[ CAS No. 99817-36-4 ] {[proInfo.proName]}

Name: 99817-36-4|2,4-Dichloro-3-ethyl-6-nitrophenol|98%
Brand: Ambeed
SKU: A267601
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Quality Control of [ 99817-36-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 99817-36-4 ]

CAS No. :	99817-36-4	MDL No. :	MFCD00270764
Formula :	C₈H₇Cl₂NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YTVCECQSAPGJBB-UHFFFAOYSA-N
M.W :	236.05	Pubchem ID :	7020339
Synonyms :

Calculated chemistry of [ 99817-36-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	57.08
TPSA :	66.05 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.9 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.83
Log Po/w (XLOGP3) :	4.0
Log Po/w (WLOGP) :	3.17
Log Po/w (MLOGP) :	2.1
Log Po/w (SILICOS-IT) :	1.3
Consensus Log Po/w :	2.28

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.01
Solubility :	0.0231 mg/ml ; 0.000098 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.09
Solubility :	0.00192 mg/ml ; 0.00000815 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-3.23
Solubility :	0.138 mg/ml ; 0.000583 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.93

Safety of [ 99817-36-4 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P264-P270-P272-P273-P280-P301+P310+P330-P302+P352+P333+P313+P363-P305+P351+P338+P310-P391-P405-P501	UN#:	2811
Hazard Statements:	H301-H317-H318-H410	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 99817-36-4 ]

* 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 [ 99817-36-4 ]

[ 99817-36-4 ] Synthesis Path-Downstream 1~10

1
[ 99817-36-4 ]
[ 99817-37-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen In isopropyl alcohol at 60 - 70℃;

Reference： [1]Current Patent Assignee: KONICA MINOLTA, INC. - JP2005/289835, 2005, A Location in patent: Page/Page column 6

2
[ 99817-36-4 ]
[ 7440-44-0 ]
2,4-dichloro-3-ethyl-6-aminophenol hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride In methanol	12.3 Production of 2-(2,4-di-t-amylphenoxy)-N-(3,5-dichloro-4-ethyl-2-hydroxyphenyl)butyramide (3) 2,4-Dichloro-3-ethyl-6-nitrophenol (20 g, 98.4% purity) was dissolved in methanol (80 g), to which Raney nickel (0.8 g) and activated carbon (0.2 g) were added and into which hydrogen gas was introduced at a hydrogen pressure of 4 kg/cm2 at 40° to 45° C. until no absorption of hydrogen gas was found. After completion of the reaction, Raney nickel was removed in air, and hydrochloric acid (17.7 g) was added dropwise, and the reaction mixture was cooled to 20° C., which resulted in a deposition of crystals. The deposited crystals were washed with acetone (28 g) and dried, which afforded 16.2 g of 2,4-dichloro-3-ethyl-6-aminophenol hydrochloride.

Reference： [1]Current Patent Assignee: SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Chemical (w/o Dongwoo Fine-Chem) - US5442114, 1995, A

Yield	Reaction Conditions	Operation in experiment
90%		3 EXAMPLE 3 EXAMPLE 3 Reaction was conducted in the same manner as in Example 2 except that 1.3 g of aluminium chloride is used as a catalyst of chlorination. As a result, 136.0 g of 2,4-dichloro-3-ethyl-6-nitrophenol is obtained (yield, 90%).
70.9%		15 EXAMPLE 15 EXAMPLE 15 In the same manner as in Example 13 except that 1,2-dichloroethane is used in place of the monochlorobenzene as a solvent, 2,4-dichloro-3-ethyl-6-nitrophenol is obtained. Yield, 106.9 g (70.9% yield based on 4-chloro-3-ethylphenol).
63.1%		15 EXAMPLE 15 EXAMPLE 15 Example 10 was repeated, provided that the hydrolysis reaction was carried out using sodium hydroxide (24 parts) in place of potassium hydroxide (32 parts), thereby obtaining 2,4-dichloro-3-ethyl-6-nitrophenol (12.6 parts) in a yield of 63.1%.

47.4%		9 EXAMPLE 9 EXAMPLE 9 Example 7 was repeated, provided that the hydrolysis reaction was carried out using sodium hydroxide (20 parts) in place of potassium hydroxide (33 parts), thereby obtaining 2,4-dichloro-3-ethyl-6-nitrophenol (13.0 parts) in the over all yield of 47.4%.
24%		8 EXAMPLE 8 EXAMPLE 8 When the amount of methanol in Example 5 was replaced by the same volume of acetone, a yield of 24% of 2,4-dichloro-3-ethyl-6-nitrophenol was obtained after a reaction time of 4 hours in the boiling solvent mixture.
		7 Example 7 Successively, the product (25.4 parts) was placed in a solution of methanol (180 parts), water (23 parts) and potassium hydroxide (33 parts), and the mixture was stirred under reflux for 4 hours. Thereafter, the reaction mixture was cooled to ambient temperature to produce dark red crystals. The crystals separated and washed with methanol and then water were placed in a 20% aqueous sulfuric acid solution (59 parts). The mixture was stirred at a temperature of 70° to 75° C. for 3 hours, and then cooled to produce crystalline 2,4-dichloro-3-ethyl-6-nitrophenol, which was separated by filtration, washed with water and then dried. Thus, the desired product (16.2 parts), m.p. 45.2° to 46.2° C., was obtained in the over-all yield of 58.6%.

4
[ 103145-09-1 ]
[ 98-69-1 ]
[ 99817-36-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; iodine; nitric acid In methanol; sulfuric acid; water	5 EXAMPLE 5 EXAMPLE 5 Iodine (5 parts) was dissolved in 96% sulfuric acid (1000 parts) and 4-ethylbenzenesulfonic acid (186 parts) was added thereto. Chlorine (about 235 parts) was introduced therein, while being stirred at a temperature of 40° to 60° C. Then, a 2,3,5-trichloro-4-ethylbenzenesulfonic acid content in the reaction mixture reached 78.3%. Successively, water (200 parts) was added to the reaction mixture so as to make a ratio of sulfuric acid to water 8:2, and the reaction mixture was subjected to steam distillation at a temperature of 160° to 200° C., thereby performing desulfonation reaction. Mixed acid consisting of 67% nitric acid (110 parts) and concentrated sulfuric acid (174 parts) was added dropwise to the desulfonation reaction product isolated from water, while being stirred at a temperature of 20° to 40° C., and the mixture was kept at that temperature for 1 to 3 hours. Thereafter, the reaction mixture was poured into water (950 parts) at a temperature of 30° C. or below. The reaction product was separated from water and then washed with water. The crude product of 2,3,5-trichloro-4-ethylnitrobenzene (220 parts) was added to a mixture of methanol (1560 parts), water (200 parts) and potassium hydroxide (240 parts), and the resulting mixture was refluxed for 4 hours. Thereafter, the reaction mixture was cooled to ambient temperature to deposit precipitate. The precipitate separated and washed with methanol and then water was placed in 20 % sulfuric acid (510 parts). The mixture was stirred for 3 hours at a temperature of 70° to 75° C., and then cooled to produce crystals of 2,4-dichloro-3-ethyl-6-nitrophenol. The crystals were collected on a filter, washed with water and then dried to obtain a desired product (141.8 parts).

Reference： [1]Current Patent Assignee: Sumitomo Chemical (w/o Dongwoo Fine-Chem); SUMITOMO CHEMICAL COMPANY LIMITED - US5012015, 1991, A

5
sodium 2,3,5-trichloro-4-ethylbenzenesulfonate [ No CAS ]
[ 99817-36-4 ]

Yield	Reaction Conditions	Operation in experiment
78.1%	With potassium hydroxide; nitric acid In sulfuric acid; water; ethylene glycol	10 EXAMPLE 10 EXAMPLE 10 Potassium hydroxide (32 parts) was dissolved in ethylene glycol (200 parts), and successively the crude sodium 2,3,5-trichloro-4-ethylbenzenesulfonate (32 parts) obtained in Example 1 was added thereto. The mixture was allowed to react at a temperature of 140° to 160° C. for 12 hours. After the reaction was over, the reaction mixture was mixed with water (200 parts), and adjusted the pH within a range of 3 to 6 to produce crystals. Water containing crystals collected on a filter was placed in 25% sulfuric acid (350 parts), and 62% nitric acid (74 parts) was dropwise added thereto, while being stirred at a temperature of 25° to 50° C. The mixture was stirred at that temperature for 1 hour, and thereafter cooled to 5° C. to produce crystals, which were collected on a filter, washed with water and then dried to obtain 2,4-dichloro-3-ethyl-6-nitrophenol (15.6 parts) having a melting point of 46.2° to 47.2° C. in a yield of 78.1%. Elementary analysis: Found: C: 40.49% H: 3.04% N: 5.83% Cl: 29.8% Calculated: C: 40.71% H: 2.99% N: 5.93% Cl: 30.04%

Reference： [1]Current Patent Assignee: Sumitomo Chemical (w/o Dongwoo Fine-Chem); SUMITOMO CHEMICAL COMPANY LIMITED - US5012015, 1991, A

6
[ 75-34-3 ]
[ 14143-32-9 ]
[ 99817-36-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogenchloride; chlorosulfonic acid; aqueous nitric acid; dihydrogen peroxide	1 EXAMPLE 1 EXAMPLE 1 In a 1-liter four-necked glass flask is prepared a solution mixture of 100 g of 4-chloro-3-ethylphenol and 350 g of dichloroethane. While the mixture is maintained at a temperature of 35°-45° C., 80 g of chlorosulfonic acid is added dropwise and the mixture is maintained at a temperature of 40°-45° C. for 1 hour. Next, 326 g of a 14.3% hydrochloric acid solution is added, and 68 g of a 35% aqueous hydrogen peroxide solution is added dropwise while maintaining the temperature at 40°-45° C. After the mixture is maintained at the same temperature for 8 hours, it is cooled to 20° C. After the oily layer is separated, the aqueous layer is placed in a dropping funnel and added dropwise, at 30°-40° C., to 230 g of a 35% aqueous nitric acid solution which has been preliminarily charged in a 1-liter four-necked glass flask. The liquid becomes turbid and turns yellowish white and the reaction is initiated. After the addition is over, the reaction mixture is maintained at the same temperature for 2 hours. The reaction mixture is cooled to 5° C. and filtered. The product is washed with water and dried to give 2,4-dichloro-3-ethyl-6-nitrophenol. Yield, 143 g (95% yield based on 4-chloro-3-ethylphenol),
94%	With hydrogenchloride; chlorosulfonic acid; aqueous nitric acid; dihydrogen peroxide	8 EXAMPLE 8 EXAMPLE 8 In a 1-liter four-necked glass flask is prepared a solution mixture of 100 g of 4-chloro-3-ethylphenol and 350 g of dichloroethane. While the mixture is maintained at a temperature of 35°-45° C., 80 g of chlorosulfonic acid is added dropwise and the mixture is maintained at a temperature of 40°-45° C. for 1 hour. Next, 326 g of a 14.3% hydrochloric acid solution is added, and 68 g of a 35% aqueous hydrogen peroxide solution is added dropwise while maintaining the temperature at 40°-45° C. After the mixture is maintained at the same temperature for 8 hours, it is cooled to 20° C. After the oily layer is separated, the aqueous layer obtained is charged in a 2-liter four-necked glass flask. A 460 g portion of the filtrate (A) obtained in the nitration reaction in Example 7 is added to the aqueous layer, and the mixture is maintained at a temperature of 20°-30° C. On the other hand, 115 g of the filtrate (B) obtained in Example 7 and 115 g of a 70% aqueous nitric acid solution are placed in a dropping funnel and added dropwise to the aforementioned flask. The liquid becomes turbid and turns yellowish white, as soon as the addition is initiated. After the addition is over, the reaction mixture is further maintained at the same temperature for 3 hours. The reaction mixture is cooled to 5° C. and filtered. The product is washed with water and dried to give 2,4-dichloro-3-ethyl-6-nitrophenol. Yield, 143 g (94% yield based on 4-chloro-3-ethylphenol),
92%	With hydrogenchloride; chlorosulfonic acid; dihydrogen peroxide In aqueous nitric acid	6 EXAMPLE 6 EXAMPLE 6 In a 1-liter four-necked glass flask is prepared a solution mixture of 100 g of 4-chloro-3-ethylphenol and 350 g of dichloroethane. While the mixture is maintained at a temperature of 35°-45° C., 80 g of chlorosulfonic acid is added dropwise and the mixture is maintained at a temperature of 40°-45° C. for 1 hour. Next, 326 g of a 14.3% hydrochloric acid solution is added, and 68 g of a 35% aqueous hydrogen peroxide solution is added dropwise while maintaining the temperature at 40°- 45° C. After the mixture is maintained at the same temperature for 8 hours, it is cooled to 20° C. After the oily layer is separated, the aqueous layer is placed in a dropping funnel and added dropwise at 30°-40° C. to 172.5 g of a 70% aqueous nitric acid solution which has been preliminarily charged in a 1-liter four-necked glass flask. The liquid becomes turbid and turns yellowish white as soon as the addition is initiated. After the addition is over, the reaction mixture is maintained at the same temperature for 2 hours. The reaction mixture is cooled to 5° C. and filtered. The product is washed with water and dried to give 2,4-dichloro-3-ethyl-6-nitrophenol. Yield, 143 g (92% yield based on 4-chloro-3-ethylphenol),

84%	With hydrogenchloride; chlorosulfonic acid; aqueous nitric acid; dihydrogen peroxide In water	5 EXAMPLE 5 EXAMPLE 5 In a 500 ml four-necked glass flask is prepared a solution mixture of 100 g of 4-chloro-3-ethylphenol and 350 g of dichloroethane. While the mixture is maintained at a temperature of 25°-30° C., 80 g of chlorosulfonic acid is added dropwise. After the mixture is maintained at the same temperature for 3 hours, it is discharged in a 1-liter four-necked glass flask in which 200 g of water has been charged. Next, 133 g of a 35% hydrochloric acid solution and 1.3 g of aluminium chloride are added, and then 181 g of a 18% aqueous hydrogen peroxide solution is added dropwise while maintaining the temperature at 30° C. After the mixture is maintained at the temperature, it is cooled to 20° C. After the oily layer is separated, 319 g of a 70% aqueous nitric acid solution is added dropwise to the aqueous layer while keeping the temperature at 30° C. After the addition is completed, the mixture is heated to 45° C. and maintained at the temperature for 4 hours. The reaction mixture is cooled to 5° C. and filtered. The product is washed with water and dried to give 2,4-dichloro-3-ethyl-6-nitrophenol. Yield, 126.8 g (84% yield based on 4-chloro-3-ethylphenol).
82%	With hydrogenchloride; chlorosulfonic acid; dihydrogen peroxide; nitric acid	9 EXAMPLE 9 EXAMPLE 9 In a 1-liter four-necked glass flask is prepared a solution mixture of 100 g of 4-chloro-3-ethylphenol and 350 g of dichloroethane. While the mixture is maintained at a temperature of 35°-45° C., 80 g of chlorosulfonic acid is added dropwise and the mixture is maintained at a temperature of 40°-45° C. for 1 hour. Next, 326 g of a 14.3% hydrochloric acid solution is added, and 68 g of a 35% aqueous hydrogen peroxide solution is added dropwise while maintaining the temperature at 40°-45° C. After the mixture is maintained at the same temperature for 8 hours, it is cooled to 20° C. After the oily layer is separated, the aqueous layer obtained is charged in a 1-liter four-necked glass flask, and 34.5 g of a 70% nitric acid solution is added dropwise to the aqueous layer at a temperature of 30°-40° C. The liquid becomes turbid and turns yellowish white after 35 minutes from the addition. The temperature is raised about 3° C. Next, 138 g of a 70% nitric acid solution is added dropwise, and the mixture is maintained at a same temperature for 1 hour. The reaction mixture is cooled to 5° C. and filtered. The product is washed with water and dried to give 2,4-dichloro-3-ethyl-6-nitrophenol. Yield, 123.5 g (82% yield based on 4-chloro-3 -ethylphenol),
78%	With hydrogenchloride; chlorosulfonic acid; dihydrogen peroxide; nitric acid	10 EXAMPLE 10 EXAMPLE 10 In a 1-liter four-necked glass flask is prepared a solution mixture of 100 g of 4-chloro-3-ethylphenol and 350 g of dichloroethane. While the mixture is maintained at a temperature of 35°-45° C., 80 g of chlorosulfonic acid is added dropwise and the mixture is maintained at a temperature of 40°-45° C. for 1 hour. Next, 326 g of a 14.3% hydrochloric acid solution is added, and 68 g of a 35% aqueous hydrogen peroxide solution is added dropwise while maintaining the temperature at 40°-45° C. After the mixture is maintained at the same temperature for 8 hours, it is cooled to 20° C. After the oily layer is separated, the aqueous layer obtained is charged in a 1-liter four-necked glass flask, and 172 g of a 70% nitric acid solution is added dropwise to the aqueous a temperature of 30°-40° C. The liquid becomes turbid and turns yellowish white. The temperature is raised about 15° C. After the addition, the reaction mixture is maintained at the same temperature for 1 hour. The reaction mixture is cooled to 5° C. and filtered. The product is washed with water and dried to give 2,4-dichloro-3-ethyl-6-nitrophenol. Yield, 117.5 g (78% yield based on 4-chloro-3-ethylphenol),
	With hydrogenchloride; chlorosulfonic acid; dihydrogen peroxide In aqueous nitric acid	7 EXAMPLE 7 Yield, 142 g (94% yield based on 4-chloro-3-ethylphenol), Purity, 99.1% (percentage based on LC area). On the other hand, in a 1-liter four-necked glass flask is prepared a solution mixture of 100 g of 4-chloro-3-ethylphenol and 350 g of dichloroethane. While the mixture is maintained at a temperature of 35°-40° C., 80 g of chlorosulfonic acid is added dropwise and the mixture is maintained at a temperature of 40°-45° C. for 1 hour. Next, 326 g of a 14.3% hydrochloric acid solution is added, and 68 g of a 35% aqueous hydrogen peroxide solution is added dropwise while maintaining the temperature at 40°-45° C. After the mixture is maintained at the same temperature for 8 hours, it is cooled to 20° C. After the oily layer is separated, the aqueous layer is placed in a dropping funnel and added dropwise to 115 g of a 70% aqueous nitric acid solution and a 115 g portion of the filtrate (A) obtained by the aforementioned manner which have been preliminarily charged in a 1-liter four-necked glass flask and maintained at a temperature of 20°-30° C. The liquid becomes turbid and turns yellowish white as soon as the addition is initiated. After the addition is over, the reaction mixture is further maintained at the same temperature for 3 hours. The reaction mixture is cooled to 5° C. and filtered. The filtrate (B) is obtained in an amount of about 650 g. The product is washed with water and dried to give 2,4-dichloro-3-ethyl-6-nitrophenol. Yield, 145 g (96% yield based on 4-chloro-3-ethylphenol),
	With hydrogenchloride; chlorosulfonic acid; dihydrogen peroxide In aqueous nitric acid	7 EXAMPLE 7 EXAMPLE 7 In a 1-liter four-necked glass flask is prepared a solution mixture of 100 g of 4-chloro-3-ethylphenol and 350 g of dichloroethane. While the mixture is maintained at a temperature of 35°-45° C., 80 g of chlorosulfonic acid is added dropwise and the mixture is maintained at a temperature of 40°-45° C. for 1 hour. Next, 326 g of a 14.3% hydrochloric acid solution is added, and 68 g of a 35% aqueous hydrogen peroxide solution is added dropwise while maintaining the temperature at 40°-45° C. After the mixture is maintained at the same temperature for 8 hours, it is cooled to 20° C. After the oily layer is separated, the aqueous layer is placed in a dropping funnel and added dropwise to 230 g of a 35% aqueous nitric acid solution which has been preliminarily charged in a 1-liter four-necked glass flask and maintained at a temperature of 30°-40° C. The liquid becomes turbid and turns yellowish white as soon as the addition is initiated. After the addition is over, the reaction mixture is further maintained at the same temperature for 3 hours. The reaction mixture is cooled to 5° C. and filtered. The filtrate (A) is obtained in an amount of about 650 g. The cake is washed with water and dried to give 2,4-dichloro-3-ethyl-6-nitrophenol.

Reference： [1]Current Patent Assignee: SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Chemical (w/o Dongwoo Fine-Chem) - US5136109, 1992, A
[2]Current Patent Assignee: SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Chemical (w/o Dongwoo Fine-Chem) - US5136109, 1992, A
[3]Current Patent Assignee: SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Chemical (w/o Dongwoo Fine-Chem) - US5136109, 1992, A
[4]Current Patent Assignee: SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Chemical (w/o Dongwoo Fine-Chem) - US5136109, 1992, A
[5]Current Patent Assignee: SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Chemical (w/o Dongwoo Fine-Chem) - US5136109, 1992, A
[6]Current Patent Assignee: SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Chemical (w/o Dongwoo Fine-Chem) - US5136109, 1992, A
[7]Current Patent Assignee: SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Chemical (w/o Dongwoo Fine-Chem) - US5136109, 1992, A
[8]Current Patent Assignee: SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Chemical (w/o Dongwoo Fine-Chem) - US5136109, 1992, A

7
[ 14143-32-9 ]
[ 108-90-7 ]
[ 99817-36-4 ]

Yield	Reaction Conditions	Operation in experiment
89%	With hydrogenchloride; chlorosulfonic acid; aqueous nitric acid; dihydrogen peroxide In water	2 EXAMPLE 2 EXAMPLE 2 In a 500 ml four-necked glass flask is prepared a solution mixture of 100 g of 4-chloro-3-ethylphenol and 200 g of monochlorobenzene. While the mixture is maintained at a temperature of 25°-30° C., 80 g of chlorosulfonic acid is added dropwise. After the mixture is maintained at the same temperature for 3 hours, it is discharged in a 1-liter four-necked glass flask in which 200 g of water has been charged. Next, 133 g of a 35% hydrochloric acid solution is added, and 93 g of a 35% aqueous hydrogen peroxide solution is added dropwise while maintaining the temperature at 30° C. After the mixture is maintained at the same temperature for 3 hours, it is cooled to 20° C. After the oily layer is separated, 319 g of a 70% aqueous nitric acid solution is added dropwise to the aqueous layer while keeping the temperature at 20°-25° C. After the addition is completed, the mixture is heated to 45° C. and maintained at the temperature for 4 hours. The reaction mixture is cooled to 5° C. and filtered. The product is washed with water and dried to give 2,4-dichloro-3-ethyl-6-nitrophenol. Yield, 134.5 g (89% yield based on 4-chloro-3-ethylphenol).
85%	With hydrogenchloride; chlorosulfonic acid; aqueous nitric acid; dihydrogen peroxide In water	4 EXAMPLE 4 EXAMPLE 4 In a 500 ml four-necked glass flask is prepared a solution mixture of 100 g of 4-chloro-3-ethylphenol and 200 g of monochlorobenzene. While the mixture is maintained at a temperature of 25°-30° C., 80 g of chlorosulfonic acid is added dropwise. After the mixture is maintained at the same temperature for 3 hours, it is discharged in a 1-liter four-necked glass flask in which 200 g of water has been charged. After the oily layer is separated, 133 g of a 35% hydrochloric acid solution is added to the aqueous layer and 93 g of a 35% aqueous hydrogen peroxide solution is added dropwise to the aqueous layer while keeping the temperature at 30° C. After the mixture is maintained at the temperature for 3 hours, the reaction mixture is cooled to 20° C. To the mixture is added dropwise 319 g of a 70% aqueous nitric acid solution with maintaining the temperature at 20°-25° C. After the addition is completed, the mixture is heated to 45° C. and maintained at the temperature for 4 hours. The reaction mixture is cooled to 5° C. and filtered. The product is washed with water and dried to give 2,4-dichloro-3-ethyl-6-nitrophenol. Yield, 128.4 g (85% yield based on 4-chloro-3-ethylphenol).

8
[ 14143-32-9 ]
[ 99817-36-4 ]

Yield	Reaction Conditions	Operation in experiment
77%		13 EXAMPLE 13 The product is washed with water and dried to give 2,4-dichloro-3-ethyl-6-nitrophenol. Melting point, 46.3°-47.3° C. Yield, 116 g (77.0% yield based on 4-chloro-3-ethylphenol).

Reference： [1]Current Patent Assignee: SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Chemical (w/o Dongwoo Fine-Chem) - US5136109, 1992, A

9
[ 104207-31-0 ]
[ 99817-36-4 ]

Yield	Reaction Conditions	Operation in experiment
83.4%	With aqueous nitric acid	16 EXAMPLE 16 EXAMPLE 16 In the same manner as in Example 13 except that an aqueous solution of 3,5-dichloro-4-ethyl-2-hydroxybenzenesulfonic acid is added dropwise to a 50% aqueous nitric acid solution which have been preliminarily charged, the aimed product of 2,4-dichloro-3-ethyl-6-nitrophenol is obtained. Yield, 125.7 g (83.4% yield based on 4-chloro-3-ethylphenol).

Reference： [1]Current Patent Assignee: SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Chemical (w/o Dongwoo Fine-Chem) - US5136109, 1992, A

10
[ 103145-09-1 ]
[ 7732-18-5 ]
[ 99817-36-4 ]

Yield	Reaction Conditions	Operation in experiment
96%	With sodium hydroxide In methanol	5 EXAMPLE 5 EXAMPLE 5 A mixture of 900 ml of methanol, 100 ml of H2 O and 80 g of NaOH was initially introduced into a round-bottomed flask, then heated to reflux temperature and, with stirring, 103.5 g of 1,3,4-trichloro-2-ethyl-5-nitrobenzene, distilled material from the crude product from Example 1, was very rapidly run in as a melt (38° C.). After refluxing for 4 hours, the solution was dark red in color, and starting material was no longer detectable. The reaction mixture was cooled to room temperature, 2,000 ml of H2 O were added, and the mixture was acidified to pH 1 with 50% strength sulphuric acid and then extracted with 3*200 ml of chloroform. After evaporation of the solvent followed by steam distillation, 59.4 g of 2,4-dichloro-3-ethyl-6-nitrophenol were obtained, =63% of theory as 96% pure material.

Reference： [1]Current Patent Assignee: BAYER AG - US4670608, 1987, A

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Isomers

Technical Information

• Acid-Catalyzed α -Halogenation of Ketones • Acidity of Phenols • Addition of a Hydrogen Halide to an Internal Alkyne • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • Alcohols React with PX3 • Alkyl Halide Occurrence • Alkylation of an Alkynyl Anion • An Alkane are Prepared from an Haloalkane • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Chan-Lam Coupling Reaction • Chloroalkane Synthesis with SOCI2 • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Conjugate Additions of p-Benzoquinones • Conversion of Amino with Nitro • Convert Haloalkanes into Alcohols by SN2 • Decomposition of Arenediazonium Salts to Give Phenols • Deprotonation of Methylbenzene • Diazo Coupling • Directing Electron-Donating Effects of Alkyl • Electrophilic Chloromethylation of Polystyrene • Electrophilic Substitution of the Phenol Aromatic Ring • Etherification Reaction of Phenolic Hydroxyl Group • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation of Benzene with Haloalkanes • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Alkenes • Halogenation of Benzene • Halogenation of Phenols • Hiyama Cross-Coupling Reaction • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Kinetics of Alkyl Halides • Kolbe-Schmitt Reaction • Kumada Cross-Coupling Reaction • Methylation of Ammonia • Nitration of Benzene • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Oxidation of Phenols • Pechmann Coumarin Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Dihalides • Reductive Removal of a Diazonium Group • Reimer-Tiemann Reaction • Reverse Sulfonation——Hydrolysis • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Sulfonation of Benzene • Suzuki Coupling • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Nitro Group Conver to the Amino Function • Vilsmeier-Haack Reaction

Historical Records

Related Functional Groups of
[ 99817-36-4 ]

Aryls

[ 39549-27-4 ]

2,4-Dichloro-3-methyl-6-nitrophenol

Similarity: 0.93

[ 7147-89-9 ]

4-Chloro-5-methyl-2-nitrophenol

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[ 100278-74-8 ]

5-Chloro-4-methyl-2-nitrophenol

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[ 101080-03-9 ]

1-Chloro-4-methoxy-2-methyl-5-nitrobenzene

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[ 609-89-2 ]

2,4-Dichloro-6-nitrophenol

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Chlorides

[ 39549-27-4 ]

2,4-Dichloro-3-methyl-6-nitrophenol

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[ 7147-89-9 ]

4-Chloro-5-methyl-2-nitrophenol

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[ 100278-74-8 ]

5-Chloro-4-methyl-2-nitrophenol

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[ 101080-03-9 ]

1-Chloro-4-methoxy-2-methyl-5-nitrobenzene

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[ 609-89-2 ]

2,4-Dichloro-6-nitrophenol

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Nitroes

[ 39549-27-4 ]

2,4-Dichloro-3-methyl-6-nitrophenol

Similarity: 0.93

[ 7147-89-9 ]

4-Chloro-5-methyl-2-nitrophenol

Similarity: 0.90

[ 100278-74-8 ]

5-Chloro-4-methyl-2-nitrophenol

Similarity: 0.84

[ 101080-03-9 ]

1-Chloro-4-methoxy-2-methyl-5-nitrobenzene

Similarity: 0.83

[ 609-89-2 ]

2,4-Dichloro-6-nitrophenol

Similarity: 0.80

Ghs Precautionary Statements

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

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 99817-36-4 ] {[proInfo.proName]}

Quality Control of [ 99817-36-4 ]

Related Doc. of [ 99817-36-4 ]

Product Details of [ 99817-36-4 ]

Calculated chemistry of [ 99817-36-4 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 99817-36-4 ]

Application In Synthesis of [ 99817-36-4 ]

[ 99817-36-4 ] Synthesis Path-Downstream 1~10

Technical Information

Related Functional Groups of [ 99817-36-4 ]

Aryls

Chlorides

Nitroes

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 99817-36-4 ]