3,5-Dinitrobenzoic acid

HCID 7433CAS 99-34-3
Substructure searchFind similar structures

Basic information

Standard SMILES
O=C(O)c1cc([N+](=O)[O-])cc([N+](=O)[O-])c1
InChIKey
VYWYYJYRVSBHJQ-UHFFFAOYSA-N
Molecular formula
C7H4N2O6
Average molar mass
212.12 g/mol
Monoisotopic mass
212.00693585

Overview

3,5-dinitrobenzoic acid is a member of the class of benzoic acids that is benzoic acid in which the hydrogens at positions 3 and 5 are replaced by nitro groups. It is a member of benzoic acids and a C-nitro compound.

Names & identifiers

Preferred name
3,5-Dinitrobenzoic acid
IUPAC
3,5-dinitrobenzoic acid
English name
3,5-Dinitrobenzoic acid
Molecular formula
C7H4N2O6
Molecular weight
212.12

Names & synonyms

3,5-DINITROBENZOIC ACID99-34-3Benzoic acid, 3,5-dinitro-DNBADinitrobenzoic acid3-Carboxy-1,5-dinitrobenzene4V3F9Q018PNSC-8732DTXSID7059195CHEBI:73914RefChem:916264-carboxy-2,6-dinitrophenyl
Show more names
3,5-DINITROBENZOATEDNBA)3,5-Dinitrobenz3,5-Dinitrobenzoic acid Solution, 100ppm3.5-Dinitr3,5-dinitrobenzoicRARECHEM AL BO 0231TIMTEC-BB SBB0078403,5-DNBAfreeofsulfur
DTXCID5049104202-751-1695-040-4MFCD000072533,5-Dinitro-benzoic acid3,5-DNBA3,5-dinitrobenzenecarboxylic acid3,5-Dinitrobenzoic acid, 99%

Database identifiers

CAS
99-34-3
PubChem CID
7433
DTXSID
DTXSID7059195
ChEMBL
CHEMBL118713
ChEBI
CHEBI:73914
UNII
4V3F9Q018P
EC Number
202-751-1、695-040-4
Nikkaji
J401.383B、J62.022J

Properties

Computed structural properties

XLogP
1.5
Topological polar surface area
129 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
6
Rotatable bonds
1
Heavy atoms
15

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Nitrobenzoic Acids
SpringerMaterials PropertiesCrystal structure
LogP1.75
Vapor Pressure0.00000141 [mmHg]
Physical DescriptionSolid; [Merck Index] Light yellow crystalline solid; [Sigma-Aldrich MSDS]
Ionization Efficiency · 6 items

Negative

0.79

10.5

Agilent XCT

Electrospray ionization

ammonia (10nM)

Physicochemical properties

Melting point
204 · 204-206 °C (lit.)
Boiling point
351.93 °C · 351.93°C (rough estimate)
Density
1.683 · 1.683
refractive index
1.53 · 1.5300 (estimate)
storage temp.
Sealed in dry,Room Temperature
solubility
0.5 g/10 · ethanol: soluble0.5g/10 mL, clear, yellow to very deep greenish-yellow

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H302 (99.1%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 111 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

Hazard information

Regulatory Information · 3 items

Chemical: Benzoic acid, 3,5-dinitro-

Status: Active Update: 09-04-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/5821

3,5-Dinitrobenzoic acid: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryA skin and strong eye irritant; Harmful by ingestion; [Sigma-Aldrich MSDS] See 3-Nitrobenzoic acid.
Hazard Classes and CategoriesAcute Tox. 4 (99.1%)

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
DG9140700
ridadr
UN1325
hs_code
29163900

Chemistry & industry

Uses & manufacturing

UsesUsed to identify alcohols and alkyl halides and in chromatographic determination of essential oil constituents; [Merck Index] Used as an intermediate; [ExPub: ECHA REACH Registrations]
General Manufacturing InformationBenzoic acid, 3,5-dinitro-: ACTIVE
Applications · 3 items

Uses3,5-nitrobenzoic acid is an important intermediate for organic synthesis, in the pharmaceutical industry for the synthesis sulfachrysoidine and for the detection of ampicillin.

Uses3,5-Dinitrobenzoic acid, is used as a reagent used in the derivatization of resins and the determination of ampicillin.

General Description3,5-Dinitrobenzoic acid forms an adduct with 3,5-dimethylpyridine and the crystal structure of adduct has been studied at room temperature and 80K for both undeuterated and deuterated compounds. It forms 1:1 cocrystal with analgesic drug, ethenzamide and exists in two polymorphic forms.

Preparation methods · 1 item

Preparation3,5-Dinitrobenzoic acid is synthesized by nitration of benzoic acid. Sulfuric acid was added to the dry reaction pot, and benzoic acid was added under stirring. Heat to 60°C, add fuming nitric acid dropwise, and complete the dropwise addition below 85°C. React at 80-85°C for 1 h, 100°C for 0.5-1h, and then heat up to 135°C for 2h. Leave overnight. The reaction solution was put into ice water to separate out crystals, filtered, washed with water and then washed with 50% ethanol to obtain 3,5-dinitrobenzoic acid. Yield 70%.

Upstream & downstream products

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
爱斯特（成都）生物制药股份有限公司+86-28-85122536 85324413 · [email protected]

Additional notes

DefinitionChEBI: 3,5-dinitrobenzoic acid is a member of the class of benzoic acids that is benzoic acid in which the hydrogens at positions 3 and 5 are replaced by nitro groups. It is a C-nitro compound and a member of benzoic acids.

Related reactions

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Linked notes

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