Basic information
- Standard SMILES
O=C(O)c1cccc([N+](=O)[O-])c1C(=O)O- InChIKey
KFIRODWJCYBBHY-UHFFFAOYSA-N- Molecular formula
- C8H5NO6
- Average molar mass
- 211.13 g/mol
- Monoisotopic mass
- 211.01168688
Overview
structure in first source
Names & identifiers
- Preferred name
- 3-Nitrophthalic acid
- IUPAC
- 3-nitrophthalic acid
- English name
- 3-Nitrophthalic acid
- Molecular formula
- C8H5NO6
- Molecular weight
- 211.13
Names & synonyms
3-Nitrophthalic acid603-11-2Phthalic acid, 3-nitro-1,2-Benzenedicarboxylic acid, 3-nitro-MC7W4GB97CNSC-3120DTXSID9060528RefChem:95046DTXCID1042786210-030-83-nitrobenzene-1,2-dicarboxylic acid3-Nitrophthalicacid
Show more names
3-NPAo-Nitrophthalic acidPomalidomide Impurity 8NSC 3120AKOS B0287343-nitrophthalic3-nitro-phthalateRARECHEM AL BO 0803
3-nitro-phthalic acidMFCD00007138Pomalidomide Impurity 5m-Nitrophthalic acid3-Nitro-1,2-benzenedicarboxylic acidUNII-MC7W4GB97CSCHEMBL304456STR03241
Database identifiers
- CAS
603-11-2- PubChem CID
- 69043
- DTXSID
DTXSID9060528- UNII
- MC7W4GB97C
- EC Number
- 210-030-8
- Nikkaji
- J3.288.228E、J62.025D
Properties
Computed structural properties
- XLogP
- 0.7
- Topological polar surface area
- 120 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 2
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 296
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Nitrobenzoic Acids
Vapor Pressure0.00000018 [mmHg]
Physical DescriptionOff-white powder; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 210 °C · 210 °C (dec.) (lit.)
- Boiling point
- 350.79 °C · 350.79°C (rough estimate)
- Density
- 1.6342 · 1.6342 (rough estimate)
- vapor density
- 7.3 · 7.3 (vs air)
- refractive index
- 1.5282 · 1.5282 (estimate)
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 5 %, · water: soluble5%, clear to slightly hazy, colorless to faint yellow or tan
- pka
- 1 · pK1:1.88 (25°C)
- form
- Powder
- color
- Off-white to light yellow
- Water Solubility
- 20 g/L · 20 g/L (25 ºC)
- Decomposition
- 216 °C · 216 °C
- BRN
- 2054269 · 2054269
- Stability
- Stable. Incompatible with strong oxidizing agents.
- InChI
- 1S/C8H5NO6/c10-7(11)4-2-1-3-5(9(14)15)6(4)8(12)13/h1-3H,(H,10,11)(H,12,13)
- InChIKey
- KFIRODWJCYBBHY-UHFFFAOYSA-N
- SMILES
- OC(=O)c1cccc(c1C(O)=O)[N+]([O-])=O
- CAS DataBase Reference
- 603 · 603-11-2(CAS DataBase Reference)
- FDA UNII
- 7 W4GB97C · MC7W4GB97C
- NIST Chemistry Reference
- 3 · 3-Nitrophthalic acid(603-11-2)
- EPA Substance Registry System
- 3 · 3-Nitrophthalic acid (603-11-2)
- UNSPSC Code
- 12352106 · 12352106
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05,GHS07
- Signal word
- Danger
- Hazard statements
- 315 · H315-H318-H335
- Precautionary statements
- 261 · P261-P280-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38-41
- Safety Statements
- 26 · 26-36/39-37/39-36
- WGK Germany
- 3 · 3
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HS Code
- 29173980 · 29173980
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 1 Skin · Eye Dam. 1Skin Irrit. 2STOT SE 3
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Danger
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 87 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 1,2-Benzenedicarboxylic acid, 3-nitro-
Status: Active Update: 06-07-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/21660
3-Nitrophthalic acid: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryA skin and strong eye irritant; [Alfa Aesar MSDS] See 3-Nitrobenzoic acid.
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29173980
- risk_code
- 36/37/38-41
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 26-36/39-37/39-36
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H318-H335
- REACH Registrations
- Active
- Hazard Classifications
- Eye Dam. 1Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P280-P305+P351+P338
Chemistry & industry
Uses & manufacturing
General Manufacturing Information1,2-Benzenedicarboxylic acid, 3-nitro-: ACTIVE
Applications
Uses3-Nitrophthalic Acid is a useful chemical in organic synthesis. It is also an impurity of Apremilast.
Uses3-Nitrophthalic acid may be used as starting reagent in the synthesis of modified 2-iodoxybenzoic acid derivatives. It may be used in the synthesis of brucinium 2-carboxy-6-nitrophthalate dihydrate (systematic name: 2,3-dimethoxy-10-oxostrychnidinium 2-carboxy-6-nitrophthalate dihydrate), via heating with brucine.
General Description3-Nitrophthalic acid is a degradation product of isoxaben herbicide. It acts as ligand and forms rare-earth complexes.
Preparation methods
PreparationPhthalic anhydride was added to concentrated sulfuric acid, stirring under the passage of water vapor heating to 80 °C, fuming nitric acid was added dropwise, the reaction temperature to maintain 100-110°C, add the end of the heat above 110°C for 2h, placed in the overnight pour into the water, and filtered. The filter cake was recrystallized with water to obtain 3-Nitrophthalic acid. Yield of about 30%.
Upstream & downstream products
Upstream raw materials
Downstream products
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