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Home > Encyclopedia > N-Isopropylaniline

N-Isopropylaniline

N-Isopropylaniline structure

N-Isopropylaniline 

structure
  • CAS No:

    768-52-5

  • Formula:

    C9H13N

  • Chemical Name:

    N-Isopropylaniline

  • Synonyms:

    Benzenamine,N-(1-methylethyl)-;Aniline,N-isopropyl-;N-(1-Methylethyl)benzenamine;N-Isopropylaniline;N-Phenylisopropylamine;N-Isopropylbenzenamine;Isopropylphenylamine;N-Phenyl-N-(1-methylethyl)amine;N-(1-Methylethyl)phenylamine

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

Clear light yellow liquid


N-isopropylaniline is a clear brown liquid. (NTP, 1992)|YELLOW LIQUID.|Clear, yellowish liquid with a sweet, aromatic odor.


N-isopropylaniline is a clear brown liquid. (NTP, 1992)

N-Isopropylaniline Basic Attributes

135.21

135.21

2205871

212-196-7

I7Y9616F3R

0909

2810

DTXSID7025479

Yellowish liquid|Clear, yellowish liquid.

29214990

Characteristics

12

2.5

N-isopropylaniline is a clear brown liquid. (NTP, 1992)

0.9526 g/cm3

-10 °C

203 °C @ Press: 760 Torr

185 °F

1.546

H2O: <0.01 g/100 mL at 21 ºC

Vapour pressure, Pa at 25°C: 4

Relative vapour density (air = 1): 4.7

Oral-Rat  LD50: 560 mg/kg; Abdominal cavity-mouse  LD50: 547 mg/kg

Combustible; Fire site decomposes toxic nitrogen oxide gas

Sweet, aromatic odor.

pKa = 5.30 at 25 °C (conjugate acid)

Insoluble in water.

Amines, Aromatic

N-ISOPROPYLANILINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Class IIIB Combustible Liquid: Fl.P. at or above 200°F.

Safety Information

III

6.1(b)

2810

3

22-23-36/37/38

26-36-45-7/9

BY4190000

T

Storeroom low temperature, ventilated, dry; fireproof; stored separately from oxidants, strong acids

P260-P284-P305 + P351 + P338-P310

H302-H315-H319-H330-H335

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

This chemical is combustible. (NTP, 1992)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 82 °C explosive vapour/air mixtures may be formed.|Flammable - 2nd degree

|Danger|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P271, P280, P284, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P320, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 77 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H227: Combustible liquid [Warning Flammable liquids]|P201, P202, P210, P260, P261, P264, P270, P271, P280, P281, P301+P312, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P314, P330, P337+P313, P370+P378, P403+P233, P403+P235, P405, and P501

Fires involving this compound should be controlled with a dry chemical, carbon dioxide or halon extinguisher. (NTP, 1992)|Use powder, foam, carbon dioxide.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an 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, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck 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, 2016)

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. STORAGE PRECAUTIONS: You should keep this container tightly closed under an inert atmosphere and store it under refrigerated conditions. (NTP, 1992)

Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: No recommendation is made specifying the need for the worker to change clothing after the work shift. Provide: Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.] (NIOSH, 2016)|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.]|(See protection codes)

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|The worker should immediately wash the skin when it becomes contaminated.|Work clothing that becomes wet or significantly contaminated should be removed and replaced.

Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 2 ppm (10 mg/cu m), skin.

Personal protection: complete protective clothing including self-contained breathing apparatus. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Separated from food and feedstuffs. Keep in a well-ventilated room.

A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C.

The substance is mildly irritating to the eyes and skin. The substance may cause effects on the blood. This may result in the formation of methaemoglobin. The effects may be delayed. Medical observation is indicated.

Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the blood. This may result in the formation of methaemoglobin.

NO open flames. Above 82 °C use a closed system and ventilation.

PREVENT GENERATION OF MISTS! STRICT HYGIENE! IN ALL CASES CONSULT A DOCTOR!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear face shield or eye protection in combination with breathing protection.

N-Isopropylaniline was detected in soils in Canada after application of propachlor at concns of 0.34-2.2 mg/kg(1).

Toxicity

moderately toxic

LD50 Rat oral 560 mg/kg|LC50 Rat ihl 218 ppm/4 hr|LD50 Rabbit skin 3550 mg/kg

N-Isopropylaniline's production and use as a dye and chemical intermediate(1) may result in its release to the environment through various waste streams(SRC). N-Isopropylaniline is also a metabolite of the microbial degradation of the herbicide propachlor(2).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 566(SRC), determined from an estimated log Kow of 2.53(2) and a regression-derived equation(3), indicates that N-isopropylaniline is expected to have low mobility in soil(SRC). A pKa value of 5.3(4) suggests that N-isopropylaniline will partially exist in the protonated form in moist soils and the protonated form of N-isopropylaniline is expected to bind strongly to soil surfaces(SRC). Volatilization of N-isopropylaniline from moist soil surfaces is expected to be an important fate process for the neutral species(SRC) given an estimated Henry's Law constant of 7.4X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(5). N-Isopropylaniline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.44 mm Hg(SRC), determined from a fragment constant method(6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 566(SRC), determined from an estimated log Kow of 2.53(2) and a regression-derived equation(3), indicates that N-isopropylaniline is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 7.4X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 4 and 47 days, respectively(SRC). A pKa of 5.3(5) suggests that N-isopropylaniline will partially exist in the protonated form in aqueous environments and the protonated form of N-isopropylaniline is not expected to volatilize from water. According to a classification scheme(6), an estimated BCF of 17(SRC), from an estimated log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low.|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), N-isopropylaniline, which has an estimated vapor pressure of 0.44 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase N-isopropylaniline is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 6 hours(SRC), calculated from its estimated rate constant of 6.1X10-11 cu cm/molecule-sec at 25 °C(3) determined using a structure estimation method(3).

The rate constant for the vapor-phase reaction of N-isopropylaniline with photochemically-produced hydroxyl radicals has been estimated as 6.1X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 6 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Aniline has UV absorption which extends beyond 290 nm(2). Therefore, it is likely that N-isopropylaniline will also absorb light in the environmental UV spectrum and potentially undergo direct photolysis in the environment(SRC). A pKa value of 5.3(3) suggests that N-isopropylaniline will partially exist in the protonated form in moist soil and water(SRC).

An estimated BCF of 18 was calculated for N-isopropylaniline(SRC), using an estimated log Kow of 2.53(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

The Koc of N-isopropylaniline is estimated as 566(SRC), using an estimated log Kow of 2.53(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that N-isopropylaniline is expected to have low mobility in soil. A pKa value of 5.3(4) suggests that N-isopropylaniline will partially exist in the protonated form in moist soils and the protonated form of N-isopropylaniline is expected to bind strongly to soil surfaces(SRC).

The Henry's Law constant for N-isopropylaniline is estimated as 7.4X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that N-isopropylaniline is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 4 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 47 days(SRC). N-Isopropylaniline's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). N-Isopropylaniline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.44 mm Hg(SRC), determined from a fragment constant method(3). A pKa value of 5.3(4), suggests that N-isopropylaniline will partially exist in the protonated form in aqueous environments and the protonated form of N-isopropylaniline is not expected to volatilize from water or moist soil surfaces(SRC).

N-Isopropylaniline was detected in onions grown in Canada after application of propachlor at concns of 0.01-1.2 mg/kg(1).

Occupational exposure to N-isopropylaniline may occur through inhalation and dermal contact with this compound at workplaces where N-isopropylaniline is produced or used. (SRC)

Drug Information

THE N-ISOPROPYLANILINE METABOLITES AFTER IP INJECTION OF (14)C-LABELED N-ISOPROPYLANILINE-HCL WERE ANALYZED CHROMATOGRAPHICALLY IN COMBINED URINE SAMPLES FROM FOUR RATS EVERY 24 HR FOR A TOTAL OF 96 HR. 24 HR URINE SAMPLES CONTAINED NO METABOLITES. 4-HYDROXY-N-ISOPROPYLANILINE & P-AMINOPHENOL CONSTITUTING THE MAJOR & MINOR METABOLITE WITH 61 & 8, RESPECTIVELY. N-PHENYL-2-AMINOPROPIONIC ACID, A TRACE METABOLITE, REPRESENTED LESS THAN 1 OF THE TOTAL RADIOACTIVITY.

Exposure Routes: inhalation, skin absorption, ingestion, skin and/or eye contact Symptoms: Irritation eyes, skin; headache, lassitude (weakness, exhaustion), dizziness; cyanosis; ataxia; dyspnea (breathing difficulty) on effort; tachycardia; methemoglobinemia Target Organs: Eyes, skin, respiratory system, blood, cardiovascular system, liver, kidneys (NIOSH, 2016)

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. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. 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: 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. Generally, the induction of vomiting is NOT recommended outside of a physician's care due to the risk of aspirating the chemical into the victim's lungs. However, if the victim is conscious and not convulsing and if medical help is not readily available, consider the risk of inducing vomiting because of the high toxicity of the chemical ingested. Ipecac syrup or salt water may be used in such an emergency. IMMEDIATELY transport the victim to a hospital. 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)|(See procedures)


Fresh air, rest. Administration of oxygen may be needed. Refer immediately for medical attention.


Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer immediately for medical attention.


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aniline and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious. Monitor cardiac rhythm and treat arrhythmias as necessary... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation... . /Aniline and related compounds/

N-isopropylaniline

The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.|inhalation, skin absorption, ingestion, skin and/or eye contact

irritation eyes, skin; headache, lassitude (weakness, exhaustion), dizziness; cyanosis; ataxia; dyspnea (breathing difficulty) on effort; tachycardia; methemoglobinemia


Blue lips, fingernails and skin. Dizziness. Headache. Laboured breathing.


MAY BE ABSORBED! See Inhalation.


Redness. Pain.

Eyes, skin, respiratory system, blood, cardiovascular system, liver, kidneys

N-Isopropylaniline Use and Manufacturing

Uses

Used as pharmaceutical intermediate

Benzenamine, N-(1-methylethyl)-: ACTIVE|N-Isopropylaniline is also a metabolite of the microbial degradation of the herbicide propachlor.

Fire Hazards -> Flammable - 2nd degree

Computed Properties

Molecular Weight:135.21
XLogP3:2.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:135.104799419
Monoisotopic Mass:135.104799419
Topological Polar Surface Area:12
Heavy Atom Count:10
Complexity:82.7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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