o-Phenetidine

HCID 7203CAS 1321-31-9

Basic information

Standard SMILES
CCOc1ccccc1N
InChIKey
ULHFFAFDSSHFDA-UHFFFAOYSA-N
Molecular formula
C8H11NO
Average molar mass
137.18 g/mol
Monoisotopic mass
137.08406397

Names & identifiers

Preferred name
o-Phenetidine
IUPAC
2-ethoxyaniline
English name
o-Phenetidine
Molecular formula
C8H11NO
Molecular weight
137.18

Names & synonyms

o-Phenetidine2-ETHOXYANILINE94-70-22-Aminophenetoleo-EthoxyanilineBenzenamine, 2-ethoxy-2-Ethoxybenzenamineo-Aminophenetole2-Ethoxyphenylamine1-Amino-2-ethoxybenzeneETHOXYANILINECCRIS 4697
Show more names
o-HltSUBgt/SUBgtAKOS 91146Catechol-d42-EthoxyaniL
DTXSID5025863NSC 9818EINECS 202-356-4BRN 0637069AI3-09043I76155S2AAPHENETIDINE, O-NSC-9818

Database identifiers

CAS
1321-31-9、94-70-2
PubChem CID
7203
DTXSID
DTXSID5025863
ChEMBL
CHEMBL1525301
ChEBI
CHEBI:190954
UNII
I76155S2AA
EC Number
202-356-4
Nikkaji
J7.480B

Properties

Computed structural properties

XLogP
1.5
Topological polar surface area
35.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
10

Experimental & physicochemical properties

Density1.044 at 69.4 °F (NTP, 1992) - Denser than water; will sink
Solubility5 to 10 mg/mL at 76.1 °F (NTP, 1992)
Flash Pointgreater than 200 °F (NTP, 1992)
Boiling Point444 to 450 °F at 760 mmHg (NTP, 1992)
Melting Pointless than -4 °F (NTP, 1992)
Vapor Pressure · 2 items

1 mmHg at 152.6 °F ; 25 mmHg at 271 °F (NTP, 1992)

0.02 [mmHg]

Physicochemical properties

Melting point
-20 °C · -20 °C
Boiling point
231 · 231-233 °C(lit.)
Density
1.051 g/mL · 1.051 g/mL at 25 °C(lit.)
vapor pressure
1 mm · 1 mm Hg ( 67 °C)
refractive index
20 · n20/D 1.555(lit.)
Flash point
177 °F · 177 °F

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral];H311: Toxic in contact with skin [Danger Acute toxicity, dermal];H331: Toxic if inhaled [Danger Acute toxicity, inhalation];H373 **: May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]

P260, P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P319, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

Hazard information

Regulatory Information · 3 items

Chemical: Benzenamine, 2-ethoxy-

Status: Active Update: 08-05-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/10083

2-Aminophenetole: Does not have an individual approval but may be used under an appropriate group standard

DOT LabelPoison
Fire HazardsThis chemical is probably combustible. (NTP, 1992)
Health Hazards · 1 item

SYMPTOMS: Exposure to this compound may cause cyanosis, hypothermia, headache, drowsiness, vomiting, irritation of the alimentary tract and nephritis.;ACUTE/CHRONIC HAZARDS: This compound and its vapors may cause irritation of the eyes, skin and mucous membranes. (NTP, 1992)

Hazards Summary · 1 item

Toxic (vapor is also hazardous); Can be absorbed through skin; [Merck Index] Liquid or vapor may cause skin, eye, and mucous membrane irritation; Other symptoms may include cyanosis, headache, drowsiness, vomiting, alimentary tract irritation, and nephritis; [NTP] May induce methemoglobinemia; Harmful by ingestion; Toxic by inhalation and skin absorption; [Sigma-Aldrich MSDS] See p-Phenetidine.

Reactive GroupAmines, Aromatic

Safety & protection

Fire FightingFires involving this material can be controlled with 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.;SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.;INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.;INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

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 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.;STORAGE PRECAUTIONS: You should protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under refrigerated temperatures. STORE AWAY FROM SOURCES OF IGNITION. (NTP, 1992)

Isolation and Evacuation · 1 item

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:;IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.;SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.;FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)

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)

Toxicology

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect

Regulatory information

Regulatory Information · 3 items

Chemical: Benzenamine, 2-ethoxy-

Status: Active Update: 08-05-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/10083

2-Aminophenetole: Does not have an individual approval but may be used under an appropriate group standard

Safety data

F
8-10-23
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
2
tsca
TSCA listed
rtecs
SI6465300
ridadr
UN 2311 6.1/PG 3

Chemistry & industry

Uses & manufacturing

UsesUsed to make dyes; [Merck Index] Used to make fine chemicals; [ExPub: ECHA REACH Registrations]
General Manufacturing InformationBenzenamine, 2-ethoxy-: ACTIVE

Applications

Usesmanufacture of dyes.

General DescriptionReddish brown oily liquid.

Preparation methods

Preparationo-Phenetidine is produced from 2- ethoxynitrobenzene by reduction with iron or by catalytic hydrogenation in the presence of precious-metal catalysts or Raney nickel.

Additional notes

DefinitionChEBI: o-Phenetidine is a substituted aniline and an aromatic ether. It is used in the manufacture of acetophenetidin.

Related reactions

33 records

Linked notes

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