89639-98-5|(2-Chloro-3-nitrophenyl)methanol| Ambeed

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Quality Control of [ 89639-98-5 ] Purity: 98% SDS Specification

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Product Details of [ 89639-98-5 ]

CAS No. :	89639-98-5
Formula :	C₇H₆ClNO₃
M.W :	187.58
SMILES Code :	OCC1=C(Cl)C(=CC=C1)[N+]([O-])=O
MDL No. :	MFCD08236803
InChI Key :	MOCPJIDJALBRIX-UHFFFAOYSA-N
Pubchem ID :	15132843

Safety of [ 89639-98-5 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H319-H372-H410
Precautionary Statements:	P501-P273-P260-P270-P264-P280-P391-P314-P337+P313-P305+P351+P338-P301+P312+P330
Class:	9
UN#:	3077
Packing Group:	Ⅲ

Application In Synthesis of [ 89639-98-5 ]

* 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.

Downstream synthetic route of [ 89639-98-5 ]

[ 89639-98-5 ] Synthesis Path-Downstream 1~35

1
[ 89639-98-5 ]
[ 58755-57-0 ]

Yield	Reaction Conditions	Operation in experiment
79.7%	With pyridinium chlorochromate; In dichloromethane; at 20℃; for 12h;	8.43 g (39.09 mmol) of pyridinium chlorochromate (PCC) were added to a solution of 6.11 g (32.57 mmol) of <strong>[89639-98-5](2-chloro-3-nitrophenyl)methanol</strong> in 120 ml of dichloromethane, and the mixture was stirred at room temperature for 12 hours. After complete conversion, the solvent was evaporated to dryness under reduced pressure. The residue obtained was purified chromatographically on silica gel (mobile phase dichloromethane/methanol 20:1). This gave 4.82 g (25.97 mmol, 79.7% of theory) of the title compound.GC-MS (method 3): Rt=5.09 min; m/z=186 (M+H)+.1H-NMR (400 MHz, DMSO-d6): δ=10.35 (s, 1H), 8.33 (dd, 1H), 8.13 (dd, 1H), 7.77 (t, 1H).
78%		A solution of oxalyl chloride in dichloromethane (2.0M, 116 mmol) was chilled to -70 C. (internal temperature) under a nitrogen atmosphere. DMSO (15 mL, 211.3 mmol) was added dropwise maintaining -65 C. and then stirring was continued for 45 min. at -70 C. A solution of the 3-nitro-2-chlorobenzyl alcohol (14.4 g, 76.6 mmol) in dichloromethane (250 mL) was then added and the reaction stirred at -70 C. for 2 h. Triethylamine (54 mL, 387 mmol) was added dropwise and the reaction stirred for 2 h at -70 C. and then 12 h at room temperature. The reaction was quenched by the addition of 500 mL of water. The aqueous phase was extracted twice with dichloromethane. The combined organic layers were washed with brine, dried with MgSO4, filtered, and evaporated to obtain a light brown solid. Column Chromatography (silica gel, 30% dichloromethane/hexanes to 70% dichloromethane/hexanes) produced 11.1 g (78%) of the desired 3-nitro-2-chlorobenzaldehyde as a yellow solid. 3-Nitro-2-chlorobenzaldehyde (11.1 g, 59.5 mmol) was dissolved in DMF (100 mL) and potassium carbonate (9.1 g, 66.2 mmol) was added. By slow addition, methyl thioglycoate (5.4 mL, 60.4 mmol) was added and a slight exotherm was observed. The reaction mixture was stirred 12 h at room temperature. Water (200 mL) was added to the reaction mixture which was then cooled on an ice/water bath. The solid was filtered and washed water until the filtrate was colorless, leaving the 13.3 g (94%) of the desired 7-nitro-benzo[b]thiophene-2-carboxylic acid methyl ester as a white solid.
74%		Step 2. 2-Chloro-3-nitrobenzaldehyde; A 250-mL 3-necked round-bottom flask was charged with a solution of oxalyl chloride (5.42 g, 42.70 mmol, 1.10 equiv) in DCM (100 mL). To this was added a solution of DMSO (6.65 g, 85.11 mmol, 2.20 equiv) in DCM (15 mL) drop wise -78 C. 2-Chloro-3-nitrophenyl)methanol (7.23 g, 38.54 mmol, 1.00 equiv) in DCM (35 mL) was added into the solution at -78 C. and allowed to stir for 1 hour. Then, TEA (30 mL) was added at this temperature and allowed to stir for an additional hour. Upon completion, the reaction was quenched with water and extracted with DCM (3×100 mL). Combined organic layers were dried over anhydrous sodium sulfate, filtered off and concentrated on a rotary evaporator. The residue was purified by a silica gel column chromatography eluted with PE:EA (10:1) affording 2-chloro-3-nitrobenzaldehyde as light yellow solid (5.3 g, 74%).

With manganese(IV) oxide; In dichloromethane; at 20℃;

General procedure: MnO2 (508 g, 5.84 mol) was added to (2-bromo-4-nitro-phenyl)methanol (135.1 g, 0.582 mol) in DCM (1 L) and the reaction mixture was stirred overnight at rt. The mixture was filtered and the filtrate was evaporated to afford the title compound 18 (110.8 g, 83%) as a yellow solid

References: [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 936 - 944.
[2]Patent: US2011/34450,2011,A1 .Location in patent: Page/Page column 101; 102.
[3]Patent: US2003/225053,2003,A1 .Location in patent: Page 24.
[4]Patent: US8080566,2011,B1 .Location in patent: Page/Page column 72.
[5]Tetrahedron,2000,vol. 56,p. 165 - 173.
[6]Journal of Medicinal Chemistry,2005,vol. 48,p. 4009 - 4024.
[7]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 1992 - 2000.
[8]Tetrahedron,2014,vol. 70,p. 6613 - 6622.

2
[ 89639-98-5 ]
[ 108772-93-6 ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 1166 - 1176.

3
[ 3970-35-2 ]
[ 89639-98-5 ]

Yield	Reaction Conditions	Operation in experiment
99%		Intermediate 1 2-Chloro-3-nitrobenzyIbromide2-Chloro-3-nitrobenzoic acid (0.30 g, 1.5 mmol) was added to BH3 (IM, 4.0 mL, 4.0 mmol). The reaction was refluxed for 3 hours and then cooled to room temperature. The reaction was quenched with water and extracted with diethyl ether (3x15 mL). Purification on silica (100% dichloromethane) gave 0.28g, (99% yield) of the 2-chloro-3- nitrobenzylalcohol.
98%		Step 1. (2-Chloro-3-nitrophenyl)methanol; A 500-mL 3-necked round-bottom flask was charged with a solution of NaBH4 (4 g, 105.26 mmol, 2.10 equiv) in THF (100 mL). To this was added a solution of 2-chloro-3-nitrobenzoic acid (10 g, 49.75 mmol) in THF (100 mL) at 0 C. After 10 minutes, BF3.Et2O (15 mL) in THF (50 mL) was added dropwise over 10 minutes. The resulting solution was stirred at room temperature overnight. The reaction progress was monitored by TLC (DCM: MeOH=5:1). Upon completion, the reaction was quenched with water (500 mL) and extracted with ethyl acetate (3×300 mL). Combined organic layers were dried over anhydrous sodium sulfate, filtered off and concentrated on a rotary evaporator affording (2-chloro-3-nitrophenyl)methanol as light yellow solid (9 g, 98%).
84%	In tetrahydrofuran; water;	Example 132 Synthesis of (2-chloro-3-nitrophenyl)methanol A borane-tetrahydrofuran complex (1.0 M, 20 ml) was added dropwise to a solution of 2-chloro-3-nitrobenzoic acid (5.0 g) in anhydrous tetrahydrofuran (30 ml) in a nitrogen atmosphere and the mixture was heated under reflux for 16 h. Water was added to the reaction mixture which was extracted with ethyl acetate; the organic layer was washed successively with a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, dried with anhydrous-sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=5:2) to give 3.5 g of the titled compound (yield, 84%). 1H-NMR(CDCl3) δ: 2.04(1H, t, J=5.9 Hz), 4.88(2H, d, J=5.9 Hz), 7.45(1H, dd, J=7.9, 7.9 Hz), 7.72-7.82(2H,m)

61%		The following procedure for the synthesis of the intermediate 7-nitro-benzo[b]thiophene-2-carboxylic acid is a modification of the procedure in the chemical literature (L. K. A. Rahaman and R. M. Scrowston, J. Chem. Soc. Perkin Trans. I, 19, 1984, 385). 3-Nitro-2-chlorobenzoic acid (25.51 g, 126.56 mmol) was dissolved in anhydrous THF (400 mL) under a nitrogen atmosphere. The solution was cooled to -70 C. (internal temperature) under N2 flush. DIBAL-H (260 mL, 1.0M in hexanes) was added dropwise over about 11/2 h (internal temperature was maintained below -65 C.). The reaction was allowed to slowly warm to room temperature and was stirred 12 h. The reaction was cooled to -70 C. and 50 mL of MeOH was added dropwise. The reaction mixture was placed in an H2O/ice bath and a 1M Rochelle's salt solution was slowly added in. This solution was stirred for 1 h at room temperature, then filtered through diatomaceous earth. The THF was concentrated in vacuo and the remaining aqueous solution was extracted 3 times with EtOAc. The combined organic layers were washed with brine, dried with MgSO4, filtered, and evaporated to obtain 14.4 g (61%) of the desired 3-nitro-2-chlorobenzyl alcohol as a yellow solid.
43%	In tetrahydrofuran; hydrogenchloride; hexane;	EXAMPLE 9 2-Chloro-3-nitrobenzenemethanol A solution of 2-chloro-3-nitrobenzoic acid (1.0 g, 5.0 mmol) in tetrahydrofuran (10 mL) is cooled to 0 C. under an argon atmosphere. Boranetetrahydrofuran complex (6.4 mL of a 1.0 M solution) is added dropwise, maintaining a reaction temperature of less than 5 C. After the addition is complete, the reaction mixture is stirred for 6 hours at room temperature. It is then cooled in an ice bath and quenched by the addition of 10 mL of 1.0 N HCl. The reaction mixture is heated at reflux for 30 minutes and concentrated by distilling the THF. The remaining aqueous solution is extracted with methylene chloride, and the organic layer is washed with saturated aqueous bicarbonate and brine. Evaporation of the organic layer followed by recrystallization of the residue from hexane gives 2-chloro-3-nitrobenzenemethanol (0.4 g, 43%), mp=69-70 C.
	With dimethylsulfide borane complex; triethylamine; In tetrahydrofuran; at 0℃; for 3h;Reflux;	General procedure: Triethylamine (94.3 g, 0.932 mol) and 10 N BH3·SMe2 in DMS (281 mL, 2.81 mol) were added to 2-bromo-4-nitro-benzoic acid 17 (230 g, 0.935 mol, sourced commercially) in THF (1.5 L) at 0 C, then the reaction mixture was heated at reflux for 3 h. The reaction mixture was allowed to cool to rt, then slowly quenched with water (100 mL) and acidified with concd aq HCl to pH=1, heated at reflux for 30 min, then allowed to cool to rt. The mixture was extracted three times with DCM (3*500 mL), and the combined organic layers were evaporated and purified by flash chromatography, eluting with 17-33% EtOAc in petroleum ether, to afford the title compound (135.1 g, 62%) as a yellow solid;

References: [1]Patent: WO2007/39125,2007,A2 .Location in patent: Page/Page column 34.
[2]Patent: US8080566,2011,B1 .Location in patent: Page/Page column 72.
[3]Journal of Medicinal Chemistry,1987,vol. 30,p. 1166 - 1176.
[4]Patent: US6534546,2003,B1 .
[5]Journal of Medicinal Chemistry,1988,vol. 31,p. 936 - 944.
[6]Patent: US2003/225053,2003,A1 .Location in patent: Page 23, 24.
[7]Patent: US5017604,1991,A .
[8]Tetrahedron,2000,vol. 56,p. 165 - 173.
[9]Journal of Medicinal Chemistry,2005,vol. 48,p. 4009 - 4024.
[10]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 1992 - 2000.
[11]Tetrahedron,2014,vol. 70,p. 6613 - 6622.

4
[ 89639-98-5 ]
[ 145457-72-3 ]
3-nitro-2-<5-<(tert-butyldimethylsilyl)oxy>pentyl>thiobenzyl alcohol [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 119 - 129.

6
[ 89639-98-5 ]
[ 857040-81-4 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 4009 - 4024.
[2]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 1992 - 2000.

7
[ 89639-98-5 ]
[ 857040-99-4 ]