Basic information
- Standard SMILES
Cn1ccnc1- InChIKey
MCTWTZJPVLRJOU-UHFFFAOYSA-N- Molecular formula
- C4H6N2
- Average molar mass
- 82.1 g/mol
- Monoisotopic mass
- 82.05309819
Overview
1-methyl-1H-imidazole is a 1H-imidazole having a methyl substituent at the N-1 position.
Names & identifiers
- Preferred name
- 1-Methylimidazole
- IUPAC
- 1-methylimidazole
- English name
- 1-Methylimidazole
- Molecular formula
- C4H6N2
- Molecular weight
- 82.1
Names & synonyms
1-methylimidazole1-Methyl-1H-imidazole616-47-7N-Methylimidazole1H-Imidazole, 1-methyl-IMIDAZOLE, 1-METHYL-DTXSID6052291P4617QS63YNSC-880641-methyl-1H-imidazol-3-iumDTXCID6030863CHEBI:113454
Show more names
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
Database identifiers
- CAS
616-47-7- PubChem CID
- 1390
- DTXSID
DTXSID6052291- ChEMBL
CHEMBL543- ChEBI
CHEBI:113454- UNII
- P4617QS63Y
- EC Number
- 210-484-7
- Nikkaji
- J1.664K
Properties
Computed structural properties
- XLogP
- -0.1
- Topological polar surface area
- 17.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 6
- Formal charge
- 0
- Complexity
- 44.8
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Imidazoles
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesDensity
Density1.0325 @25 °C
Boiling Point196 °C @760 [mm Hg]
Melting Point-6 °C
Vapor Pressure0.47 [mmHg]
Physical Description
Liquid
Colorless to yellow hygroscopic liquid; [Alfa Aesar MSDS]
Dissociation Constants6.95 (at 25 °C)
Physicochemical properties
- Melting point
- 60 °C · −60 °C(lit.)
- Boiling point
- 198 °C · 198 °C(lit.)
- Density
- 1.03 g/mL · 1.03 g/mL at 25 °C(lit.)
- vapor pressure
- 0.4 mm · 0.4 mm Hg ( 20 °C)
- refractive index
- 20 · n20/D 1.495(lit.)
- Flash point
- 198 °F · 198 °F
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- form
- Liquid
- pka
- 6.95 · 6.95(at 25℃)
- Specific Gravity
- 1.031 · 1.031
- color
- Clear colorless to yellow
- PH
- 9.5 · 9.5-10.5 (50g/l, H2O, 20℃)
- PH Range
- 9.5 · 9.5 - 11.5 at 100 g/l at 20 °C
- biological source
- synthetic
- explosive limit
- 2.7 · 2.7-15.7%(V)
- Water Solubility
- Miscible with water.
- Sensitive
- Hygroscopic
- BRN
- 105197 · 105197
- Henry's Law Constant
- 6.9 · 6.9×101 mol/(m3Pa) at 25℃, Du et al. (2017)
- Stability
- Stable, but moisture sensitive. Incompatible with acids, acid anhydrides, strong oxidizing agents, moisture, carbon dioxide, acid chlorides.
- InChI
- 1S/C4H6N2/c1-6-3-2-5-4-6/h2-4H,1H3
- InChIKey
- MCTWTZJPVLRJOU-UHFFFAOYSA-N
- SMILES
- Cn1ccnc1
- LogP
- -0.19 at · -0.19 at 25℃
- CAS DataBase Reference
- 616 · 616-47-7(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 4617 QS63Y · P4617QS63Y
- NIST Chemistry Reference
- 1 H-Imidazole, · 1H-Imidazole, 1-methyl-(616-47-7)
- EPA Substance Registry System
- 1 H-Imidazole, · 1H-Imidazole, 1-methyl- (616-47-7)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05,GHS06
- Signal word
- Danger
- Hazard statements
- 302 · H302-H311-H314
- Precautionary statements
- 270 · P270-P280-P301+P312-P301+P330+P331-P303+P361+P353-P305+P351+P338
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- Hazard Codes
- C,Xn,F,T
- Risk Statements
- 21 · 21/22-34-19-11-20/21/22-52/53-24-22-40-37-21
- Safety Statements
- 26 · 26-36-45-1/2-36/37/39-16-33-29-61
- RIDADR
- 3267 · UN 3267 8/PG 2
- WGK Germany
- 1 · 1
- RTECS
- 7000000 · NI7000000
- F
- 3 · 3-10
- Autoignition Temperature
- 977 °F · 977 °F
- TSCA
- TSCA listed
- HazardClass
- 8 · 8
- PackingGroup
- III
- HS Code
- 29332990 · 29332990
- Storage Class
- 6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- Hazard Classifications
- 3 DermalAcute · Acute Tox. 3 DermalAcute Tox. 4 OralEye Dam. 1Repr. 2Skin Corr. 1B
- Toxicity
- 50 orally · LD50 orally in Rabbit: 1144 mg/kg LD50 dermal Rabbit > 400 - < 640 mg/kg
- REACH Registrations
- Active
- Limited Quantities
- 1 L · 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
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]
Hazard information
Regulatory Information
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
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
Acute Tox. 4 (96.9%)
Acute toxicity (ingestion) - category 4
Acute Tox. 4 *
Safety & protection
Protective Action Criteria (PAC)
2.3 [mg/m3]
25 [mg/m3]
150 [mg/m3]
Toxicology
Adverse EffectsDermatotoxin - Skin burns.
Safety data
- F
- 3-10
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- NI7000000
- ridadr
- UN 3267 8/PG 2
- hs_code
- 29332990
- Toxicity
- LD50 orally in Rabbit: 1144 mg/kg LD50 dermal Rabbit > 400 - < 640 mg/kg
- risk_code
- 21/22-34-19-11-20/21/22-52/53-24-22-40-37-21
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS06
- hazard_code
- C,Xn,F,T
- safety_code
- 26-36-45-1/2-36/37/39-16-33-29-61
- hazard_class
- 8
- Storage Class
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- packing_group
- III
- Hazard statements
- H302-H311-H314
- Limited Quantities
- 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 3 DermalAcute Tox. 4 OralEye Dam. 1Repr. 2Skin Corr. 1B
- Autoignition Temperature
- 977 °F
- Precautionary statements
- P270-P280-P301+P312-P301+P330+P331-P303+P361+P353-P305+P351+P338
Chemistry & industry
Uses & manufacturing
U.S. Production2023: 50,000 - <75,000 lb
Industry UsesProcessing aids not otherwise specified
General Manufacturing Information
All Other Basic Organic Chemical Manufacturing
1H-Imidazole, 1-methyl-: ACTIVE
Applications
Uses1-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].
General DescriptionThis 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.
Preparation methods
Preparation1-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
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: 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.
Related reactions
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