(4-Nitrophenyl)acetic acid (HCID 4661)

Overview

(4-nitrophenyl)acetic acid is a member of the class of phenylacetic acids that is phenylacetic acid in which the phenyl grup is substituted at the para- position by a nitro group. It is a member of phenylacetic acids and a C-nitro compound. It is functionally related to a phenylacetic acid. It is a conjugate acid of a (4-nitrophenyl)acetate.

Names & identifiers

Preferred name: (4-Nitrophenyl)acetic acid
IUPAC: 2-(4-nitrophenyl)acetic acid
English name: 4-Nitrophenylacetic acid
Molecular formula: C8H7NO4
Molecular weight: 181.15

Names & synonyms

4-Nitrophenylacetic acid104-03-02-(4-NITROPHENYL)ACETIC ACIDp-nitrophenylacetic acid(4-Nitrophenyl)acetic acid4-Nitrobenzeneacetic acidBenzeneacetic acid, 4-nitro-2-(p-Nitrophenyl)acetic acidAcetic acid, (p-nitrophenyl)-KLB4P626REDTXSID6059289NSC-5398

Show more names

4-NITRO-A-TOLUIC ACIDparaNitro Phenyl Acetic Acid4-NitrophenylaceticRARECHEM AL BO 0237-Nitro-a-toluic acid4-Nitrobenzencaceticp-Nitro-α-toluicacidNitrophenylacetic aci

CHEBI:40443RefChem:858156DTXCID8032837203-168-52-(4-Nitrophenoxy)acetic acidMFCD000073834-nitrophenylacetate(4-Nitro-phenyl)-acetic acid

Database identifiers

CAS: 104-03-0
PubChem CID: 4661
DTXSID: DTXSID6059289
ChEBI: CHEBI:40443
UNII: KLB4P626RE
EC Number: 203-168-5
Nikkaji: J10.498A、J714.504G

Properties

Computed structural properties

XLogP: 1.4
Topological polar surface area: 83.1 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 4
Rotatable bonds: 2
Heavy atoms: 13
Formal charge: 0
Complexity: 203

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Other Aromatics (Nitrogen)

DrugsPharmaceuticals -> Listed in ZINC15

SpringerMaterials PropertiesChemical shift

LogP1.54

Vapor Pressure0.0000291 [mmHg]

Physical DescriptionPale yellow solid; [Merck Index] Yellow powder; [Alfa Aesar MSDS]

Physicochemical properties

Melting point: 150 · 150-155 °C(lit.)
Boiling point: 314.24 °C · 314.24°C (rough estimate)
Density: 1.4283 · 1.4283 (rough estimate)
refractive index: 1.5468 · 1.5468 (estimate)
storage temp.: Sealed in dry,Room Temperature
form: Crystalline Powder
pka: 3.85 · 3.85(at 25℃)
color: Beige to yellow
PH: 2.98 at · 2.98 at 22.8℃ and 10g/L
Water Solubility: slightly soluble
Merck: 14 · 14,6621
BRN: 1911801 · 1911801
InChI: 1S/C8H7NO4/c10-8(11)5-6-1-3-7(4-2-6)9(12)13/h1-4H,5H2,(H,10,11)
InChIKey: YBADLXQNJCMBKR-UHFFFAOYSA-N
SMILES: OC(=O)Cc1ccc(cc1)[N+]([O-])=O
LogP: 0.3 at · 0.3 at 30℃ and pH7.72
CAS DataBase Reference: 104 · 104-03-0(CAS DataBase Reference)
FDA UNII: 4 P626RE · KLB4P626RE
EPA Substance Registry System: 4 · 4-Nitrophenylacetic acid (104-03-0)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 5 · GHS05,GHS09
Signal word: Danger
Hazard statements: 318 · H318-H410
Precautionary statements: 273 · P273-P280-P305+P351+P338-P391-P501
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36-37/39
RIDADR: 3077 · UN 3077 9 / PGIII
WGK Germany: 3 · 3
RTECS: 1130010 · AJ1130010
Hazard Note: Irritant
TSCA: TSCA listed
HS Code: 29163900 · 29163900
Storage Class: 13 · 13 - Non Combustible Solids
Hazard Classifications: 1 Aquatic · Aquatic Acute 1Aquatic Chronic 1Eye Dam. 1
Toxicity: 500 mg/disc · dnr-bcs 500 mg/disc MUREAV170,11,86
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (93.3%): 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 90 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Status: Active Update: 18-11-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/16775

Benzeneacetic acid, 4-nitro-: 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 Nitrobenzene and Phenylacetic acid.

Hazard Classes and CategoriesSkin Irrit. 2 (93.3%)

Safety data

wgk: 3
tsca: TSCA listed
rtecs: AJ1130010
ridadr: UN 3077 9 / PGIII
hs_code: 29163900
Toxicity: dnr-bcs 500 mg/disc MUREAV170,11,86
risk_code: 36/37/38
Signal word: Danger
Symbol(GHS): GHS05,GHS09
hazard_code: Xi
hazard_note: Irritant
safety_code: 26-36-37/39
Storage Class: 13 - Non Combustible Solids
Hazard statements: H318-H410
REACH Registrations: Active
Hazard Classifications: Aquatic Acute 1Aquatic Chronic 1Eye Dam. 1
Precautionary statements: P273-P280-P305+P351+P338-P391-P501

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationBenzeneacetic acid, 4-nitro-: ACTIVE

Applications

Uses(4-Nitrophenyl)acetic Acid used in the synthesis of 5,7-dimethyl-2-aryl-3H-pyrrolizin-3-ones which may act as angiogenesis inhibitors. Also used in the one step construction of amino-substituted squaraine dye.

UsesIntermediate for dyestuffs, pharmaceuticals, penicillin precursors, local anesthetics.