67233-85-6

Basic information

• Product Name: 2-Methoxy-5-nitrophenol sodium salt
• Synonyms: 2-methoxy-5-nitro;AtonikG;nitroguaiacolsodiumsalt;Sodium2-methoxy-5-nitrophenoxide;ATONIK;5-NITROGUAIACOL SODIUM SALT;2-METHOXY-5-NITROPHENOL SODIUM SALT;SODIUM 2-METHOXY-5-NITROPHENOL
• CAS NO: 67233-85-6
• Molecular Formula: C₇H₆NO₄*Na
• Molecular Weight: 191.12
• EINECS: 1312995-182-4
• Mol File: 67233-85-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 105-106°C
• Boiling Point: 291 °C at 760 mmHg
• Flash Point: 147.1 °C
• Appearance: /
• Vapor Pressure: 0.00115mmHg at 25°C
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: DMSO (Sparingly, Heated), Methanol (Slightly)
• Water Solubility: soluble
• Stability: Hygroscopic
• CAS DataBase Reference: 2-Methoxy-5-nitrophenol sodium salt(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methoxy-5-nitrophenol sodium salt(67233-85-6)
• EPA Substance Registry System: 2-Methoxy-5-nitrophenol sodium salt(67233-85-6)

Safety Data

• RTECS: SL7807000
• Hazardous Substances Data: 67233-85-6(Hazardous Substances Data)

Usage

Chemical Properties

Sodium 5-nitroguaiacol is soluble in methanol, ethanol, acetone and other organic solvents. It is compounded with sodium o-nitrophenolate and sodium p-nitrophenolate to obtain sodium nitrophenolate, which has been widely used in agriculture.

Uses

Sodium 5-nitroguaiacol is the most active monomer in sodium nitrophenolate, and has been designated and recommended as a green food engineering plant growth regulator by the United Nations and the Food and Agriculture Organization (FAO). It has a very obvious synergistic effect in the compounding of fertilizers, pesticides, fungicides, and seed coating agents; when applied in animal husbandry and fishery, it can significantly improve the yield and quality of meat, eggs and skins, and also It can enhance the immunity of animals and prevent various diseases.

Toxicology

The acute oral LD50 of 5-nitroguaiacol sodium on female and male rats was 3100 and 1270 mg/kg, respectively, and had no irritating effect on eyes and skin toxicity too.

InChI:InChI=1/C7H7NO4.Na/c1-12-7-3-2-5(8(10)11)4-6(7)9;/h2-4,9H,1H3;/q;+1/p-1

Synthetic route

2-methoxy-5-nitrophenyl acetate (53606-41-0) → sodium 5-nitroguaiacolate (67233-85-6)

Conditions	Yield
With sodium hydroxide at 100℃; for 1h; Temperature;	87.15%

3,4-dimethoxynitrobenzene (709-09-1) → Sodium; 2-methoxy-4-nitro-phenolate (4569-55-5) + sodium 5-nitroguaiacolate (67233-85-6)

Conditions	Yield
In potassium hydroxide Quantum yield; Irradiation;	A 0.3 % Spectr. B 99.7 % Spectr.

2-methoxy-phenol (90-05-1) → sodium 5-nitroguaiacolate (67233-85-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 5,5-dimethyl-1,3-cyclohexadiene / 7 h / 45 °C 2: nitric acid; acetic acid / 6 h / 75 °C / 712.57 Torr 3: sodium hydroxide / 1 h / 100 °C View Scheme

sodium 5-nitroguaiacolate (67233-85-6) + ethylene dibromide (106-93-4) → 1-(2-methoxy-5-nitrophenoxy)-2-bromoethane (92878-94-9)

Conditions	Yield
With 1-n-butyl-3-methylimidazolim bromide; sodium hydroxide at 100℃; for 6h;	82%
With 1-butyl-3-methylimidazole bromide; sodium hydroxide at 100℃; for 6h;	82%
With 1-n-butyl-3-methylimidazolim bromide; sodium hydroxide at 100℃; for 6h;	82%

sodium 5-nitroguaiacolate (67233-85-6) + 1,2-dichloro-ethane (107-06-2) → 2-(2-methoxy-5-nitrophenoxy)chloroethane

Conditions	Yield
With 1-butyl-3-methylimidazole bromide; sodium hydroxide at 130℃; under 4560.31 - 6080.41 Torr; for 9h; Inert atmosphere; Autoclave;	80%

2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) + sodium 5-nitroguaiacolate (67233-85-6) → N,N-diethyl-2-(2-methoxy-5-nitrophenoxy)-ethylamine (733700-14-6)

Conditions	Yield
With tetrabutylammomium bromide; sodium hydroxide In water at 80℃;	75.3%

sodium 5-nitroguaiacolate (67233-85-6) + allyl bromide (106-95-6) → 3-allyloxy-4-methoxynitrobenzene (142072-71-7)

Conditions	Yield
In DMF (N,N-dimethyl-formamide) at 65℃; for 2h;
In DMF (N,N-dimethyl-formamide) at 65℃; for 2h;
In DMF (N,N-dimethyl-formamide) at 65℃; for 2h;
In DMF (N,N-dimethyl-formamide) at 65℃; for 2h;

sodium 5-nitroguaiacolate (67233-85-6) + methyl chloroacetate (96-34-4) → C10H11NO6 (183803-02-3)

Conditions	Yield
With tetrabutylammomium bromide In water at 75 - 85℃;

sodium 5-nitroguaiacolate (67233-85-6) → N-[2-(2-methoxy-5-nitrophenoxy)ethyl]pyridine chloride

Conditions	Yield
Multi-step reaction with 2 steps 1: 1-butyl-3-methylimidazole bromide; sodium hydroxide / 9 h / 130 °C / 4560.31 - 6080.41 Torr / Inert atmosphere; Autoclave 2: 6 h / 110 °C View Scheme

Upstream product

• 53606-41-0 2-methoxy-5-nitrophenyl acetate 
• 90-05-1 2-methoxy-phenol 
• 709-09-1 3,4-dimethoxynitrobenzene 

Downstream Products

• 61324-40-1 3-benzyloxy-4-methoxybenzeneamine 
• 75167-86-1 2-(benzyloxy)-1-methoxy-4-nitrobenzene 
• 92878-94-9 1-(2-methoxy-5-nitrophenoxy)-2-bromoethane 
• 733700-14-6 N,N-diethyl-2-(2-methoxy-5-nitrophenoxy)-ethylamine 
• 183803-02-3 C₁₀H₁₁NO₆ 
• 142072-71-7 3-allyloxy-4-methoxynitrobenzene 

Relevant articles and documents

Preparation method of plant growth regulation compound sodium nitrophenolate

The invention relates to the field of preparation of agricultural auxiliaries, in particular to a preparation method of plant growth regulation compound sodium nitrophenolate. According to the invention, acetyl chloride is adopted to replace acetic anhydride which is a precursor to serve as a protecting group for hydroxyl acetylation, so that the acquisition difficulty of process raw materials is reduced, and the production cost of 5-nitroguaiacol sodium salt is controlled; and besides, a phase transfer catalyst is applied to the hydrolysis reaction of 5-nitroacetyl guaiacol, so that the hydrolysis of the product can be effectively promoted, the yield of the hydrolysis reaction is greatly improved, and the overall yield of the 5-nitroguaiacol sodium salt is further improved. The prepared 5-nitroguaiacol sodium salt has the advantage of low cost, and as a main effective component of the compound sodium nitrophenolate, the 5-nitroguaiacol sodium salt can improve the market competitiveness of the compound sodium nitrophenolate product, avoid the behavior that the drug effect of the compound sodium nitrophenolate product is reduced due to the fact that the cost of the 5-nitroguaiacol sodium salt is high and the ratio is reduced by bad manufacturers, and make contribution for promoting the benign development of the market.