N-Isopropylaniline

HCID 13032

Basic information

CAS
768-52-5
Standard SMILES
CC(C)Nc1ccccc1
InChIKey
FRCFWPVMFJMNDP-UHFFFAOYSA-N
Molecular formula
C9H13N
Average molar mass
135.21 g/mol
Monoisotopic mass
135.10479942

Overview

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

Names & identifiers

Preferred name
N-Isopropylaniline
IUPAC
N-propan-2-ylaniline
English name
N-Isopropylaniline
Molecular formula
C9H13N
Molecular weight
135.21

Names & synonyms

N-ISOPROPYLANILINE768-52-5IsopropylanilineBenzenamine, N-(1-methylethyl)-Aniline, N-isopropyl-N-PhenylisopropylamineN-isopropyl anilineDTXSID7025479N-IPAI7Y9616F3RDTXCID005479N-(1-Methylethyl)-benzenamine
Show more names
N-IsopropylaniISO-PROPYLANILINEN-isopropylanilinN-isopropy anilinen-isopropyl-anilinN-isoproyl anilineTIMTEC-BB SBB007921
RefChem:163621CHEBI:21742212-196-7N-propan-2-ylanilineN-Isopropylaniline-d6isopropylphenylaminePhenylisopropylamineMFCD00026347

Database identifiers

CAS
768-52-5
PubChem CID
13032
DTXSID
DTXSID7025479
ChEMBL
CHEMBL1529910
UNII
I7Y9616F3R
EC Number
212-196-7
Nikkaji
J150.019H

Properties

Computed structural properties

XLogP
2.5
Topological polar surface area
12 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
2
Heavy atoms
10

Experimental & physicochemical properties

Chemical Classes · 2 items

Nitrogen Compounds -> Amines, Aromatic

Flammable agents - 2nd degree

SpringerMaterials Properties13C nuclear magnetic resonance spectrum
OdorSweet, aromatic odor.
Density · 5 items

0.93 at 60 °F (NIOSH, 2024) - Less dense than water; will float

0.9526 g/cu cm

Density (at 25 °C): 0.93 g/cm³

0.93 at 60 °F

(60 °F): 0.93

Color/Form · 2 items

Yellowish liquid

Clear, yellowish liquid.

Solubility · 3 items

less than 0.1 mg/mL at 70 °F (NTP, 1992)

Sol in alcohol, ether, acetone, benzene

Solubility in water: insoluble

Physicochemical properties

Melting point
-32 °C · -32°C
Boiling point
55 °C0.3 · 55 °C0.3 mm Hg(lit.)
Density
0.934 g/mL · 0.934 g/mL at 25 °C(lit.)
refractive index
20 · n20/D 1.539(lit.)
Flash point
185 °F · 185 °F
storage temp.
Keep in dark place,Inert atmosphere,Room temperature

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

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

P260, P261, P264, P264+P265, P270, P271, P280, P284, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P319, P320, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 82 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H227: Combustible liquid [Warning Flammable liquids]

Hazard information

Regulatory Information · 2 items

Chemical: Benzenamine, N-(1-methylethyl)-

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelPoison
Fire Hazards · 2 items

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.

Health HazardsExcerpt from NIOSH Pocket Guide for N-Isopropylaniline:
Hazards SummaryLike aniline and N,N-dimethylaniline, N-isopropylaniline can cause methemoglobinemia after skin and inhalation exposure in the workplace. [ACGIH] Can induce methemoglobinemia; May cause skin sensitization; [ICSC]
Reactive GroupAmines, Aromatic

Safety & protection

Fire Fighting · 2 items

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

Use powder, foam, carbon dioxide.

First Aid Measures · 4 items

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.

Rinse mouth. Do NOT induce vomiting. Refer immediately for medical attention.

First Aid · 2 items

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.

(General first aid procedures)

Safe StorageSeparated from food and feedstuffs. Keep in a well-ventilated room.
Exposure Control and Personal ProtectionBiological Exposure Indices (BEI) [ACGIH] - Methemoglobin in blood = 1.5% of hemoglobin during or at end of shift. [ACGIH]
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.

Toxicology

Target OrgansEyes, skin, respiratory system, blood, cardiovascular system, liver, kidneys
Environmental Fate · 3 items

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).

Food Survey ValuesN-Isopropylaniline was detected in onions grown in Canada after application of propachlor at concns of 0.01-1.2 mg/kg(1).
Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as primary toxic effect.
Exposure Routes · 2 items

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

Signs and Symptoms · 5 items

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

MAY BE ABSORBED! See Inhalation.

Redness. Pain.

Nausea. Further see Inhalation.

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

Regulatory information

TSCA Requirements · 2 items

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble in 51 FR 41329.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. N-Isopropylaniline is included on this list.

Safety data

OEB
B
OEL
TWA: 2 ppm (10 mg/m3) [skin]
wgk
3
tsca
TSCA listed
rtecs
BY4190000
ridadr
2810

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

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.

Uses & manufacturing

Uses · 2 items

Used in synthesis of dyes for acrylic fibers and other chemicals; [ACGIH]

Dyeing acrylic fibers; chem intermediate

General Manufacturing Information · 2 items

Benzenamine, N-(1-methylethyl)-: ACTIVE

N-Isopropylaniline is also a metabolite of the microbial degradation of the herbicide propachlor.

Applications · 3 items

UsesDyeing of acrylic fibers and as a chemical intermediate

UsesN-Isopropylaniline is a microbial metabolite of Propachlor (P757300), an acylanilide herbicide that is used to maintain crop protection from weeds. Propachlor is also known to induce Glutathione (G597951)-dependent cytotoxicity and sister chromatid exchanges in human cells.

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

Suppliers100 total

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]
武汉欣扬瑞和化学科技有限公司153-07155313 15307155313 · [email protected]
河北展药生物科技有限公司15369953316 +8615369953316 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]

Related reactions

420 records

Compound notes

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