22539-55-5|8-Chloro-5-nitroquinoline| Ambeed

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Quality Control of [ 22539-55-5 ] Purity: 98% SDS Specification

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Product Details of [ 22539-55-5 ]

CAS No. :	22539-55-5
Formula :	C₉H₅ClN₂O₂
M.W :	208.60
SMILES Code :	O=[N+](C1=C2C=CC=NC2=C(Cl)C=C1)[O-]
MDL No. :	MFCD00466079
InChI Key :	XSJNIKQCTPVESL-UHFFFAOYSA-N
Pubchem ID :	252444

Safety of [ 22539-55-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 22539-55-5 ]

* 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 [ 22539-55-5 ]

[ 22539-55-5 ] Synthesis Path-Downstream 1~34

1
[ 22539-55-5 ]
[ 108-98-5 ]
[ 855761-38-5 ]

References: [1]Journal of the American Chemical Society,1940,vol. 62,p. 3508,3511.

2
[ 22539-55-5 ]
[ 107-15-3 ]
N-(5-nitro-[8]quinolyl)-ethylenediamine [ No CAS ]

References: [1]Annales de l'Institut Pasteur,1930,vol. 44,p. 719,738.

3
[ 22539-55-5 ]
8-chloro-5-nitro-quinoline-1-oxide [ No CAS ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1948,vol. 68,p. 209.
Chem.Abstr.,1953,p. 8075.

4
[ 22539-55-5 ]
[ 855763-38-1 ]

References: [1]Journal of the American Chemical Society,1940,vol. 62,p. 173.

5
[ 22539-55-5 ]
[ 54717-96-3 ]

References: [1]Journal of the American Chemical Society,1940,vol. 62,p. 3508,3511.

6
[ 22539-55-5 ]
[ 75793-58-7 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1893,vol. <2> 48,p. 140.
[2]Journal of the Chemical Society,1932,p. 2104,2106.

7
[ 611-33-6 ]
[ 22539-55-5 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1893,vol. <2> 48,p. 140.
[2]Journal fur praktische Chemie (Leipzig 1954),1893,vol. <2> 48,p. 140.

8
[ 6283-25-6 ]
[ 56-81-5 ]
[ 22539-55-5 ]

References: [1]Bulletin de la Societe Chimique de France,1930,vol. <4> 47,p. 749.

9
[ 22539-55-5 ]
[ 3337-86-8 ]
[ 102244-04-2 ]

References: [1]Pharmaceutical Chemistry Journal,1986,vol. 20,p. 103 - 106.
Khimiko-Farmatsevticheskii Zhurnal,1986,vol. 20,p. 168 - 171.

10
[ 22539-55-5 ]
[ 6596-82-3 ]
[ 87236-38-2 ]

References: [1]Pharmaceutical Chemistry Journal,1983,vol. 17,p. 476 - 479.
Khimiko-Farmatsevticheskii Zhurnal,1983,vol. 17,p. 798 - 801.

11
[ 22539-55-5 ]
[ 16629-40-6 ]
[ 87236-39-3 ]

References: [1]Pharmaceutical Chemistry Journal,1983,vol. 17,p. 476 - 479.
Khimiko-Farmatsevticheskii Zhurnal,1983,vol. 17,p. 798 - 801.

12
[ 22539-55-5 ]
[ 139366-38-4 ]

References: [1]Polish Journal of Chemistry,1991,vol. 65,p. 1077 - 1084.

13
5-nitro-8-oxy-quinoline [ No CAS ]
[ 22539-55-5 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1892,vol. <2> 45,p. 540.

14
[ 7647-01-0 ]
[ 22539-55-5 ]
tin dichloride [ No CAS ]
[ 75793-58-7 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1893,vol. <2> 48,p. 140.

15
[ 22539-55-5 ]
[ 1826-67-1 ]
[ 260049-35-2 ]

Yield	Reaction Conditions	Operation in experiment
21%	In tetrahydrofuran;	5-Chloro-1H-pyrrolo[2,3-f]quinoline To a stirred solution of <strong>[22539-55-5]8-chloro-5-nitroquinoline</strong> (5.0 g, 24 mmol) in tetrahydrofuran (70 mL) at -78 C. under Ar was added a solution of vinylmagnesium bromide (1.0 M in tetrahydrofuran, 72 mL, 72 mmol) over 5 min. The mixture was stirred for 40 minutes, poured into aqueous ammonium chloride solution (200 mL) and extracted with ether (3*100 mL). The combined organic extracts were washed (water, brine), dried (sodium sulfate), concentrated in vacuo and purified by column chromatography [SiO2; ethyl acetate-heptane (1:1)] to give 5-chloro-1H-pyrrolo[2,3-f]quinoline as an orange solid (1.0 g, 21%): mp 248-250 C.; IR νmax (Nujol)/cm-1 3198, 2924, 2854, 1500, 1465, 1377, 1364, 1290, 1162, 1126, 1085, 949, 887, 810, 780, 744, 706, 633, 599 and 512; NMR δH (400 Mz, CDCl3) 6.64 (1H, d, J 3 Hz) 7.56 (1H, t, J 4 Hz) 7.65 (1H, dd, J2.5, 8.5 Hz) 8.14 (1H, s) 8.83 (1H, d, J 8.5 Hz) 8.88 (1H, d, J 2.5 Hz) 12.37 (1H, m).

References: [1]Patent: US6365598,2002,B1 .
[2]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 677 - 680.

16
[ 22539-55-5 ]
[ 260049-36-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 677 - 680.

17
[ 22539-55-5 ]
[ 260049-37-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 677 - 680.

18
[ 22539-55-5 ]
2-(5-chloro-pyrrolo[2,3-f]quinolin-1-yl)-1-methyl-ethylamine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 677 - 680.

19
[ 22539-55-5 ]
[ 876135-29-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 677 - 680.

20
[ 22539-55-5 ]
N-(8-chloro-[5]quinolyl)-acetamide [ No CAS ]

References: [1]Journal of the Chemical Society,1932,p. 2104,2106.

21
[ 22539-55-5 ]
8-phenylsulfanyl-[5]quinolylamine [ No CAS ]

References: [1]Journal of the American Chemical Society,1940,vol. 62,p. 3508,3511.

22
[ 22539-55-5 ]
8-benzenesulfonyl-[5]quinolylamine [ No CAS ]

References: [1]Journal of the American Chemical Society,1940,vol. 62,p. 3508,3511.

23
[ 22539-55-5 ]
8-benzenesulfinyl-5-nitro-quinoline [ No CAS ]

References: [1]Journal of the American Chemical Society,1940,vol. 62,p. 3508,3511.

24
[ 22539-55-5 ]
[ 855761-34-1 ]

References: [1]Journal of the American Chemical Society,1940,vol. 62,p. 3508,3511.

25
[ 22539-55-5 ]
[ 703-32-2 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1893,vol. <2> 48,p. 140.

26
[ 22539-55-5 ]
bis-(5-nitro-[8]quinolyl)-sulfone [ No CAS ]

References: [1]Journal of the American Chemical Society,1940,vol. 62,p. 173.

27
[ 95-51-2 ]
[ 22539-55-5 ]

References: [1]Bulletin de la Societe Chimique de France,1930,vol. <4> 47,p. 749.

28
[ 4008-48-4 ]
[ 33513-42-7 ]
[ 22539-55-5 ]
N,N-dimethyl-5-nitroquinolin-8-amine [ No CAS ]

References: [1]ChemMedChem,2011,vol. 6,p. 1872 - 1883.

29
[ 22539-55-5 ]
[ 6258-60-2 ]
[ 1602769-85-6 ]

References: [1]ChemMedChem,2014,vol. 9,p. 129 - 150.

30
[ 6283-25-6 ]
[ 107-02-8 ]
[ 22539-55-5 ]

References: [1]ChemMedChem,2014,vol. 9,p. 129 - 150.

31
[ 22539-55-5 ]
[ 1226501-67-2 ]
1-morpholino-3-(5-nitroquinolin-8-ylthio)propan-1-one [ No CAS ]

References: [1]ChemMedChem,2014,vol. 9,p. 129 - 150.

32
[ 22539-55-5 ]
[ 163210-63-7 ]
[ 1602769-90-3 ]

References: [1]ChemMedChem,2014,vol. 9,p. 129 - 150.

33
[ 22539-55-5 ]
[ 89929-31-7 ]
[ 1602769-91-4 ]

References: [1]ChemMedChem,2014,vol. 9,p. 129 - 150.

34
[ 22539-55-5 ]
[ 1568-80-5 ]
C₃₉H₃₂N₄O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
6.0003 g		In a 250 mL three-necked flask equipped with a mechanical stirring device,Add 10 mmol of methyl diphenol compound,24mmol of potassium carbonate,The system was reacted for half an hour using an ultrasonic method at a frequency of 20 KHz.Obtaining a phenolic ionic liquid,Add 24mmol 2-chloro-5-nitroquinoline,The total solid content of the reaction system is 20%, and the system is stirred and heated to 100 C.The TLC detects that the disappearance of the raw material point is the end of the reaction.After the system is cooled, the material is discharged and deionized water, filtered, dried,The crude product is obtained, and the obtained crude product is dissolved in N,N-dimethylformamide.Heat the system to reflux temperature and add deionized water.Until the system just precipitates and does not dissolve, turn off the heating, cool down and filter,6.0003 g of a dinitro compound was obtained.

References: [1]Patent: CN109535069,2019,A .Location in patent: Paragraph 0114; 0115.

Historical Records

Technical Information

• Alkyl Halide Occurrence • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

Related Functional Groups of
[ 22539-55-5 ]

Chlorides

A619682 [75586-66-2]

4,9-Dichloro-1-nitroacridine

Similarity: 0.95

A602085 [121465-04-1]

8-Chloro-6-nitroquinoline

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A584648 [101860-71-3]

3-Chloro-6-nitroquinoline

Similarity: 0.94

A278776 [196205-09-1]

7-Chloro-5-nitro-1H-indole

Similarity: 0.91

A629174 [1076199-85-3]

7-Chloro-4-nitroquinoline

Similarity: 0.91

Nitroes

A619682 [75586-66-2]

4,9-Dichloro-1-nitroacridine

Similarity: 0.95

A602085 [121465-04-1]

8-Chloro-6-nitroquinoline

Similarity: 0.94

A584648 [101860-71-3]

3-Chloro-6-nitroquinoline

Similarity: 0.94

A278776 [196205-09-1]

7-Chloro-5-nitro-1H-indole

Similarity: 0.91

A629174 [1076199-85-3]

7-Chloro-4-nitroquinoline

Similarity: 0.91

Related Parent Nucleus of
[ 22539-55-5 ]

Quinolines

A602085 [121465-04-1]

8-Chloro-6-nitroquinoline

Similarity: 0.94

A584648 [101860-71-3]

3-Chloro-6-nitroquinoline

Similarity: 0.94

A629174 [1076199-85-3]

7-Chloro-4-nitroquinoline

Similarity: 0.91

A106628 [40106-98-7]

4-Chloro-5-nitroquinoline

Similarity: 0.87

Precautionary Statements-General
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Response
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P321
P322
P330	Rinse mouth.
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P342	If experiencing respiratory symptoms:
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P378
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P391	Collect spillage. Hazardous to the aquatic environment
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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.
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P370 + P378	In case of fire:
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Storage
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P401
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H260	In contact with water releases flammable gases which may ignite spontaneously
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Code	Phrase
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H310	Fatal in contact with skin
H311	Toxic in contact with skin
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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

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CAS No.: 22539-55-5

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