827-95-2

Basic information

• Product Name: Sodium 3-nitrobenzoate
• Synonyms: 3-nitro-benzoicacisodiumsalt;3-NITROBENZOIC ACID SODIUM SALT;SODIUM M-NITROBENZOATE;SODIUM 3-NITROBENZOATE;SODIUM 3-NITROBENZOATE TRIHYDRATE;M-NITROBENZOIC ACID SODIUM SALT;Sodium 3-nitrobenzoate hydrate;M-NITROBENZOIC ACID SODIUM
• CAS NO: 827-95-2
• Molecular Formula: C₇H₄NO₄*Na
• Molecular Weight: 189.1
• EINECS: 212-578-3
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
• Mol File: 827-95-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: >300°C
• Boiling Point: 340.7 °C at 760 mmHg
• Flash Point: 157.5 °C
• Appearance: off-white to yellow/crystalline
• Density: 1.13g/cm³
• Vapor Pressure: 0.000139mmHg at 25°C
• Refractive Index: 1.492
• Storage Temp.: Store below +30°C.
• Solubility: 10.9g/l
• Water Solubility: Soluble in water.
• BRN: 4166479
• CAS DataBase Reference: Sodium 3-nitrobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium 3-nitrobenzoate(827-95-2)
• EPA Substance Registry System: Sodium 3-nitrobenzoate(827-95-2)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38-22
• Safety Statements: 16-26-36-36/37-22
• RIDADR: UN 1325 4.1/PG 2
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 4.1
• PackingGroup: III
• Hazardous Substances Data: 827-95-2(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow solid

Uses

Sodium 3-nitrobenzoate is an important organic intermediate. It can be used in agrochemical, pharmaceutical and dyestuff field.

InChI:InChI=1/C12H19NO4/c1-2-3-4-5-6-7-12(16)17-13-10(14)8-9-11(13)15/h2-9H2,1H3

Synthetic route

2-acetoxy-1-(3-nitrophenyl)ethanone (90945-65-6) + sodium methylate (124-41-4) → Dimethyl ether (115-10-6) + acetic acid methyl ester (79-20-9) + sodium m-nitrobenzoate (827-95-2)

Conditions	Yield
In methanol at 30℃; Rate constant; Mechanism; other temperature (10 to 30 deg C);

3-Nitro-benzoic acid 9H-fluoren-9-ylmethyl ester (85055-67-0) → 9-methylene-fluorene (4425-82-5) + sodium m-nitrobenzoate (827-95-2)

Conditions	Yield
With sodium methylate In methanol at 25℃; Rate constant; other reagent, other solvent;

3-nitro-benzaldehyde (99-61-6) → sodium m-nitrobenzoate (827-95-2)

Conditions	Yield
With sodium hydroxide; sodium periodate; ruthenium trichloride In water at 35℃; Rate constant; Mechanism; other temperatures; dependence on the concentration of substrate;

3-nitrobenzoic acid (121-92-6) → sodium m-nitrobenzoate (827-95-2)

Conditions	Yield
With sodium hydroxide

sodium m-nitrobenzoate (827-95-2) + propargyl alcohol (107-19-7) → prop-2-yn-1-yl 3-nitrobenzoate (108521-49-9)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; triethylamine In N,N-dimethyl-formamide for 4h; Heating;	90%

dichlorobis(η5-methylcyclopentadienyl)titanium(IV) (1282-40-2) + sodium m-nitrobenzoate (827-95-2) → bis(methylcyclopentadienyl)bis(m-nitrobenzoate)titanium

Conditions	Yield
In benzene 30°C, stirring, 12 h; removing pptd. salt by filtration, concg. filtrate in vac., addn. of petroleum ether, refrigerating at 0°C overnight, washing crystals with petroleum ether; elem. anal.;	82%

sodium m-nitrobenzoate (827-95-2) + tri(α-naphthyl)antimony(III) dichloride (444307-81-7, 52762-61-5) → tri(α-naphthyl)antimony(V) (OOCC6H4NO2-meta)(Cl)

Conditions	Yield
In methanol; benzene byproducts: NaCl; at reflux temp.; elem. anal.;	82%

zirconocene dichloride (1291-32-3) + sodium m-nitrobenzoate (827-95-2) → bis(η5-cyclopentadienyl)zirconium(IV)(m-NO2C6H4)chloride

Conditions	Yield
In benzene byproducts: NaCl; under N2; anhydrous sodium salt of acid, complex and benzene stirred for 10h at 30°C, pptn. of NaCl; filtered, concd. (reduced pressure), addn. of petroleum ether, recrystd. (benzene/petroleum ether), dried (vac.); elem. anal.;	75.2%

manganese(II) perchlorate hexahydrate + (S)-1,2-bis(1-methyl benzimidazol-2-yl)ethanol + sodium m-nitrobenzoate (827-95-2) → [Mn4((S)-1,2-bis(N-methyl-benzimidazol-2-yl)ethanol)4(m-nitrobenzoate)2](ClO4)2*5H2O

Conditions	Yield
With triethylamine In ethanol for 3h; Inert atmosphere;	71%

sodium m-nitrobenzoate (827-95-2) + chloromethyl methyl ether (107-30-2) → 3-Nitrobenzoesaeure-methoxymethylester

Conditions	Yield
In N,N,N,N,N,N-hexamethylphosphoric triamide for 4h; Ambient temperature;	69%

Ni3(2,2'-dipyridylaminato)4(ClO4)2 + sodium m-nitrobenzoate (827-95-2) → [Ni3(2,2'-dipyridylaminato)4(3-nitrobenzoato)2]

Conditions	Yield
In methanol; water for 336h;	69%

sodium m-nitrobenzoate (827-95-2) + Chloroacetamide (79-07-2) → 2-(3-Nitrobenzoyloxy)acetamid

Conditions	Yield
In N,N-dimethyl-formamide at 90 - 95℃;	64%

sodium m-nitrobenzoate (827-95-2) → 3,3'-dinitro-1,1'-biphenyl (958-96-3)

Conditions	Yield
With copper(I) oxide; oxygen; palladium dichloride In water at 100℃; under 760.051 Torr; for 28h; Sealed tube; Green chemistry;	60%

bis(cyclopentadienyl)titanium dichloride (1271-19-8) + sodium m-nitrobenzoate (827-95-2) → (C5H5)2Ti(OCOC6H4NO2)2

Conditions	Yield
In benzene a mixt. of (η-C5H5)2TiCl2 and Na salt of the substituted benzoic acid in anhydrous benzene stirred at 30°C for 4 h; orange soln. filtered, concd., crystn. (refrigerator), recrystd. (benzene);	44%

sodium m-nitrobenzoate (827-95-2) → m-nitrobenzoyl bromide (13277-62-8)

Conditions	Yield
With Oxalyl bromide In benzene for 2h; Heating;

sodium m-nitrobenzoate (827-95-2) + N-phenyl-benzimidoyl chloride (4903-36-0) → N-(3-nitrobenzoyl)-N-phenylbenzamide (61582-63-6)

Conditions	Yield
In 1,4-dioxane; water at 25℃; Rate constant; pH:7;

sodium m-nitrobenzoate (827-95-2) + benzenesulfonyl chloride (98-09-9) → benzenesulfonic acid-(3-nitro-benzyl ester) (107625-10-5)

Conditions	Yield
In methanol at 25℃; Rate constant; Kinetics; Thermodynamic data; ΔH(excit), ΔS(excit.), Ea, var. temperature;

sodium m-nitrobenzoate (827-95-2) + N-(4-nitro-phenyl)-benzimidoyl chloride (34918-79-1) → N-(3-Nitro-benzoyl)-N-(4-nitro-phenyl)-benzamide

Conditions	Yield
In 1,4-dioxane; water at 55℃; Rate constant; pH:7;

sodium m-nitrobenzoate (827-95-2) → (3-Nitrobenzoyloxy)essigsaeure (98386-18-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 64 percent / dimethylformamide / 90 - 95 °C 2: 78 percent / conc. HCl / dioxane / 0.1 h / 75 °C View Scheme

sodium m-nitrobenzoate (827-95-2) + copper(II) sulfate (7758-99-8) → copper meta-nitrobenzoate dihydrate

Conditions	Yield
In water stoich. amts., 40-50°C;

p-tolyl triflate (29540-83-8) + sodium m-nitrobenzoate (827-95-2) → 4-methyl-3'-nitrobiphenyl (53812-68-3)

Conditions	Yield
With tol-BINAP; copper(I) oxide; palladium(II) acetylacetonate; 1,10-Phenanthroline In 1-methyl-pyrrolidin-2-one at 170℃; for 16h;	11 %Chromat.

1,3,5-trichloro-2,4,6-triazine (108-77-0) + sodium m-nitrobenzoate (827-95-2) → C24H12N6O12

Conditions	Yield
In acetonitrile at 20℃; for 0.166667h;

manganese(II) perchlorate hexahydrate + S-1-(1H-benzimidazol-2-yl)2-(N-methyl-benzimidazol-2-yl)ethanol + sodium m-nitrobenzoate (827-95-2) → [Mn4(S-1-(1H-benzimidazol-2-yl)2-(N-methyl-benzimidazol-2-yl)ethanol)4(m-nitrobenzoate)2](ClO4)2*3H2O

Conditions	Yield
With triethylamine In ethanol

Iron(III) nitrate nonahydrate + cobalt(II) chloride hexahydrate + sodium m-nitrobenzoate (827-95-2) → C42H30CoFe2N6O28(1+)*NO3(1-)*2H2O

Conditions	Yield
Stage #1: Iron(III) nitrate nonahydrate; cobalt(II) chloride hexahydrate; sodium m-nitrobenzoate In methanol for 4h; Stage #2: With dihydrogen peroxide In methanol for 5h; Reflux;

Upstream product

• 90945-65-6 2-acetoxy-1-(3-nitrophenyl)ethanone 
• 124-41-4 sodium methylate 
• 99-61-6 3-nitro-benzaldehyde 
• 121-92-6 3-nitrobenzoic acid 
• 85055-67-0 3-Nitro-benzoic acid 9H-fluoren-9-ylmethyl ester 

Downstream Products

• 107625-10-5 benzenesulfonic acid-(3-nitro-benzyl ester) 
• 108521-49-9 prop-2-yn-1-yl 3-nitrobenzoate 
• 98386-18-6 (3-Nitrobenzoyloxy)essigsaeure 
• 61582-63-6 N-(3-nitrobenzoyl)-N-phenylbenzamide 

Relevant articles and documents

Influence of axial ligands on diverse properties in three trinickel string complexes

Three new trinickel string complexes, [Ni3(dpa)4(3-nba) 2](1), [Ni3(dpa)4(4-nba)2]·(CH 3OH) (2), and [Ni3(dpa)4(3,5-dnba)2](3) where dpa- is the anion of 2,2-dipyridylamine, 3-nba- is 3-nitrobenzoate anion, 4-nba is 4-nitrobenzoate anion, and 3,5-dnba- is 3,5-dinitrobenzoate anion, were synthesized in good yield and characterized by X-ray crystallography, infrared spectra, elemental analysis, magnetic susceptibility, cyclic voltammogram (CV), UV-vis spectra, fluorescence spectra, and TG analysis. The magnetic susceptibilities suggested that the terminal Ni atoms in all three complexes are in high-spin state while the central Ni atom is in a low-spin state. The CVs of complexes 1-3 showed reversible one-electron redox waves at E1/2 = 1.1395 V for 1, 1.108 V for 2, and 1.109 V for 3 corresponding to Ni3 7+/Ni3 6+. The Ni-Ni distances in three complexes are somewhat different, indicating the axial nitrobenzoate ligands have significant effect on the structural assembly. Supplemental materials are available for this article. Go to the publisher's online edition of Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry to view the supplemental file.

Studies of the Borderline between Concerted and Stepwise Mechanisms of Elimination : E1cB Elimination of Fluoren-9-ylmethyl Carboxylate Esters

Rates of β-elimination of carboxylate leaving groups from fluoren-9-ylmethyl carboxylate esters in methanolic sodium methoxide at 25 deg C are reported.An E1cB mechanism with rate-determining formation of a carbanion intermediate is assigned on the basis of near identity of measured elimination rates and rates of carbanion formation predicted from a Taft correlation, and the similarity with elimination of 1-(1-acetoxy-1-methylethyl)indene for which the mechanism has been established by Ahlberg and Thibblin.Values of ρ=0.42 and βlg=0.27 measured for substituted benzoate leaving groups are a little larger than expected (ca. 0.24 and 0.18, respectively) and the discrepancy is tentatively ascribed to conformational enhancement of remote substituent effects, rather than to a contribution of E2 elimination.The effects of alkyl and aryl substitution α to the leaving group are discussed, especially in relation to the borderline between concerted and stepwise mechanisms.The measurements fail to confirm an earlier inference that the borderline shows a discontinuity in transition-state structure at the point of mechanistic change.