[ CAS No. 17289-19-9 ] {[proInfo.proName]}

Name: 17289-19-9|Methyl 1-methyl-1H-imidazole-4-carboxylate|98%
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Quality Control of [ 17289-19-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 17289-19-9 ]

Product Details of [ 17289-19-9 ]

CAS No. :	17289-19-9	MDL No. :	MFCD02179561
Formula :	C₆H₈N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KZPZTVKOJSKVBV-UHFFFAOYSA-N
M.W :	140.14	Pubchem ID :	2773510
Synonyms :

Calculated chemistry of [ 17289-19-9 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.33
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	34.77
TPSA :	44.12 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) :	-7.01 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.5
Log Po/w (XLOGP3) :	0.2
Log Po/w (WLOGP) :	0.21
Log Po/w (MLOGP) :	-0.43
Log Po/w (SILICOS-IT) :	0.16
Consensus Log Po/w :	0.33

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.07
Solubility :	11.8 mg/ml ; 0.0846 mol/l
Class :	Very soluble
Log S (Ali) :	-0.69
Solubility :	28.9 mg/ml ; 0.206 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.85
Solubility :	20.0 mg/ml ; 0.143 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.78

Safety of [ 17289-19-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 17289-19-9 ]

* 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 [ 17289-19-9 ]
Downstream synthetic route of [ 17289-19-9 ]

[ 17289-19-9 ] Synthesis Path-Upstream 1~1

1
[ 67-56-1 ]
[ 19485-38-2 ]
[ 17289-19-9 ]
[ 17289-20-2 ]

Reference： [1] Organic Letters, 2006, vol. 8, # 5, p. 923 - 926

[ 17289-19-9 ] Synthesis Path-Downstream 1~33

1
[ 67-56-1 ]
[ 143165-09-7 ]
[ 17289-19-9 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1980,vol. 53,p. 557 - 558

2
[ 67-56-1 ]
[ 41716-18-1 ]
[ 17289-19-9 ]

Reference： [1]Synthesis,1988,p. 767 - 771

3
[ 67-56-1 ]
[ 53629-38-2 ]
[ 17289-19-9 ]

Reference： [1]Tetrahedron,1982,vol. 38,p. 2687 - 2696

5
[ 17289-19-9 ]
1-methyl-5-imidazolecarboxylic acid hydrochloride [ No CAS ]

Reference： [1]Organic Letters,2006,vol. 8,p. 923 - 926

6
[ 67-56-1 ]
[ 19485-38-2 ]
[ 17289-19-9 ]
[ 17289-20-2 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 923 - 926

7
[ 19485-35-9 ]
[ 17289-19-9 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 923 - 926
[2]Synthesis,1988,p. 767 - 771

8
[ 19485-38-2 ]
[ 17289-19-9 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1980,vol. 53,p. 557 - 558
[2]Synthesis,1988,p. 767 - 771

9
[ 41716-18-1 ]
[ 17289-19-9 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1980,vol. 53,p. 557 - 558

10
[ 67-56-1 ]
[ 201230-82-2 ]
[ 71759-87-0 ]
[ 17289-19-9 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;bis-triphenylphosphine-palladium(II) chloride; at 100℃; under 12929.0 Torr; for 48h;	Methyl (1-N-methyl)imidazole-4-carboxylate. A mixture of 4-iodo-1-methyl-1H-imidazole (500 mg, 2.40 mmol), trans-dichlorobis(triphenylphosphine)palladium(II) (255 mg, 0.30 mmol) and triethylamine (3 mL) in methanol (30 mL) in a pressure vessel was purged with argon for 10 min. The vessel was then pressurized with carbon monoxide to 250 psi and heated at 100 C. for 2 days. After cooling to room temperature, the reaction mixture was filtered through Celite, and concentrated under vacuum. The resultant residue was purified by flash chromatograph on silica gel (5% MeOH in CHCl3) to give title compound. 1H NMR (400 MHz, CDCl3) delta 7.60 (s, 1H), 7.28 (s, 1H), 3.90 (s, 3H), 3.78 (s, 3H).

Reference： [1]Patent: US2003/229079,2003,A1 .Location in patent: Page 37

11
[ 17289-17-7 ]
[ 17289-19-9 ]

Yield	Reaction Conditions	Operation in experiment
	With manganese dioxide;	19.0 g of manganese dioxide was added to a stirred solution of 4.7 g of 38D in ethanol-free, chloroform and the mixture was stirred overnight at room temperature. The mixture was heated at reflux for 1 hour, cooled, 9.5 g of manganese dioxide was added; the mixture was stirred at room temperature for 2 hours and at reflux for 30 minutes. The mixture was cooled and filtered and the filtrate was stripped of solvent to give methyl 1-methylimidazole-4-carboxylate (38E), as a yellow solid, m.p.: 72.5-81 C.

Reference： [1]Patent: US4853027,1989,A

12
[ 17289-19-9 ]
[ 74857-56-0 ]
[ 317332-46-0 ]

Yield	Reaction Conditions	Operation in experiment
		1-(3-Benzylphenyl)-3-(1-N-methylimidazole-4-yl)propane-1,3-dione (5E). To a solution of 1-(3-benzylphenyl) methyl ketone (4B) (213 mg, 1.01 mmol) in dry THF (5 mL) under argon was added potassium bis(trimethylsilyl)amide (0.5 M solution in toluene, 2.0 mL, 1.0 mmol) at 0 C. and stirred for 30 min. Methyl (1-N-methyl)imidazole-4-carboxylate was then added and the reaction mixture was stirred at 0 C. for 10 min then ambient temperature for 15 min. The reaction was quenched with 1N HCl to pH 8. The reaction mixture was extracted with CHCl3 three times. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated under vacuum. The residue was triturated with ether/hexanes to give 5E. 1H NMR (400 MHz, CDCl3) delta 7.86-7.90 (m, 2H), 7.63 (d, 1H), 7.50 (d, 1H), 7.25-7.40 (m, 4H), 7.18-7.22 (m, 3H), 7.07 (s, 1H), 4.04 (s, 2H), 3.77 (s, 3H).

Reference： [1]Patent: US2003/229079,2003,A1 .Location in patent: Page 37

13
[ 17289-19-9 ]
Tebbe's reagent [ No CAS ]
[ 1202769-48-9 ]

Yield	Reaction Conditions	Operation in experiment
		Methyl 1 -methyl- lH-imidazole-4-carboxylate B.48 (250mg, 1.178mmol) was dissolved in 5ml of anhydrous pyridine and cooled to ~0C under an atmosphere of nitrogen. Tebbe Reagent (0.5M in toluene) (3.57mL) was added slowly. The reaction was warmed to room temperature and stirred 2hours. After cooling to O0C, the reaction was quenched with ImI of 40%NaOH and 2ml of water. The solution was diluted with 10ml of pyridine and stirred at r.t. for lhour. Solvents were removed under vacuum. The residue obtained was partially dissolved in methanol and filtered. The filtrate was then purified by CombiFlash chromatography eluting with a gradient of 2%methanol/dichloromethane to 10%methanol/dichloromethane. The fractions containing the product were combined and concentrated under vacuum to give 4-(l- methoxyethenyl)-l -methyl- lH-imidazole B.49 as a brownish oil (249mg). ESI-MS: M + H+ 139.1 m/z.

Reference： [1]Patent: WO2009/158011,2009,A1 .Location in patent: Page/Page column 176

14
[ 754225-84-8 ]
[ 17289-19-9 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 6232 - 6235

15
[ 17289-19-9 ]
methyl 2-bromo-1-methyl-1H-imidazole-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With N-Bromosuccinimide; In tetrahydrofuran; at 20℃; for 72h;	To a stirring solution of methyl 1-methyl-1 H-imidazole-4-carboxylate (5 g , 46.38 mmol) in THF (100 ml) was added NBS (8.25 g , 46.38 mmol). The reaction mixture was allowed to stir at room temperature for 72 h. The mixture was concentrated and the crude residue was dissolved in EtOAc (80 ml), washed with sat.Na2S203 (100 ml) and a ~pH 12 solution of NaOH (50 ml). The NaOH solution was extracted using 1 :4 IPA : CHCI3 (5 x 10 ml) and the organic layers were combined, dried over MgSQ, filtered and concentrated to give the crude product. Purification by column chromatography with a gradient of 0100% EtOAc / heptane gave the purified product which was dissolved in a pH~12 solution of NaOH (50 ml) and extracted using DCM. The organic layers were combined, dried over MgSQ, filtered and concentrated to give the title compound (5.58 g, 71 %) as a white solid . 1 H-NMR (DMSO-d6, 250 MHz): d[ppm]= 8.08 (s, 1 H), 3.74 (s, 3H), 3.63 (s, 3H) HPLCMS (Method A): [m/z]: 218.8, 220.75 [M+H]+
17%	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 60℃; for 4h;	To a solution of methyl 1 -methyl-1 H-imidazole-4-carboxylate (14.3 mmol, 2 g) in CCI4 (40 ml_), NBS (15.3 mmol, 2.72 g) and AIBN (0.715 mmol, 1 17 mg) were added. The reaction mixture was stirred 4h at 605C and then cooled to room temperature. The solvent was evaporated. The reaction crude was purified by flash chromatography on silica gel using an elution of 8% methanol in ethyl acetate to afford methyl 2-bromo-1 -methyl-1 H-imidazole-4-carboxylate (529 mg, Yield: 17%). 1 H NMR (400 MHz, CDCI3) delta 7.59 (1 H, s), 3.91 (3H, s), 3.67 (3H, s) LC-MS: tR = 1 .60 [M+H] + = 219/221 (method 3)
17%	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 60℃; for 4h;	To a solution of <strong>[17289-19-9]methyl 1-methyl-1H-imidazole-4-carboxylate</strong> (14.3 mmol, 2 g) in CCl4 (40 mL), NBS (15.3 mmol, 2.72 g) and AIBN (0.715 mmol, 117 mg) were added. The reaction mixture was heated for 4 h at 60 C and then cooled to RT. The solvent was evaporated. The reaction crude was purified by flash chromatography over silica gel using an elution of 8% methanol in ethyl acetate to afford 529 mg (Yield: 17%) of the title compound 18. 1H NMR (400 MHz, CDCl3): delta 7.59 (1H, s), 3.91 (3H, s), 3.67 (3H, s); ESI-MS: m/z 219 [M + H]+

Reference： [1]Patent: WO2017/68089,2017,A2 .Location in patent: Page/Page column 303; 304
[2]Patent: WO2013/149997,2013,A1 .Location in patent: Page/Page column 99
[3]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2016,vol. 55B,p. 1117 - 1130

16
[ 17289-19-9 ]
methyl 1-methyl-2-styryl-1H-imidazole-4-carboxylate [ No CAS ]

Reference： [1]Patent: WO2013/149997,2013,A1
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2016,vol. 55B,p. 1117 - 1130

17
[ 17289-19-9 ]
methyl 2-formyl-1-methyl-1H-imidazole-4-carboxylate [ No CAS ]

Reference： [1]Patent: WO2013/149997,2013,A1
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2016,vol. 55B,p. 1117 - 1130
[3]Patent: WO2017/68089,2017,A2

18
[ 17289-19-9 ]
[ 39971-65-8 ]
methyl 1-methyl-5-(trifluoromethyl)-1H-imidazole-4-carboxylate [ No CAS ]
methyl 1-methyl-2-(trifluoromethyl)-1H-imidazole-4-carboxylate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 11868 - 11871
Angew. Chem.,2014,vol. 126,p. 12062 - 12065,4

19
[ 17289-19-9 ]
bis(((difluoromethyl)sulfinyl)oxy)zinc [ No CAS ]
methyl 5-(difluoromethyl)-1-methyl-1H-imidazole-4-carboxylate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 11868 - 11871
Angew. Chem.,2014,vol. 126,p. 12062 - 12065,4

20
[ 17289-19-9 ]
methyl 2-((3aS,4R,9bR)-8-chloro-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinolin-4-yl)-1-methyl-1H-imidazole-4-carboxylate [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2016,vol. 55B,p. 1117 - 1130

21
[ 17289-19-9 ]
methyl 2-(1-hydroxy-2-nitroethyl)-1-methyl-1H-imidazole-4-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/68089,2017,A2

22
[ 17289-19-9 ]
methyl 1-methyl-2-[(E)-2-nitroethenyl]-1H-imidazole-4-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/68089,2017,A2

23
[ 17289-19-9 ]
methyl 2-(2-[(tert-butoxy)carbonyl]amino}ethyl)-1-methyl-1H-imidazole-4-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/68089,2017,A2

24
[ 17289-19-9 ]
[ 120781-01-3 ]

Yield	Reaction Conditions	Operation in experiment
22.8%	With N-Bromosuccinimide; In chloroform; at 50℃; for 18h;	To a solution of Example 63a (1.40 g, 10.0 mmol) in CHC13 (30.0 mL) was added NBS (2.13g, 12.0 mmol). The reaction mixture was then stirred 18hrs at 50C and then cooled to room temperature. The residue was extracted with EtOAc (200 mL * 2). The combined organic phase was washed with brine, dried over Na2S04, filtrated and concentrated under reduced pressure to give the crude product which was further purified by silica gel chromatography to give the pure product Example 63b (500 mg, yield 22.8%). NMR (400 MHz, Chloroform- ) delta 7.60 (s, 1H), 3.91 (s, 3H), 3.67 (s, 3H).

Reference： [1]Patent: WO2017/218960,2017,A1 .Location in patent: Paragraph 00617

25
[ 17289-19-9 ]
C₁₂H₁₆N₄O₂ [ No CAS ]

Reference： [1]Patent: WO2017/218960,2017,A1

26
[ 17289-19-9 ]
C₁₁H₁₆N₄O [ No CAS ]

Reference： [1]Patent: WO2017/218960,2017,A1

27
[ 17289-19-9 ]
C₁₁H₁₅ClN₄ [ No CAS ]

Reference： [1]Patent: WO2017/218960,2017,A1

28
[ 17289-19-9 ]
2-hydroxy-6-((5-(1-isopropyl-1H-pyrazol-5-yl)-1-methyl-1H-imidazol-4-yl)methoxy)benzaldehyde [ No CAS ]

Reference： [1]Patent: WO2017/218960,2017,A1

29
[ 17289-19-9 ]
[ 129003-87-8 ]

Reference： [1]Patent: WO2009/158011,2009,A1

30
[ 17289-19-9 ]
[ 756-79-6 ]
[ 1402838-49-6 ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 6705 - 6733

31
[ 17289-19-9 ]
[ 1402838-81-6 ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 6705 - 6733

32
[ 17289-19-9 ]
[ 1402837-01-7 ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 6705 - 6733

33
[ 17289-19-9 ]
[ 275818-95-6 ]
C₇H₈F₂N₂O₂ [ No CAS ]

Reference： [1]Nature Communications,2020,vol. 11

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Ghs Precautionary Statements

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P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

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. 17289-19-9 ] {[proInfo.proName]}

Quality Control of [ 17289-19-9 ]

Related Doc. of [ 17289-19-9 ]

Product Details of [ 17289-19-9 ]

Calculated chemistry of [ 17289-19-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 17289-19-9 ]

Application In Synthesis of [ 17289-19-9 ]

[ 17289-19-9 ] Synthesis Path-Upstream 1~1

[ 17289-19-9 ] Synthesis Path-Downstream 1~33

Related Functional Groups of [ 17289-19-9 ]

Esters

Related Parent Nucleus of [ 17289-19-9 ]

Imidazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 17289-19-9 ]

Related Parent Nucleus of
[ 17289-19-9 ]