[ CAS No. 3034-42-2 ] {[proInfo.proName]}

Name: 3034-42-2|1-Methyl-5-nitroimidazole|98%
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SKU: A103808
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DV 2D 3D

3d Animation Molecule Structure of 3034-42-2

Structure of 3034-42-2 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 3034-42-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 3034-42-2 ]

SDS Specification

Alternatived Products of [ 3034-42-2 ]

Product Details of [ 3034-42-2 ]

CAS No. :	3034-42-2	MDL No. :	MFCD00126968
Formula :	C₄H₅N₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JLZXSFPSJJMRIX-UHFFFAOYSA-N
M.W :	127.10	Pubchem ID :	18210
Synonyms :

Calculated chemistry of [ 3034-42-2 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.25
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	32.31
TPSA :	63.64 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.96 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.93
Log Po/w (XLOGP3) :	0.16
Log Po/w (WLOGP) :	0.33
Log Po/w (MLOGP) :	-1.16
Log Po/w (SILICOS-IT) :	-1.67
Consensus Log Po/w :	-0.28

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.07
Solubility :	10.7 mg/ml ; 0.0843 mol/l
Class :	Very soluble
Log S (Ali) :	-1.05
Solubility :	11.2 mg/ml ; 0.0884 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.14
Solubility :	92.5 mg/ml ; 0.728 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.95

Safety of [ 3034-42-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 3034-42-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 3034-42-2 ]
Downstream synthetic route of [ 3034-42-2 ]

[ 3034-42-2 ] Synthesis Path-Upstream 1~20

1
[ 3034-38-6 ]
[ 77-78-1 ]
[ 3034-42-2 ]

Yield	Reaction Conditions	Operation in experiment
82%	for 2 h; Reflux	5-Nitroimidazole (2) (1 g, 8.85 mmol) and dimethyl sulfate (1.2 mL) were added in dioxane (5 mL). Reaction mixture was refluxed for 2 h. The solvent was then evaporated under vacuum, and the oily acidic residue was neutralized by a NaHCO₃ saturated aqueous solution. The formed solid and the aqueous solution were extracted with dichloromethane (3 x 5 mL). Mixture was dried with magnesium sulfate and organic solvent evaporated on vacuum, crude was purified using flash column chromatography (dichloromethane/ethylacetate; 97:3) to obtained 1-Methyl-5-nitro-1H-imidazole (4a) (0.92 g, 82percent); m.p. 60 °C.

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 3, p. 1015 - 1018
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 5, p. 1274 - 1278
[3] Journal of Medicinal Chemistry, 2003, vol. 46, # 3, p. 427 - 440

2
[ 3034-38-6 ]
[ 3034-42-2 ]

Yield	Reaction Conditions	Operation in experiment
82%	With dimethyl sulfate In formic acid; water	EXAMPLE 2 202 parts of 5-nitroimidazole is dissolved in 600 parts of formic acid (90percent by weight), 250 parts of dimethyl sulfate is added and the whole is heated for 6 hours. The formic acid is distilled off in vacuo. 420 parts of water is added to the residue, the whole cooled to from 0° to 5° C. and the unreacted 5-nitroimidazole (60 parts) is centrifuged off. The mixture is adjusted to pH 10 with aqueous ammonia solution (25percent by weight) and the precipitate is separated at 0° to 5° C. 130 parts of 1-methyl-5-nitroimidazole having a melting point of 58° to 60° C. is obtained; this is equivalent to a yield of 82percent of theory based on reacted 4(5)-nitroimidazole.

Reference： [1] Patent: US4021442, 1977, A,

3
[ 3034-38-6 ]
[ 80-48-8 ]
[ 3034-42-2 ]

Reference： [1] Patent: US4010176, 1977, A,

4
[ 553-90-2 ]
[ 3034-38-6 ]
[ 3034-41-1 ]
[ 3034-42-2 ]

Reference： [1] Tetrahedron Letters, 1984, vol. 25, # 18, p. 1957 - 1960

5
[ 5709-48-8 ]
[ 3034-42-2 ]

Reference： [1] Patent: US4925949, 1990, A,

6
[ 3034-38-6 ]
[ 74-88-4 ]
[ 3034-42-2 ]

Reference： [1] Chemistry - A European Journal, 2010, vol. 16, # 13, p. 3983 - 3993

7
[ 616-47-7 ]
[ 3034-41-1 ]
[ 3034-42-2 ]

Reference： [1] Journal of the Chemical Society, 1924, vol. 125, p. 1434
[2] Synthesis, 2011, # 17, p. 2859 - 2864

8
[ 3034-38-6 ]
[ 77-78-1 ]
[ 3034-41-1 ]
[ 3034-42-2 ]

Reference： [1] Liebigs Annalen der Chemie, 1987, p. 77 - 80
[2] Journal of the Chemical Society, 1925, vol. 127, p. 576
[3] Tetrahedron Letters, 1984, vol. 25, # 18, p. 1957 - 1960

9
[ 616-47-7 ]
[ 3034-42-2 ]
[ 19183-15-4 ]

Reference： [1] Synthesis, 2011, # 17, p. 2859 - 2864

10
[ 616-47-7 ]
[ 3034-41-1 ]
[ 3034-42-2 ]
[ 19183-15-4 ]

Reference： [1] Synthesis, 2011, # 17, p. 2859 - 2864

11
[ 3034-38-6 ]
[ 77-78-1 ]
[ 3034-42-2 ]

Reference： [1] New Journal of Chemistry, 2006, vol. 30, # 3, p. 349 - 358
[2] Antimicrobial Agents and Chemotherapy, 2003, vol. 47, # 1, p. 302 - 308
[3] Journal of the Chemical Society, 1924, vol. 125, p. 1434

12
[ 13182-96-2 ]
[ 77-78-1 ]
[ 3034-42-2 ]

Reference： [1] Synthesis, 1995, # 9, p. 1183 - 1189

13
[ 77-78-1 ]
[ 3034-42-2 ]

Reference： [1] Synthesis, 1995, # 9, p. 1183 - 1189

14
[ 3034-38-6 ]
[ 3034-42-2 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 2819 - 2828

15
[ 212248-40-3 ]
[ 74-88-4 ]
[ 3034-41-1 ]
[ 3034-42-2 ]

Reference： [1] Russian Journal of Organic Chemistry, 1997, vol. 33, # 12, p. 1764 - 1766

16
[ 109540-97-8 ]
[ 3034-42-2 ]

Reference： [1] Journal of the Chemical Society, vol. 232, p. 236

17
[ 186581-53-3 ]
[ 60-29-7 ]
[ 3034-38-6 ]
[ 3034-41-1 ]
[ 3034-42-2 ]

Reference： [1] Journal of the Chemical Society, 1925, vol. 127, p. 576

18
[ 3034-38-6 ]
[ 77-78-1 ]
[ 3034-41-1 ]
[ 3034-42-2 ]

Reference： [1] Journal of the Chemical Society, 1925, vol. 127, p. 576

19
[ 50-00-0 ]
[ 3034-42-2 ]
[ 936-05-0 ]

Yield	Reaction Conditions	Operation in experiment
62%	at 140℃; for 48 h;	In a sealed glass tube, formaldehyde (1 g, 33.54 mmol) and 1-Methyl-5-nitro-1H-imidazole (4a) (1 g, 7.8 mmol) solution were added in DMSO (5 mL). The tube was heated at 140 °C for 48 h. After that solution was poured into water (5 mL) and extracted with ethyl acetate (3 x 5 mL). Then mixture was dried (MgSO₄) and solvent evaporation under vacuum, gave crude in the form of solid, which was recrystallized (THF/heptane, 1:1) and product (5a) was isolated (0.76 g, 62percent yield) as white powder; m.p. 117 °C.

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 2819 - 2828
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 3, p. 1015 - 1018
[3] Journal of Medicinal Chemistry, 2003, vol. 46, # 3, p. 427 - 440
[4] Tetrahedron, 2000, vol. 56, # 4, p. 645 - 657
[5] Patent: WO2014/205414, 2014, A1, . Location in patent: Paragraph 0298

20
[ 3034-42-2 ]
[ 936-05-0 ]

Reference： [1] Patent: US4010176, 1977, A,

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[ 3034-42-2 ]

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Ghs Precautionary Statements

Precautionary Statements-General
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P101	If medical advice is needed,have product container or label at hand.
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Code	Phrase
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P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
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P264	Wash hands thoroughly after handling.
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P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
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Code	Phrase
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P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
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P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
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P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
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P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
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Yield	Reaction Conditions	Operation in experiment
62%	In dimethyl sulfoxide; at 140℃; for 48h;	In a sealed glass tube, formaldehyde (1 g, 33.54 mmol) and 1-Methyl-5-nitro-1H-imidazole (4a) (1 g, 7.8 mmol) solution were added in DMSO (5 mL). The tube was heated at 140 C for 48 h. After that solution was poured into water (5 mL) and extracted with ethyl acetate (3 x 5 mL). Then mixture was dried (MgSO4) and solvent evaporation under vacuum, gave crude in the form of solid, which was recrystallized (THF/heptane, 1:1) and product (5a) was isolated (0.76 g, 62% yield) as white powder; m.p. 117 C.
62%	In dimethyl sulfoxide; at 130℃; for 48h;Sealed tube;	Weigh <strong>[3034-42-2]1-methyl-5-nitroimidazole</strong> 160mg (1.26mmol) and paraformaldehyde 162mg (5.41mmol) in a sealed tube, 3ml dissolved in dimethyl sulfoxide DMSO, the reaction at 130 C for 48h, cooled water (30ml ) and ethyl acetate (30ml * 3). the combined organic phase was washed with saturated aqueous sodium chloride (50ml * 3), dried over anhydrous sodium sulfate organic phase is filtered, the filtrate was concentrated and the residue purified by silica gel column chromatography (neat ethyl acetate) to give compound 1-methyl-2-hydroxymethyl-5-nitroimidazole 122mg, 62% yield.
	In dimethyl sulfoxide;	[0298] (1-Methyl-5-nitro-1H-imidazol-2-yl)methanol (2-CH20H). The titlecompound was prepared according to the literature procedure (116). 1H NMR (400 MHz, d6-DMSO) 8= 8.00 (s, 1H), 5.67 (t, J=6.0 Hz, 1H), 4.58 (d, J=6.0 Hz, 2H), 3.92 (s, 3H). 13CNMR (100 MHz, d6-DMSO) 8= 152.3, 139.2, 131.4, 56.0, 33.2. ESI MS (MeOH) for[M+Hf = 158.2 Da.

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 3034-42-2 ] {[proInfo.proName]}

Quality Control of [ 3034-42-2 ]

Related Doc. of [ 3034-42-2 ]

Product Details of [ 3034-42-2 ]

Calculated chemistry of [ 3034-42-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 3034-42-2 ]

Application In Synthesis of [ 3034-42-2 ]

[ 3034-42-2 ] Synthesis Path-Upstream 1~20

[ 3034-42-2 ] Synthesis Path-Downstream 1~54

Related Functional Groups of [ 3034-42-2 ]

Nitroes

Related Parent Nucleus of [ 3034-42-2 ]

Imidazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 3034-42-2 ]

Related Parent Nucleus of
[ 3034-42-2 ]