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2-Nitrobenzoic acid

HCID 11087
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
552-16-9
Standard SMILES
O=C(O)c1ccccc1[N+](=O)[O-]
InChIKey
SLAMLWHELXOEJZ-UHFFFAOYSA-N
Molecular formula
C7H5NO4
Average molar mass
167.12 g/mol
Monoisotopic mass
167.02185764

Overview

Yellowish white crystals with an intensely sweet taste. (NTP, 1992)

Names & identifiers

Preferred name
2-Nitrobenzoic acid
IUPAC
2-nitrobenzoic acid
English name
2-Nitrobenzoic acid
Molecular formula
C7H5NO4
Molecular weight
167.12

Names & synonyms

2-NITROBENZOIC ACID552-16-9o-Nitrobenzoic acidBenzoic acid, 2-nitro-DTXSID5025738ortho-nitrobenzoic acidCCRIS 2334S6S4653K7ZNSC 9576EINECS 209-004-9DTXCID005738AI3-08821
Show more names
2-nitrobenzoic2-NITRODRACYLIC ACID2-Nitrobenzoicacid,95%Nitrobenzoic aci2-nitro-benzoicacio-Nitrobenaoicacido-nitro-benzoicaciRARECHEM AL BO 0202ORTHO-NITROBENZOATE
NSC-9576UNII-S6S4653K7ZNITROBENZOIC ACID, 2-CCRIS-2334CHEBI:25620oNitrobenzoic acidoCarboxynitrobenzeneNitrobenzoicacid, o

Database identifiers

CAS
552-16-9
PubChem CID
11087
DTXSID
DTXSID5025738
ChEMBL
CHEMBL114719
ChEBI
CHEBI:25620
UNII
S6S4653K7Z
EC Number
209-004-9
Nikkaji
J1.389.648H、J1.613F

Properties

Computed structural properties

XLogP
1.5
Topological polar surface area
83.1 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
1
Heavy atoms
12
Formal charge
0
Complexity
198

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Nitrobenzoic Acids
SpringerMaterials PropertiesChemical shift
LogP1.46
Density1.575 at 68 °F (NTP, 1992) - Denser than water; will sink
Solubilityless than 1 mg/mL at 73 °F (NTP, 1992)
Melting Point297 to 298 °F (NTP, 1992)
Vapor Pressure0.0000714 [mmHg]
Physical Description · 2 items

Yellowish white crystals with an intensely sweet taste. (NTP, 1992)

Yellowish-white solid; [CAMEO] Off-white powder; [Alfa Aesar MSDS]

Ionization Efficiency · 6 items

Positive

1.57

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

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

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 70 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Chemical: Benzoic acid, 2-nitro-

Benzoic acid, 2-nitro-: Does not have an individual approval but may be used under an appropriate group standard

Fire HazardsFlash point data concerning this compound are not available, however, it is probably combustible. (NTP, 1992)
Health HazardsACUTE/CHRONIC HAZARDS: When this compound is heated to decomposition it emits very toxic fumes. (NTP, 1992)
Hazards SummaryA skin and strong eye irritant; [Alfa Aesar MSDS] See Benzoic acid and Nitrobenzene. See 3-Nitrobenzoic acid.
Reactive GroupAcids, Carboxylic
Reactivity ProfileO-NITROBENZOIC ACID is incompatible with strong oxidizing agents. Also incompatible with strong bases. May react with cyanides (NTP, 1992).
Air and Water ReactionsInsoluble in water.
Hazard Classes and Categories

Chemistry & industry

Uses & manufacturing

UsesUsed as a reagent for protection of amine groups and in organic synthesis; [NTP]
General Manufacturing InformationBenzoic acid, 2-nitro-: ACTIVE
Applications · 3 items

UsesNH2-protecting reagent.

Uses2-Nitrobenzoic Acid is used as a reagent in the synthesis of several organic compounds including that of novel triazoles and a tetrazole of escitalopram which act as cholinesterase inhibitors. It is also used in the one pot synthesis of 1,4-disubstituted 1,2,3-triazoles.

General DescriptionYellowish white crystals with an intensely sweet taste.

Upstream & downstream products

Upstream raw materials

2-Nitrotoluene

Downstream products

Methyl anthranilate2-Nitrobenzoyl chlorideFomesafenBenzoic acid, 2-nitro-, 1,1'-anhydrideN-(2-Amino-4-chlorophenyl)anthranilic acid1,2-Dihydro-4-hydroxy-2-oxo-3-quinolinecarboxylic acid ethyl ester2-Nitrophenyl isocyanate

Related reactions

66 records
New reaction record
HRID 2431 reaction equation
HRID 2431As reactantuspto-grants-1998_03
HRID 9752 reaction equation
HRID 9752As productuspto-grants-2006_08
HRID 93827 reaction equation
HRID 93827As productTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 109326 reaction equation
HRID 109326As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 125502 reaction equation
HRID 125502As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 176733 reaction equation
HRID 176733As reactantTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 203610 reaction equation
HRID 203610As reactantTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 221294 reaction equation
HRID 221294As reactantuspto-grants-2012_06
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Compound notes

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Physicochemical properties

Melting point
146 · 146-148 °C(lit.)
Boiling point
295.67 °C · 295.67°C (rough estimate)
Density
1 · 1,58 g/cm3
refractive index
1.628 · 1.6280 (estimate)
storage temp.
Sealed in dry,Room Temperature
solubility
7.8 g/l · 7.8g/l
form
Fine Powder
pka
2.16 · 2.16(at 18℃)
color
Off-white
Specific Gravity
1.58 · 1.58
Water Solubility
6.8 g/L · 6.8 g/L
Merck
14 · 14,6588
BRN
1910632 · 1910632
Stability
Stable. Incompatible with strong oxidizing agents, strong bases.
InChI
1S/C7H5NO4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4H,(H,9,10)
InChIKey
SLAMLWHELXOEJZ-UHFFFAOYSA-N
SMILES
OC(=O)c1ccccc1[N+]([O-])=O
CAS DataBase Reference
552 · 552-16-9(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
6 S4653K7Z · S6S4653K7Z
NIST Chemistry Reference
2 · Benzoic acid, 2-nitro-(552-16-9)
EPA Substance Registry System
o-Nitrobenzoic acid (552-16-9)
UNSPSC Code
12352100 · 12352100
NACRES
22 · NA.22
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
Hazard Codes
Xi,Xn
Risk Statements
36 · 36/37/38-68-22
Safety Statements
26 · 26-36/37/39
WGK Germany
3 · 3
RTECS
5050000 · DH5050000
TSCA
TSCA listed
HS Code
29163900 · 29163900
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
Skin Irrit. 2 (100%)

Safety & protection

Fire FightingFires involving this compound can be controlled using 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: 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 ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 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 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) · 1 item

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

wgk
3
tsca
TSCA listed
rtecs
DH5050000
hs_code
29163900
risk_code
36/37/38-68-22
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi,Xn
safety_code
26-36/37/39
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
4-Hydroxyquinoline-3-carboxylic acid
Methyl 2-nitrobenzoate
2,5-diaminobenzoic acid
2,2'-Dinitrodibenzyl
4-Oxo-1,4-dihydroquinoline-3-carboxylic acid

Additional notes

DefinitionChEBI: A nitrobenzoic acid carrying the nitro substituent at position 2.