P-PHENETIDINE

p-Phenetidine is used as an intermediate in the synthesis of pharmaceutical drugs, dyes, and the sweetener dulcin.
p-Phenetidine is also used as a chemical intermediate in the manufacture of bucetin, phenacetin, ethoxyquin, and phenacaine.
p-Phenetidine is widely used as an intermediate in the synthesis of dyes, pharmaceutical actives and other fine chemicals.

CAS Number: 156-43-4
EC Number: 205-854-1
Molecular Formula: C₈H₁₁NO
Molecular Weight: 137.18 g/mol

SYNONYMS:
4-Ethoxyaniline, para-Phenetidine, 4-Aminophenetole, P-PHENETIDINE,4-ETHOXYANILINE,PARA PHENETIDINE,ethoxyaniline,Benzenamine, 4-ethoxy-,p-Aminophenolethylether,p-Phenetidin,4-Ethoxyanilin,P-ETHOXYANILINE,PARA-PHENETIDIN, p-Phenetidine, 4-ETHOXYANILINE, 156-43-4, Phenetidine, 4-Aminophenetole, p-Ethoxyaniline, p-Phenetidin, Benzenamine, 4-ethoxy-, p-Aminophenetole, Phenethidine, 1-Amino-4-ethoxybenzene, Aniline, p-ethoxy-, 4-Phenetidine, 4-Aminoethoxybenzene, Ethyl p-aminophenol, DTXSID0025864, 9TSL224ZSE, CP 5685, NSC-3116, DTXCID505864, CHEBI:85505, RefChem:858162, 205-855-5, Aminophenetole, 4-Ethoxybenzenamine, p-Aminofenetol, p-Fenetidin, 4-ETHOXY-ANILINE, NSC 3116, MFCD00007865, 4-Ethoxybenzeneamine, Aniline, 4-ethoxy-, 4-ethoxyphenylamine, p-Fenetidin [Czech], p-Aminofenetol [Czech], CAS-156-43-4, CCRIS 2878, p-aminophenyl ethyl ether, EINECS 205-855-5, UNII-9TSL224ZSE, BRN 0606666, phenetylamine, 4-ethoxyanilin, AI3-09042, p-aminoethoxybenzene, 4-ethoxy-phenylamine, Para-aminoethoxybenzene, (4-ethoxyphenyl) amine, (4-ethoxyphenyl)-amine, PHENETIDINE, P-, 4-Ethoxyaniline, 98%, 4-aminophenyl ethyl ether, P-ETHOXYPHENYLAMINE, EC 205-855-5, P-PHENETIDINE [MI], WLN: ZR DO2, SCHEMBL15703, 4-13-00-01017 (Beilstein Handbook Reference), MLS002454444, UN 2311 (Salt/Mix), BIDD:GT0388, SCHEMBL366829, CHEMBL250969, SCHEMBL7470630, SCHEMBL7993749, NSC3116, HMS3041D03, STR01492, Tox21_201946, Tox21_303334, EBC-12924, SBB040442, STK397546, AKOS000100572, FP26875, MSK406070-100M, VS-0323, NCGC00091785-01, NCGC00091785-02, NCGC00257138-01, NCGC00259495-01, PD055436, SMR001252219, NS00011443, P0090, ST45026313, EN300-17982, E78819, 4-Ethoxyaniline Solution in Methanol, 100ug/mL, F230478, Q27158608, Z57127438, F2190-0444, InChI=1/C8H11NO/c1-2-10-8-5-3-7(9)4-6-8/h3-6H,2,9H2,1H, 4-Ethoxybenzenamine, 1-Amino-4-ethoxybenzene, 4-Aminophenetole, 4-Ethoxyaniline, 4-Ethoxybenzenamine, 4-Ethoxyphenylamine, NSC 3116, p-Aminophenetole, p-Ethoxyaniline, p-Ethoxyphenylamine, p-Phenetidin, p-Phenetidine, 4-Phenetidine, 4-Ethoxyaniline, para-Phenetidine, p-Ethoxyaniline, 1-Amino-4-ethoxybenzene, Benzenamine, 4-ethoxy-, p-Aminophenetole

p-Phenetidine, also known as 4-phenetidine or 4-aminophenetole, belongs to the class of organic compounds known as aminophenyl ethers.
These are aromatic compounds that contain a phenol ether, which carries an amine group on the benzene ring.
p-Phenetidine is a secondary metabolite.

Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules.
In some cases, they are simply molecules that arise from the incomplete metabolism of other secondary metabolites.
p-Phenetidine belongs to the class of organic compounds known as aminophenyl ethers.

These are aromatic compounds that contain a phenol ether, which carries an amine group on the benzene ring.
Characterized by its high purity, p-Phenetidine functions as a chemical intermediate in pharmaceutical synthesis and conforms to industry-grade specifications.
p-Phenetidine (4-ethoxyaniline, C8H11NO) is an aromatic amine and one of three positional isomers of phenetidine.

p-Phenetidine is a colorless to pale yellow liquid (melting point 2.4–4°C, boiling point 250–255°C) with a density of 1.065 g/mL at 25°C and a water solubility of approximately 20 g/L at 20°C.
p-Phenetidine, also known as 4-Phenetidine, is an aromatic amine belonging to the aniline derivative family.

p-Phenetidine contains an amino group (-NH₂) and an ethoxy group (-OCH₂CH₃) positioned opposite each other on a benzene ring (para position).
p-Phenetidine has historically been an important intermediate in the manufacture of pharmaceuticals, dyes, pigments, and specialty organic chemicals.
p-Phenetidine (4-ethoxyaniline) is a chemical compound with the molecular formula C8H11NO.

p-Phenetidine is one of the three isomers of phenetidine.
p-Phenetidine is a colourless to light yellow clear liquid that turns red to brown on exposure to air and light.
p-Phenetidine is a versatile aromatic intermediate for dyes, pharmaceuticals, and fine chemicals.

p-Phenetidine (C₈H₁₁NO), also known as 4-ethoxyaniline, is a colourless to light yellow clear liquid that is sensitive to air and light and turns red to brown on exposure.
This aromatic amine, p-Phenetidine, is a valued chemical intermediate for a broad range of synthesis routes.
Its defined reactivity makes p-Phenetidine a reliable building block in multistage syntheses where consistent quality is essential.
Because of its sensitivity to air and light, p-Phenetidine benefits from appropriate handling and storage to preserve product quality.

 
USES and APPLICATIONS of P-PHENETIDINE:
p-Phenetidine has long been recognized as an important industrial intermediate in organic chemistry.
One of its most significant historical applications was the manufacture of phenacetin, where p-Phenetidine underwent acetylation to produce the pharmaceutical compound.
Although phenacetin has largely disappeared from modern medicine, the synthetic importance of p-Phenetidine remains well established.

p-Phenetidine is also widely used in the production of azo dyes and pigments, where its amino group undergoes diazotization and coupling reactions to create colored compounds used in textiles, inks, plastics, and coatings.
In specialty chemical manufacturing, p-Phenetidine serves as a precursor for antioxidants, stabilizers, laboratory reagents, and fine chemicals.

p-Phenetidine is also employed in research laboratories investigating aromatic amine chemistry, reaction mechanisms, and synthetic methodology.
Modern applications of p-Phenetidine are generally restricted to industrial manufacturing and laboratory use rather than direct consumer exposure.
One of p-Phenetidine's best-known historical applications was as a precursor in the synthesis of phenacetin, an analgesic and antipyretic drug that is no longer widely used because of safety concerns.

Today, p-Phenetidine remains valuable primarily as an industrial intermediate in controlled manufacturing processes rather than as a direct consumer product.
p-Phenetidine is used as an intermediate in the synthesis of pharmaceutical drugs, dyes, and the sweetener dulcin.
p-Phenetidine is a metabolite of the pharmaceutical drugs bucetin and phenacetin and of the preservative ethoxyquin.

p-Phenetidine is also used as a chemical intermediate in the manufacture of bucetin, phenacetin, ethoxyquin, and phenacaine.
This ethoxy-substituted aniline, p-Phenetidine, is widely used as an intermediate in the synthesis of dyes, pharmaceutical actives and other fine chemicals.
p-Phenetidine is used in the manufacture of acetophenetidin.
p-Phenetidine is used as intermediate for several materials also used as medicine, dye, food preservatives, feed additives and rubber age-resistant intermediates.

KEY FEATURES of P-PHENETIDINE:
Clear, colourless to light yellow liquid (darkens on air/light exposure)
Versatile aromatic intermediate based on 4-ethoxyaniline

Suitable for the manufacture of dyes, pharmaceuticals and fine chemicals
Defined, reproducible reactivity for multistage synthesis
Reliable quality with global supply support

BENEFITS AND FUNCTIONAL CHARACTERISTICS of P-PHENETIDINE:
p-Phenetidine possesses several characteristics that make it valuable in chemical manufacturing.
p-Phenetidine's amino group offers excellent synthetic versatility, allowing conversion into numerous derivatives through well-established reactions.
p-Phenetidine enhances reactivity during aromatic substitution while also influencing the physical properties of resulting compounds.

p-Phenetidine is relatively easy to purify because of its crystalline nature and moderate melting point.
p-Phenetidine also dissolves well in many organic solvents, simplifying industrial processing.
These characteristics have made p-Phenetidine an efficient intermediate for producing pharmaceuticals, dyes, pigments, and specialty organic chemicals.

CHEMICAL PROPERTIES of P-PHENETIDINE:
p-Phenetidine is a colourless liquid.
p-Phenetidine also reduces COX-1 and COX-2 expression in neutrophils.

p-Phenetidine is an aromatic ether that is aniline in which the hydrogen at position 4 is replaced by an ethoxy group.
p-Phenetidine is a hydrolysis metabolite of phenacetin.
p-Phenetidine is a colorless to dark red liquid.

p-Phenetidine is slightly soluble in water.
p-Phenetidine, or 4-ethoxyaniline, is an aromatic ether that is aniline in which the hydrogen at position 4 is replaced by an ethoxy group.
p-Phenetidine is a hydrolysis metabolite of phenacetin.

p-Phenetidine has a role as a drug metabolite.
p-Phenetidine is an aromatic ether, a substituted aniline and a primary amino compound.
p-Phenetidine (4-ethoxyaniline) is a chemical compound with the molecular formula C8H11NO.

ALTERNATIVE PARENTS of P-PHENETIDINE:     
*Phenoxy compounds 
*Aniline and substituted anilines 
*Alkyl aryl ethers 
*Primary amines 
*Organopnictogen compounds 
*Hydrocarbon derivatives 

SUBSTITUENTS of P-PHENETIDINE:     
*Aminophenyl ether
*Phenoxy compound
*Aniline or substituted anilines
*Alkyl aryl ether
*Monocyclic benzene moiety
*Ether
*Organic nitrogen compound
*Organic oxygen compound
*Organopnictogen compound
*Hydrocarbon derivative
*Primary amine
*Organooxygen compound
*Organonitrogen compound
*Amine
*Aromatic homomonocyclic compound

PHYSICAL AND CHEMICAL CHARACTERISTICS of P-PHENETIDINE:
p-Phenetidine is a moderately reactive aromatic amine whose amino group serves as the primary reactive site during chemical synthesis.
The ethoxy substituent, p-Phenetidine, increases electron density on the aromatic ring, making electrophilic substitution reactions easier than in unsubstituted aniline.
p-Phenetidine is only slightly soluble in water but dissolves readily in many common organic solvents, making it convenient for industrial organic synthesis.

Exposure to oxygen and light can slowly oxidize p-Phenetidine, causing yellow, brown, or reddish discoloration during storage.
Because of its moderate lipophilicity, p-Phenetidine shows greater affinity for organic phases than water, although it is considerably less hydrophobic than heavily chlorinated aromatic compounds.

CHEMICAL CHARACTERISTICS of P-PHENETIDINE:
p-Phenetidine belongs to the primary aromatic amines and exhibits chemical behavior typical of aniline derivatives.
The amino group participates readily in diazotization reactions, acylation, alkylation, and condensation reactions, while the ethoxy group activates the aromatic ring toward electrophilic substitution.
p-Phenetidine serves as an important synthetic building block because both functional groups can be selectively modified during multi-step organic synthesis.

PHYSICAL and CHEMICAL PROPERTIES of P-PHENETIDINE:
Chemical Name: p-Phenetidine
IUPAC Name: 4-Ethoxyaniline
Common Name: p-Phenetidine
CAS Number: 156-43-4
EC Number: 205-854-1
Molecular Formula: C₈H₁₁NO
Molecular Weight: 137.18 g/mol
Chemical formula: C8H11NO
Molar mass: 137.182 g·mol−1

Appearance: Colorless liquid; turns red to brown on exposure to air
Density: 1.07 g/mL
Melting point: 3 °C (37 °F; 276 K)
Boiling point: 254 °C (489 °F; 527 K)
Solubility in water: 20 g/L (20 °C)
Molecular Formula / Molecular Weight: C8H11NO = 137.18
Physical State (20 deg.C): Liquid
Storage Temperature: Refrigerated (0-10°C)
Store Under Inert Gas: Store under inert gas
Condition to Avoid: Light Sensitive,Air Sensitive,Heat Sensitive

CAS RN: 156-43-4
Reaxys Registry Number: 606666
PubChem Substance ID: 87574351
SDBS (AIST Spectral DB): 1657
Merck Index (14): 7228
MDL Number: MFCD00007865
CBNumber: CB0386144
Molecular Formula: C8H11NO
Molecular Weight: 137.18
MDL Number: MFCD00007865

MOL File: 156-43-4.mol
Melting point: 2-5 °C(lit.)
Boiling point: 250 °C(lit.)
Density: 1.065 g/mL at 25 °C(lit.)
vapor pressure: 2.93Pa at 25℃
refractive index: n20/D 1.559(lit.)
Flash point: 240 °F
storage temp.: 2-8°C
solubility: 20g/l

pka: 5.2(at 28℃)
form: A liquid
color: Clear Yellow
PH: 8 (1g/l, H2O, 20℃)
Water Solubility: practically insoluble
Sensitive: Air Sensitive
Merck: 14,7228
BRN: 606666
Dielectric constant: 7.3（21℃）

Stability: Stable, but light and air sensitive. 
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: 156-43-4(CAS DataBase Reference)
EWG's Food Scores: 2-6
FDA UNII: 9TSL224ZSE

NIST Chemistry Reference: 4-Ethoxyaniline(156-43-4)
EPA Substance Registry System: p-Phenetidine (156-43-4)
UNSPSC Code: 12352100
NACRES: NA.22
Molecular Weight: 137.18 g/mol
XLogP3: 1.2
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 2

Exact Mass: 137.084063974 Da
Monoisotopic Mass: 137.084063974 Da
Topological Polar Surface Area: 35.3 Ų
Heavy Atom Count: 10
Formal Charge: 0
Complexity: 87.3
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0

Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Appearance: White to slightly pink crystalline solid
Physical State: Solid
Color: White, off-white, or faint pink
Odor: Mild aromatic amine odor
Molecular Formula: C₈H₁₁NO
Molecular Weight: 137.18 g/mol
Melting Point: 57–60°C
Boiling Point: 253–255°C

Density: Approximately 1.06 g/cm³
Vapor Pressure: Low at room temperature
Water Solubility: Slightly soluble
Solubility in Organic Solvents: Soluble in ethanol, ether, benzene, chloroform, acetone, and methanol
Log Kow: Approximately 1.5–2.0
Flash Point: Approximately 120°C
Refractive Index: Around 1.56
pKa: Approximately 5.3
Stability: Stable under recommended storage conditions
Light Sensitivity: May gradually discolor upon prolonged exposure to light and air
Oxidation: Readily oxidizes in air, producing darker-colored products
Decomposition Products: Carbon oxides and nitrogen oxides

FIRST AID MEASURES of P-PHENETIDINE:
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation: 
Fresh air.
*In case of skin contact: 
Take off immediately all contaminated clothing. 
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact: 
Rinse out with plenty of water. 
Call in ophthalmologist. 
Remove contact lenses.
*If swallowed:
After swallowing: 
Immediately make victim drink water (two glasses at most). 
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available

ACCIDENTAL RELEASE MEASURES of P-PHENETIDINE:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains. 
Collect, bind, and pump off spills. 
Observe possible material restrictions. 
Take up dry. 
Dispose of properly. 
Clean up affected area.

FIRE FIGHTING MEASURES of P-PHENETIDINE:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2) 
Foam 
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.

EXPOSURE CONTROLS/PERSONAL PROTECTION of P-PHENETIDINE:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection. 
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A 
-Control of environmental exposure:
Do not let product enter drains.

HANDLING and STORAGE of P-PHENETIDINE:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed. 
Dry.

STABILITY and REACTIVITY of P-PHENETIDINE:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available

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