1H-Imidazole, 1-methyl-

1H-Imidazole, 1-methyl- - Names and Identifiers

Name	1-Methylimidazole
Synonyms	DY 070 NSC 88064 Araldite DY 070 methyl imidazole 1-methyl-imidazol N-methyl midazole 1-Methylimidazole N-Methylimidazole N-methyl imidazole 1-Methylglyoxaline N1-Methylimidazole Methylimidazole,1- N-methyl glyoxaline Methylimidazole, 1- Imidazole, 1-methyl- 1-methyl-1H-imidazole 1H-Imidazole, 1-methyl- N-methyl midazoleN-methyl glyoxaline N-methylimidazole (1-methylimidazole)
CAS	616-47-7
EINECS	210-484-7
InChI	InChI=1/C4H6N2/c1-6-3-2-5-4-6/h2-4H,1H3
InChIKey	MCTWTZJPVLRJOU-UHFFFAOYSA-N

1H-Imidazole, 1-methyl- - Physico-chemical Properties

Molecular Formula	C4H6N2
Molar Mass	82.1
Density	1.03g/mLat 25°C(lit.)
Melting Point	−60°C(lit.)
Boling Point	198°C(lit.)
Flash Point	198°F
Water Solubility	Miscible with water.
Vapor Presure	0.4 mm Hg ( 20 °C)
Appearance	Clear Liquid
Specific Gravity	1.031
Color	Clear colorless to yellow
BRN	105197
pKa	6.95(at 25℃)
PH	9.5-10.5 (50g/l, H2O, 20℃)
Storage Condition	Store below +30°C.
Stability	Stable, but moisture sensitive. Incompatible with acids, acid anhydrides, strong oxidizing agents, moisture, carbon dioxide, acid chlorides.
Sensitive	Hygroscopic
Explosive Limit	2.7-15.7%(V)
Refractive Index	n20/D 1.495(lit.)
MDL	MFCD00005292
Physical and Chemical Properties	Density 1.03 melting point -60°C boiling point 198°C refractive index 1.4955-1.4975 flash point 92°C
Use	Used as organic synthesis intermediates and resin curing agent, adhesive, etc

1H-Imidazole, 1-methyl- - Risk and Safety

Risk Codes	R21/22 - Harmful in contact with skin and if swallowed. R34 - Causes burns R19 - May form explosive peroxides R11 - Highly Flammable R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R52/53 - Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R24 - Toxic in contact with skin R22 - Harmful if swallowed R40 - Limited evidence of a carcinogenic effect R37 - Irritating to the respiratory system R21 - Harmful in contact with skin
Safety Description	S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S1/2 - Keep locked up and out of the reach of children. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S16 - Keep away from sources of ignition. S33 - Take precautionary measures against static discharges. S29 - Do not empty into drains. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets.
UN IDs	UN 3267 8/PG 2
WGK Germany	1
RTECS	NI7000000
FLUKA BRAND F CODES	3-10
TSCA	Yes
HS Code	29332990
Hazard Class	8
Packing Group	III
Toxicity	LD50 orally in Rabbit: 1144 mg/kg LD50 dermal Rabbit > 400 - < 640 mg/kg

1H-Imidazole, 1-methyl- - Introduction

Soluble in water, soluble in organic solvent.

Last Update：2022-10-16 17:27:09

1H-Imidazole, 1-methyl- - Security information

dangerous goods mark	C,Xn,F,T
hazard category code	21/22-34-19-11-20/21/22-52/53-24-22-40-37-21
safety instructions	26-36-45-1/2-36/37/39-16-33-29-61
dangerous goods transport number	UN 3267 8/PG 2
WGK Germany	1
RTECS number	NI7000000
F	3-10
auto-ignition temperature	977 °F
TSCA	Yes
HazardClass	8
PackingGroup	III
customs code	29332990
Toxicity	LD50 orally in Rabbit: 1144 mg/kg LD50 dermal Rabbit > 400 - < 640 mg/kg

Last Update：2024-04-10 22:29:15

1H-Imidazole, 1-methyl- - Preparation

A continuous preparation method of N-methylimidazole, using Hβ molecular sieve as a catalyst, in a tubular reactor, mixed ammonia containing ammonia and methylamine, and mixed aldehyde containing formaldehyde and glyoxal carry out a gas phase catalytic reaction, and the obtained reaction product is separated by rectification to obtain N-methylimidazole. The specific steps are:

Add Hβ molecular sieve catalyst to the tubular reactor, heat and vaporize the raw materials mixed with ammonia and mixed aldehyde, and continuously pass into the tubular reactor. The mixed gas generated by the gas phase catalytic reaction is condensed to obtain N-methyl imidazole crude product;
the crude N-methylimidazole product obtained in step (1) is added to the decompression side line rectification column for rectification and separation, the pressure of the decompression side line rectification column is controlled to be 0.20MPa, the side line discharge of the decompression side line rectification column is N-methylimidazole with a content of ≥ 99.0wt%, the top of the decompression side line rectification column is obtained with water with a purity of more than 99.0wt%;
The water obtained from the top of the decompression side line distillation tower with a purity of more than 99.0wt% is added to the distillation tower, and after distillation separation, the top of the distillation tower obtains an aqueous solution of mixed ammonia and mixed aldehyde as raw materials for recycling, and the bottom of the distillation tower is discharged as water.

Last Update：2024-04-10 22:29:15

1H-Imidazole, 1-methyl- - Nature

melting point	−60 °C(lit.)
boiling point	198 °C(lit.)
density	1.03 g/mL at 25 °C(lit.)
Vapor pressure	0.4mm Hg ( 20 °C)
refractive index	n20/D 1.495(lit.)
flash point	198 °F
storage conditions	Store below +30°C.
morphology	Liquid
acidity coefficient (pKa)	6.95(at 25℃)
color	Clear colorless to yellow
Specific gravity	1.031
PH value	9.5-10.5 (50g/l, H2O, 20℃)
pH range of acid-base indicator discoloration	9.5 - 11.5 at 100 g/l at 20 °C
explosion limit value (explosive limit)	2.7-15.7%(V)
water solubility	Miscible with water.
sensitivity	Hygroscopic
BRN	105197
stability	Stable, but moisture sensitive. Incompatible with acids, acid anhydrides, strong oxidizing agents, moisture, carbon dioxide, acid chlorides.
InChIKey	MCTWTZJPVLRJOU-UHFFFAOYSA-N
NIST chemical information	1H-Imidazole, 1-methyl-(616-47-7)
EPA chemical information	1H-Imidazole, 1-methyl- (616-47-7)

Last Update：2024-04-09 21:31:46

1H-Imidazole, 1-methyl- - Introduction

N-methylimidazole, or 1-methylimidazole, is mainly used as organic synthesis intermediates, ionic liquids and resin curing agents, adhesives, etc., such as deoxyribonucleic acid synthesis and hydroxyacetylation catalysts and Used in pouring, bonding and glass fiber reinforced plastic and other fields. Therefore, optimizing the synthesis process of N-methylimidazole has good application value and practical significance. At present, the research on the preparation methods of N-methylimidazole mainly focuses on 6 methods: 1, 2-dicarbonyl compound synthesis, Van Leusen synthesis, Phillips synthesis, Wohl-Marckwald synthesis, Witting synthesis and N-methylation synthesis.

Last Update：2024-04-09 20:52:54

1H-Imidazole, 1-methyl- - Use

N-methylimidazole is an important raw material for the synthesis of pharmaceutical intermediates. It is used to prepare losartan, nidazofenone, 1-methylimidazole-5-formyl chloride hydrochloride and naphthalimidazole hydrochloride, etc.; In the field of pesticides, it is widely used in the synthesis of fungicides and plant growth-promoting agents, such as: N-methylimidazole is used as a; in addition, N-methylimidazole is also used as curing agent and adhesive for epoxy resin and other resins. N-methylimidazole also has great application in pouring and glass fiber reinforced plastic

Last Update：2024-04-09 20:52:54

1H-Imidazole, 1-methyl- - Use

is mainly used as curing agent for epoxy resin and other resins. Used in pouring, bonding, glass fiber reinforced plastic and other fields.
organic synthesis intermediates and resin curing agents, adhesives, etc. Can be used in pouring, bonding and glass fiber reinforced plastic and other fields.
organic synthesis intermediates and used as epoxy resin curing agent, adhesive, etc.; can be widely used in epoxy resin bonding, coating, pouring, encapsulation, impregnation and composite materials.
used as organic synthesis intermediates and resin curing agents, adhesives, etc.

Last Update：2024-04-09 21:31:46

1H-Imidazole, 1-methyl- - Reference Information

pH range of acid-base indicator discoloration	9.5 - 11.5 at 100g/l at 20°C
LogP	-0.19 at 25℃
NIST chemical information	information provided by: webbook.nist.gov (external link)
EPA chemical substance information	information provided by: ofmpeb.epa.gov (external link)
Overview	N-methylimidazole (1-methylimidazole) is mainly used as organic synthesis intermediates, ionic liquids and resin curing agents, adhesives, such as deoxyribonucleic acid synthesis and hydroxyl acetylation catalyst and used in casting, bonding and glass fiber reinforced plastic and other fields. Therefore, the optimization of N-methyl imidazole synthesis process has good application value and practical significance. At present, the research on the preparation methods of N-methylimidazole mainly focuses on the synthesis of 1, 2-dicarbonyl compounds, Van Leusen synthesis, Phillips synthesis, Wohl-Marckwald synthesis, witting synthesis method and N-methylation synthesis method in 6 ways.
Application	N-methylimidazole is an important raw material for the synthesis of pharmaceutical intermediates, for the preparation of losartan, 1-methylimidazole-5-formyl chloride hydrochloride and naphthyl methyl imidazole hydrochloride, etc.; In the field of pesticides, are widely used in the synthesis of fungicides and plant growth promoters, such: N-methylimidazole was used as the cationic matrix to produce imidazolium-based ionic liquids by quaternization. In addition, N-methylimidazole was also used as curing agent and adhesive for epoxy resin and other resins; N-methylimidazole is also widely used in the field of casting and FRP.
preparation	a continuous preparation method of N-methylimidazole, using H beta molecular sieve as catalyst, in the tubular reactor, the mixed ammonia containing ammonia and methylamine and the mixed aldehyde containing formaldehyde and glyoxal are subjected to gas phase catalytic reaction, and the obtained reaction product is separated by distillation to obtain N-methylimidazole. The specific steps are as follows:(1) The H beta molecular sieve catalyst is added to the tubular reactor, and the mixed ammonia and mixed aldehyde of the raw material are heated and vaporized, and then continuously passed into the tubular reactor, the mixed gas generated by the gas-phase catalytic reaction is condensed to obtain a crude N-methylimidazole product;(2) the crude N-methylimidazole product obtained in step (1) is added to a vacuum side-line rectification column for rectification and separation, the pressure of the vacuum side-line rectification column is controlled to be 0.20MPa, the side-line discharge of the vacuum side-line rectification column is N-methylimidazole with a content of ≥ 99.0wt%, and water with a purity of more than 99.0wt% is obtained at the top of the vacuum side-line rectification column, the bottom discharge of the vacuum side-line rectification column is a high boiling point mixture containing a trace amount of N-methylimidazole;(3) water with a purity of more than 99.0wt% obtained at the top of the vacuum side-line rectification column is added to the rectification column, after distillation separation, the aqueous solution of mixed ammonia and mixed aldehyde is obtained at the top of the distillation column as raw materials for recycling, and the bottom discharge of the distillation column is water.
Application	is mainly used for curing agent of epoxy resin and other resins; Used for casting, bonding and glass fiber reinforced plastic and other fields. organic synthesis intermediates and resin curing agents, adhesives, etc. Can be used for casting, bonding and glass fiber reinforced plastic and other fields. organic synthesis intermediates and used as epoxy resin curing agent, adhesive, etc.; Can be widely used in epoxy resin bonding, coating, casting, encapsulation, impregnation and composite materials. used as organic synthesis intermediates and resin curing agent, adhesive, etc.
autoignition temperature	977 ° F.