oil | [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.)
| [Fp ]
205 °F
| [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Soluble in chloroform and insoluble in water | [form ]
Oil | [pka]
5.31±0.10(Predicted) | [color ]
Colorless to yellow to brown liquid | [Water Solubility ]
insoluble | [Usage]
A useful synthetic intermediate | [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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
2933299090 |
| Hazard Information | Back Directory | [Chemical Properties]
Pale Yellow Oil | [Uses]
5-Chloro-1-methylimidazole is a labelled useful synthetic intermediate.
| [Uses]
A useful synthetic intermediate | [Uses]
A 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 |
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