[ CAS No. 612-28-2 ] {[proInfo.proName]}

Name: 612-28-2|N-Methyl-2-nitroaniline|98%
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Quality Control of [ 612-28-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 612-28-2 ]

Product Details of [ 612-28-2 ]

CAS No. :	612-28-2	MDL No. :	MFCD00007090
Formula :	C₇H₈N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KFBOUJZFFJDYTA-UHFFFAOYSA-N
M.W :	152.15	Pubchem ID :	69157
Synonyms :

Calculated chemistry of [ 612-28-2 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	44.57
TPSA :	57.85 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.68 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.57
Log Po/w (XLOGP3) :	2.18
Log Po/w (WLOGP) :	1.45
Log Po/w (MLOGP) :	0.61
Log Po/w (SILICOS-IT) :	-0.66
Consensus Log Po/w :	1.03

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.43
Solubility :	0.567 mg/ml ; 0.00373 mol/l
Class :	Soluble
Log S (Ali) :	-3.03
Solubility :	0.143 mg/ml ; 0.000937 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.2
Solubility :	0.96 mg/ml ; 0.00631 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.99

Safety of [ 612-28-2 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P280-P301+P310	UN#:	2811
Hazard Statements:	H301+H311+H331-H373	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 612-28-2 ]

* 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.

Downstream synthetic route of [ 612-28-2 ]

[ 612-28-2 ] Synthesis Path-Downstream 1~43

1
[ 612-28-2 ]
[ 89937-90-6 ]

Reference： [1]Journal of the Iranian Chemical Society,2011,vol. 8,p. 857 - 861
[2]Monatshefte fur Chemie,2012,vol. 143,p. 467 - 470
[3]Journal fur praktische Chemie (Leipzig 1954),1890,vol. <2>41,p. 164
[4]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 573 - 578

2
[ 612-28-2 ]
[ 53484-26-7 ]

Yield	Reaction Conditions	Operation in experiment
93%	With N-Bromosuccinimide; In acetic acid; for 7h;Heating / reflux;	5.0 g (33 mmol) of N-methyl-2-nitroaniline and 5.9 g (33 mmol) of N-bromosuccinimide were added with 60 mL of acetic acid, and the whole was refluxed under heating for 7 hours. After the completion of the reaction, the reaction solution was poured into 500 mL of water, and the precipitated solid was filtered out. The solid that had been filtered out was dissolved into ethyl acetate and dried with magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the residue was dried at room temperature under reduced pressure to obtain 7.1 g of the orange solid of 4-bromo-N-methyl-2-nitroaniline (93% yield).
93%	With N-Bromosuccinimide; acetic acid; for 7h;Heating / reflux;	(1) Synthesis of 4-bromo-N-methyl-2-nitroaniline Pouring 60 milliliter of acetic acid over 5.0 g (33 mmol) of N-methyl-2-nitroaniline and 5.9 g (33 mmol) of N-bromosuccinimide, the resultant solution was refluxed with heating for 7 hours. After completion of the reaction, the reacted solution was poured into 500 milliliter of water, and precipitated solids were separated with filtration. Dissolving the resultant solids into ethyl acetate, the resultant solution was dried with the use of magnesium sulfate. After filtration, the solvent was removed by distillation under reduced pressure, and after drying the solids under reduced pressure at room temperature, 7.1 g of 4-bromo-N-methyl-2-nitroaniline as orange solids were obtained (yield: 93 %).
93%	With N-Bromosuccinimide; acetic acid; for 7h;Reflux;	(E-1) Synthesis of 4-bromo-N-methyl-2-nitroanilline 60 mL of acetic acid was added to 5.0g (33 mmol) of N-methyl-2-nitroaniline and 5.9g (33 mmol) of N-bromosuccinimide, and the resultant was heated under reflux for 7 hours. After completion of the reaction, the reaction solution was poured to 500 mL of water, and deposited solids were filtered off. The solids which were filtered off were dissolved in ethyl acetate, and dried with magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure at room temperature, whereby 7.1g (yield 93%) of orange solids of 4-bromo-N-methyl-2-nitroaniline were obtained.

88%

With bromine; acetic acid; at 20℃; for 4h;

In a 1000 mL three-neck flask equipped with an electric stirrer and a constant pressure funnel, 60 g (394 mmol) of N-methyl-2-nitroaniline,N-methyl-2-nitroaniline was dissolved in 230 mL of anhydrous acetic acid into a three-necked flask, and 35 mL of anhydrous acetic acid and 69.7 g (436 mmol) of anhydrous liquid bromineStirring at room temperature to open the constant pressure funnel drops of bromine in acetic acid solution,Reaction exothermic, after the completion of the reaction at room temperature 25 4h,Thin layer chromatography reaction was complete (developing solvent: methylene chloride), in the late reaction of a large number of orange solidAfter the reaction, the material in the three-necked flask was suction-filtered, and the filtrate was added with no water to precipitate solid. The solid obtained by filtration was washed once with 260 mL of 5% sodium carbonate aqueous solution and then with deionized water twice, The final standard was the final wash water pH of 7.0.The washed solid was dried in vacuo to give 80.33 g of an orange-yellow solid product in 88% yield.

Reference： [1]Patent: EP1734038,2006,A1 .Location in patent: Page/Page column 44-45
[2]Patent: EP1602648,2005,A1 .Location in patent: Page/Page column 39
[3]Patent: EP2524913,2012,A1 .Location in patent: Page/Page column 32
[4]Patent: CN105399683,2016,A .Location in patent: Paragraph 0023-0028
[5]Recueil des Travaux Chimiques des Pays-Bas,1902,vol. 21,p. 258
Recueil des Travaux Chimiques des Pays-Bas,1908,vol. 27,p. 35 Anm. 2

3
[ 612-28-2 ]
[ 4760-34-3 ]

Yield	Reaction Conditions	Operation in experiment
88%	With palladium on activated charcoal; In ethanol; at 50℃; for 4h;Inert atmosphere;	20 g of compound b1 was placed in a 300 mL flask,Add 200 mL of absolute ethanol,Then add in a nitrogen atmosphere5% palladium carbon catalyst 1g,Heat to 50 C,After 4 hours of reaction, the temperature was lowered to room temperature.Filtering and concentrating the filtrate to obtain compound c1 (14.1 g, yield 88%).
83%	With palladium on activated charcoal; ammonium formate; In methanol; at 20℃; for 2h;Inert atmosphere;	2. Synthesis of intermediate 110-2 Under a nitrogen atmosphere, the intermediate 110-1 (15.0 g, 98.6 mmol) as a raw material was dissolved in in 500 mL of methanol in 1000 mL three-necked flask at room temperature, and palladium on carbon containing water (5.0 g, 9.86 mmol) and ammonium formate (30.0 g, 476 mmol) were sequentially added into the flask, then the reaction was carried out at room temperature for 2h. After detecting the reaction was completed, the reaction system was filtered under suction; the filtrate was collected, concentrated to dryness. 200 mL of water was added into the residue, and the resulting mixture was extracted with 100 mL of dichloromethane three times. The organic phases were combined, dried over anhydrous sodium sulfate and concentrated to dryness to give 10.0 g of the intermediate 110-2 (83%) as a yellow solid. LCMS: 123.0.
60%	With hydrogen; In ethanol; at 20℃; under 760.051 Torr; for 3h;	A solution of compound 4 (R1=H, 760mg, 5mmol) and Raney Nickel (3g) in ethanol was hydrogenated under 1atm at room temperature for 3h. The mixture was filtered over a pad of Celite. The filtrate was concentrated in vacuo and purified by silica gel column chromatography (eluent: n-Hex/EA=5:1) to give the product 5 (366mg, yield 60%) as oil. 1H NMR (400MHz, CDCl3) delta 6.86 (t, J=8.4 Hz, 1H), 6.69 (m, 3H), 3.32 (NH, 2H), 2.87 (s, 3H); LC/MS (electrospray) m/z (M+H)+ 123.98.

	With phosphoric acid;palladium/charcoal; In isopropyl alcohol;	EXAMPLE 2 A mixture of 190 kg of o-nitro-N-methylaniline, 0.95 kg of palladium/charcoal catalyst (10% Pd) and 570 L of isopropanol is hydrogenated in a 1200 L-VA-Hydrogenator at 60 - max. of 85 C. under a hydrogen pressure of 2-6 bar until the uptake of hydrogen has stopped. 99 kg of crystalline phosphoric acid and 238 L of isopropanol are placed in another 1200 L apparatus and the contents of hydrogenation apparatus are allowed to flow into it, with stirring, while the catalyst is filtered off. The filter and the filtered catalyst are washed with 95 L of isopropanol, cooled to 10-20 C., and stirred for a further 30-60 minutes. The product is centrifuged, washed with 238 L of isopropanol, and dried in vacuo at 40-60 C. Yield: 225 kg of N-methylphenylenediamine, 0.77 phosphate (90% of theory)
	With cyclohexene;palladium 10% on activated carbon; In ethanol; for 16h;Heating / reflux;	Starting material IiJV-Methyl-l,2-phenyIenediamine<strong>[612-28-2]N-methyl-2-nitroaniline</strong> (3.0 g; 0.05 mol) was dissolved in ca. 120 mL ethanol to a clear, yellow solution. Cyclohexene (40 mL; 0.4 mol) and 10% palladium-on-carbon (2.65 g; 5 mol%) were sequentially added as single portions. The resulting suspension was heated to reflux and maintained for 16 h. The reaction mixture was filtered hot through a pad of diatomaceous earth and the filter cake washed with a few portions of hot ethanol. The filtrate was concentrated under reduced pressure to yield the product as a red-brown oil, which was EPO <DP n="131"/>used directly in the subsequent step. 1H NMR (300 MHz, CDCl3): delta 2.84 (s, 3 H) 3.32 (s, 3 H) 6.49 - 6.82 (m, 3 H) 6.78 - 7.01 (m, 1 H) M/Z = 123.
	With ammonium chloride; zinc; In water;Microwave irradiation;	General procedure: N1- methyl/ethyl-o-Phenylenediamine(5 mM), Zinc dust (0.25 gm) and ammonium chloride(10 mM) in 5 ml water were mixed thoroughly in asmall beaker (25 ml). The reaction solid mixture wasplaced in a microwave oven (300Watt) at 50%power level for 8 to 15 min; the progress of thereaction was monitored by checking the solubilityof the solid reaction mixture product in dilute HCl,when the entire organic solid dissolved it wasfiltered to separate Zinc dust, and neutralized withaqueous solution. The solid was separated byfiltration and recrystallized from an appropriatesolvent (aqueous Ethanol)
	With hydrogen; In toluene; at 120℃; under 6000.6 Torr; for 10h;Autoclave;	The chemoselective hydrogenation of nitroarenes was performed in batch reactors. The reactant, internal standard (dodecane), solvent (toluene or THF), and powder catalyst, as well as a magnetic bar, were added into the batch reactor. After the reactor was sealed, air was purged by flushing two times with 10 bar of hydrogen. Then the autoclave was pressurized with H2 to the corresponding pressure. The stirring speed was kept at 800 rpm and the size of the catalyst powder was below 0.02 mm to avoid either external or internal diffusion limitation. Finally, the batch reactor was heated to the target temperature. For the kinetic studies, 50 muL of the mixture was taken out for GC analysis at different reaction times. For the scope studies, 100 muL of the mixture wastaken out for GC analysis. The products were also analyzed byGC-MS.
222.8 mg	With tin(II) chloride hydrate; In ethanol; for 4h;Reflux;	General procedure: 4-(Methylamino)-3-nitrobenzenesulfonamide (2) (250 mg, 1.081 mmol, 1 equiv) dissolved in EtOH and SnCl2.2H2O (1219.8mg, 5.4058 mmol, 5 equiv) was added in five parts, and refluxed for 4h. After EtOH was evaporated, the reaction mixture was diluted with water and neutralized with NaHCO3, ethyl acetate was added, and the mixture filtered from Celite pad. The phases were separated and aqueous phase extracted with ethyl acetate. The combined organic phase was dried, filtered and concentrated. The crude 3 (153.9 mg, 70% yield) was used in the next step without purification. Mp 170.7-172.1 C, (171C [4]). HRMS m/z calculated for C7H11N3O2S [M+H]+ 202.0650 , found: 202.0644. CAS No. 66315-22-8.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2918 - 2922
[2]Angewandte Chemie - International Edition,2015,vol. 54,p. 11516 - 11520
    Angew. Chem.,2015,vol. 127,p. 11678 - 11682
[3]Journal of Organic Chemistry,2008,vol. 73,p. 8631 - 8634
[4]Patent: CN108774266,2018,A .Location in patent: Paragraph 0070; 0071; 0074
[5]Patent: EP3216786,2017,A1 .Location in patent: Paragraph 0571-0572
[6]Journal of the Chemical Society. Perkin transactions I,1991,p. 2525 - 2529
[7]Journal of the Chemical Society. Perkin transactions I,1980,p. 2387 - 2391
[8]Gazzetta Chimica Italiana,1996,vol. 126,p. 329 - 338
[9]European Journal of Medicinal Chemistry,2014,vol. 78,p. 35 - 42
[10]Journal of Organic Chemistry,1941,vol. 6,p. 25,28
[11]Journal of the American Chemical Society,1954,vol. 76,p. 1891
[12]Chemische Berichte,1891,vol. 24,p. 2682 Anm.1
    Chemische Berichte,1892,vol. 25,p. 2841
[13]Journal of the Chemical Society,1929,p. 2828
[14]Journal of the Chemical Society,1928,p. 198,199
    Journal of the Chemical Society,1931,p. 1274,1277
[15]Journal of the Chemical Society,1955,p. 1804,1806
[16]Chemische Berichte,1942,vol. 75,p. 1936,1942
[17]Chemische Berichte,1990,vol. 123,p. 1149 - 1154
[18]Journal of the American Chemical Society,1998,vol. 120,p. 2251 - 2255
[19]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 187 - 190
[20]Patent: US6169204,2001,A
[21]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 2414 - 2419
[22]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1573 - 1576
[23]Patent: WO2008/56150,2008,A1 .Location in patent: Page/Page column 128-129
[24]Journal of Medicinal Chemistry,2009,vol. 52,p. 5703 - 5711
[25]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5191 - 5194
[26]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3138 - 3141
[27]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 738 - 742
[28]Molecules,2012,vol. 17,p. 4545 - 4559
[29]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 4790 - 4793
[30]Organic Process Research and Development,2007,vol. 11,p. 81 - 85
[31]Oriental Journal of Chemistry,2014,vol. 30,p. 1855 - 1863
[32]Journal of Catalysis,2016,vol. 340,p. 1 - 9
[33]Patent: US2400872,1942,
[34]Applied Organometallic Chemistry,2019,vol. 33
[35]Bioorganic Chemistry,2020,vol. 95
[36],2020,vol. 22

4
[ 88-73-3 ]
[ 74-89-5 ]
[ 612-28-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With copper; In water; at 100℃; for 8h;Sealed tube;	A solution of 1-chloro-2-nitrobenzene (1.57g, 10mmol), 40% aqueous methylamine (4.3mL, 50mmol), and copper powder (31mg, 0.5mmol) was sealed in a 30mL screw-cap tube and stirred at 100C for 8h. The reaction mixture was then cooled-down to room temperature and extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo to give crude product 4 (1.4g, yield 95%) as oil. The crude product was used directly in next reaction step. 1H NMR (400MHz, CDCl3) delta 8.18 (d, J=8.0 Hz, 1H), 8.16 (NH, 1H), 7.45 (t, J=7.8Hz, 1H), 6.84 (d, J=8.0Hz, 1H), 6.65 (t, J=7.8Hz, 1H), 3.02 (d, J=5.2Hz, 3H); LC/MS (electrospray) m/z (M+H)+ 153.05.
93%	at 100℃; under 4125.41 Torr; for 7h;Large scale;	In the reactor, 40 kg of 40% monomethylamine and 200 kg of o-nitrochlorobenzene were charged.The temperature is sealed to about 100 C, and the reaction pressure is controlled to 0.55 MPa.The reaction time is 7 hours.Sampling analysis of o-nitrophenyl chloride content less than 0.7% to complete the reaction, pressure relief,Cool to a temperature below 10 C and filter to give N-methyl o-nitroaniline181.5kg (dry goods) The HPLC analysis content was 99.2%, and the yield was 93%.The mother liquor obtained by filtration recovers the monomethylamine cycle.The 181.5kg filter cake of N-methyl-o-nitroaniline obtained in the previous step was put into 570kg of methanol.Add 1.8 kg of ammonia water and 8 kg of 1% palladium on carbon catalyst containing 60% moisture.Heating and heating to a reaction temperature of about 75 C, catalytic hydrogenation reduction at a reaction pressure of 0.4 MPa, until the hydrogen is no longer absorbed,Sampling analysis of the content of N-methyl o-nitroaniline is less than 0.5%. After the reaction is completed, the pressure is released, the temperature is cooled to room temperature, and the palladium carbon catalyst is filtered and recycled.After the filtrate was distilled to recover methanol, 200 kg of water was added, and hydrochloric acid was added dropwise to pH 7.5.After cooling to 10 C or lower, the product was filtered to obtain 137.1 kg. Yield 95%Example
190 g	In water; at 90 - 120℃; under 3750.38 - 9000.9 Torr; for 5h;Autoclave; Inert atmosphere;	200 g of o-chloronitrobenzene and 197 g of monomethylamine aqueous solution were added to a 1 L autoclave, sealed, and pressurized with nitrogen to 0.5 MPa, and the temperature was slowly increased. When T=90 C,When the heating is stopped, the reaction enters a spontaneous state, the heat is released, and the temperature continues to rise (the highest temperature can reach 110 C, the maximum pressure is 1.2 MPa). When the temperature is no longer rising, the temperature is further raised to 120 C, and the reaction is kept for 5 hours. After completion of the reaction, the temperature was lowered, and the layers were allowed to stand still, and the lower oil phase was taken to obtain 190 g of N-methyl-o-nitroaniline

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 1180 - 1183
[2]Dalton Transactions,2015,vol. 44,p. 2529 - 2540
[3]European Journal of Medicinal Chemistry,2014,vol. 78,p. 35 - 42
[4]Chemistry - A European Journal,2018,vol. 24,p. 16873 - 16888
[5]Patent: CN108774140,2018,A .Location in patent: Paragraph 0004; 0015-0020
[6]Synthetic Communications,2003,vol. 33,p. 2899 - 2906
[7]Collection of Czechoslovak Chemical Communications,2001,vol. 66,p. 1638 - 1658
[8]Recueil des Travaux Chimiques des Pays-Bas,1902,vol. 21,p. 258
Recueil des Travaux Chimiques des Pays-Bas,1908,vol. 27,p. 35 Anm. 2
[9]Patent: CN110272347,2019,A .Location in patent: Paragraph 0031-0033; 0036; 0037; 0040; 0041

5
[ 88-74-4 ]
[ 74-88-4 ]
[ 612-28-2 ]

Yield	Reaction Conditions	Operation in experiment
74.5%	With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; In toluene; at 80℃;Inert atmosphere;	Method As described in step (1) of Example 1,The reactants were replaced by p-tert-butylbromobenzene to methyl iodide,Get a red oily liquid,Namely N-methyl-2-o-nitroaniline, yield:4.53 g, 74.5%.
70%	With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In toluene; for 2h;Reflux;	Tri-tert-butylphosphine(4.4 mL of a 1.0 M solution in toluene, 1.48 g, 0.05 mmol),Palladium acetate (0.4 g, 1.83 mmol) and sodium tert-butoxide (22.8 g, 238 mmol)Add to 2-nitroaniline (25.2g, 183mmol) and methyl iodide(25.8g, 183mmol)a solution in degassed toluene (1 L),And the mixture was heated under reflux for 2 hours.The reaction mixture was cooled to room temperature, diluted with toluene and filtered over EtOAc.The filtrate was diluted with water and extracted with toluene, and the organic phases were combined and evaporated.The residue was filtered through silica gel and recrystallized.Compound b1 (19.5 g, yield 70%) was obtained.

Reference： [1]Patent: CN107188853,2017,A .Location in patent: Paragraph 0027; 0028; 0029; 0081; 0082; 0083
[2]Patent: CN108774266,2018,A .Location in patent: Paragraph 0070-0073
[3]Chemische Berichte,1894,vol. 27,p. 372
Chemische Berichte,1899,vol. 32,p. 1804
[4]Chemische Berichte,1905,vol. 38,p. 321
[5]Journal of the Chemical Society. Perkin Transactions 2 (2001),1997,p. 915 - 919

6
[ 1493-27-2 ]
[ 74-89-5 ]
[ 612-28-2 ]

Yield	Reaction Conditions	Operation in experiment
3.53 g	In ethanol; at 18 - 25℃; for 2h;	Step 1: Intermediate 2 [00426j A solution of Intermediate 1 (3.0 g, 21.3 mmol) in methanamine (ethanol solution, 30 mL) was allowed to stir at ambient temperature for 2 h after which the volatiles were evaporated under reduced pressure. To the residue was added aqueous solution of NaHCO3 (50 mL) and the mixture was extracted with EtOAc (30 mL x 3). The combined organic layers were dried over Na2504 and concentrated to give 3.53 g of the title compound. ?H NMR (400MHz, CDC13) : oe 3.03 (d, 3H), 6.63-6.67 (m, 1H), 6.84 (d, 1H), 7.43-7.48 (m, 1H), 7.99 (br s, 1H), 8.17 (dd, 1H).
	With potassium carbonate; In N,N-dimethyl-formamide; for 0.166667h;Microwave irradiation; Cooling;	General procedure: N1-methyl/ethyl-2-nitroaniline (2) wassynthesized by using 25ml (33.5 gm, 0.24 mol) of 2-fluronitrobenzene (1) dissolved in DMF andanhydrous K2CO3was added to it. 115 ml (6 mol) ofmethylamine/ethylamine was slowly added itthrough dropping funnel in cold condition. Aftercomplete addition of methylamine/ethylaminesolution the reaction mixture was kept in microwavefor 10 min. The completion of reaction was checkedby monitoring TLC. After completion, the reactionmixture was poured into ice cold water with stirringand extracted with the product with ether, the etherlayer was separated and dried with sodiumsulphate, and then ether was removed by distillationto get products 2a, 2b.
	In dimethyl sulfoxide; at 140℃; for 7h;	1-Fluoro-2-nitrobenzene (750 muL, 7.112 mmol, 1 equiv) dissolved in DMSO and methylamine (2462.6 muL, 28.44 mmol, 4 equiv) was added and the reaction mixture was stirred at 140?C in an oil bath for 7h. Reaction mixture was poured into water and extracted with ethyl acetate. Organic layer was dried, filtered and evaporated. The crude 8 (1030 mg, 95% yield) was used in the next step without purification [7]. Mp 36.2-37.8 C (36-37 C [8]). HRMS m/z calculated for C7H8N2O2 [M+H]+ 153.0664, found: 153.0637. CAS # 612-28-2

Reference： [1]Molecules,2012,vol. 17,p. 4545 - 4559
[2]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2918 - 2922
[3],2020,vol. 22
[4]Bulletin de la Societe Chimique de France,1956,p. 311,315
[5]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1573 - 1576
[6]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 6067 - 6070
[7]Journal of Medicinal Chemistry,2009,vol. 52,p. 5703 - 5711
[8]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5191 - 5194
[9]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3138 - 3141
[10]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 738 - 742
[11]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 4790 - 4793
[12]Patent: WO2014/144737,2014,A1 .Location in patent: Paragraph 00426
[13]Oriental Journal of Chemistry,2014,vol. 30,p. 1855 - 1863
[14]Bioorganic Chemistry,2020,vol. 95

7
[ 50-00-0 ]
[ 612-28-2 ]
[ 100974-85-4 ]

Reference： [1]Tetrahedron,1998,vol. 54,p. 5991 - 6000
[2]Journal of the American Chemical Society,1992,vol. 114,p. 7440 - 7451

8
[ 612-28-2 ]
[ 100-46-9 ]
[ 2622-63-1 ]
[ 716-79-0 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1980,vol. 19,p. 655 - 658

9
[ 612-28-2 ]
[ 814-68-6 ]
[ 169330-12-5 ]

Yield	Reaction Conditions	Operation in experiment
583 mg	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 18 - 25℃; for 2.5h;	[00427j To a solution of Intermediate 3 (500 mg, 3.29 mmol) and DIPEA(900 mg, 7.0 mmol) in DMF (5 mL), was added acrylol chloride (1.92 g, 21.4 mmol). The reaction was stirred at ambient temperature for 2.5 h. The mixture was partitioned between EtOAc and water. The organic layer was separated and washed with water, brine, dried over Na2SO4 and the crude product was subjected to flash chromatography on silica gel (eluting with 6 % MeOH in DCM) to afford 583 mg of the title compound. MS mlz: 207.2 (M+1).?H NMR (400MHz, CDC13) : oe 3.32 (s, 3H), 5.53 (d, 1H), 5.82-5.89 (m, 1H), 6.37 (d,1H), 7.37 (d, 1H), 7.56 (t, 1H), 7.67-7.71 (m, 1H), 8.01 (d, 1H).

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1995,p. 1349 - 1358
[2]Patent: WO2014/144737,2014,A1 .Location in patent: Paragraph 00427

10
[ 610-17-3 ]
[ 13351-73-0 ]
[ 89937-90-6 ]
[ 614-00-6 ]
[ 612-28-2 ]

Reference： [1]Canadian Journal of Chemistry,1997,vol. 75,p. 469 - 473

11
[ 610-17-3 ]
[ 13351-73-0 ]
[ 89937-90-6 ]
[ 612-28-2 ]
[ 98-95-3 ]

Reference： [1]Canadian Journal of Chemistry,1997,vol. 75,p. 469 - 473

12
[ 88-73-3 ]
[ 60-34-4 ]
[ 13351-73-0 ]
[ 22713-36-6 ]
[ 612-28-2 ]
[ 95-51-2 ]

Reference： [1]Heterocycles,1999,vol. 50,p. 693 - 702

13
[ 88-74-4 ]
[ 77-78-1 ]
[ 612-28-2 ]

Reference： [1]Synthetic Communications,2000,vol. 30,p. 3523 - 3526
[2]Angewandte Chemie - International Edition,2015,vol. 54,p. 11516 - 11520
Angew. Chem.,2015,vol. 127,p. 11678 - 11682
[3]Organic Process Research and Development,2007,vol. 11,p. 81 - 85

14
[ 201230-82-2 ]
[ 612-28-2 ]
[ 1849-01-0 ]

Reference： [1]European Journal of Organic Chemistry,2005,p. 1675 - 1679

15
[ 612-28-2 ]
[ 2044-88-4 ]

Yield	Reaction Conditions	Operation in experiment
62%	With bismuth (III) nitrate pentahydrate; palladium diacetate; In 2,2,2-trifluoroethanol; trifluoroacetic acid; at 20 - 90℃; for 24h;Inert atmosphere;	General procedure: Bi(NO3)3.5H2O (2 equiv, 0.6 mmol), Pd(OAc)2 (0.015 mmol, 5 mol %) were added into a 25mL oven-dried Schlenk tube, the tube was evacuated and backfilled with Ar (repeated three times in 30 min). Under a counter flow of Ar, N-substituted aniline (1 equiv, 0.3 mmol) was added by syringe firstly, 1.5 mL TFE and 0.5 mL TFA were then added by disposable medical syringes. The flask was sealed and the mixture was stirred firstly at room temperature for15 min, then allowed to stir in a preheated oil bath at 90 C for 24 h.The mixture was cooled to room temperature when the reaction was completed. Next, the solution was diluted by 10 mL ethyl acetate and filtered the insoluble matters, washed the organic phases by 5% NaHCO3 solution after the extraction, and extracted the aqueous phases by ethyl acetate (3x15 mL) to collect organic phases. All the organic solutions were washed by brine, dried 30 min with anhydrous MgSO4, filtered and concentrated under reduced pressure. The crude products were purified by chromatography on silica gel, eluting with ethyl acetate/petroleum ether(5/1-2/1).

Reference： [1]Tetrahedron,2015,vol. 71,p. 3827 - 3832
[2]Russian Journal of General Chemistry,2006,vol. 76,p. 64 - 75

16
[ 612-28-2 ]
[ 1849-01-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2918 - 2922

17
[ 612-28-2 ]
[ 2876-08-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: palladium; aqueous ethanolic hydrochloric acid / Hydrogenation 2: diethyl ether
	Multi-step reaction with 2 steps 1: tin; hydrochloric acid 2: hydrochloric acid
	Multi-step reaction with 3 steps 1: tin; hydrochloric acid 3: hydrochloric acid

	Multi-step reaction with 3 steps 1: sulfuric acid 2: iron; diluted acetic acid 3: hydrochloric acid
	Multi-step reaction with 4 steps 1: sulfuric acid 2: iron; diluted acetic acid 4: hydrochloric acid
	Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / 25 °C / Inert atmosphere 2: triphenylphosphine / decane / 12 h / 168 - 178 °C / Inert atmosphere

Reference： [1]Roeder; Day [Journal of Organic Chemistry, 1941, vol. 6, p. 25,28]
[2]Phillips [Journal of the Chemical Society, 1929, p. 2828]
[3]Phillips [Journal of the Chemical Society, 1929, p. 2828]
[4]Phillips [Journal of the Chemical Society, 1929, p. 2828]
[5]Phillips [Journal of the Chemical Society, 1929, p. 2828]
[6]Duchek, Jan; Vasella, Andrea [Helvetica Chimica Acta, 2011, vol. 94, # 6, p. 977 - 986]

18
[ 612-28-2 ]
[ 20934-51-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: palladium/charcoal; ethanol / Hydrogenation
	Multi-step reaction with 2 steps 1: sodium hydroxide; CaCl₂ / diethyl ether; ethanol

Reference： [1]Cheeseman [Journal of the Chemical Society, 1955, p. 1804,1806]
[2]Current Patent Assignee: UNIVERSITY OF CALIFORNIA; OREGON STATE BOARD OF HIGHER EDUCATION - US5514680, 1996, A

19
[ 612-28-2 ]
[ 205642-00-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Raney nickel; ethanol / Hydrogenation 2: pyridine

Reference： [1]Elderfield; Meyer [Journal of the American Chemical Society, 1954, vol. 76, p. 1891]

20
[ 612-28-2 ]
[ 78-39-7 ]
[ 2876-08-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	With 10% Pd/C; hydrogen; acetic acid In methanol at 20℃;

Reference： [1]Location in patent: scheme or table Liu, Zheng; Li, Haihong; Zhao, Qingjie; Shen, Jingshan [Heterocycles, 2008, vol. 75, # 8, p. 1907 - 1911]

21
[ 1190092-27-3 ]
[ 612-28-2 ]
[ 528560-93-2 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: methyl 4'-((6-formyl-4-methyl-2-n-propyl-1H-benzimidazol-1-yl)methyl)biphenyl-2-carboxylate; 2-nitro-N-methylaniline In N,N-dimethyl-formamide for 0.5h; Stage #2: With sodium dithionite In water; N,N-dimethyl-formamide at 10 - 45℃;	7 To the solution of aldehyde (5) (2 g, 4,7 mmol) in N,N- dimethylformamide (DMF) (40 mL) λT-methyl-o-nitroaniline (0,89 g, 5,9 mol) was added and stirred over -0,5 h. The reaction mixture was cooled to +100C and IM aqueous solution of sodium dithionite Na2S2U4 (3,5 g, 20,0 mmol, prepared freshly before the use) was added dropwise, keeping the temperature of the mixture below 15°C. When the addition was complete the reaction mixture was heated at temperature 45°C for 5 h, and stirred for 24 h at room temperature. After the completion of the reaction, 5M aqueous ammonia solution (25 mL) and water (25 mL) were added to the reaction mixture. The formed precipitate was filtrated, washed with water (2x25 mL) and dried to give 1,85 g (yield 74,6 %) of the crude product. The product was purified by maceration in ethyl acetate to obtain 1,7 g of the title compound.1H NMR (200 MHz, CDCl3), δ (ppm): 7,02-7,96 (m, 14H, aromatic); 5,39 (s, 2H, N-CH2-Ph) 3,69 (s, 3H, CH3-N benzimidazole); 3,54 (s, 3H, OCH3); 2,86-3,0 (t, 2H, CH2-CH2-CH3); 2,77 (s, 3H, CH3-Ph benzimidazole); 1,76-2,0 (m, 2H, CH2-CH2-CH3); 0,98-1,12 (t, 3H, CH2-CH2-CH3);13C NMR (135 MHz, CDCl3), δ (ppm): 168,39; 156,19; 154,37; 142,92; 142,65; 141,44; 140,82; 136,43; 134,76; 134,56; 131,12; 130,42; 130,30; 129,65; 129, 17; 128,72; 127, 13; 125,70; 123,58; 122,20; 122,01; 119, 19; 109,31; 108,65; 51,61; 46,79; 31,50; 29,58; 21,57; 16,55; 13,86

Reference： [1]Current Patent Assignee: ZAKLADY FARMACEUTYCZNE POLPHARMA S.A. - WO2009/123483, 2009, A1 Location in patent: Page/Page column 17-18

22
[ 1190092-31-9 ]
[ 612-28-2 ]
[ 144702-26-1 ]

Yield	Reaction Conditions	Operation in experiment
64.0%		To the solution of tert-butyl 4'-((6-formyl-4-methyl-2-n- propyl- Jff-benzimidazol- 1 -yl) methyl) biphenyl-2-carboxylate ( 150 mg, 0,32 mmol) in ethanol (9 mL), iV-methyl-o-nitroaniline (48 mg, 0,32 mmol) was added and stirred over -0,5 h. IM aqueous solution of sodium dithionite Na2S2theta4 (1 mL, 3,0 eq., prepared freshly before the use) was added. The mixture was stirred at <n="21"/>temperature 500C for 2 h and kept overnight (ok. 16 h). An additional amount of N- methyl- o-nitroaniline (20 mg) and IM aqueous solution of sodium dithionite Na2S2U4 (0,5 mL) were added and stirred at temperature 500C for 4 h.To the cooled reaction mixture IM HCl (5 mL) and water (20 mL) were added. The mixture was extracted with CH2CI2 (4x 10 mL). The combined organic phases were washed with IM HCl (15 mL) and water (15 mL) and dried over MgSO4. The solution was filtered and concentrated to give 223 mg compounds as an intensively yellow film.The film was purified by chromatography on silica gel, using as eluent CHCI3 with gradually added MeOH (0-3%). There was obtained 117 mg (yield 64,0 %) of telmisartan tert- butyl ester as colorless film.

Reference： [1]Patent: WO2009/123483,2009,A1 .Location in patent: Page/Page column 18-19

23
[ 64-17-5 ]
[ 612-28-2 ]
[ 2876-08-6 ]

Yield	Reaction Conditions	Operation in experiment
96 %Chromat.	With Pt-TiO₂ at 32℃; for 4h; UV-irradiation; Inert atmosphere;	The photocatalytic and catalytic synthesis was carried out using the following procedure. Appropriate amounts of catalyst and 2-nitrodiphenylamine or 2-aminodiphenylamine in 25 mL of alcohol were taken in a reaction tube. The reaction tube was sealed with a rubber septum and purged with nitrogen for 30 min. The reaction mixture was irradiated with UV (365 nm) medium-pressure mercury lamp (Sankyo Denki, Japan; intensity I = 1.381 × 10-6 einstein L-1 s-1)/ solar light at constant stirring. The temperature of the reaction medium during UV irradiation was 32 °C and it was nearly constant. With solar light, the temperature of the solution changed gradually from 32 to 48 °C for all the experiments. The progress of the reaction was monitored using thin layer chromatography (TLC). Product analysis was performed by GC analysis, Perkin-Elmer GC-9000 with a capillary column of DB-5 and flame ionization detector was used. GC-MS analysis was carried out using Varian 2000 Thermo with the following features: capillary column VF5MS (5% phenyl-95% methylpolysiloxane), 30 m length, 0.25 mm internal diameter, 0.25 μm film thickness, temperature of column range from 50-280 °C (10 °C/min) and injector temperature 250 °C, attached with mass spectrometer model SSQ 7000. The isolation was performed by column chromatography on a silica gel column by eluting with a co-solvent of dichloromethane and methanol (volume ratio: 8:2). For solar experiments, all reactions have been carried out under similar conditions on sunny days of different months of 2008-2009 between 10 A.M. and 2 P.M. The intensity of solar light was measured using a LT Lutron LX-10/A digital Lux meter and it was found to be 1250 × 100 (+/-100) lux. The intensity was nearly constant during the experiments.

Reference： [1]Location in patent: experimental part Selvam; Swaminathan [Tetrahedron Letters, 2011, vol. 52, # 26, p. 3386 - 3392]

24
[ 39621-11-9 ]
[ 612-28-2 ]
[ 1160492-68-1 ]

Reference： [1]Advanced Synthesis and Catalysis,2011,vol. 353,p. 3023 - 3030
[2]Inorganic Chemistry,2014,vol. 53,p. 5171 - 5178

25
[ 612-28-2 ]
[ 760212-73-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; acetic acid / 7 h / Reflux 2.1: pyridine / 7 h / 90 °C / Inert atmosphere 3.1: water; sodium dithionite / tetrahydrofuran; methanol / 3 h / 20 °C / Inert atmosphere 3.2: 1 h / 20 °C 4.1: toluene-4-sulfonic acid / xylene / 7 h / Reflux
	Multi-step reaction with 4 steps 1: acetic acid; bromine / 4 h / 20 °C 2: pyridine / 7 h / 90 °C / Inert atmosphere 3: sodium dithionite / tetrahydrofuran; methanol; water / 3 h / 20 °C 4: toluene-4-sulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 7 h / Reflux

Reference： [1]Current Patent Assignee: IDEMITSU KOSAN CO LTD - EP2524913, 2012, A1
[2]Current Patent Assignee: JIANGSU UNIVERSITY OF TECHNOLOGY - CN105399683, 2016, A

26
[ 612-28-2 ]
[ 100-51-6 ]
N-Methyl-N'-[1-phenyl-meth-(E)-ylidene]-benzene-1,2-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%Spectr.	In toluene; at 130℃; for 24h;Schlenk technique; Inert atmosphere; Sealed tube;	General procedure: In a typical reaction, 2 wt% Pd/HT catalyst (0.05 g, 2 mol% Pd relative to nitrobenzene) was added to a pressure tube (25 mL)equipped with a stir bar. The tube was sealed with a rubber septum, and vacuumed for several times. Substrates nitrobenzene(0.5 mmol, 50 L), benzyl alcohol (1.5 mmol, 150 L), and solvent toluene (2 mL) were added into the tube though the rubber septum using syringes, and then the septum was replaced by a Teflon screwcap under a nitrogen flow. The tube was sealed and the mixture was allowed to stir in a preheated oil bath at 130C for 24 h. After the reaction was completed, a GC internal standard dodecane(10 L) was added to the mixture. The mixture was diluted with ethyl acetate and filtered through a pad of silica gel. The pad of thesilica gel was washed again with small amount of ethyl acetate and the final volume of the clear solution was marked up to 25 mL. Theliquid products were then analyzed using a gas chromatographyequipment (Agilent 7820A).

Reference： [1]Applied Catalysis A: General,2014,vol. 470,p. 1 - 7

27
[ 612-28-2 ]
[ 100-46-9 ]
[ 2622-63-1 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 6218 - 6221

28
[ 612-28-2 ]
[ 3282-30-2 ]
[ 1579960-85-2 ]

Yield	Reaction Conditions	Operation in experiment
46%		N-Methyl-o-nitroaniline(1.0 g, 6.58 mmol, 1.0 equiv.) was added to sodiumhydride (0.32 g, 13.16mmol, 2.0 equiv.) in dry THF (50 ml) and the mixture stirred for 2 h. To this mixture was addeddropwise a solution of PivCl (2.10 g, 19.74 mmol, 3.0 equiv.) and the mixturestirred for 24 h. Further PivCl (2.10 g, 19.74 mmol, 3.0 equiv.) was added tothe mixture which was then stirred for a further 24 h. The reaction mixture wasthen evaporated to dryness and the residue dissolved in dichloromethane (100 ml) and the solution washed with water (100 ml), and aqueous sodium hydroxide (2 mol/L), dried (MgSO4) and evaporated to dryness.Purification of the residue by column chromatography (10% diethylether-dichloromethane) gave the product as yellow solid (0.67 g, 46%), mp 83-84 C. The product was dissolved in MeOH (18 mL), treated with 10%Pd/C (20 mg), then subjected to hydrogenation at atmospheric pressure for 2 hours.The mixture was filtered through Celite and washed with MeOH. The combinedfiltrates were concentrated in vacuo. The residue was triturated with Et2O,filtered, and then dried under vacuum to give the title compound 5o as a light yellow solid (0.51 g, 88%).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 1557 - 1561

29
1-phenyl-3-methyl-1H-pyrazole-5-carbonyle chloride [ No CAS ]
[ 612-28-2 ]
N,3-dimethyl-N-(2-nitrophenyl)-1-phenyl-1H-pyrazole-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With triethylamine; In acetonitrile; for 10h;Reflux;	A solutioncontaining 13 obtained as above and <strong>[612-28-2]N-methyl-2-nitroaniline</strong> (3.34 g, 22 mmol) in dryacetonitrile (50 ml) was refluxed for 10 h. The solution was evaporated under reduced pressure,and the residue was washed with ethyl ether (2x10 ml) and then crystallized from ethyl acetate/light petroleum ether (b.p. 40-70 C) to give 14, as a pale yellow solid, in 70% yield (referred toto 3-Methyl-1-phenyl-1H-pyrazole-5-carboxylic acid), 2.6 g, mp: 150-52 C. MS (m/z): 336(M+). IR (numax, cm-1): 1660 (CO). 1H-NMR: deltaH 2.16 (3H, s, Me), 3.36 (3H, s, Me), 6.00 (1H,s,pyrazole H-C(4) ), 7.26 - 8.03 (9H, m, C6H5 and C6H4); Anal. Calcd. for C18H16N4O3 (336.34) :C, 64.28; H, 4.79; N, 16.66. Found: C, 64.28; H, 4.99; N, 16.90%.

Reference： [1]ARKIVOC,2014,vol. 2014,p. 80 - 90

30
[ 612-28-2 ]
[ 100-51-6 ]
[ 2622-63-1 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium sulfide hydrate; iron(III) chloride hexahydrate; at 150℃; for 24h;Inert atmosphere;	General procedure: A 20-mL test-tube equipped with a magnetic stirring bar was charged with o-nitroaniline 1 (2.5 mmol, 1 equiv), alcohol 2 or 5 (3 mmol, 1.2equiv), Na2S·nH2O (?60percent, 130 mg, 1 mmol, 40 molpercent) and FeCl3·6H2O(7 mg, 0.025 mmol, 1 molpercent). The resulting mixture was stirred for 24h under an argon atmosphere at the indicated temperature (see Schemes 2 and 3 and Table 2). After cooling to r.t., the mixture was purified in different ways. (i) For NH benzimidazole products, the mixture was washed with CH2Cl2 (3 × 2 mL) then dissolved in MeOH.The MeOH solution was filtered through a short pad of silica gel. The filtrate was concentrated in vacuo to afford the NH benzimidazole product. Further purification by column or recrystallization was carried out if necessary. (ii) For N-methyl-2-phenylbenzimidazole 3ha and quinoxalines 5, the crude mixture was dissolved in a minimum volume of CH2Cl2 and purified by column chromatography (silica gel or alumina, heptane?EtOAc, EtOAc, EtOAc?MeOH, hexane?Et2O). We noted that some 13C NMR signals of NH-benzimidazoles are missing or difficult to observe.

Reference： [1]Synthesis,2015,vol. 47,p. 1741 - 1748
[2]Organic and Biomolecular Chemistry,2018,vol. 16,p. 2088 - 2096
[3]Chemical Communications,2014,vol. 50,p. 6145 - 6148

31
[ 64-18-6 ]
[ 612-28-2 ]
[ 1632-83-3 ]

Yield	Reaction Conditions	Operation in experiment
98%	With palladium 10% on activated carbon; triethylamine; at 150℃; for 0.133333h;Microwave irradiation;	The 0.152g (1.0mmol) <strong>[612-28-2]N-methyl-2-nitroaniline</strong> is dissolved in 0.8gTEAF (4.0mmol, 4 . 0equiv), and add 5.5mg10% Pd/C (0.5mol %). Suspension in the microwave heated to 150 C and lasts for 5 minutes. The reaction with TLC monitoring. The reaction mixture is added in 15 ml methanol and infusorial earth filtering to remove the catalyst. Removing the spin vaporization of methanol and add 10 ml saturated aqueous solution of sodium bicarbonate. After the gas of the escape, the reaction solution with 15 ml ethyl acetate extraction three times, and combined with the organic layer is dried with sodium sulfate. Removing the spin vaporization of the product of the ethyl ester of acetic acid 0.130g, the yield is 98%.

Reference： [1]RSC Advances,2015,vol. 5,p. 11132 - 11135
[2]Patent: CN105732519,2016,A .Location in patent: Paragraph 0041; 0042; 0043

32
[ 612-28-2 ]
[ 616-38-6 ]
[ 3097-21-0 ]

Reference： [1]Green Chemistry,2015,vol. 17,p. 2480 - 2486

33
[ 5470-96-2 ]
[ 612-28-2 ]
[ 54709-54-5 ]

Yield	Reaction Conditions	Operation in experiment
46%	With sodium dithionite; In water; N,N-dimethyl-formamide; for 12h;Reflux;	A mixture of quinoline-2-carbaldehyde (1.57 g, 10.0 mmol), <strong>[612-28-2]N-methyl-2-nitrobenzenamine</strong> (1.52 g, 10.0 mmol), Na2S2O4 (3.20 g), and DMF : H2O (3 : 1) was refluxed for 12 h. The solvent was evaporated on a rotary evaporator and the resulting solid was elutedwith petroleum ether on an alumina column. The second fraction was collected and concentrated to give L2 as a yellow solid in 46% yield. deltaH (400 MHz; CDCl3; Me4Si) 8.55 (1H,d, J = 8.6 Hz), 8.28 (1H, d, J = 8.6 Hz), 8.16 (1H, d, J = 8.6 Hz), 7.87 (2H, t, J = 10.9 Hz),7.76 (1H, t, J = 10.1 Hz), 7.59 (1H, t, J = 10.1 Hz), 7.48 (1H, d, J = 7.8 Hz), 7.35 (2H, m),4.46 (3H, s, -CH3). deltaC (100 MHz; CDCl3; Me4Si) 150.4, 149.8, 147.1, 142.6, 137.5, 136.3,129.6, 129.5, 127.6, 127.5, 127.1, 123.5, 122.6, 121.6, 120.2, 110.0, 32.99. Anal. Calcd for C17H13N3 (259.31): C, 78.74; H, 5.05; N, 16.20. Found: C, 78.64; H, 5.15; N, 16.10. FTIR(diamond disk, cm-1): 3047, 1616, 1598, 1466, 1446, 1390, 1332, 1211, 1115, 1053,1008, 838, 764, 734.

Reference： [1]Journal of Coordination Chemistry,2015,vol. 68,p. 3825 - 3838

34
[ 88-74-4 ]
[ 68-12-2 ]
[ 612-28-2 ]

Yield	Reaction Conditions	Operation in experiment
94%	With zinc(II) acetate dihydrate; In neat (no solvent); at 120℃; under 7600.51 Torr; for 18h;Autoclave; Inert atmosphere; Green chemistry;	General procedure: Zn(OAc)2·2H2O (5.0 mol%) was transferred to a 100 mL autoclavereactor equipped with an overhead stirrer and an automatic temperature-control system. The appropriate benzene-1,2-diamine 1 (2 mmol), DMF (10.0 mmol), and PMHS (5.0 mmol)were successively introduced. The reactor was sealed, flushedthree times with N2 (10 atm), and heated to the required temperature with vigorous stirring (600 rpm). During the course ofthe reaction, an increase of pressure was observed, due to thegeneration of Me2NH and HCHO at 120 C.15 (For this reason, the protocol needs to be performed in a sealed high-pressurereactor.) When the reaction was complete, the autoclave wascooled to r.t., and the pressure generated during the reactionwas carefully released. Basic hydrolysis was then carried out atr.t. for 30 min to remove unreacted PMHS from the mixture.13aThe mixture was then extracted with EtOAc (3 × 20 mL). Thecombined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The crude products were further purified bycolumn chromatography [silica gel (100-200 mesh), PE-EtOAc(20:4 to 10:2)]. The spectroscopic data for the products wereconsistent with those reported in the literature.

Reference： [1]Synlett,2015,vol. 26,p. 2835 - 2842

35
[ 88-74-4 ]
[ 616-38-6 ]
[ 612-28-2 ]
[ 13725-30-9 ]
[ 93675-40-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 130℃; under 760.051 Torr; for 24h;Green chemistry;	General procedure: A reaction flask was charged with amine substrate, PTC, base, solvent, and DMC. The mixture was heated to 130C, and the reaction was monitored by thin-layer chromatography (TLC). After reaction completion, the mixture was extracted with EtOAc and washed with H2O. The combined organic extracts were dried over anhydrous MgSO4 and concentrated under vacuum. The residue was purified by flash chromatography (silica gel, petroleum ether/EtOAc) to afford the desired compound.

Reference： [1]Research on Chemical Intermediates,2016,vol. 42,p. 5951 - 5960

36
[ 612-28-2 ]
[ 2835-06-5 ]
[ 2622-63-1 ]

Yield	Reaction Conditions	Operation in experiment
79%	With potassium carbonate; In toluene; at 140℃; for 24h;Schlenk technique; Sealed tube;	In a clean dry 10 ml Schlenk reaction tube, sequentially adding a 2-nitro-N-methylaniline 38 mg, benzene glycine 113 mg, potassium carbonate 80 mg, in order to 1 ml of toluene as a solvent, the reaction tube seal, in 140 °C reaction under 24 hours. After the reaction, the reaction mixture directly by rotating the evaporimeter turns on lathe does, then the volume ratio of 8:1 of petroleum ether and ethyl acetate as the eluant, by separating by silica gel column, to obtain 39 mg light yellow solid, yield 79percent.

Reference： [1]Patent: CN105777662,2016,A .Location in patent: Paragraph 0090; 0091; 0092

37
[ 593-51-1 ]
[ 1493-27-2 ]
[ 612-28-2 ]

Yield	Reaction Conditions	Operation in experiment
83%	In ethanol; water; at 100℃;Inert atmosphere;	Example 110 1. Synthesis of intermediate 110-1 Under a nitrogen atmosphere, 2-nitrofluorobenzene (20 g, 141 mmol) as a raw material was dissolved in 500 mL of anhydrous ethanol in a 1000 mL of three-necked flask at room temperature, followed by adding methylamine hydrochloride (28.5 g, 422 mmol) and 50 mL of water into the reaction system. The reaction was raised to 100C and carried out overnight. Next day, after detecting the reaction was completed, the reaction system was cooled to room temperature, concentrated to dryness. The resulting residue was purified by silica gel column chromatography (eluent: PE: EA = 5: 1). The product was collected, concentrated to dryness to give 18.0 g of the intermediate 110-1 (83%) as a yellow solid. LCMS: 153.0.

Reference： [1]Patent: EP3216786,2017,A1 .Location in patent: Paragraph 0568-0570

38
[ 612-28-2 ]
[ 594-44-5 ]
C₉H₁₂N₂O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87.21%		To a solution of <strong>[612-28-2]N-methyl-2-nitroaniline</strong> (0.5g, 3.28mmol, 1.Oeq) in dimethylformamide (lOmL) at 0 C, sodium hydride (0.33g, 8.2mmol, 2.5eq) was added portionwise. Reaction mixture was stirred at 0 C for 30 mm. Then ethanesulfonyl chloride (0.84g, 6.57mmol, 2.Oeq) was added dropwise. Reaction mixture was allowed to stir at 110 C for 1 8h. After completion of the reaction, the reaction mixture was transferred into ice- cold water and extracted with ethyl acetate. Organic layers were combined, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to obtain crude product. This was purified by column chromatography using 15% ethyl acetate in hexane as eluant to obtain pure 190.1 (0.7g, 87.2 1%). MS(ES): m/z 245.16 [M+H]t

Reference： [1]Patent: WO2018/75937,2018,A1 .Location in patent: Paragraph 00974; 00975

39
[ 612-28-2 ]
N-methyl-o-phenylenediamine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%		In the reactor, 40 kg of 40% monomethylamine and 200 kg of o-nitrochlorobenzene were charged.The temperature is sealed to about 100 C, and the reaction pressure is controlled to 0.55 MPa.The reaction time is 7 hours.Sampling analysis of o-nitrophenyl chloride content less than 0.7% to complete the reaction, pressure relief,Cool to a temperature below 10 C and filter to give N-methyl o-nitroaniline181.5kg (dry goods) The HPLC analysis content was 99.2%, and the yield was 93%.The mother liquor obtained by filtration recovers the monomethylamine cycle.The 181.5kg filter cake of N-methyl-o-nitroaniline obtained in the previous step was put into 570kg of methanol.Add 1.8 kg of ammonia water and 8 kg of 1% palladium on carbon catalyst containing 60% moisture.Heating and heating to a reaction temperature of about 75 C, catalytic hydrogenation reduction at a reaction pressure of 0.4 MPa, until the hydrogen is no longer absorbed,Sampling analysis of the content of N-methyl o-nitroaniline is less than 0.5%. After the reaction is completed, the pressure is released, the temperature is cooled to room temperature, and the palladium carbon catalyst is filtered and recycled.After the filtrate was distilled to recover methanol, 200 kg of water was added, and hydrochloric acid was added dropwise to pH 7.5.After cooling to 10 C or lower, the product was filtered to obtain 137.1 kg. Yield 95%.

Reference： [1]Patent: CN108774140,2018,A .Location in patent: Paragraph 0004; 0015-0020

40
[ 612-28-2 ]
[ 2622-63-1 ]

Reference： [1]Patent: CN108774266,2018,A

41
[ 612-28-2 ]
[ 100-52-7 ]
[ 2622-63-1 ]

Reference： [1]Journal of Materials Chemistry A,2018,vol. 6,p. 23766 - 23772

42
[ 612-28-2 ]
benzene-1,3,5-triyl triformate [ No CAS ]
[ 1849-01-0 ]

Reference： [1]European Journal of Organic Chemistry,2019,vol. 2019,p. 5161 - 5164

43
[ 612-28-2 ]
[ 81684-80-2 ]

Yield	Reaction Conditions	Operation in experiment
		To a 1 L reaction bottle, 120 g of ethanol, 100 g of N-methyl o-nitroaniline, and 10 g of a supported lacquer raw nickel were sequentially added, and the mixture was stirred and heated to between 70 and 75 C. The micro reflux was maintained, and hydrazine hydrate was slowly added thereto, and the dropwise addition was completed, and the reaction was kept at 80 C for 20 hours. After the reaction is completed, the mixture is filtered off, the activated carbon is discarded, and the filtered mother liquor is retained

Reference： [1]Patent: CN110272347,2019,A .Location in patent: Paragraph 0031; 0032; 0034-0036; 0038-0040; 0042; 0043

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
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.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
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.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
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.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
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

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. 612-28-2 ] {[proInfo.proName]}

Quality Control of [ 612-28-2 ]

Related Doc. of [ 612-28-2 ]

Product Details of [ 612-28-2 ]

Calculated chemistry of [ 612-28-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 612-28-2 ]

Application In Synthesis of [ 612-28-2 ]

[ 612-28-2 ] Synthesis Path-Downstream 1~43

Related Functional Groups of [ 612-28-2 ]

Aryls

Amines

Nitroes

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 612-28-2 ]