[ CAS No. 3383-72-0 ] {[proInfo.proName]}

Name: 3383-72-0|1-(2-Chloroethoxy)-4-nitrobenzene|98%
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SKU: A323910
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Quality Control of [ 3383-72-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 3383-72-0 ]

SDS Specification

Alternatived Products of [ 3383-72-0 ]

Product Details of [ 3383-72-0 ]

CAS No. :	3383-72-0	MDL No. :	MFCD00674505
Formula :	C₈H₈ClNO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OBCFOPGCTNULTG-UHFFFAOYSA-N
M.W :	201.61	Pubchem ID :	2764587
Synonyms :

Calculated chemistry of [ 3383-72-0 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	51.36
TPSA :	55.05 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.58 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.68
Log Po/w (XLOGP3) :	2.75
Log Po/w (WLOGP) :	2.21
Log Po/w (MLOGP) :	2.07
Log Po/w (SILICOS-IT) :	0.51
Consensus Log Po/w :	1.85

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.9
Solubility :	0.254 mg/ml ; 0.00126 mol/l
Class :	Soluble
Log S (Ali) :	-3.56
Solubility :	0.0554 mg/ml ; 0.000275 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.95
Solubility :	0.227 mg/ml ; 0.00112 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	3.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.9

Safety of [ 3383-72-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 3383-72-0 ]

* 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.

Upstream synthesis route of [ 3383-72-0 ]
Downstream synthetic route of [ 3383-72-0 ]

[ 3383-72-0 ] Synthesis Path-Upstream 1~15

1
[ 3383-72-0 ]
[ 50609-01-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 12, p. 2668 - 2673

2
[ 288-32-4 ]
[ 3383-72-0 ]
[ 2301-25-9 ]
[ 75912-69-5 ]

Reference： [1] Journal of Medicinal Chemistry, 1985, vol. 28, # 10, p. 1427 - 1432

3
[ 100-02-7 ]
[ 107-04-0 ]
[ 3383-72-0 ]

Yield	Reaction Conditions	Operation in experiment
66%	With caesium carbonate In ethanol at 80℃; for 8 h;	l-(2-Chloro-ethoxy)-4-nitro-benzene can be synthesized by the following procedure. To a solution of 4-nitro-ρhenol (28.7 mmol) in absolute ethanol (15 mL) is added cesium carbonate (28.7 mmol) followed by l-bromo-2-chloro-ethane (86.2 mmol). The reaction mixture is heated at 80 ⁰C for 8 h. The reaction mixture is cooled down and quenched with water and extracted with EtOAc. The organic layer is washed with water, brine, dried over Na₂SO_4, and concentrated to afford an orange residue that upon trituration with EtOH gives l-(2-chloro-ethoxy)-4-nitro-benzene (66percent). MS (m/z) (M+l)⁺ 202.2.

Reference： [1] Patent: WO2007/38669, 2007, A2, . Location in patent: Page/Page column 170
[2] Journal of Medicinal Chemistry, 2006, vol. 49, # 16, p. 4981 - 4991
[3] Patent: WO2005/68452, 2005, A1, . Location in patent: Page/Page column 41
[4] Journal of Medicinal Chemistry, 2008, vol. 51, # 6, p. 1637 - 1648
[5] Patent: WO2004/5282, 2004, A1, . Location in patent: Page 39

4
[ 16365-27-8 ]
[ 3383-72-0 ]

Reference： [1] Journal of the Indian Chemical Society, 1936, vol. 13, p. 334
[2] Yakugaku Zasshi, 1954, vol. 74, p. 238,240[3] Chem.Abstr., 1955, p. 3163
[4] Patent: US2005/14939, 2005, A1, . Location in patent: Page 23
[5] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 12, p. 2668 - 2673

5
[ 100-02-7 ]
[ 3383-72-0 ]

Reference： [1] Patent: US2002/28832, 2002, A1,
[2] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 12, p. 2668 - 2673
[3] Patent: US2002/55524, 2002, A1,
[4] Patent: US2002/128236, 2002, A1,

6
[ 100-02-7 ]
[ 16670-48-7 ]
[ 3383-72-0 ]

Reference： [1] Patent: US4891372, 1990, A,
[2] Patent: EP307121, 1989, A1,

7
[ 100-00-5 ]
[ 3383-72-0 ]

Reference： [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 26, p. 4895 - 4899

8
[ 16365-27-8 ]
[ 144-55-8 ]
[ 3383-72-0 ]

Reference： [1] Patent: US5804686, 1998, A,
[2] Patent: US6211365, 2001, B1,
[3] Patent: US2002/55524, 2002, A1,
[4] Patent: US2002/128236, 2002, A1,

9
[ 100-02-7 ]
[ 107-06-2 ]
[ 3383-72-0 ]

Reference： [1] European Journal of Medicinal Chemistry, 2005, vol. 40, # 5, p. 481 - 493
[2] Patent: WO2004/35534, 2004, A2, . Location in patent: Page/Page column 10

10
[ 75-21-8 ]
[ 100-02-7 ]
[ 16365-27-8 ]
[ 3383-72-0 ]

Reference： [1] Patent: US5138054, 1992, A,

11
[ 100-02-7 ]
[ 107-07-3 ]
[ 3383-72-0 ]

Reference： [1] Tetrahedron Letters, 2016, vol. 57, # 8, p. 905 - 909

12
[ 107-06-2 ]
[ 824-78-2 ]
[ 3383-72-0 ]

Reference： [1] Journal of medicinal chemistry, 1963, vol. 6, p. 343 - 346

13
[ 28341-54-0 ]
[ 3383-72-0 ]

Reference： [1] Journal of the Indian Chemical Society, 1936, vol. 13, p. 334

14
[ 3383-72-0 ]
[ 85176-37-0 ]
[ 115287-37-1 ]

Reference： [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 4, p. 1151 - 1155
[2] Patent: US4959366, 1990, A,

15
[ 3383-72-0 ]
[ 115256-11-6 ]

Reference： [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 4, p. 1151 - 1155

[ 3383-72-0 ] Synthesis Path-Downstream 1~9

1
[ 288-32-4 ]
[ 3383-72-0 ]
[ 2301-25-9 ]
[ 75912-69-5 ]

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1427 - 1432

2
[ 3383-72-0 ]
[ 85176-37-0 ]
[ 115287-37-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium iodide; potassium carbonate; In acetonitrile;	(A) 1-(4-Nitrophenoxy)-2-[N-methyl-N-(4-nitrophenethyl)amino]ethane STR25 To a solution of N-methyl-4-nitrophenethylamine (1.5 g) (J.O.C., [1956], 21, 45) and 2-[4-nitrophenoxy]ethyl chloride (1.55 g) (C.A., [1955], 49, 3163e) in acetonitrile (50 ml) was added potassium carbonate (1.25 g) and sodium iodide (1.2 g) and the suspension was stirred at reflux for 72 hours. After evaporation to dryness, the residual oily solid was partitioned between a 2N aqueous sodium bicarbonate solution and ethyl acetate. After two further extractions with ethyl acetate, the organic portions were combined, washed with a saturated aqueous brine solution, dried over magnesium sulphate, filtered and evaporated. The resultant orange solid (2.7 g) was crystallized from ethanol to give the title compound, (1.9 g), m.p. 74. Analysis %: Found: C,58.75; H,5.4; N,12.15; Calculated for C17 H19 N3 O4: C,59.1; H,5.5; N,12.2.

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 1151 - 1155
[2]Patent: US4959366,1990,A

3
[ 3383-72-0 ]
[ 72141-41-4 ]
[ 329003-83-0 ]

Yield	Reaction Conditions	Operation in experiment
94%	With potassium carbonate; sodium iodide In acetonitrile Heating;

Reference： [1]Kanojia, Ramesh M.; Salata, Joseph J.; Kauffman, Jack [Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 24, p. 2819 - 2823]

4
[ 3383-72-0 ]
[ 87691-88-1 ]
[ 690978-22-4 ]

Yield	Reaction Conditions	Operation in experiment
89 - 92%	With potassium carbonate; potassium iodide; In acetonitrile; at 150℃; for 1.5h;Microwave irradiation;	Excess dried, -325 mesh potassium carbonate (257 mg, 1.86 MMOL) was diluted in 4 mL acetonitrile and 3-piperazin-1-yl-benzoisothiazole hydrochloride (395 mg, 1.55 MMOL), catalytic potassium iodide, and 1 (2- chloroethoxy)-4-nitrobenzene (250 mg, 1.20 MMOL) were added. This mixture was sealed in a Smith microwave vial and heated on the Smith Workstation at 150 C for 1.5 h. After cooling, the salts were filtered off and washed with ACETONITRILE and the filtrate was concentrated. The residue was taken up in methylene chloride and washed with water. The organic layer was dried over sodium sulfate, and concentrated to afford 530 mg of a yellow solid. Yield 89%; 92% HPLC purity at 214 nm; mp 115 C ; MS (APCI) : 385 [M+H] +.

Reference： [1]Patent: WO2004/41793,2004,A1 .Location in patent: Page 49

5
[ 3383-72-0 ]
[ 50609-01-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 2668 - 2673

6
[ 3383-72-0 ]
[ 38948-27-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: palladium on activated charcoal; hydrogen / methanol / 20 °C

Reference： [1]Luo, Guoshun; Chen, Mingqi; Lyu, Weiting; Zhao, Ruheng; Xu, Qian; You, Qidong; Xiang, Hua [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 12, p. 2668 - 2673]

7
[ 3383-72-0 ]
[ 52481-41-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 2668 - 2673
[2]Bioorganic and Medicinal Chemistry,2020,vol. 28

8
[ 123-75-1 ]
[ 3383-72-0 ]
[ 265654-77-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 100℃; for 4.0h;Inert atmosphere;	General procedure: Various secondary amines a-f (7.44 mmol) was added to a solution of1-(2-chloroethoxy)-4-nitrobenzene 9 (0.5 g, 2.48 mmol), anhydrous K2CO3 (1.71 g, 12.4 mol) andcatalytic amount of KI in DMF (10 mL), and the mixture was refluxed for 4 h at 100C under anargon atmosphere. After the reaction was completed, the mixture was slowly added to ice waterand extracted with EtOAc. The combined organic phases were washed sequentially with saturatedNaCl, and then dried over anhydrous Na2SO4, and evaporated to dryness under reduced pressureto give corresponding compounds 10a-f as yellow oil, which were used without furtherpurification.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 2668 - 2673

9
[ 110-91-8 ]
[ 3383-72-0 ]
[ 65300-53-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 100℃; for 4h;Inert atmosphere;	General procedure: Various secondary amines a-f (7.44 mmol) was added to a solution of1-(2-chloroethoxy)-4-nitrobenzene 9 (0.5 g, 2.48 mmol), anhydrous K2CO3 (1.71 g, 12.4 mol) andcatalytic amount of KI in DMF (10 mL), and the mixture was refluxed for 4 h at 100C under anargon atmosphere. After the reaction was completed, the mixture was slowly added to ice waterand extracted with EtOAc. The combined organic phases were washed sequentially with saturatedNaCl, and then dried over anhydrous Na2SO4, and evaporated to dryness under reduced pressureto give corresponding compounds 10a-f as yellow oil, which were used without furtherpurification.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 2668 - 2673
[2]Organic and Biomolecular Chemistry,2018,vol. 16,p. 4895 - 4899
[3]Bioorganic and Medicinal Chemistry,2020,vol. 28

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Physical hazards
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
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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. 3383-72-0 ] {[proInfo.proName]}

Quality Control of [ 3383-72-0 ]

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[ 3383-72-0 ] Synthesis Path-Upstream 1~15

[ 3383-72-0 ] Synthesis Path-Downstream 1~9

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Aryls

Chlorides

Ethers

Nitroes

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[ 3383-72-0 ]