5-Nitroisoquinoline Chemical Properties

Melting point:

106-109 °C (lit.)

Boiling point:

305.12°C (rough estimate)

Density 

1.3146 (rough estimate)

refractive index 

1.5651 (estimate)

storage temp. 

Sealed in dry,Room Temperature

pka

3.55±0.13(Predicted)

form 

powder to crystal

color 

Light yellow to Amber to Dark green

BRN 

134858

CAS DataBase Reference

607-32-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-38-20/21/22-40

Safety Statements 

26-37/39-36/37/39-36-22

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29334900

MSDS

• Language:English Provider:5-Nitroisoquinoline
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

5-Nitroisoquinoline Usage And Synthesis

Chemical Properties

light yellow crystal powder

Uses

5-Nitroisoquinoline (cas# 607-32-9) is a compound useful in organic synthesis.

Uses

5-Nitroisoquinoline was used to prepare a number of pyrroloisoquinolines.

General Description

5-Nitroisoquinoline reacted with vinylmagnesium bromide to form a number of pyrroloisoquinolines. 5-Nitroisoquinoline derivatives (potential antimalarial drugs) were evaluated for mutagenic (MUT) and chromosome-damaging (CHR) activities by the Salmonella test.

Synthesis

General procedure for the synthesis of 5-nitroisoquinoline from isoquinoline: 1. dissolve isoquinoline (3.0 g, 23.2 mmol) in 40 mL of concentrated sulfuric acid at -15 °C and slowly add solid potassium nitrate (2.8 g, 27.8 mmol) in four equal portions, each at 30 min intervals. 2. The reaction mixture was gradually warmed to room temperature and stirring was continued for 3 hours. 3. The reaction mixture was poured into ice water (100 mL) and the pH was adjusted to 8-10 with ammonia. 4. The precipitated yellow solid was collected by filtration, washed with methyl tert-butyl ether (100 mL x 2) and dried to give 5-nitroisoquinoline (4.0 g, 100% yield). 5. 5-Nitroisoquinoline (2.5 g, 14.4 mmol) was dissolved in methanol (50 mL), 10% palladium/carbon catalyst (300 mg) was added, and stirred at room temperature for 3 hours under hydrogen atmosphere. 6. The reaction mixture was filtered and the filtrate was concentrated in vacuum to give 5-aminoisoquinoline (0.85 g, 41% yield) as a brown solid.

References

[1] Bioorganic Chemistry, 2019, vol. 82, p. 100 - 108
[2] Patent: WO2012/146724, 2012, A2. Location in patent: Page/Page column 49
[3] Patent: US2014/57942, 2014, A1. Location in patent: Paragraph 0337-0338
[4] Patent: WO2014/68035, 2014, A1. Location in patent: Page/Page column 35
[5] Journal of Organic Chemistry, 1986, vol. 51, # 11, p. 2011 - 2021

5-Nitroisoquinoline(607-32-9)Related Product Information

• Isoquinoline
• 5-Nitroquinoline
• 3-Methylisoquinoline
• 4-Nitrobenzoic acid
• 1-METHYLISOQUINOLINE
• Nitrobenzene
• TRITON
• 4-Nitrophenol
• Nitromethane
• 8-BROMO-5-NITRO-ISOQUINOLINE
• 3-METHYL-5-NITROISOQUINOLINE
• 3-CHLORO-5-NITROISOQUINOLINE
• 7-(trifluoromethyl)-1,2,3,4-tetrahydro-5-nitroisoquinoline hydrochloride
• 5-BROMO-8-NITROISOQUINOLINE
• 4-NITROISOQUINOLINE
• 6-Methoxy-5-nitroisoquinoline
• 4-METHYL-5-NITROISOQUINOLINE
• METHYL 5-NITRO-3-ISOQUINOLINECARBOXYLATE