2,2,4-Trimethyl-1,2-dihydroquinoline

HCID 8981

Basic information

CAS
147-47-7
Standard SMILES
CC1=CC(C)(C)Nc2ccccc21
InChIKey
ZNRLMGFXSPUZNR-UHFFFAOYSA-N
Molecular formula
C12H15N
Average molar mass
173.25 g/mol
Monoisotopic mass
173.12044948

Overview

1,2-dihydro-2,2,4-trimethylquinoline appears as dark cloudy copper-colored or yellow liquid. Odorless. (NTP, 1992)

Names & identifiers

Preferred name
2,2,4-Trimethyl-1,2-dihydroquinoline
IUPAC
2,2,4-trimethyl-1H-quinoline
English name
1,2-Dihydro-2,2,4-trimethylquinoline
Molecular formula
C12H15N
Molecular weight
173.25

Names & synonyms

2,2,4-Trimethyl-1,2-dihydroquinoline147-47-71,2-DIHYDRO-2,2,4-TRIMETHYLQUINOLINEFlectol H2,2,4-trimethyl-1H-quinolineQuinoline, 1,2-dihydro-2,2,4-trimethyl-Flectol pastillesFlectol APolnox RVulkanox HS/LGVulkanox HS/powderNCI-C60902
Show more names
Acetone anilRALOX TMQ MonomerQuinoline,1,2-dihydro2,2,4-Arimethyl-1H-quinoline1,2-hydro-2,2,4-trimethylquinoline
Acetone anil (quinoline derivative)Trimethyl dihydroquinolineTrimethyl-1,2-dihydroquinoline2,2,4-Trimethyl-1,2-dihydroquinoneDTXSID0025070Acetone anil (quinoline deriv.)ANTIOXIDANT FR-SBNSC-4175

Database identifiers

CAS
147-47-7、26780-96-1
PubChem CID
8981
DTXSID
DTXSID0025070
ChEMBL
CHEMBL294154
UNII
0553M374Q3
EC Number
205-688-8
Nikkaji
J2.551H

Properties

Computed structural properties

XLogP
2.8
Topological polar surface area
12 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
13

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Quinolines
Density · 2 items

1.03 at 77 °F (NTP, 1992) - Denser than water; will sink

1.08 @ 25 °C

Color/FormLIGHT TAN POWDER
Solubilityless than 0.1 mg/mL at 66 °F (NTP, 1992)
Flash Point · 2 items

214 °F (NTP, 1992)

101 °C

Boiling Point491 to 500 °F at 743 mmHg (NTP, 1992)

Physicochemical properties

Melting point
120 °C · 120 °C
Boiling point
293.92 °C · 293.92°C (rough estimate)
Density
1.0215 · 1.0215 (rough estimate)
refractive index
1.568 · 1.5680 (estimate)
storage temp.
2 · 2-8°C(protect from light)
solubility
Chloroform (Soluble), DMSO (Slightly), Ethyl Acetate (Slightly)

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 13.2% (14 of 106) of reports.

Warning

H302 (86.8%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 106 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Chemical: Quinoline, 1,2-dihydro-2,2,4-trimethyl-

Quinoline, 1,2-dihydro-2,2,4-trimethyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Fire HazardsThis chemical is combustible. (NTP, 1992)
Fire PotentialSLIGHT
Health HazardsACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes of nitrogen oxides. (NTP, 1992)
Hazards Summary · 1 item

Weight loss, decreased hemoglobin, CNS depression, and abnormal liver function observed in rats dosed long-term by intragastric tube; [HSDB] No evidence of carcinogenicity in mice or female rats and some evidence of carcinogenicity in male rats in 2-year dermal studies; [NTP] Causes thymus and liver changes and weight loss in 13-week intermittent dermal study of rats; Causes changes in urine and serum composition and weight loss in 21-week intermittent inhalation study of rats; Causes impaired liver function in 30-day intermittent oral study of rats; [RTECS] May cause skin sensitization, eye irritation, and respiratory tract irritation; [Redox MSDS] Search for 147-47-7 AND (sensitizer OR sensitization OR allergic): no results; [PubMed]

Reactive GroupAmines, Phosphines, and Pyridines

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.

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.

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 EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Ongoing Test Status · 1 item

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=147-47-7]

Carcinogen Classification · 6 items

1,2-Dihydro-2,2,4-Trimethylquinoline (Monomer)

TR-456: Toxicology and Carcinogenesis Studies of 1,2-Dihydro-2,2,4-Trimethylquinoline (CASRN 147-47-7) in F344/N Rats and B6C3F1 Mice (Dermal Studies) and the Initiation/Promotion (Dermal Study) in Female Sencar Mice (1997 )

06/20/95

Some Evidence

No Evidence

No Evidence

Non-Human Toxicity Excerpts · 3 items

LONG-TERM INTRAGASTRIC ADMINISTRATION OF 1,2-DIHYDRO-2,2,4-TRIMETHYLQUINOLINE TO RATS DECREASED BODY WEIGHT, DEPRESSED THE NERVOUS SYSTEM, AND DISRUPTED LIVER FUNCTION. IT ALSO DECREASED THE AMOUNT OF HEMOGLOBIN & THE NUMBER OF ERYTHROCYTES IN THE BLOOD.

1,2-Dihydro-2,2,4-trimethylquinoline (DTQ) was evaluated for mutagenicity in the Salmonella/microsome preincubation assay using a standard protocol approved by the National Toxicology Program. DTQ was tested at doses of 0, 1, 3.3, 10, 33, 100, and 220 ug/plate in four Salmonella typhimurium strains (TA98, TA100, TA1535, and TA1537) in the presence and absence of Aroclor-induced rat or hamster liver S9. DTQ was negative in these tests and the highest ineffective dose level tested in all four Salmonella tester strains without slight or total clearing of the background lawn was 33 ug/plate.

... CONCLUSIONS: Under the conditions of these 2 yr dermal studies, there was some evidence of carcinogenic activity of 1,2-dihydro-2,2,4-trimethylquinoline in male F344/N rats, based on increased incidences of renal tubule adenoma and adenoma or carcinoma (combined). There was no evidence of carcinogenic activity of 1,2-dihydro-2,2,4-trimethylquinoline in female F344/N rats receiving 36, 60, or 100 mg/kg, or in male or female B6C3Fl mice receiving 3.6, 6, or 10 mg/kg.

National Toxicology Program Studies · 1 item

Male and female F344/N rats and B6C3F1 mice received topical applications of 1,2-dihydro-2,2,4-trimethylquinoline in acetone (greater than 90% pure) for ... 2 yr. ... 2 YEAR STUDY IN RATS: Groups of 60 male and 60 female F344/N rats were topically administered 0, 36, 60, or 100 mg 1,2-dihydro-2,2,4-trimethylquinoline/kg body weight in acetone, 5 days/wk for 103 (males) or 104 (females) wk. ... 2 YEAR STUDY IN MICE: Groups of 60 male and 60 female B6C3Fl mice were topically administered 0, 3.6, 6, or 10 mg 1,2-dihydro-2,2,4-trimethylquinoline/kg body weight in acetone, 5 days/wk for 103 (males) or 104 (females) wk. CONCLUSIONS: Under the conditions of these 2 yr dermal studies, there was some evidence of carcinogenic activity of 1,2-dihydro-2,2,4-trimethylquinoline in male F344/N rats, based on increased incidences of renal tubule adenoma and adenoma or carcinoma (combined). There was no evidence of carcinogenic activity of 1,2-dihydro-2,2,4-trimethylquinoline in female F344/N rats receiving 36, 60, or 100 mg/kg, or in male or female B6C3Fl mice receiving 3.6, 6, or 10 mg/kg.

Safety data

tsca
TSCA listed
hs_code
2933499090
Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H315-H319
Precautionary statements
P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Chemistry & industry

Uses & manufacturing

Uses · 2 items

Used as a monomer; The polymer is a rubber antioxidant; [HSDB]

MONOMER POLYMERIZED FOR USE AS A RUBBER ANTIOXIDANT

U.S. Exports(1975) No Data
U.S. Imports(1975) No Data
U.S. Production(1975) GREATER THAN 9.08X10+5 GRAMS
Consumption Patterns100% POLYMERIZED FOR USE AS A RUBBER ANTIOXIDANT (1976)
Methods of ManufacturingREACTION OF QUINOLINE AND ACETONE
Applications · 3 items

Uses1,2-Dihydro-2,2,4-trimethylquinoline is used as an antioxidant in styrene-butadiene and nitrile-butadiene rubbers and latexes. It was selected for evaluation because it is a derivative of quinoline, a known rodent carcinogen, and was regarded as having potential carcinogenic activity.

Uses1,2-Dihydro-2,2,4-trimethylquinoline (>85%) is used as an antioxidant in styrene-butadiene and nitrile-butadiene rubbers and latexes. It was selected for evaluation because it is a derivative of quinoline, a known rodent carcinogen, and was regarded as having potential carcinogenic activity.

General DescriptionDark cloudy copper-colored or yellow liquid. Odorless.

Upstream & downstream products

Suppliers100 total

湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
武汉欣扬瑞和化学科技有限公司153-07155313 15307155313 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
Hebei Yanxi Chemical Co., Ltd.+86-17531190177 · [email protected]

Related reactions

7 records

Compound notes

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