287119-83-9|2-(2-Methyl-5-nitrophenyl)acetic acid| Ambeed

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 287119-83-9 ] Purity: 98% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 287119-83-9 ]

CAS No. :	287119-83-9
Formula :	C₉H₉NO₄
M.W :	195.17
SMILES Code :	CC1=C(CC(O)=O)C=C(C=C1)[N+]([O-])=O
MDL No. :	MFCD11655591
InChI Key :	JCSRJKWRJVUXSQ-UHFFFAOYSA-N
Pubchem ID :	22475338

Safety of [ 287119-83-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 287119-83-9 ]

* 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.

Downstream synthetic route of [ 287119-83-9 ]

[ 287119-83-9 ] Synthesis Path-Downstream 1~35

1
[ 67-56-1 ]
[ 287119-83-9 ]
[ 287119-84-0 ]

Yield	Reaction Conditions	Operation in experiment
98%	With thionyl chloride; at 0 - 85℃; for 3h;	Compound 1-2 (20.0 g, 102 mmol)Was dissolved in methanol (250 mL)0 ~ 5 the following was slowly added thionyl chloride (27.5g, 204mmol),Maintaining the temperature at 75 ~ 85 reaction 3 hours;After the reaction is cooled to room temperature,Add water plus ethyl acetate extraction,The organic phase was washed twice with sodium bicarbonate,Dried over anhydrous sodium sulfate, concentrated,Compound 1-3 (21.0 g) was obtained in a yield of 98.0%.
95%	With hydrogenchloride; In 1,4-dioxane; for 2h;	Step 2: hydrochloric acid solution (10.8 mL, 43.12 mmol) was added to a solution of <strong>[287119-83-9]2-<strong>[287119-83-9](2-methyl-5-nitrophenyl)acetic acid</strong></strong> Ex.4a (4.21 g, 21.56 mmol) in methanol. The reaction mixture was refluxed for 2h. LCMS showed the formation of theexpected product as the only peak. After cooling to rt and removing the solvent in vacuo, the crude product was dissolved in water and basified to pH>12 using 2N NaOH. The solution was extracted using EtOAc and the combined organic layer were washed with brine, dried, filtered and the solution was concentrated under reduced pressure. The resulting solid methyl 2-(2-methyl-5-n itrophenyl )acetate (4.31 g, 95%) was used as such in the next synthetic step.
23%	With hydrogenchloride; In 1,4-dioxane; at 65℃; for 15h;	- Step 2: 4 M HCI in dioxane (26.6 mL, 106.46 mmol)) was added to a solution of previously synthesized nitro derivative Ex.3a (10.39 g, 53.23 mmol) in methanol (150 mL). The reaction mixture was refluxed for 1 5h. After cooling to rt and removing the excess of solvent under reduced pressure, the crude product was dissolved in water and basified to pH>12 using 2N NaOH. The aqueous layer was extracted with EtOAc. The combined organic layer was washed with brine, dried over Mg504, filtered and the solution was concentrated to reduced pressure. The residue was purified by flash chromatography on silica gel eluting with heptanes and EtOAc to afford methyl 2-(2-methyl-5-nitrophenyl)acetate Ex.3b (2.55 g, 23%).

	With hydrogenchloride; In 1,4-dioxane; for 14h;Heating / reflux;	<strong>[287119-83-9]2-(2-Methyl-5-nitrophenyl)acetic acid</strong> 13 (30 g, 154 mmol) is dissolved in methanol (700 mL) and HCl (79 mL of a 4 M solution in 1,4-dioxane, 316 mmol) is added. The reaction is heated to reflux for 14 h. After cooling to rt and removing solvent in vacuo, the crude product is dissolved in water (500 mL) and basified to pH > 12 using 2N sodium hydroxide. The solution is extracted using ethyl acetate and the combined organic layer is washed with brine, dried over sodium sulfate and filtered. After removing the solvent in vacuo, the product 14 is obtained as a dark yellow solid. 1H NMR (300MHz, CDCl3) delta 8.06 (m, 2H), 7.33 (d, J= 8.4 Hz, IH), 3.73 (s, 3H), 3.72 (s, 2H), 2.41 (s, 3H).
		[00125] <strong>[287119-83-9]2-(2-Methyl-5-nitrophenyl)acetic acid</strong> 13 (30 g, 154 mmol) was dissolved in methanol (700 mL) and HCl (79 mL of a 4 M solution in 1,4-dioxane, 316 mmol) was added. The reaction was heated to reflux for 14 h. After cooling to rt and removing solvent in vacuo, the crude product was dissolved in of water (500 mL) and basified to pH > 12 using 2N sodium hydroxide. The solution was extracted using ethyl acetate and the combined organic layer was washed with brine, dried over sodium sulfate and filtered. After removing the solvent in vacuo, the product 14 was obtained as a dark yellow solid. 1H NMR (300MHz, CDCl3) delta 8.06 (m, 2H), 7.33 (d, J= 8.4 Hz, IH), 3.73 (s, 3H), 3.72 (s, 2H), 2.41 (s, 3H).
	With hydrogenchloride; In 1,4-dioxane; for 14h;Heating / reflux;	2- (2-methyl-5-nitrophenyl)-acetic acid (1.9g, 9. 7mmol) is dissolved in 50mL methanol and 5mL 4M HC1 in 1,4-dioxane is added. The reaction is heated to reflux for 14 hours. After cooling down and removing solvent, the crude product is dissolved in 50mL water and basified by 2N sodium hydroxide water solution to pH>12. The solution is extracted by ethyl acetate, and the combined organic layer is washed by brine and dried over sodium sulfate and filtered. After removing solvent, the final product compound (16) 2- (2- methyl-5-nitrophenyl)-acetic acid methyl ester is the dark yellow solid, 1.85g.

References: [1]Patent: CN106336382,2017,A .Location in patent: Paragraph 0099; 0104; 0105; 0106.
[2]Patent: WO2018/138354,2018,A1 .Location in patent: Paragraph 38.
[3]Patent: WO2018/138359,2018,A1 .Location in patent: Page/Page column 41.
[4]Journal of the Chemical Society. Perkin Transactions 1 (2001),2000,p. 1601 - 1608.
[5]Patent: WO2008/51757,2008,A1 .Location in patent: Page/Page column 33; 34.
[6]Patent: WO2009/105712,2009,A1 .Location in patent: Page/Page column 37-38.
[7]Patent: WO2005/34869,2005,A2 .Location in patent: Page/Page column 41-42.

2
[ 644-36-0 ]
[ 287119-83-9 ]

Yield	Reaction Conditions	Operation in experiment
42%	With sulfuric acid; nitric acid; In dichloromethane; at -20 - 20℃;	Intermediate 80A: Preparation of 2-(2-methyl-5-nitrophenyl)acetic acid [00224] A solution of 2-o-tolylacetic acid (3.54 g, 23.6 mmol) in DCM (12 mL) was added to a pre-cooled mixture of concentrated sulfuric acid (10 mL, 188 mmol) and 90% nitric acid (1 mL, 22.4 mmol) at - 20 0C. The reaction mixture was stirred at - 20 0C for 30 minutes, then slowly warmed to room temperature and stirred overnight. The reaction mixture was poured into ice-water. The white solid was collected by filtration, rinsed with water, and concentrated. The solid was triturated with ether and filtered to obtain Intermediate 8OA (2.4 g, 42%) as a white solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 12.62 (1 H, br. s.), 8.13 (1 H, d, J = 2.51 Hz), 8.04 (1 H, dd, J = 8.28, 2.51 Hz), 7.47 (1 H, d, J = 8.53 Hz), 3.80 (2 H, s), 2.34 (3 H, s).
34.6%		The starting material 2-methyl-phenylacetic acid (200.0 g, 1.33 mol)Was dissolved in dichloromethane (700 mL)0 C below slowly addedConcentrated sulfuric acid (584 mL),After the addition reaction was continued for 0.5 hours,Then concentrated nitric acid (30 mL)Maintain the temperature at -2 ~ 3 reaction 16 hours;After the reaction,Poured into 500 mL of water,Extracted with dichloromethane, dried,Concentrated to give Compound 1-2 (90.0 g) in a yield of 34.6%.
32%	With sulfuric acid; nitric acid; In dichloromethane; at -10℃; for 1h;	Step 1: a 500 mL round bottom flask was charged with conc. sulfuric acid (130 mL) and cooled to -10C. A solution of o-tolyacetic acid (10 g, 66.58 mmol) in CH2CI2 (35 mL) was added dropwise. After that, a solution of conc. sulfuric acid(27 mL) and nitric acid (2.7 mL) was slowly added dropwise. The reaction mixture was stirred at -10C for 1 h and then poured onto ice. The aqueous phase was extracted with EtOAc. The organic layer was washed with water and brine, dried, filtered and the solution was concentrated under reduced pressure. The resulting solid was triturated in Et20 and filtered off to afford 2-(2-methyl-5-nitrophenyl)acetic acid as white solid (4.21 g, 32%).

	With sulfuric acid; nitric acid; In dichloromethane;	A. Acylating Reagent (2-Methyl-5-nitrophenyl)acetic acid A 1 L round bottom flask was charged with conc. sulfuric acid (500 mL) and cooled to -12 C. (ethyleneglycol-dry ice). (2-Methylphenyl)acetic acid (35.4 g, 0.24 mol) dissolved in dichloromethane (120 mL) was added during 10 minutes and the mixture was then treated dropwise during two hours with a pre-cooled (ethylene glycol-dry ice) solution of conc. sulfuric acid (100 mL) and 100% nitric acid (10 mL). The reaction mixture was stirred for one hour at -12 C. and then poured on ice. The aqueous phase was extracted with ethyl acetate (31 L). The combined organic phases were washed with brine (21L) and water (2*1 L), dried (Na2SO4) and concentrated in vacuo to give the 38.1 g crude mixture (38 g). 1H NMR showed a 70:30 mixture of the title compound and (2-methyl-3-nitrophenyl)acetic acid, and the title compound was purified by trituration with diethyl ether.
	With sulfuric acid; nitric acid; In dichloromethane; at -20 - 20℃; for 0.75h;	- Step 1: a solution of o-tolyacetic acid (5.0 g, 33.29 mmol), in CH2CI2 (15 mL) was added dropwise to a pre-cooled mixture of conc. sulfuric acid (26 mL, 266.3 mmol) and 99.5% nitric acid (1.35 mL, 31.63 mmol) at -20C. The reaction mixture was stirred at that temperature for 30 mm, then slowly warmed to rt and stirred for 1 5h. The reaction mixture was poured into ice-water. The white solid was collected by filtration and washed with water. The solid was triturated with Et20 and filtered to obtain the mono and di-nitration products in a 1:1 ratio (4.78 g), that will be separated after the next esterification step.

References: [1]Patent: WO2010/42699,2010,A1 .Location in patent: Page/Page column 112-113.
[2]Patent: CN106336382,2017,A .Location in patent: Paragraph 0099; 0101; 0102; 0103.
[3]Patent: WO2018/138354,2018,A1 .Location in patent: Page/Page column 38.
[4]Patent: US2003/166664,2003,A1 .
[5]Patent: WO2018/138359,2018,A1 .Location in patent: Page/Page column 41.

3
[ 644-36-0 ]
2-methyl-3,5-dinitrophenylacetic acid [ No CAS ]
[ 287119-83-9 ]