1975-44-6

Basic information

• Product Name: 5-NITRO-NAPHTHALENE-1-CARBOXYLIC ACID
• Synonyms: 5-NITRO-NAPHTHALENE-1-CARBOXYLIC ACID;1-naphthalenecarboxylic acid, 5-nitro-;5-Nitro-1-naphthoic acid;5-NITRO-PHTHALENE-1-CARBOXYLIC ACID
• CAS NO: 1975-44-6
• Molecular Formula: C₁₁H₇NO₄
• Molecular Weight: 217.18
• Product Categories: Naphthalene series
• Mol File: 1975-44-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 241.5°C
• Boiling Point: 357.72°C (rough estimate)
• Flash Point: 199.2 °C
• Appearance: /
• Density: 1.3654 (rough estimate)
• Vapor Pressure: 7.4E-09mmHg at 25°C
• Refractive Index: 1.4900 (estimate)
• Storage Temp.: 2-8°C
• PKA: 2.61±0.10(Predicted)
• CAS DataBase Reference: 5-NITRO-NAPHTHALENE-1-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-NITRO-NAPHTHALENE-1-CARBOXYLIC ACID(1975-44-6)
• EPA Substance Registry System: 5-NITRO-NAPHTHALENE-1-CARBOXYLIC ACID(1975-44-6)

Safety Data

• Hazardous Substances Data: 1975-44-6(Hazardous Substances Data)

Usage

General Description

5-Nitro-naphthalene-1-carboxylic acid, also known as 5-NNCA, is a chemical compound with the molecular formula C12H7NO4. It is a derivative of naphthalene and contains a nitro group and a carboxylic acid group. 5-NNCA is known for its use in the synthesis of various pharmaceuticals and organic compounds. It is also used as a dye intermediate and as a chemical reagent in organic chemistry research. The compound has potential applications in the pharmaceutical industry due to its ability to act as an anti-inflammatory and analgesic agent. Additionally, 5-NNCA is also used in the synthesis of various chemical dyes and pigments.

InChI:InChI=1/C11H7NO4/c13-11(14)9-5-1-4-8-7(9)3-2-6-10(8)12(15)16/h1-6H,(H,13,14)

Synthetic route

1-naphthalenecarboxylic acid (86-55-5) → 5-nitro-1-naphthoic acid (1975-44-6) + 8-nitro-1-naphthalenecarboxylic acid (2216-13-9)

Conditions	Yield
With nitric acid for 4h;	A 37% B 44%
With nitric acid Trennung durch Behandeln mit Soda anschliessend mit Salzsaeure und Umkrystallisieren aus Alkohol;
With nitric acid

1-naphthalenecarboxylic acid (86-55-5) → 5-nitro-1-naphthoic acid (1975-44-6)

Conditions	Yield
With nitric acid; acetic acid Isolierung aus dem Reaktionsprodukts ueber den Methylester;
With nitric acid; acetic acid Isolierung aus dem Reaktionsprodukts ueber den Aethylester;
With X-NO2

8-chloro-5-nitro-[1]naphthoic acid (27683-83-6) → 5-nitro-1-naphthoic acid (1975-44-6)

Conditions	Yield
With copper; toluene

5-nitro-1-hydroxymethylnaphthalene (99972-57-3) → 5-nitro-1-naphthoic acid (1975-44-6)

Conditions	Yield
With chromium(VI) oxide; acetic acid

8-bromo-5-nitro-naphthalene-1-carboxylic acid (25029-79-2) + decalin (91-17-8) + copper-powder → 5-nitro-1-naphthoic acid (1975-44-6)

methyl 1-naphthoate (2459-24-7) + sulfuric acid (7664-93-9) + nitric acid (7697-37-2) → 5-nitro-1-naphthoic acid (1975-44-6) + 8-nitro-1-naphthalenecarboxylic acid (2216-13-9) + 4,5-dinitro-[1]naphthoic acid (99972-07-3) + 4.5-dinitro-naphthoic acid-(1)-methyl ester

hydrogenchloride (7647-01-0) + 5-Nitro-1-naphthalenecarbonitrile (23245-64-9) → 5-nitro-1-naphthoic acid (1975-44-6)

Conditions	Yield
at 150 - 160℃; im geschlossenen Rohr;

5-nitro-naphthoic acid-(1)-nitrile → 5-nitro-1-naphthoic acid (1975-44-6)

Conditions	Yield
With hydrogenchloride at 150 - 160℃; im geschlossenen Rohr;

8-bromo-5-nitro-naphthoic acid-(1) → 5-nitro-1-naphthoic acid (1975-44-6)

Conditions	Yield
With copper; decalin

amide of/the/ α-naphthoic acid → 5-nitro-1-naphthoic acid (1975-44-6) + 8-nitro-[1]naphthoic acid amide (38514-76-0)

Conditions	Yield
With nitric acid

1-naphthalenecarboxylic acid (86-55-5) + nitric acid (7697-37-2) → 1-Nitronaphthalene (86-57-7) + 5-nitro-1-naphthoic acid (1975-44-6) + 8-nitro-1-naphthalenecarboxylic acid (2216-13-9)

1-naphthalenecarboxylic acid (86-55-5) + nitric acid (7697-37-2) + acetic acid (64-19-7) → 1-Nitronaphthalene (86-57-7) + 5-nitro-1-naphthoic acid (1975-44-6) + 8-nitro-1-naphthalenecarboxylic acid (2216-13-9)

1-naphthalenecarboxylic acid (86-55-5) + acetic acid (64-19-7) + red fuming nitric acid → 5-nitro-1-naphthoic acid (1975-44-6) + 8-nitro-1-naphthalenecarboxylic acid (2216-13-9) + 6.8(?)-dinitro-naphthoic acid-(1)

1-naphthylcarboxamide (2243-81-4) → 5-nitro-1-naphthoic acid (1975-44-6) + amide of/the/ 8-nitro-naphthoic acid-(1)

Conditions	Yield
With nitric acid

1-naphthylcarboxamide (2243-81-4) + nitric acid (7697-37-2) → 5-nitro-1-naphthoic acid (1975-44-6) + amide of/the/ 8-nitro-naphthoic acid-(1)

5-nitro-1-naphthaldehyde (6639-35-6) + acetone (67-64-1) + aqueous KMnO4-solution → 5-nitro-1-naphthoic acid (1975-44-6)

8-chloro-5-nitro-[1]naphthoic acid (27683-83-6) + toluene (108-88-3) + copper-powder → 5-nitro-1-naphthoic acid (1975-44-6)

hydrogenchloride (7647-01-0) + 8-carboxy-4-nitro-[1]naphthylmercury (1+)-betaine → 5-nitro-1-naphthoic acid (1975-44-6)

4-nitronaphthalic-1,8-anhydride (6642-29-1) → 4-nitro-1-naphthoic acid (1975-43-5) + 5-nitro-1-naphthoic acid (1975-44-6)

Conditions	Yield
Stage #1: 4-nitronaphthalic-1,8-anhydride With sodium hydroxide In water at 100℃; for 0.0166667h; microwave irradiation; Stage #2: With mercury(II) diacetate In water at 200℃; for 0.5h; Pesci reaction; microwave irradiation; Stage #3: With hydrogenchloride In water at 120℃; for 0.25h; microwave irradiation; Title compound not separated from byproducts;

5-nitro-1-chloromethylnaphthalene (6625-54-3) → 5-nitro-1-naphthoic acid (1975-44-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous Na2CO3 2: CrO3; acetic acid View Scheme

(1RS,2SR)-2-amino-1-(4-fluorophenyl)-3-[4-(trifluoromethyl)phenyl]propan-1-ol + 5-nitro-1-naphthoic acid (1975-44-6) → N-[(1RS,2SR)-2-(4-fluorophenyl)-2-hydroxy-1-[4-(trifluoromethyl)benzyl]ethyl]-5-nitronaphthalene-1-carboxamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃;	95%

ethanol (64-17-5) + 5-nitro-1-naphthoic acid (1975-44-6) → ethyl 5-nitro-1-naphthoate (91901-43-8)

Conditions	Yield
With sulfuric acid for 24h; Heating / reflux;	92%
With sulfuric acid Heating;	88%

Met-OMe (10332-17-9) + 5-nitro-1-naphthoic acid (1975-44-6) → (S)-4-Methylsulfanyl-2-[(5-nitro-naphthalene-1-carbonyl)-amino]-butyric acid methyl ester (174638-32-5)

Conditions	Yield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide for 20h;	72%

methanol (67-56-1) + 5-nitro-1-naphthoic acid (1975-44-6) → methyl 5-nitronaphthalene-1-carboxylate (59866-98-7)

Conditions	Yield
With sulfuric acid
With hydrogenchloride

1-naphthalenecarboxylic acid (86-55-5) + 5-nitro-1-naphthoic acid (1975-44-6) → 5-nitro-[1]naphthoic acid ; compound with naphthoic acid-(1)

Conditions	Yield
With ethanol

5-nitro-1-naphthoic acid (1975-44-6) → 5-amino-1-naphthoic acid (32018-88-5)

Conditions	Yield
With ammonia; iron(II) sulfate
With ammonium hydroxide; iron(II) sulfate
(electrochemical reduction);

5-nitro-1-naphthoic acid (1975-44-6) → 5-nitro-[1]naphthoic acid amide

Conditions	Yield
With thionyl chloride Einw. von Ammoniak;

5-nitro-1-naphthoic acid (1975-44-6) → 5-nitro-1-naphthoic acid chloride (5333-16-4)

Conditions	Yield
With thionyl chloride
With phosphorus pentachloride In ethyl acetate Ambient temperature;
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h;

5-nitro-1-naphthoic acid (1975-44-6) → 4,5-dinitro-[1]naphthoic acid (99972-07-3)

Conditions	Yield
With nitric acid Reaktion ueber mehrere Stufen;

5-nitro-1-naphthoic acid (1975-44-6) → 5,8-dinitro-[1]naphthoic acid

Conditions	Yield
With nitric acid Reaktion ueber mehrere Stufen;

5-nitro-1-naphthoic acid (1975-44-6) → 1-Hydroxylamino-5-carboxynaphthalin

Conditions	Yield
(electrochemical reduction);

5-nitro-1-naphthoic acid (1975-44-6) → 5-nitro-1-hydroxymethylnaphthalene (99972-57-3)

Conditions	Yield
With borane-THF In tetrahydrofuran	0.9 g

5-nitro-1-naphthoic acid (1975-44-6) + 5-diethylamino-2-pentylamine (140-80-7) → 5-Nitro-naphthalene-1-carboxylic acid (4-diethylamino-1-methyl-butyl)-amide (345584-86-3)

5-nitro-1-naphthoic acid (1975-44-6) + nitric acid (7697-37-2) → 3-nitrophthalic acid (603-11-2)

5-nitro-1-naphthoic acid (1975-44-6) + KMnO4 + alkali → 3-nitrophthalic acid (603-11-2)

5-nitro-1-naphthoic acid (1975-44-6) + nitric acid (7697-37-2) → 1,5-dinitronaphthalene (605-71-0)

5-nitro-1-naphthoic acid (1975-44-6) + nitric acid (7697-37-2) → 4,5-dinitro-[1]naphthoic acid (99972-07-3) + 5,8-dinitro-[1]naphthoic acid + 1,5-dinitronaphthalene (605-71-0) + 5.x-dinitro-naphthoic acid-(1)

Upstream product

• 27683-83-6 8-chloro-5-nitro-[1]naphthoic acid 
• 25029-79-2 8-bromo-5-nitro-naphthalene-1-carboxylic acid 
• 91-17-8 decalin 
• 6625-54-3 5-nitro-1-chloromethylnaphthalene 
• 6642-29-1 4-nitronaphthalic-1,8-anhydride 
• 7647-01-0 hydrogenchloride 
• 108-88-3 toluene 
• 6639-35-6 5-nitro-1-naphthaldehyde 
• 67-64-1 acetone 
• 2243-81-4 1-naphthylcarboxamide 
• 7697-37-2 nitric acid 
• 86-55-5 1-naphthalenecarboxylic acid 
• 64-19-7 acetic acid 
• 23245-64-9 5-Nitro-1-naphthalenecarbonitrile 

Downstream Products

• 95092-66-3 phenyl 5-nitro-1-naphthoate 
• 95092-95-8 phenyl 5-amino-1-naphthoate * methanesulfonic acid 
• 615259-81-9 N-benzyl-5-nitronaphthalene-1-carboxamide 
• 91569-19-6 methyl 5-amino-1-naphthoate 
• 59866-98-7 methyl 5-nitronaphthalene-1-carboxylate 
• 38410-44-5 5-(Phenylazoxy)-1-naphthoesaeure 
• 6625-54-3 5-nitro-1-chloromethylnaphthalene 
• 174638-34-7 (S)-2-{[5-((R)-2-tert-Butoxycarbonylamino-3-tritylsulfanyl-propionylamino)-naphthalene-1-carbonyl]-amino}-4-methylsulfanyl-butyric acid methyl ester 
• 174638-35-8 (S)-2-{[5-((R)-2-tert-Butoxycarbonylamino-3-tritylsulfanyl-propionylamino)-naphthalene-1-carbonyl]-amino}-4-methylsulfanyl-butyric acid 
• 174638-40-5 (S)-2-{[5-((R)-2-tert-Butoxycarbonylamino-3-tritylsulfanyl-propylamino)-naphthalene-1-carbonyl]-amino}-4-methylsulfanyl-butyric acid methyl ester 
• 174638-41-6 (S)-2-{[5-((R)-2-tert-Butoxycarbonylamino-3-tritylsulfanyl-propylamino)-naphthalene-1-carbonyl]-amino}-4-methylsulfanyl-butyric acid 
• 99972-07-3 4,5-dinitro-[1]naphthoic acid 
• 605-71-0 1,5-dinitronaphthalene 
• 603-11-2 3-nitrophthalic acid 

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Process for the production of nitro derivatives of aromatic compounds

Nitroderivates of aromatic compounds which are difficult to nitrate, can readily be obtained by nitration providing that the aromatic compound is treated with nitric acid or another nitrating agent in the presence of aliphatic or cycloaliphatic hydrocarbons monosubstituted or polysubstituted by halogen, the nitro group or an alkyl sulphonyl group, and the nitro derivative formed subsequently isolated.