Basic information
- CAS
5466-84-2- Standard SMILES
O=C1OC(=O)c2cc([N+](=O)[O-])ccc21- InChIKey
MMVIDXVHQANYAE-UHFFFAOYSA-N- Molecular formula
- C8H3NO5
- Average molar mass
- 193.11 g/mol
- Monoisotopic mass
- 193.0011222
Overview
4-nitrophthalic anhydride is a yellow powder. (NTP, 1992)
Names & identifiers
- Preferred name
- 4-Nitrophthalic acid anhydride
- IUPAC
- 5-nitro-2-benzofuran-1,3-dione
- English name
- 4-Nitrophthalic anhydride
- Molecular formula
- C8H3NO5
- Molecular weight
- 193.11
Names & synonyms
Show more names
Database identifiers
- CAS
5466-84-2- PubChem CID
- 230976
- DTXSID
DTXSID6025775- ChEMBL
CHEMBL1373184- UNII
- SQN32UA63N
- EC Number
- 226-776-2
- Nikkaji
- J104.459A
Properties
Computed structural properties
- XLogP
- 1.1
- Topological polar surface area
- 89.2 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 0
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 307
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 116 · 116-120 °C(lit.)
- Boiling point
- 197 °C · 197 °C / 8mmHg
- Density
- 1.6392 · 1.6392 (rough estimate)
- refractive index
- 1.47 · 1.4700 (estimate)
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- Acetone (Slightly), Chloroform (Slightly), Methanol (Slightly)
- form
- Solid
- color
- Pale Beige
- Water Solubility
- Hydrolysis
- Sensitive
- Moisture Sensitive
- BRN
- 179682 · 179682
- InChI
- InChI=1S/C8H3NO5/c10-7-5-2-1-4(9(12)13)3-6(5)8(11)14-7/h1-3H
- InChIKey
- MMVIDXVHQANYAE-UHFFFAOYSA-N
- SMILES
- C1(=O)C2=C(C=C([N+]([O-])=O)C=C2)C(=O)O1
- CAS DataBase Reference
- 5466 · 5466-84-2(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 32 UA63N · SQN32UA63N
- NIST Chemistry Reference
- 4 · 4-Nitrophthalic anhydride(5466-84-2)
- EPA Substance Registry System
- 5 · 5-Nitrophthalic anhydride (5466-84-2)
- UNSPSC Code
- 12162002 · 12162002
- NACRES
- 23 · NA.23
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi,Xn
- Risk Statements
- 36 · 36/37/38-20/22
- Safety Statements
- 26 · 26-36-36/37/39-22
- WGK Germany
- 3 · 3
- RTECS
- 3328000 · TI3328000
- F
- 10 · 10-21
- TSCA
- TSCA listed
- HS Code
- 29173990 · 29173990
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, 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 46 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Health Hazards
SYMPTOMS: Symptoms of exposure to this compound include coughing, sneezing, burning in respiratory system, dermatitis, and skin irritation. Symptoms of chronic exposure include bronchitis, eye irritation, inflammation of respiratory tract and bloody nasal discharge.
Reactivity Profile
4-NITROPHTHALIC ANHYDRIDE reacts exothermically with water. The reactions are usually slow, but might become violent if local heating accelerates their rate. Acids accelerate the reaction with water. Incompatible with acids, strong oxidizing agents, alcohols, amines, and bases.
Safety & protection
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
Personal Protective Equipment (PPE)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
Safety data
- F
- 10-21
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- TI3328000
- hs_code
- 29173990
- risk_code
- 36/37/38-20/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,Xn
- safety_code
- 26-36-36/37/39-22
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Uses & manufacturing
Applications
Uses4-Nitrophthalic anhydride is used an an intermediate for the synthesis of a benzimidazole PARP inhibitor I (succinate salt) (ABT-472).
Uses5-Nitrophthalic Anhydride is used in the preparation of phthalic acids as well as compounds with anticonvulsant activities.
General DescriptionYellow powder.
Preparation methods
Preparation4-Nitrophthalic anhydride is synthesized by hydrolysis of 4-nitrophthalimide and then dehydration. The 4-nitrophthalimide was added to the sodium hydroxide solution, heated and boiled for 15min. Adjust pH to 6-8 with nitric acid, and add nitric acid to boil for 5 min. Cooling, filtering, the filtrate was extracted with ether, the extract was dried and then the ether was evaporated, that is, 4-Nitrophthalic anhydride crystals were precipitated. Yield 95%.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
Related reactions
Compound notes
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