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4-Nitrobenzoyl chloride

HCID 8502
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
122-04-3
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

4-Nitrobenzoyl chloride122-04-3P-NITROBENZOYL CHLORIDEBenzoyl chloride, 4-nitro-4-Nitrobenzoic acid chloridep-Nitrobenzoic acid chlorideBenzoyl chloride, p-nitro-DTXSID9025742X3H8PW2GC4NSC-5381DTXCID905742RefChem:525932
Show more names
PNBC4-NitrobenzoylSKL7484-Nitrobenzoyl chlorp-Nitrobenzoyl chloriLABOTEST-BB LT000772604-nitro-benzoylchloridp-nitro-benzoylchloridNITROBENZOYL-4 CHLORIDE
204-517-44-Nitro-benzoyl chlorideMFCD00007345para-nitrobenzoyl chlorideNitrobenzoyl chloride, 4-4-Nitrobenzoyl-d4ChlorideCCRIS 31364-nitro benzoyl chloride

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 propertiesFilling in

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

Chemical ClassesToxic Gases & Vapors -> Acid Halides
SpringerMaterials PropertiesChemical shift
SolubilityDecomposes (NTP, 1992)
Boiling Point396 to 401 °F at 105 mmHg (NTP, 1992)
Melting Point167 °F (NTP, 1992)
Physical Description · 2 items

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)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

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 · 4 items

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

DOT LabelCorrosive
Fire HazardsFlash point data are not available for this chemical, but it is combustible. (NTP, 1992)
Health HazardsExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Hazards Summary · 1 item

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.

Chemistry & industry

Uses & manufacturing

UsesUsed as an intermediate for dye stuffs and other chemicals; [NTP]
U.S. Production2023: <50,000 lb
General Manufacturing InformationBenzoyl chloride, 4-nitro-: ACTIVE
Applications · 3 items

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

4-Nitrobenzoic acidPhosphorus oxitrichlorideThionyl chloride

Downstream products

7-Amino-3-[(5-methyl-1,3,4-thiadiazol-2-ylthio)methyl]-3-cephem-4-carboxylic AcidN-(p-Aminobenzoyl)glutamic acidP-NITROBENZOYL-L-GLUTAMIC ACID

Related reactions

905 records
New reaction record
HRID 1339 reaction equation
HRID 1339As reactantuspto-grants-1998_03
HRID 2446 reaction equation
HRID 2446As reactantuspto-grants-1998_03
HRID 3522 reaction equation
HRID 3522As reactantuspto-grants-1998_03
HRID 3526 reaction equation
HRID 3526As reactantuspto-grants-1998_03
HRID 3533 reaction equation
HRID 3533As reactantuspto-grants-1998_03
HRID 3538 reaction equation
HRID 3538As reactantuspto-grants-1998_03
HRID 3543 reaction equation
HRID 3543As reactantuspto-grants-1998_03
HRID 3548 reaction equation
HRID 3548As reactantuspto-grants-1998_03
Page 1 of 114

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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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)
Reactive GroupNitro, Nitroso, Nitrate, and Nitrite Compounds, Organic
Reactivity AlertsWater-Reactive
Reactivity Profile · 1 item

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].

Air and Water ReactionsUnstable in moist surroundings and should be kept in a tightly-closed container. React with water or steam (NTP, 1992).
Hazard Classes and CategoriesSkin Corr. 1B (100%)

Safety & protection

Fire FightingFires involving this compound should be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

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 · 1 item

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.

Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Personal Protective Equipment (PPE)MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves.

Toxicology

Adverse EffectsDermatotoxin - Skin burns.

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
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