4-Ethoxyaniline

HCID 9076CAS 156-43-4

Basic information

Standard SMILES
CCOc1ccc(N)cc1
InChIKey
IMPPGHMHELILKG-UHFFFAOYSA-N
Molecular formula
C8H11NO
Average molar mass
137.18 g/mol
Monoisotopic mass
137.08406397

Overview

P-phenetidine is a colorless to dark red liquid. (NTP, 1992)

Names & identifiers

Preferred name
4-Ethoxyaniline
IUPAC
4-ethoxyaniline
English name
Phenetidine
Molecular formula
C8H11NO
Molecular weight
137.18

Names & synonyms

p-Phenetidine4-ETHOXYANILINE156-43-4Phenetidine4-Aminophenetolep-Ethoxyanilinep-Phenetidinp-AminophenetoleBenzenamine, 4-ethoxy-Phenethidine1-Amino-4-ethoxybenzeneAniline, p-ethoxy-
Show more names
PARA PHENETIDINEethoxyanilinep-Aminophenolethylether4-EthoxyanilinPARA-PHENETIDIN
4-Phenetidine4-AminoethoxybenzeneEthyl p-aminophenolDTXSID00258649TSL224ZSECP 5685NSC-3116DTXCID505864

Database identifiers

CAS
156-43-4
PubChem CID
9076
DTXSID
DTXSID0025864
ChEMBL
CHEMBL250969
ChEBI
CHEBI:85505
UNII
9TSL224ZSE
EC Number
205-855-5
Nikkaji
J2.032J

Properties

Computed structural properties

XLogP
1.2
Topological polar surface area
35.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
10

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Amines, Aromatic
SpringerMaterials PropertiesBoiling point
LogP · 2 items

1.24

1.24

Density · 3 items

1.0652 at 61 °F (NTP, 1992) - Denser than water; will sink

1.1 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.0

Solubility · 2 items

5 to 10 mg/mL at 68 °F (NTP, 1992)

Solubility in water, g/100ml at 20 °C: 2 (moderate)

Flash Point · 2 items

240 °F (NTP, 1992)

120 °C c.c.

Physicochemical properties

Melting point
2 · 2-5 °C(lit.)
Boiling point
250 °C · 250 °C(lit.)
Density
1.065 g/mL · 1.065 g/mL at 25 °C(lit.)
vapor pressure
2.93 Pa · 2.93Pa at 25℃
refractive index
20 · n20/D 1.559(lit.)
Flash point
240 °F · 240 °F

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P318, P321, P330, P333+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P318, P321, P330, P333+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 4 items

Chemical: Benzenamine, 4-ethoxy-

Benzenamine, 4-ethoxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenamine, 4-ethoxy- 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: 08-05-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/10853

Phenetidine: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Benzenamine, 4-ethoxy-: Human health tier II assessment
DOT LabelPoison
Fire Hazards · 2 items

This compound is combustible. (NTP, 1992)

Combustible.

Health HazardsSYMPTOMS: Symptoms of exposure to this compound may include cyanosis, hypothermia, headache, drowsiness, vomiting, nephritis and irritation of the alimentary tract.
Hazards Summary · 1 item

An eye irritant; May induce methemoglobinemia; [ICSC] Causes methemoglobinemia in repeated-dose oral studies of rats; [RTECS] Toxic by ingestion, inhalation, and skin absorption; May cause contact irritation, cyanosis, hypothermia, headache, drowsiness, vomiting, nephritis, and alimentary tract irritation; [NTP] Case report of methemoglobinemia from occupational exposure; Sensitizing in 2 of 3 maximization tests of guinea pigs; Not a lung sensitizer in guinea pigs; Some evidence of skin sensitization in humans; [IUCLID] A strong eye irritant; May cause skin sensitization; Harmful by ingestion, inhalation, and skin absorption; Suspected mutagen; [Alfa Aesar MSDS] See m-Phenetidine. See p-Anisidine.

Safety & protection

Fire Fighting · 2 items

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Use powder, alcohol-resistant foam, water spray, carbon dioxide.

First Aid Measures · 4 items

Fresh air, rest.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

Rinse with plenty of water (remove contact lenses if easily possible).

Rinse mouth. Seek medical attention if you feel unwell.

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.

Safe StorageSeparated from strong oxidants and food and feedstuffs.
Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed 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.

Spillage Disposal · 1 item

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Toxicology

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
Exposure RoutesThe substance can be absorbed into the body by inhalation of its vapour and by ingestion.
Signs and SymptomsRedness.
ICSC Environmental DataEnvironmental effects from the substance have not been investigated adequately.
Toxicity DataLCLo (rat) = 487 mg/m3/4hr

Safety data

F
8-10
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
1
tsca
TSCA listed
rtecs
SI6465500
ridadr
UN 2311 (PHENETIDINES)

Chemistry & industry

Uses & manufacturing

UsesUsed to make acetophenetidine, phenocoll, dulcin, and dyes; [Merck Index] Used to make fine chemicals; [ExPub: ECHA REACH Registrations]
U.S. Production2023: 50,000 - <250,000 lb
Industry UsesOther
General Manufacturing Information · 2 items

Explosives Manufacturing

Benzenamine, 4-ethoxy-: ACTIVE

Applications

UsesA toxic metabolite of Phenacetin (P294580) which exhibits high renal toxicity. p-Phenetidine also reduced COX-1 and COX-2 expression in neutrophils.

General DescriptionColorless to dark red liquid.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
玉门市海鼎化工有限公司09376971818 13079324666 · [email protected]

Additional notes

DefinitionChEBI: An aromatic ether that is aniline in which the hydrogen at position 4 is replaced by an ethoxy group. It is a hydrolysis metabolite of phenacetin.

Related reactions

258 records

Linked notes

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