1-メチルイミダゾール

1-Methylimidazole

HCID 1390CAS 616-47-7

基本情報

標準SMILES
Cn1ccnc1
InChIKey
MCTWTZJPVLRJOU-UHFFFAOYSA-N
分子式
C4H6N2
平均分子量
82.1 g/mol
単同位体質量
82.05309819

概要

1-methyl-1H-imidazole is a 1H-imidazole having a methyl substituent at the N-1 position.

名称と識別子

優先名称
1-Methylimidazole
IUPAC
1-methylimidazole
現地名
1-メチルイミダゾール
英語名
1-Methylimidazole
分子式
C4H6N2
分子量
82.1

名称と別名

1-methylimidazole1-Methyl-1H-imidazole616-47-7N-Methylimidazole1H-Imidazole, 1-methyl-IMIDAZOLE, 1-METHYL-DTXSID6052291P4617QS63YNSC-880641-methyl-1H-imidazol-3-iumDTXCID6030863CHEBI:113454
名称をさらに表示
1-メチルイミダゾールメチルイミダゾール1‐メチルイミダゾール1-メチル-1H-イミダゾール1-メチルイミダゾール, 99%15vol% 1-メチルイミダゾール,アセトニトリル溶液20vol% 1-メチルイミダゾール, アセトニトリル溶液MIMMeImmethyl imidazoleN-methylimidazole (1-methylimidazole)1-MethylimdazoleN-methyl midazoleN-methyl glyoxaline
RefChem:76394210-484-7N-methylimidazol1-methylimidazoln-methyl imidazoleMFCD00005292Methimazole Impurity 2; Thiamazole EP Impurity B1-methyl-imidazole

データベース識別子

CAS
616-47-7
PubChem CID
1390
DTXSID
DTXSID6052291
ChEMBL
CHEMBL543
ChEBI
CHEBI:113454
UNII
P4617QS63Y
EC Number
210-484-7
Nikkaji
J1.664K

物性

構造計算による物性

XLogP
-0.1
極性表面積
17.8 Ų
水素結合供与体数
0
水素結合受容体数
1
回転可能結合数
0
重原子数
6

実験および物理化学的性質

Chemical ClassesNitrogen Compounds -> Imidazoles
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesDensity
Density1.0325 @25 °C
Boiling Point196 °C @760 [mm Hg]
Melting Point-6 °C

物理化学的性質

融点
60 °C · −60 °C(lit.)
沸点
198 °C · 198 °C(lit.)
比重(密度)
1.03 g/mL · 1.03 g/mL at 25 °C(lit.)
蒸気圧
0.4 mm · 0.4 mm Hg ( 20 °C)
屈折率
20 · n20/D 1.495(lit.)
闪点
198 °F · 198 °F
化学的性質 · 1 件

化学的特性1-Methylimidazole or N-methylimidazole is an aromatic heterocyclic organic compound with the formula CH3C3H3N2. It is a colorless to yellow liquid, with an amine-like odor. It is miscible with water. N-methylimidazole is an important raw material for the synthesis of pharmaceutical intermediates, used in the preparation of losartan, nizofenone, 1-Methyl-1H-imidazole-5-carbonyl chloride hydrochloride and naphazoline hydrochloride, etc. It is also used as a specialty solvent, a base, and as a precursor to some ionic liquids.

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P260, P264, P270, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P362+P364, P363, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 0.1% (1 of 797) of reports.

Danger

H302 (96.9%): Harmful if swallowed [Warning Acute toxicity, oral]

危険有害性情報

Regulatory Information · 4 件

Chemical: 1H-Imidazole, 1-methyl-

1H-Imidazole, 1-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1H-Imidazole, 1-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 03-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/10038

1-Methylimidazole: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - 1H-Imidazole, 1-methyl-
Hazards Summary · 1 件

Causes convulsions in oral and intraperitoneal lethal-dose studies of mice; [RTECS] Dermal LD50 (rabbit) = 400-640 mg/kg; Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; Harmful by ingestion and skin absorption; [Alfa Aesar MSDS] See Imidazole.

Hazard Classes and Categories · 3 件

Acute Tox. 4 (96.9%)

Acute toxicity (ingestion) - category 4

Acute Tox. 4 *

安全と保護具

Protective Action Criteria (PAC) · 3 件

2.3 [mg/m3]

25 [mg/m3]

150 [mg/m3]

毒性情報

Adverse EffectsDermatotoxin - Skin burns.

安全データ

F
3-10
wgk
1
tsca
TSCA listed
rtecs
NI7000000
ridadr
UN 3267 8/PG 2
毒性
LD50 orally in Rabbit: 1144 mg/kg LD50 dermal Rabbit > 400 - < 640 mg/kg

化学と産業

用途と製造

U.S. Production2023: 50,000 - <75,000 lb
Industry UsesProcessing aids not otherwise specified
General Manufacturing Information · 2 件

All Other Basic Organic Chemical Manufacturing

1H-Imidazole, 1-methyl-: ACTIVE

応用分野 · 3 件

用途工業化学物質

使用1-Methylimidazole is an aprotic solvent. It is a derivative of imidazole used in the production of pharmaceuticals, pesticides, ion exchange resins, dye intermediates, textile auxiliaries, photographic chemicals, and corrosion inhibitors. It can also be used as a catalyst for the manufacture of polyurethane and a curing agent for epoxy resins. For example, when 1-methylimidazole is added to an aqueous diethylenetriamine (DETA) solution, high CO2 loading can be achieved through phase separation of the absorbent during CO2 absorption[1].

一般的な説明This product has been enhanced for catalysis. 1-Methylimidazole is a derivative of imidazole that is utilized in the manufacture of such classes of items as pharmaceuticals, pesticides, ion-exchange resins, dye intermediates, textile auxiliaries, photographic chemicals, and corrosion inhibitors. It is also used as a catalyst for manufacturing polyurethanes and a curing agent for epoxy resins.

調製方法 · 2 件

製造方法1-Methylimidazole is prepared mainly by two routes industrially. The main one is acid-catalysed methylation of imidazole by methanol. The second method involves the Radziszewski reaction from glyoxal, formaldehyde, and a mixture of ammonia and methylamine. (CHO)2 + CH2O + CH3NH2 + NH3 → H2C2N(NCH3)CH + 3 H2O The compound can be synthesized on a laboratory scale by methylation of imidazole at the pyridine-like nitrogen and subsequent deprotonation. Similarly, 1-methylimidazole may be synthesized by first deprotonating imidazole to form a sodium salt followed by methylation. H2C2N(NH)CH + CH3I → [H2C2(NH)(NCH3)CH]I [H2C2(NH)(NCH3)CH]I + NaOH → H2C2N(NCH3)CH + H2O + NaI

純化方法Dry it with sodium metal and then distil it. Store it at 0o under dry argon. The picrate has m 159.5-160.5o (from H2O). [Beilstein 23 III/IV 568.]

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補足説明

定義ChEBI: 1-methyl-1H-imidazole is a 1H-imidazole having a methyl substituent at the N-1 position. It is a metabolite of 1-methyl-2-thioimidazole (methimazole). It inhibits bone resorption.

関連反応

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