3,5-Dinitrobenzoic acid: Difference between revisions

 

Line 34: Line 34:

|Section2={{Chembox Properties

|Section2={{Chembox Properties

| Appearance = Yellow or colourless crystals

| Appearance = Yellow or colourless crystals

| Formula = {{chem2|C7H4O6N2}}

| Formula = C₇H₄O₆N₂

| C=7 |H=4 |O=6 |N=2

| MolarMass = 212.118 g/mol

| MeltingPtC = 205 to 207

| MeltingPtC = to

| MeltingPt_notes =

| MeltingPt_notes =

| MeltingPt_ref = <ref name=”SigmaAldrich”>{{Sigma-Aldrich|id=121258|name=3,5-dinitrobenzoic acid|access-date=23 October 2025}}</ref>

| pKa = 2.82

| pKa = 2.82

| VaporPressure = {{val|0.000001|u=mmHg|fmt=none}}<ref name=”FisherSDS”>{{cite web |url=https://documents.thermofisher.com/DirectWebViewer/private/document.aspx?prd=ALFAAA16502~~PDF~~MTR~~AGHS~~EN~~2024-03-26%2004:19:18~~3%205-Dinitrobenzoic%20acid~~ |title=3,5-dinitrobenzoic acid SDS |publisher=ThermoFisher Scientific |website=thermofisher.com |date=25 March 2024 |access-date=23 October 2025}}</ref>

}}

}}

| Section7 = {{Chembox Hazards

| Section7 = {{Chembox Hazards

| GHS_ref = <ref name=”SigmaAldrich”/>

| GHSPictograms = {{GHS07}}

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|302|315|319|335|413}}

| HPhrases = {{H-phrases|302|315|319|335|413}}

| PPhrases = {{P-phrases|261|264|270|271|273|280|301+312|302+352|304+340|305+351+338|312|321|330|332+313|337+313|362|403+233|405|501}}

| PPhrases = {{P-phrases|261|264|270|271|273|280|301+312|302+352|304+340|305+351+338|332+313|337+313|362|403+233|405|501}}

| NFPA-H = 2

| NFPA-F = 1

| NFPA-I = 0

| NFPA-S =

| NFPA_ref = <ref name=”FisherSDS”/>

}}

}}

}}

}}

”’3,5-Dinitrobenzoic acid”’ is an [[organic chemistry|organic chemical]] that is an important [[corrosion inhibitor]] and is also used in [[photography]]. This [[aromatic]] compound is used by [[chemists]] to identify alcohol components in [[ester]]s and in the [[Fluorimetry|fluorometric]] analysis of [[creatinine]].

”’3,5-Dinitrobenzoic acid”’ is an [[organic chemistry|organic chemical]] that is an important [[corrosion inhibitor]] and is also used in [[photography]]. This [[aromatic]] compound is used by [[chemists]] to identify alcohol components in [[ester]]s and in the [[Fluorimetry|fluorometric]] analysis of [[creatinine]].

== Synthesis ==

== Synthesis ==

Line 55: Line 63:

:[[File:3_5_Dinitrobenzoesäure.svg|400px]]

:[[File:3_5_Dinitrobenzoesäure.svg|400px]]

The nitration can also be started with [[3-Nitrobenzoic acid|3-nitrobenzoic acid]], which leads to yields of approximately 98 %.<ref name=”Lebedev”>{{cite journal|first1=B. A.|last1=Lebedev|first2=V. Yu.|last2=Dolmatov|first3=P. S.|last3=Zubarev|first4=N. V.|last4=Latynov|first5=M. M.|last5=Aleksandrov|first6=R. I|last6=Ponamareva|title=Preparation of 3,5-dinitrobenzoic acid from meta-nitrobenzoic acid|journal=[[Pharmaceutical Chemistry Journal]]|year=1988|volume=22|issue=5|pages=399–401|doi=10.1007/BF00769656|s2cid=34335456}}.</ref>

The nitration can also be started with [[3-Nitrobenzoic acid|3-nitrobenzoic acid]], which leads to yields of approximately 98%.<ref name=”Lebedev”>{{cite journal|first1=B. A.|last1=Lebedev|first2=V. Yu.|last2=Dolmatov|first3=P. S.|last3=Zubarev|first4=N. V.|last4=Latynov|first5=M. M.|last5=Aleksandrov|first6=R. I|last6=Ponamareva|title=Preparation of 3,5-dinitrobenzoic acid from meta-nitrobenzoic acid|journal=Pharmaceutical Chemistry Journal|year=1988|volume=22|issue=5|pages=399–401|doi=10.1007/BF00769656|s2cid=34335456}}.</ref>

== Properties ==

== Properties ==

3,5-Dinitrobenzoic acid is an odorless, yellowish solid. Due to the [[mesomeric effect]] of the two nitro groups, it is more acidic (pK_a = 2.82) than benzoic acid (pK_a = 4.20) and 3-nitrobenzoic acid (pK_a = 3.47).

3,5-Dinitrobenzoic acid is an odorless, yellowish solid. Due to the [[mesomeric effect]] of the two nitro groups, it is more acidic (pKsuba = 2.82) than benzoic acid (pKsuba = 4.20) and 3-nitrobenzoic acid (pKsuba = 3.47).

== Uses ==

== Uses ==

3,5-Dinitrobenzoic acid finds use in the identification of various organic substances, especially alcohols, by [[derivatization]]. For such an analysis, the substance to be analyzed is reacted with 3,5-dinitrobenzoic acid in the presence of sulfuric acid in order to form a derivate. By doing so, many substances that are liquid or have a low melting point are converted to easily crystallized derivates with sharp melting points. For instance, alcohols can be identified by the melting point of their [[ester]]s with 3,5-dinitrobenzoic acid. This method is also applicable to a large number of [[amine]]s.

3,5-Dinitrobenzoic acid finds use in the identification of various organic substances, especially alcohols, by [[derivatization]]. For such an analysis, the substance to be analyzed is reacted with 3,5-dinitrobenzoic acid in the presence of sulfuric acid in order to form a derivate. By doing so, many substances that are liquid or have a low melting point are converted to easily crystallized derivates with sharp melting points. For instance, alcohols can be identified by the melting point of their [[ester]]s with 3,5-dinitrobenzoic acid. This method is also applicable to a large number of [[amine]]s.

:[[File:3-5-Dinitrobenzoesäure-2-propylester.svg|thumb|none|450px|Identification of [[isopropanol]] as a derivate of 3,5-dinitrobenzoic acid:<br/> 3,5-dinitrobenzoic acid-2-propylester (mp.:&nbsp;123&nbsp;°C<ref name=”CRC”>[[CRC Handbook of Tables for Organic Compound Identification]], Third Edition, 1984, {{ISBN|0-8493-0303-6}}.</ref>).]]

:[[File:3-5-Dinitrobenzoesäure-2-propylester.svg|thumb|none|450px|Identification of [[isopropanol]] as a derivate of 3,5-dinitrobenzoic acid:<br/> 3,5-dinitrobenzoic acid-2-propylester (mp.:123C<ref name=”CRC”>CRC of for , |0-8493-0303-6}}</ref>]]

Compared to [[4-nitrobenzoic acid]], another acid that is used similarly, derivates of 3,5-dinitrobenzoic acid have higher melting points, so that it is preferred when the 4-nitrobenzoic acid derivate has a melting point too low to be accurately identified.<ref name=”CRC”/>

Compared to [[4-nitrobenzoic acid]], another acid that is used similarly, derivates of 3,5-dinitrobenzoic acid have higher melting points, so that it is preferred when the 4-nitrobenzoic acid derivate has a melting point too low to be accurately identified.<ref name=”CRC”/>

Line 71: Line 79:

== References ==

== References ==

{{reflist}}

{{reflist}}

== Literature ==

* {{cite encyclopedia | title = 3,5-dinitrobenzoic acid | encyclopedia = Combined Chemical Dictionary | publisher = [[Chapman and Hall]]/[[CRC Press]] | date = 2007 }}

== External links ==

* [http://msds.chem.ox.ac.uk/DI/3,5-dinitrobenzoic_acid.html MSDS Data]

{{DEFAULTSORT:Dinitrobenzoic acid, 3,5-}}

{{DEFAULTSORT:Dinitrobenzoic acid, 3,5-}}

3,5-Dinitrobenzoic acid

Names
Preferred IUPAC name
Identifiers
	1914286
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard	100.002.501
EC Number
UNII
InChI=1S/C7H4N2O6/c10-7(11)4-1-5(8(12)13)3-6(2-4)9(14)15/h1-3H,(H,10,11) Y Key: VYWYYJYRVSBHJQ-UHFFFAOYSA-N Y InChI=1/C7H4N2O6/c10-7(11)4-1-5(8(12)13)3-6(2-4)9(14)15/h1-3H,(H,10,11) Key: VYWYYJYRVSBHJQ-UHFFFAOYAQ
O=[N+]([O-])c1cc(cc([N+]([O-])=O)c1)C(=O)O
Properties
	C7H4O6N2
Molar mass	212.117 g·mol−1
Appearance	Yellow or colourless crystals
Melting point	204 to 206 °C (399 to 403 °F; 477 to 479 K)[2]
Vapor pressure	0.000001 mmHg[1]
Acidity (pKa)	2.82
Hazards
GHS labelling:[2]
	Warning
	H302, H315, H319, H335, H413
	P261, P264, P270, P271, P273, P280, P301+P312+P330, P302+P352, P304+P340+P312, P305+P351+P338, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Chemical compound

3,5-Dinitrobenzoic acid is an organic chemical that is an important corrosion inhibitor and is also used in photography.^{[citation needed]} This aromatic compound is used by chemists to identify alcohol components in esters and in the fluorometric analysis of creatinine.

3,5-dinitrobenzoic acid is obtained from benzoic acid by the nitration reaction with nitric acid in the presence of concentrated sulfuric acid.^[3][4]

The nitration can also be started with 3-nitrobenzoic acid, which leads to yields of approximately 98%.^[5]

3,5-Dinitrobenzoic acid is an odorless, yellowish solid. Due to the mesomeric effect of the two nitro groups, it is more acidic (pK_a = 2.82) than benzoic acid (pK_a = 4.20) and 3-nitrobenzoic acid (pK_a = 3.47).^{[citation needed]}

3,5-Dinitrobenzoic acid finds use in the identification of various organic substances, especially alcohols, by derivatization. For such an analysis, the substance to be analyzed is reacted with 3,5-dinitrobenzoic acid in the presence of sulfuric acid in order to form a derivate. By doing so, many substances that are liquid or have a low melting point are converted to easily crystallized derivates with sharp melting points. For instance, alcohols can be identified by the melting point of their esters with 3,5-dinitrobenzoic acid. This method is also applicable to a large number of amines.

Compared to 4-nitrobenzoic acid, another acid that is used similarly, derivates of 3,5-dinitrobenzoic acid have higher melting points, so that it is preferred when the 4-nitrobenzoic acid derivate has a melting point too low to be accurately identified.^[6]

For more sensitive compounds, the reaction is carried out using the acid chloride, 3,5-dinitrobenzoyl chloride. This allows for example the identification of amino acids.^[3]