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4-Ethoxyaniline

HCID 9076
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
156-43-4
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 propertiesFilling in

XLogP
1.2
Topological polar surface area
35.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
10
Formal charge
0
Complexity
87.3

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.

Boiling Point · 2 items

482 °F at 760 mmHg (NTP, 1992)

253-255 °C

Melting Point · 2 items

36 to 39 °F (NTP, 1992)

2.4 °C

Vapor Density

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 · 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)

REACH registered substance: p-phenetidine (EC: 205-855-5)

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.

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.

Upstream & downstream products

Upstream raw materials

4-ChloronitrobenzeneEthanolSodium sulfide4-NITROPHENETOLE4-AminophenolMethanolSodium hydroxide

Downstream products

AethoxidumAcid Blue 83Acid Blue 90N-(4-Ethoxyphenyl)-3-hydroxy-2-naphthamide

Related reactions

258 records
New reaction record
HRID 1814 reaction equation
HRID 1814As reactantuspto-grants-1998_03
HRID 2197 reaction equation
HRID 2197As reactantuspto-grants-1998_03
HRID 3205 reaction equation
HRID 3205As reactantuspto-grants-1998_03
HRID 53250 reaction equation
HRID 53250As reactantuspto-grants-1997_04
HRID 71291 reaction equation
HRID 71291As reactantuspto-grants-2014_09
HRID 71351 reaction equation
HRID 71351As reactantuspto-grants-2014_09
HRID 71381 reaction equation
HRID 71381As reactantuspto-grants-2014_09
HRID 71489 reaction equation
HRID 71489As reactantuspto-grants-2014_09
Page 1 of 33

Compound notes

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· 2 items

4.73 (NTP, 1992) - Heavier than air; will sink (Relative to Air)

Relative vapor density (air = 1): 4.7

Vapor Pressure · 3 items

3.48 mmHg at 77 °F (NTP, 1992)

0.01 [mmHg]

Vapor pressure, Pa at 50 °C: 10

Physical Description · 4 items

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

CBI

Colorless liquid; Turns red to brown on air and light exposure; [Merck Index] Brown liquid with an unpleasant odor; [Alfa Aesar MSDS]

COLOURLESS LIQUID. TURNS DARK RED ON EXPOSURE TO AIR AND LIGHT.

Collision Cross Section139.8 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID0025864]

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
storage temp.
2 · 2-8°C
solubility
20 g/l · 20g/l
pka
5.2 · 5.2(at 28℃)
form
A liquid
color
Clear Yellow
PH
8 · 8 (1g/l, H2O, 20℃)
Water Solubility
practically insoluble
Sensitive
Air Sensitive
Merck
14 · 14,7228
BRN
606666 · 606666
Dielectric constant
7.3 · 7.3(21℃)
Stability
Stable, but light and air sensitive. Combustible. Incompatible with strong oxidizing agents.
Cosmetics Ingredients Functions
HAIR DYEING
InChI
1S/C8H11NO/c1-2-10-8-5-3-7(9)4-6-8/h3-6H,2,9H2,1H3
InChIKey
IMPPGHMHELILKG-UHFFFAOYSA-N
SMILES
CCOc1ccc(N)cc1
CAS DataBase Reference
156 · 156-43-4(CAS DataBase Reference)
EWG's Food Scores
2 · 2-6
FDA UNII
9 TSL224ZSE · 9TSL224ZSE
NIST Chemistry Reference
4 · 4-Ethoxyaniline(156-43-4)
EPA Substance Registry System
p-Phenetidine (156-43-4)
UNSPSC Code
12352100 · 12352100
NACRES
22 · NA.22
Symbol(GHS)
6 · GHS06,GHS08,GHS09
Signal word
Danger
Hazard statements
331 · H331-H302-H313-H316-H319-H361-H372-H317-H341-H411
Precautionary statements
501 · P501-P273-P272-P260-P270-P202-P201-P271-P264-P280-P302+P352-P312-P391-P337+P313-P305+P351+P338-P362+P364-P333+P313-P301+P312+P330-P304+P340+P311-P403+P233-P405
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes
T,Xi,Xn
Risk Statements
23 · 23/24/25-33-68-43-36-20/21/22
Safety Statements
28 · 28-36/37-45-46
RIDADR
2311 · UN 2311 (PHENETIDINES)
WGK Germany
1 · 1
RTECS
6465500 · SI6465500
F
8 · 8-10
Hazard Note
Irritant
TSCA
TSCA listed
HazardClass
6.1 · 6.1
PackingGroup
III
HS Code
29222200 · 29222200
Storage Class
6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Muta. 2Skin Sens. 1
Toxicity
50 orl-rat: · LD50 orl-rat: 580 mg/kg GISAAA 35(8),28,70
REACH Registrations
Active
Limited Quantities
5 L · 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
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.

Reactive GroupEthers
EC ClassificationSymbol: Xn; R: 20/21/22-36-43-68; S: (2)-36/37-46
UN ClassificationUN Hazard Class: 6.1; UN Pack Group: III
Reactivity ProfileP-PHENETIDINE reacts vigorously with powerful oxidizers.
Chemical DangersOn combustion, forms nitrogen oxides. Reacts with strong oxidants.
Physical DangersThe vapour mixes well with air, explosive mixtures are easily formed.

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.

Isolation and EvacuationExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Eye PreventionWear safety goggles.
Fire PreventionNO open flames.
Inhalation RiskNo indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
Skin PreventionProtective gloves.
Ingestion PreventionDo not eat, drink, or smoke during work.

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)
hs_code
29222200
Toxicity
LD50 orl-rat: 580 mg/kg GISAAA 35(8),28,70
risk_code
23/24/25-33-68-43-36-20/21/22
Signal word
Danger
Symbol(GHS)
GHS06,GHS08,GHS09
hazard_code
T,Xi,Xn
hazard_note
Irritant
safety_code
28-36/37-45-46
hazard_class
6.1
Storage Class
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
packing_group
III
Hazard statements
H331-H302-H313-H316-H319-H361-H372-H317-H341-H411
Limited Quantities
5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
REACH Registrations
Active
Hazard Classifications
Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Muta. 2Skin Sens. 1
Precautionary statements
P501-P273-P272-P260-P270-P202-P201-P271-P264-P280-P302+P352-P312-P391-P337+P313-P305+P351+P338-P362+P364-P333+P313-P301+P312+P330-P304+P340+P311-P403+P233-P405
Ethoxyquin
Phenacetin
2-((4-ETHOXYPHENYL)AMINO)-4-NITROBENZOIC ACID
H-GLU-LYS-OH
4-ETHOXYBENZONITRILE
2-METHYL-6-ETHOXYQUINOLINE
2-Amino-6-ethoxybenzothiazole
Acid Blue 83
Acid Blue 90
N-(4-Ethoxyphenyl)-3-hydroxy-2-naphthamide
Sulfanilamide, N4-(p-ethoxyphenyl)-3-nitro-
sodium hydrogen -2-ethoxy-5-[[4-[[4-[(4-ethoxy-3-sulphonatophenyl)amino]phenyl]-(1H-indol-3-yl-1-methyl-2-phenyl)methylene]-2,5-cyclohexadien-1-ylidene]amino]benzenesulphonate
Solvent Red 3
Mordant Yellow 38

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.