Basic information
- Standard SMILES
O=C(Cl)c1ccc([N+](=O)[O-])cc1- InChIKey
SKDHHIUENRGTHK-UHFFFAOYSA-N- Molecular formula
- C7H4ClNO3
- Average molar mass
- 185.56 g/mol
- Monoisotopic mass
- 184.98797067
Overview
P-nitrobenzoyl chloride appears as yellow needles or powder with a pungent odor. (NTP, 1992)
Names & identifiers
- Preferred name
- 4-Nitrobenzoyl chloride
- IUPAC
- 4-nitrobenzoyl chloride
- English name
- 4-Nitrobenzoyl chloride
- Molecular formula
- C7H4ClNO3
- Molecular weight
- 185.56
Names & synonyms
Show more names
Database identifiers
- CAS
122-04-3- PubChem CID
- 8502
- DTXSID
DTXSID9025742- ChEMBL
CHEMBL1599838- UNII
- X3H8PW2GC4
- EC Number
- 204-517-4
- Nikkaji
- J47.843A
Properties
Computed structural properties
- XLogP
- 2.9
- Topological polar surface area
- 62.9 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 193
Experimental & physicochemical properties
Physical Description
P-nitrobenzoyl chloride appears as yellow needles or powder with a pungent odor. (NTP, 1992)
Bright yellow solid with pungent odor; [Merck Index] Yellow crystalline solid; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 71 · 71-74 °C (lit.)
- Boiling point
- 202 · 202-205 °C/105 mmHg (lit.)
- Density
- 1.53 · 1.53
- refractive index
- 1.589 · 1.5890 (estimate)
- Flash point
- 102 °C · 102 °C
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- Soluble in terahydrofuran, dichloromethane, chloroform and pyridine.
- form
- Flakes or Crystals
- color
- Yellow
- Odor
- pungent odor
- Water Solubility
- Decomposes
- Sensitive
- Moisture Sensitive
- Merck
- 14 · 14,6589
- BRN
- 473192 · 473192
- Stability
- Stable, but moisture sensitive. Combustible. Incompatible with water, alcohols, strong oxidizing agents, strong bases.
- InChI
- 1S/C7H4ClNO3/c8-7(10)5-1-3-6(4-2-5)9(11)12/h1-4H
- InChIKey
- SKDHHIUENRGTHK-UHFFFAOYSA-N
- SMILES
- [O-][N+](=O)c1ccc(cc1)C(Cl)=O
- CAS DataBase Reference
- 122 · 122-04-3(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 3 H8PW2GC4 · X3H8PW2GC4
- NIST Chemistry Reference
- 4 · 4-Nitrobenzoic acid chloride(122-04-3)
- EPA Substance Registry System
- p-Nitrobenzoyl chloride (122-04-3)
- UNSPSC Code
- 12352106 · 12352106
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05
- Signal word
- Danger
- Hazard statements
- 314 · H314
- Precautionary statements
- 280 · P280-P305+P351+P338-P310
- PPE
- 3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- Hazard Codes
- C
- Risk Statements
- 34 · 34
- Safety Statements
- 26 · 26-36/37/39-45
- RIDADR
- 3261 · UN 3261 8/PG 2
- WGK Germany
- 2 · 2
- RTECS
- 6651000 · DM6651000
- F
- 9 · 9-19-21
- TSCA
- TSCA listed
- HazardClass
- 8 · 8
- PackingGroup
- II
- HS Code
- 29163900 · 29163900
- Storage Class
- 8 A · 8A - Combustible corrosive hazardous materials
- Hazard Classifications
- 1 Met · Eye Dam. 1Met. Corr. 1Skin Corr. 1B
- Toxicity
- 50 orally · LD50 orally in Rabbit: 5600 mg/kg
- REACH Registrations
- Active
- Limited Quantities
- 1 L · 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
Danger
H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 137 reports by companies from 9 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: Benzoyl chloride, 4-nitro-
Benzoyl chloride, 4-nitro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzoyl chloride, 4-nitro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 26-09-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/16497
4-Nitrobenzoyl chloride: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Causes ataxia and muscle contraction or spasticity in oral lethal-dose studies of mice, rabbits, and rats; Causes other changes in lungs, thorax, or respiration, pigmented or nucleated red blood cells, and changes in the spleen in 17-week intermittent inhalation studies (species not specified); Causes other changes in blood in 30-day intermittent oral studies of rats; [RTECS] Decomposed by water; [Merck Index] Reacts with water; [CAMEO] Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; [Alfa Aesar MSDS] See Nitrobenzene and Benzoyl chloride.
Reactivity Profile
P-NITROBENZOYL CHLORIDE is incompatible with bases (including amines), with strong oxidizing agents, and with alcohols. May react with reducing agents. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].
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: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone 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.
Toxicology
Safety data
- F
- 9-19-21
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- DM6651000
- ridadr
- UN 3261 8/PG 2
- hs_code
- 29163900
- Toxicity
- LD50 orally in Rabbit: 5600 mg/kg
- risk_code
- 34
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- hazard_code
- C
- safety_code
- 26-36/37/39-45
- hazard_class
- 8
- Storage Class
- 8A - Combustible corrosive hazardous materials
- packing_group
- II
- Hazard statements
- H314
- Limited Quantities
- 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- REACH Registrations
- Active
- Hazard Classifications
- Eye Dam. 1Met. Corr. 1Skin Corr. 1B
- Precautionary statements
- P280-P305+P351+P338-P310
Chemistry & industry
Uses & manufacturing
Applications
Uses4-Nitrobenzoyl chloride is used in the preparation of polysubstituted furanonaphthoquinoines. It is also involved in Michael addition, Henry reaction, O-alkylation and cycloaddition reactions. Further, it is employed as an intermediate in active pharmaceutical ingredient and dyes.
Uses4-Nitrobenzoyl Chloride is used inorganic syntheses such as Michael additions. Also used in the synthesis of polysubstituted furanonaphthoquinoines.
General DescriptionYellow needles or powder with a pungent odor.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers48 total
Related reactions
Linked notes
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