[ CAS No. 131020-36-5 ] {[proInfo.proName]}

Name: 131020-36-5|Methyl 1-methyl-1H-benzo[d]imidazole-5-carboxylate|97%
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Quality Control of [ 131020-36-5 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 131020-36-5 ]

CAS No. :	131020-36-5	MDL No. :	MFCD04492113
Formula :	C₁₀H₁₀N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HBYFGEOBNHODCG-UHFFFAOYSA-N
M.W :	190.20	Pubchem ID :	965319
Synonyms :

Safety of [ 131020-36-5 ]

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 [ 131020-36-5 ]

* 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 [ 131020-36-5 ]
Downstream synthetic route of [ 131020-36-5 ]

[ 131020-36-5 ] Synthesis Path-Upstream 1~9

1
[ 131020-36-5 ]
[ 53484-17-6 ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: at 20℃; for 4 h;	The methyl 1-methyl-1H-benzimidazole-5-carbonate (500 mg) obtained above was dissolved in methanol (10 ml). 1 N Sodium hydroxide solution (8 ml) was added thereto, and the mixture was stirred for 4 hours at room temperature. Water was added to the reaction mixture which was then acidified by formic acid. Precipitates were collected by filtration and dried under reduced pressure to give the title compound (367 mg, Y.: 79percent). ¹H NMR; (DMSO-d₆) δ (ppm): 3.8 (s, 3H), 7.6 (d, 1H), 7.8 (dd, 1H), 8.2 (d, 1H), 8.3 (s, 1H).

Reference： [1] Patent: EP1595866, 2005, A1, . Location in patent: Page/Page column 26
[2] Patent: WO2004/99131, 2004, A2, . Location in patent: Page 54

2
[ 64-18-6 ]
[ 66315-16-0 ]
[ 131020-36-5 ]

Yield	Reaction Conditions	Operation in experiment
97%	at 90℃; for 3 h;	The methyl 3-amino-4-methylaminobenzoate (3.3 g) obtained above was dissolved in formic acid (96 ml). Water (4 ml) was added thereto, and the solution was stirred for 3 hours at 90°C. The reaction solution was concentrated under reduced pressure, and ethyl acetate was added to the residue. The organic phase was washed with a saturated sodium bicarbonate solution and dried over sodium sulfate anhydrous. The product was concentrated under reduced pressure to give methyl 1-methyl-1H-benzimidazole-5-carbonate (3.4 g, Y.: 97percent). ¹H NMR; (DMSO-d₆) δ (ppm): 3.8 (s, 3H), 3.8 (s, 3H), 7.6 (d, 1H), 7.9 (dd, 1H), 8.2 (d, 1H), 8.3 (s, 1H). ESI/MS (m/z): 191 (M+H)⁺.

Reference： [1] Patent: EP1595866, 2005, A1, . Location in patent: Page/Page column 26

3
[ 66315-16-0 ]
[ 149-73-5 ]
[ 131020-36-5 ]

Reference： [1] Patent: WO2003/99814, 2003, A1, . Location in patent: Page 29
[2] Patent: WO2004/99131, 2004, A2, . Location in patent: Page 54

4
[ 131020-35-4 ]
[ 131020-36-5 ]

Yield	Reaction Conditions	Operation in experiment
43.6%	With hydrogenchloride; sodium hydroxide In methanol; water	STR11 1-Methylbenzimidazole-5-carboxylic acid hydrochloride, 20.2 g (including inorganic matters), was added to 300 ml of methanol and 5 ml of conc. hydrochloric acid was added to the mixture followed by heating to reflux for 7 hours. The solvent was distilled off and 200 ml of water was added to the residue. At 5° to 10° C., 1 N sodium hydroxide solution was added to the mixture to adjust pH to 9 to 10 followed by extraction with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate and filtered. The solvent was distilled off under reduced pressure. The resulting crystals were washed with ether to give 4.8 g of methyl 1-methyl-benzimidazole-5-carboxylate (43.6percent, based on 1,5-dimethylbenzimidazole).

Reference： [1] Patent: US4977175, 1990, A,

5
[ 26663-77-4 ]
[ 74-88-4 ]
[ 131020-36-5 ]

Reference： [1] Patent: WO2014/100695, 2014, A1, . Location in patent: Paragraph 00452

6
[ 26663-77-4 ]
[ 74-88-4 ]
[ 131020-36-5 ]

Reference： [1] Patent: WO2011/138657, 2011, A1, . Location in patent: Page/Page column 54-55

7
[ 67-56-1 ]
[ 53484-17-6 ]
[ 131020-36-5 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 5, p. 991 - 999

8
[ 15788-16-6 ]
[ 131020-36-5 ]

Reference： [1] Patent: WO2011/138657, 2011, A1,

9
[ 131020-36-5 ]
[ 115576-91-5 ]

Reference： [1] Patent: WO2003/99814, 2003, A1, . Location in patent: Page 30
[2] Patent: WO2011/138657, 2011, A1, . Location in patent: Page/Page column 54-55

[ 131020-36-5 ] Synthesis Path-Downstream 1~13

1
[ 67-56-1 ]
[ 53484-17-6 ]
[ 131020-36-5 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1996,vol. 44,p. 991 - 999

2
[ 131020-35-4 ]
[ 131020-36-5 ]

Yield	Reaction Conditions	Operation in experiment
43.6%	With hydrogenchloride; sodium hydroxide; In methanol; water;	STR11 1-Methylbenzimidazole-5-carboxylic acid hydrochloride, 20.2 g (including inorganic matters), was added to 300 ml of methanol and 5 ml of conc. hydrochloric acid was added to the mixture followed by heating to reflux for 7 hours. The solvent was distilled off and 200 ml of water was added to the residue. At 5 to 10 C., 1 N sodium hydroxide solution was added to the mixture to adjust pH to 9 to 10 followed by extraction with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate and filtered. The solvent was distilled off under reduced pressure. The resulting crystals were washed with ether to give 4.8 g of methyl 1-methyl-benzimidazole-5-carboxylate (43.6%, based on 1,5-dimethylbenzimidazole).

Reference： [1]Patent: US4977175,1990,A

3
[ 131020-36-5 ]
[ 115576-91-5 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium aluminium tetrahydride; In tetrahydrofuran; for 2h;	Example 11B : 5-Hydroxymethyl-l-methylbenzimidazole A solution of methyl [L-METHYLBENZIMIDAZOLE-5-CARBOXYLATE] (1.6 g, 8.42 mmol) in dry THF (80 mL) was treated with [LIALH4] (1.59 g, 42.1 mmol) and the mixture stirred for 2 hours. 1.5 mL of 5% [NAOH] solution was then added, and the solid which precipitated was filtered through diatomaceous earth. The filtrate was collected and the solvent removed under reduced pressure to give 0. [8] g of the title compound. [C9HLON20] NMR (400 MHz, DMSO-d6): 3.85 (3H, s, NCH3) ; 4.65 (2H, s, [CH20H)] ; 5.25 [(1H,] bs, OH); 7.3 [(1H,] dd, [J =] 1 and [8] Hz, aryl-H); 7.55 [(1H,] d, [J] [=] [8] Hz, aryl-H); 7.65 [(1H,] d, J= 1 Hz, aryl-H); 8.2 [(1H,] s, imidazole-H)
	With lithium aluminium tetrahydride;	Preparation of ( 1 -methyl- l H-benzimidazol- - l methanolThe title compound was synthesized by esterification of l//-benzimidazole-5-carboxylic acid using methanol in presence of cone, sulphuric acid followed by N-methylation using methyl iodide in presence of potassium carbonate and subsequent reduction of the ester group by lithium aluminium hydride; NMR (300 MHz, DMSO- 6) delta 3.84 (s, 3H), 4.59 (s, 2H), 5.23 (br s, l H), 7.26 (d, J = 8.4 Hz, 1H), 7.52-7.58 (m, 2H), 8.23-8.31 (m, 1 H).

Reference： [1]Patent: WO2003/99814,2003,A1 .Location in patent: Page 30
[2]Patent: WO2011/138657,2011,A1 .Location in patent: Page/Page column 54-55

4
[ 66315-16-0 ]
[ 149-73-5 ]
[ 131020-36-5 ]

Yield	Reaction Conditions	Operation in experiment
	for 16h;Heating / reflux;	Example 11A : Methyl [1-METHYLBENZIMIDAZOLE-5-CARBOXYLATE] A solution of methyl [3-AMINO-4-METHYLAMINOBENZOATE] (prepared as in DE 1990390463 Al) (2.57 g, 14 mmol) in trimethyl orthoformate (50 mL) was refluxed for 16 hours. The solvent was then removed under reduced pressure to afford 2.31 g of product. [CLOHION202] Mass (calculated): [[190]] ; (found): [[M+H+]] = 191. NMR (400 [MHZ, DMSO-D6)] : 3.95 (3H, s, NCH3) ; 4.0 (3H, s, [OCH3)] ; 7.8 [(1H,] d, [J] = 8 Hz, aryl-H); 8.0 [(1H,] dd, [J] = 1 and 8 Hz, aryl-H); 8.35 [(1H,] d, [J] = 1 Hz, aryl- H); 8. 45 [(1H,] s, imidazole-H).
	With trifluorormethanesulfonic acid; In methanol; at 20℃;	1-METHYL-1H-BENZOIMIDAZOLE-5-CARBOXYLIC acid methyl ester A slurry of PEARLMAN's catalyst (Pd (OH) 2 ON carbon, 200 mg) in a small volume of methanol was added to a slurry of 4-METHYLAMINO-3-NITRO-BENZOIC acid methyl ester (15.00 g, 71.40 MMOL) and ammonium formate (22.50 g, 357 MMOL) in MEOH (220 mL) at room temperature. Occasional cooling with a cool water bath controlled the resulting mild exotherm, and after 1 h the mixture had completely DECOLORIZED.This reaction mixture was filtered through a bed of celite and concentrated to remove most of the MEOH, then was partitioned between EtOAc and saturated aqueous NaHCO3. The EtOAc phase was dried (MGSO4) and concentrated to afford 12.92 g of crude methyl 4-methylamino-3-aminobenzoate as a brown solid. This compound was dissolved in MEOH (70 mL) with external warming, then TRIMETHYLORTHOFORMATE (15.60 mL, 143 MMOL) and 1 drop of triflic acid were added and the mixture stirred overnight at RT. After concentration to remove most of the MEOH, the resulting solid was warmed to form an oil that was crystallized from ether. The solid product was collected by filtration and vacuum dried to give 10.70 g of desired product as a green SOLID.1H NMR (300 MHz, CD30D) 6 8.36 (s, 1 H), 8.24 (s, 1 H), 8.02 (dd, J=8.65 Hz, J=1.51 Hz, 1 H), 7.62 (d, J=8.56 Hz, 1 H), 4.85 (s, 3 H), 3.93 (d, J=0.9 Hz, 3 H).

Reference： [1]Patent: WO2003/99814,2003,A1 .Location in patent: Page 29
[2]Patent: WO2004/99131,2004,A2 .Location in patent: Page 54

5
[ 131020-36-5 ]
[ 53484-17-6 ]

Yield	Reaction Conditions	Operation in experiment
79%		The <strong>[131020-36-5]methyl 1-methyl-1H-benzimidazole-5-carbonate</strong> (500 mg) obtained above was dissolved in methanol (10 ml). 1 N Sodium hydroxide solution (8 ml) was added thereto, and the mixture was stirred for 4 hours at room temperature. Water was added to the reaction mixture which was then acidified by formic acid. Precipitates were collected by filtration and dried under reduced pressure to give the title compound (367 mg, Y.: 79%). 1H NMR; (DMSO-d6) delta (ppm): 3.8 (s, 3H), 7.6 (d, 1H), 7.8 (dd, 1H), 8.2 (d, 1H), 8.3 (s, 1H).
		1-METHYL-1H-BENZOIMIDAZOLE-5-CARBOXYLIC ACID : H20 (100 mL) was added to a solution of methyl 1-METHYL-1H-BENZOIMIDAZOLE-5-CARBOXYLATE (10.00 g, 52.6 MMOL) in 1 N LiOMe in MEOH (100 mL, 100 MMOL). The resulting solution was stirred under an inert atmosphere and monitored to completion BY 1H NMR.Aqueous 1 N HCI (100 mL, 100 MMOL) was added dropwise to the reaction mixture cooled with an ice-water bath. The gray solid which formed was collected by filtration and washed with water followed with methanol. Vacuum drying afforded 8.60 g of desired PRODUCT.1H NMR (300 MHZ, D6-DMSO) B 12.75 (br s, 1 H), 8.31 (s, 1 H), 8.23 (s, 1 H), 7.89 (d, J=8.36 Hz, 1 H), 7.62 (d, J=8.35 Hz, 1 H), 3.85 (s, 3 H).

Reference： [1]Patent: EP1595866,2005,A1 .Location in patent: Page/Page column 26
[2]Patent: WO2004/99131,2004,A2 .Location in patent: Page 54

6
[ 64-18-6 ]
[ 66315-16-0 ]
[ 131020-36-5 ]

Yield	Reaction Conditions	Operation in experiment
97%	In water; at 90℃; for 3h;	The methyl 3-amino-4-methylaminobenzoate (3.3 g) obtained above was dissolved in formic acid (96 ml). Water (4 ml) was added thereto, and the solution was stirred for 3 hours at 90C. The reaction solution was concentrated under reduced pressure, and ethyl acetate was added to the residue. The organic phase was washed with a saturated sodium bicarbonate solution and dried over sodium sulfate anhydrous. The product was concentrated under reduced pressure to give methyl 1-methyl-1H-benzimidazole-5-carbonate (3.4 g, Y.: 97%). 1H NMR; (DMSO-d6) delta (ppm): 3.8 (s, 3H), 3.8 (s, 3H), 7.6 (d, 1H), 7.9 (dd, 1H), 8.2 (d, 1H), 8.3 (s, 1H). ESI/MS (m/z): 191 (M+H)+.

Reference： [1]Patent: EP1595866,2005,A1 .Location in patent: Page/Page column 26

7
[ 26663-77-4 ]
[ 74-88-4 ]
[ 131020-36-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;	Preparation of ( 1 -methyl- l H-benzimidazol- - l methanolThe title compound was synthesized by esterification of l//-benzimidazole-5-carboxylic acid using methanol in presence of cone, sulphuric acid followed by N-methylation using methyl iodide in presence of potassium carbonate and subsequent reduction of the ester group by lithium aluminium hydride; NMR (300 MHz, DMSO- 6) delta 3.84 (s, 3H), 4.59 (s, 2H), 5.23 (br s, l H), 7.26 (d, J = 8.4 Hz, 1H), 7.52-7.58 (m, 2H), 8.23-8.31 (m, 1 H).

Reference： [1]Patent: WO2011/138657,2011,A1 .Location in patent: Page/Page column 54-55

8
[ 15788-16-6 ]
[ 131020-36-5 ]

Reference： [1]Patent: WO2011/138657,2011,A1

9
[ 26663-77-4 ]
[ 74-88-4 ]
methyl 1-methyl-1H-benzo[d]imidazole-6-carboxylate [ No CAS ]
[ 131020-36-5 ]

Yield	Reaction Conditions	Operation in experiment
		A solution of methyl lH-benzo[d]imidazole-6-carboxylate (9.5 g, 53.9 mmol) in THF (100 mL) had NaH (2.59 g, 64.7 mmol) added at 0C. After stirring for 30 min, CH3I (13.23 g, 93.2 mmol) was added and the mixture was stirred at room temperature for lh. The reaction was then quenched by addition of water and extracted with DCM (3x100 mL). The combined organic layers were dried over Na2S04 and concentrated to give a mixture of two isomeric products methyl 1 -methyl- lH-benzo[d]imidazole-6-carboxylate and methyl 1- methyl-lH-benzo[d]imidazole-5-carboxylate (8.0 g, Yield 78%). LCMS (m/z): 191.06 (M+l). This crude mixture was used directly in the next step.

Reference： [1]Patent: WO2014/100695,2014,A1 .Location in patent: Paragraph 00452

Yield	Reaction Conditions	Operation in experiment
79%	With hydrogenchloride; In water; N,N-dimethyl-formamide; at 20℃;Inert atmosphere;	General procedure: Hydrochloric acid (12 N solution, 167 mu) was added to a solution of compound C (251 mg, 1.50 mmol) in triethyl orthoformate (10 mL) and N,N-dimethylformamide (added with stirring until the turbidity disappeared). The mixture was stirred at room temperature for 16 h, under a nitrogen atmosphere. The solvent was evaporated under reduced pressure and the brown oily residue was purified by flash column chromatography on silica gel, using ethyl acetate/hexane (5: 1) as eluent, Following the general method I, using methyl 3-amino-4-(methylamino)benzoate (270 mg, 1.5 mmol) gave an white solid methyl 1 -methyl- lH-benzo[d]imidazole-5-carboxylate (225 mg, 79 %): 1H NMR (400 MHz, CDC13) delta 8.54 (dd, J= 1.5, 0.6 Hz, 1H), 8.08 (dd, J= 8.5, 1.5 Hz, 1H), 7.99 (s, 1H), 7.44 (dd, J= 8.5, 0.6 Hz, 1H), 3.97 (s, 3H), 3.90 (s, 3H); 13C NMR (101 MHz, CDCI3) delta 167.56, 145.19, 143.29, 137.69, 124.57, 124.49, 122.73, 109.08, 52.08, 31.22

11
[ 75-30-9 ]
[ 131020-36-5 ]
methyl 2-isopropyl-1-methyl-1H-benzo[d]imidazole-5-carboxylate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 15309 - 15313
Angew. Chem.,2017,vol. 129,p. 15511 - 15515,5

12
[ 401-55-8 ]
[ 131020-36-5 ]
methyl 3-(2-ethoxy-1-fluoro-2-oxoethyl)-1-methyl-2-thioxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 4795 - 4806

13
[ 401-58-1 ]
[ 131020-36-5 ]
methyl 3-(2-ethoxy-1-fluoro-2-oxoethyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2020,vol. 362,p. 269 - 276

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P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
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
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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. 131020-36-5 ] {[proInfo.proName]}

Quality Control of [ 131020-36-5 ]

Related Doc. of [ 131020-36-5 ]

Product Details of [ 131020-36-5 ]

Safety of [ 131020-36-5 ]

Application In Synthesis of [ 131020-36-5 ]

[ 131020-36-5 ] Synthesis Path-Upstream 1~9

[ 131020-36-5 ] Synthesis Path-Downstream 1~13

Related Functional Groups of [ 131020-36-5 ]

Esters

Related Parent Nucleus of [ 131020-36-5 ]

Benzimidazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 131020-36-5 ]

Related Parent Nucleus of
[ 131020-36-5 ]