219312-08-0|4-Chloro-2-methyl-3-nitroaniline| Ambeed

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Quality Control of [ 219312-08-0 ] Purity: 95% SDS Specification

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Product Details of [ 219312-08-0 ]

CAS No. :	219312-08-0
Formula :	C₇H₇ClN₂O₂
M.W :	186.60
SMILES Code :	NC1=CC=C(Cl)C([N+]([O-])=O)=C1C
MDL No. :	MFCD26399863
InChI Key :	UKTHQISDMJUSCB-UHFFFAOYSA-N
Pubchem ID :	18789737

Safety of [ 219312-08-0 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H301-H311-H331
Precautionary Statements:	P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501
Class:	6.1
UN#:	2811
Packing Group:	Ⅲ

Application In Synthesis of [ 219312-08-0 ]

* 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 [ 219312-08-0 ]

[ 219312-08-0 ] Synthesis Path-Downstream 1~17

1
[ 5805-95-8 ]
[ 219312-08-0 ]

References: [1]Chemische Berichte,1907,vol. 40,p. 3330.
[2]Recueil des Travaux Chimiques des Pays-Bas,1913,vol. 32,p. 309.

2
[ 219312-08-0 ]
[ 5367-26-0 ]

References: [1]Journal of the Chemical Society,1907,vol. 91,p. 974.

3
[ 7647-01-0 ]
[ 5805-95-8 ]
[ 219312-08-0 ]

References: [1]Chemische Berichte,1907,vol. 40,p. 3330.

4
[ 7647-01-0 ]
[ 5805-95-8 ]
[ 219312-08-0 ]
[ 5806-00-8 ]

References: [1]Chemische Berichte,1907,vol. 40,p. 3330.

5
[ 7664-93-9 ]
[ 219312-08-0 ]
[ 5367-26-0 ]

References: [1]Chemische Berichte,1907,vol. 40,p. 3330.

6
[ 606-20-2 ]
[ 219312-08-0 ]

References: [1]Chemische Berichte,1907,vol. 40,p. 3330.
[2]Recueil des Travaux Chimiques des Pays-Bas,1913,vol. 32,p. 309.
[3]Patent: WO2008/137027,2008,A2 .

7
[ 219312-08-0 ]
[ 4771-47-5 ]

References: [1]Chemische Berichte,1907,vol. 40,p. 3330.

8
[ 219312-08-0 ]
[ 101420-96-6 ]

Yield	Reaction Conditions	Operation in experiment
		To 4-chloro-2-methyl-3-nitroaniline(1.63 g, 8.8 mmol) dissolved in acetic acid (75 mL) at room temperature was added a 2M aqueous solution of sodium nitrite (4.4 mL). The suspension was then diluted with acetic acid (100 mL) and then heated at reflux for 4 h. The mixture was then cooled to room temperature and concentrated under reduced pressure. The residue was then partitioned between ethyl acetate (100 mL) and saturated aqueous sodium hydrogen carbonate solution (100 mL). The separated organic layer was then washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. Column chromatography of the reside (hexane/ethyl acetate (2: 1) afforded the desired product. 1H NMR (500MHz) (DMSOd6) δ 8.32 (s, IH); 7.95 (d, J=8.7Hz, IH); 7.68 (d, J=8.7Hz, IH

References: [1]Patent: WO2005/3098,2005,A1 .Location in patent: Page/Page column 51.
[2]Patent: WO2008/137027,2008,A2 .Location in patent: Page/Page column 91.

9
tetrafluoroboric acid [ No CAS ]
[ 1493-13-6 ]
[ 5460-31-1 ]
[ 219312-08-0 ]
4-chloro-2-methyl-3-nitrophenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-chloro-succinimide; sulfuric acid; sodium sulfate; sodium nitrite; In water; acetonitrile;	4. Preparation of 4-chloro-2-methyl-3-nitrophenol A slurry of 4-chloro-2-methyl-3-nitroaniline (20.9 g), water (200 mL), and fluroboric acid (86 mL) was heated to boiling until almost complete solution took place, then cooled to 0-5 C. A solution of sodium nitrite (8.11 g) in water (20 mL) was then added dropwise to the above mixture, and then the mixture was stirred in the cold for an additional 30 min. The precipitated diazonium salt was filterd off and washed with a little cold water. The wet diazonium salt was added all at once to a hot (100-120 C.) solution of water (230 mL), concentrated sulfuric acid (115 mL), and sodium sulfate (35 g), and allowed to stir for 4 hr. The reaction mixture was cooled to room temperature and extracted with ethyl ether (700 mL in two portions). The combined ether extracts were washed with saturated sodium chloride solution, then dried over magnesium sulfate. Evaporation afforded crude product (17.5 g), which was purified by flash chromatography on silica, eluding with methylene chloride to afford 7.6 g as a yellow solid. The phenol was also prepared by the NCS chlorination of 2-methyl-3-nitrophenol, in a manner similar to that described in Oberhauser, J. Org. Chem. (1997) 62:4504-4506, as follows. STR72 2-Methyl-3-nitrophenol (25.5 g), N-chlorosuccinimide (44.5 g), and trifluormethanesulfonic acid (50.0 g) were combined in dry acetonitrile (500 mL) and allowed to stir under an atmosphere of nitrogen at 75 C. for 1.5 hr. The reaction mixture was cooled to room temperature, diluted with ethyl ether (650 mL), washed with water, 10% sodium bisulfite solution, water, and finally saturated sodium chloride solution. Evaporation of the solvent afforded a crude material which was flash chromatographed on silica and eluted with acetone:hexane (1:9) to afford 16.8 g as a yellow solid.
	With N-chloro-succinimide; sulfuric acid; sodium sulfate; sodium nitrite; In water; acetonitrile;	4. Preparation of 4-chloro-2-methyl-3-nitrophenol A slurry of 4-chloro-2-methyl-3-nitroaniline (20.9 g), water (200 mL), and fluroboric acid (86 mL) was heated to boiling until almost complete solution took place, then cooled to 0-5C. A solution of sodium nitrite (8.11 g) in water (20 mL) was then added dropwise to the above mixture, and then the mixture was stirred in the cold for an additional 30 min. The precipitated diazonium salt was filterd off and washed with a little cold water. The wet diazonium salt was added all at once to a hot (100-120C) solution of water (230 mL), concentrated sulfuric acid (115 mL), and sodium sulfate (35 g), and allowed to stir for 4 hr. The reaction mixture was cooled to room temperature and extracted with ethyl ether (700 mL in two portions). The combined ether extracts were washed with saturated sodium chloride solution, then dried over magnesium sulfate. Evaporation afforded crude product (17.5 g), which was purified by flash chromatography on silica, eluding with methylene chloride to afford 7.6 g as a yellow solid. The phenol was also prepared by the NCS chlorination of 2-methyl-3-nitrophenol, in a manner similar to that described in Oberhauser, J. Org. Chem . (1997) 62 :4504-4506, as follows. 2-Methyl-3-nitrophenol (25.5 g), N-chlorosuccinimide (44.5 g), and trifluormethanesulfonic acid (50.0 g) were combined in dry acetonitrile (500 mL) and allowed to stir under an atmosphere of nitrogen at 75 C for 1.5 hr. The reaction mixture was cooled to room temperature, diluted with ethyl ether (650 mL), washed with water, 10% sodium bisulfite solution, water, and finally saturated sodium chloride solution. Evaporation of the solvent afforded a crude material which was flash chromatographed on silica and eluted with acetone:hexane (1:9) to afford 16.8 g as a yellow solid.

References: [1]Patent: US5952362,1999,A .
[2]Patent: EP887346,1998,A2 .

10
[ 79913-56-7 ]
[ 219312-08-0 ]

Yield	Reaction Conditions	Operation in experiment
	palladium on charcoal; In diethyl ether; ethanol; cyclohexene;	3. Preparation of 4-chloro-2-methyl-3-nitroaniline A mixture of 3-chloro-2,6-dinitrotoluene (18.0 g), cyclohexene (51 mL), and 10% palladium on charcoal (4.5 g) in ethanol (350 mL) was heated at reflux under an atmosphere of nitrogen for 1.5 hr. The reaction mixture was cooled to room temperature, filtered through celite, then evaporated under reduced pressure. The residue was dissolved in ethyl ether and filtered through a short silica column. Evaporation of the ether afforded 14.8 g as an orange solid.
	With hydrogen;palladium 10% on activated carbon; In ethanol; cyclohexene; for 2.0h;Heating / reflux;	A mixture of 3-chloro-2,6- dinitrotoluene (2.46 g, 9.5 mmol), cyclohexene (10 mL) and 10% palladium on charcoal (0.6 g) in ethanol (50 mL) was heated at reflux under an atmosphere of nitrogen for 2 h. After this time the reaction mixture was cooled to room temperature, filtered through celite and then evaporated under reduced pressure. The residue was dissolved in diethyl ether and filtered through a short silica column. Evaporation of the ether afforded the product as an orange solid. 1H NMR (400MHz) (CDCl3) δ 7.15 (d, J=8.7Hz, IH); 6.72 (d, J=8.7Hz, IH); 3.80 (bs, 2H); 2.11 (s, 3H).

References: [1]Patent: EP887346,1998,A2 .
[2]Patent: WO2008/137027,2008,A2 .Location in patent: Page/Page column 90.

11
[ 10202-92-3 ]
[ 219312-08-0 ]