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

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

Uses

Used in Pharmaceutical Industry:
5-Nitro-naphthalene-1-carboxylic acid is used as a key intermediate in the synthesis of various pharmaceuticals due to its versatile chemical structure. It contributes to the development of drugs with potential anti-inflammatory and analgesic properties, making it valuable in the treatment of pain and inflammation.
Used in Organic Chemistry Research:
As a chemical reagent, 5-Nitro-naphthalene-1-carboxylic acid is utilized in organic chemistry for various research purposes. Its unique structure allows for exploration in chemical reactions and the synthesis of new organic compounds, broadening the scope of chemical research.
Used in Dye and Pigment Synthesis:
5-Nitro-naphthalene-1-carboxylic acid is used as a dye intermediate in the production of various chemical dyes and pigments. Its chemical properties make it suitable for creating a range of colorants used in different industries, including textiles, plastics, and printing inks.

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

• 86-55-5 1-naphthalenecarboxylic acid 
• 27683-83-6 8-chloro-5-nitro-[1]naphthoic acid 
• 99972-57-3 5-nitro-1-hydroxymethylnaphthalene 
• 25029-79-2 8-bromo-5-nitro-naphthalene-1-carboxylic acid 
• 91-17-8 decalin 
• 2459-24-7 methyl 1-naphthoate 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 7647-01-0 hydrogenchloride 
• 23245-64-9 5-Nitro-1-naphthalenecarbonitrile 
• 64-19-7 acetic acid 
• 2243-81-4 1-naphthylcarboxamide 
• 6639-35-6 5-nitro-1-naphthaldehyde 
• 67-64-1 acetone 

Downstream Products

• 59866-98-7 methyl 5-nitronaphthalene-1-carboxylate 
• 5333-16-4 5-nitro-1-naphthoic acid chloride 
• 91901-43-8 ethyl 5-nitro-1-naphthoate 
• 99972-57-3 5-nitro-1-hydroxymethylnaphthalene 
• 603-11-2 3-nitrophthalic acid 
• 605-71-0 1,5-dinitronaphthalene 
• 99972-07-3 4,5-dinitro-[1]naphthoic acid 
• 6625-54-3 5-nitro-1-chloromethylnaphthalene 
• 95092-66-3 phenyl 5-nitro-1-naphthoate 
• 95092-95-8 phenyl 5-amino-1-naphthoate * methanesulfonic acid 
• 38410-44-5 5-(Phenylazoxy)-1-naphthoesaeure 
• 91569-19-6 methyl 5-amino-1-naphthoate 
• 615259-81-9 N-benzyl-5-nitronaphthalene-1-carboxamide 
• 174638-34-7 (S)-2-{[5-((R)-2-tert-Butoxycarbonylamino-3-tritylsulfanyl-propionylamino)-naphthalene-1-carbonyl]-amino}-4-methylsulfanyl-butyric acid methyl ester 

Relevant articles and documents

The mercury-mediated decarboxylation (Pesci reaction) of naphthoic anhydrides investigated by microwave synthesis

The mercury-mediated decarboxylation (Pesci reaction) of several substituted naphthoic anhydrides has been investigated by microwave synthesis. A laboratory microwave reactor was found to be ideal for small-scale preparations of this slow reaction, reducing reaction times from typically four days to less than 1 h for the three-step process. The ionic reaction medium rapidly heated to high temperatures under microwave heating and could be efficiently maintained by low microwave power settings. Generation of stoichiometric CO2 was safely contained within the reaction tubes. A simplified reaction procedure has been developed. For substituted naphthoic anhydrides, 1H NMR analysis of the naphthoate ester derivatives indicated no change in the regioisomer ratio compared to previously reported thermal values.

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.