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2-Aminoanthracene

HCID 11937
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Basic information

CAS
613-13-8
Standard SMILES
Nc1ccc2cc3ccccc3cc2c1
InChIKey
YCSBALJAGZKWFF-UHFFFAOYSA-N
Molecular formula
C14H11N
Average molar mass
193.24 g/mol
Monoisotopic mass
193.08914936

Overview

2-aminoanthracene appears as yellow to brownish-yellow powder or solid. (NTP, 1992)

Names & identifiers

Preferred name
2-Aminoanthracene
IUPAC
anthracen-2-amine
English name
2-Aminoanthracene
Molecular formula
C14H11N
Molecular weight
193.24

Names & synonyms

2-Aminoanthracene613-13-82-Anthramine2-Anthrylamine2-ANTHRACENAMINE2-Anthracylaminebeta-Aminoanthracene2-AnthracenamideDTXSID20244588240818JGUNSC-400535DTXCID904458
Show more names
SKL1402-Anthranamine
RefChem:85361210-330-9anthracen-2-amine.beta.-AminoanthraceneAnthracene, 2-aminoMFCD000035822-aminoanthracenBRN 2209414

Database identifiers

CAS
613-13-8
PubChem CID
11937
DTXSID
DTXSID2024458
ChEMBL
CHEMBL83154
ChEBI
CHEBI:34260
UNII
8240818JGU
EC Number
210-330-9
Nikkaji
J3.650A

Properties

Computed structural properties

XLogP
3.5
Topological polar surface area
26 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
15
Formal charge
0
Complexity
225

Experimental & physicochemical properties

PolymersOther Classes -> Polycyclic Aromatic Hydrocarbons
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP4.13
Color/FormYellow leaflets from alcohol
Solubility · 3 items

less than 0.1 mg/mL at 72 °F (NTP, 1992)

SOL IN ALCOHOL

Slightly sol in ether

Boiling Point199 °F at 9 mmHg (sublimes) (NTP, 1992)
DecompositionWhen heated to decomposition, it emits toxic fumes of NO(x).
Melting Point · 2 items

460 to 466 °F (NTP, 1992)

238-241 °C

Vapor Pressure0.00000405 [mmHg]
Physical Description · 2 items

2-aminoanthracene appears as yellow to brownish-yellow powder or solid. (NTP, 1992)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H315 (90.9%): Causes skin irritation [Warning Skin corrosion/irritation]

P203, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 44 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information2-Anthracenamine: 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 HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health HazardsACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes. (NTP, 1992)
Hazards Summary · 1 item

Induced tumors in experimental animals by topical exposure; [HSBD] Induced liver tumors in adult fish one year after embryonic injection; Skeletal abnormalities and germ cell defects observed in pups of pregnant mice dosed with 10 mg/kg/day; [REPROTOX] An irritant and photosensitizer; [Aldrich MSDS]

Reactive GroupHydrocarbons, Aromatic
Reactivity Profile2-AMINOANTHRACENE may be unstable with prolonged exposure to air and light. Solutions of this chemical should be stable for 24 hours under normal lab conditions. (NTP, 1992)

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included.

Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes.

Uses & manufacturing

Uses · 3 items

Produced from incomplete combustion of organic substances; Also found in synthetic fuel; Used for biochemical research; Not commercially produced in the US; [HSDB] Used for organic synthesis; [NTP]

BIOCHEMICAL RESEARCH

Synthetic Polymer MALDI Matrix Compounds

U.S. Production · 2 items

(1975) NOT PRODUCED COMMERCIALLY IN USA

(1977) NOT PRODUCED COMMERCIALLY IN USA

Applications · 2 items

Uses2-Aminoanthracene can be used as a reactant to prepare: Steroid derived naphthoquinoline asphaltene compounds via multicomponent cyclocondensation reaction with 5-α-cholestan-3-one and aromatic aldehydes. Naphtho[2,3- f ]quinoline derivatives by reacting with aromatic aldehyde and acetone or acetophenone catalyzed by iodine.

General DescriptionYellow to brownish-yellow powder or solid.

Upstream & downstream products

Downstream products

Dinaphtho[2,3-a:2',3'-h]phenazine

Additional notes

Suppliers

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Related reactions

3 records
New reaction record
HRID 1179068 reaction equation
HRID 1179068As reactantuspto-grants-2007_10
HRID 1545397 reaction equation
HRID 1545397As reactantTraining data from https://doi.org/10.1039/C8SC04228D (1/10)
HRID 1682503 reaction equation
HRID 1682503As reactantuspto-grants-1997_06

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

Yellow solid; [HSDB] Deep yellow powder; [MSDSonline]

Other Experimental Properties · 3 items

Sublimes

UV: 6851 (Sadtler Research Laboratories Spectral Collection) /1-Aminoanthracenamine/

UV: 5-400 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York) /9-Aminoanthracenamine/

Physicochemical properties

Melting point
238 · 238-241 °C (lit.)
Boiling point
319.47 °C · 319.47°C (rough estimate)
Density
1.1061 · 1.1061 (rough estimate)
refractive index
1.585 · 1.5850 (estimate)
storage temp.
Keep in dark place,Inert atmosphere,Room temperature
solubility
Chloroform (Very Slightly), Dichloromethane (Slightly), DMSO (Slightly)
form
Solid
pka
4.32 · 4.32±0.30(Predicted)
color
Yellow leaflets from alcohol
Water Solubility
1.3 mg/L · 1.3mg/L(24 ºC)
BRN
2209414 · 2209414
Henry's Law Constant
3.3 · 3.3×101 mol/(m3Pa) at 25℃, HSDB (2015)
Stability
Stable. Incompatible with strong oxidizing agents.
CAS DataBase Reference
613 · 613-13-8(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
8240818 JGU · 8240818JGU
EPA Substance Registry System
2 · 2-Aminoanthracene (613-13-8)
UNSPSC Code
12352100 · 12352100
NACRES
22 · NA.22
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319-H335
Precautionary statements
261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
Hazard Codes
Xi
Risk Statements
36 · 36/37/38
Safety Statements
26 · 26-24/25
WGK Germany
3 · 3
RTECS
9275000 · CA9275000
HS Code
29214990 · 29214990
Hazardous Substances Data
613 · 613-13-8(Hazardous Substances Data)
Toxicity
6 nmol/plate · mmo-sat 6 nmol/plate BBRCA9 89,259,79
Air and Water Reactions
Insoluble in water.
Toxic Combustion ProductsWhen heated to decomposition, it emits toxic fumes of NO(x).
Clean Water Act RequirementsToxic pollutant designated pursuant to section 307(a)(1) of the Clean Water Act and is subject to effluent limitations. /Polynuclear aromatic hydrocarbons/
Hazard Classes and CategoriesSkin Irrit. 2 (90.9%)

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 a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the adsorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone 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.

Disposal Methods · 2 items

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.

The following wastewater treatment technologies have been investigated for 2-anthracenamine: Biological treatment and solvent extraction.

Preventive Measures · 1 item

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.

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

Environmental Fate · 3 items

TERRESTRIAL FATE: If released to soil, 2-anthracenamine is expected to be immobilized by strong adsorption to soil. This compound would probably photolyze on soil surfaces. Volatilization and hydrolysis are not expected to be environmentally important fate processes. Insufficient data are available to predict the significance of biodegradation. (SRC)

AQUATIC FATE: If released to water, 2-anthracenamine may adsorb strongly to suspended solids and sediments, bioaccumlate significantly in aquatic organisms or photolyze rapidly in near-surface waters (estimated midday, midsummer photolysis half-life less than 4.5 days). Chemical hydrolysis is not expected to be an environmentally significant process. Insufficient data are available to predict the significance of biodegradation. (SRC)

ATMOSPHERIC FATE: If released to the atmosphere, 2-anthracenamine is expected to exist both in the vapor phase and adsorbed to particulate matter(1,SRC). This compound may react with photochemically generated hydroxyl radicals in the atmosphere (estimated vapor phase half-life 1.8 hours(2,3,SRC)), it may undergo direct photolysis, or it may be subject to dry deposition(SRC). Adsorption of 2-anthracenamine onto particulate matter may retard direct photolysis and reaction with hydroxyl radicals(4,SRC).

Adverse EffectsDermatotoxin - PICD (photoirritant contact dermatitis).
Soil Adsorption/MobilityKoc ranging between 94276 and 15904 were measured for 2-anthracenamine in fourteen different soils and sediments(1). These Koc are indicative of extremely strong adsorption to soil and suspended solids and sediments in water(2,SRC).
Artificial Pollution Sources · 2 items

2-Anthracenamine has been identified as a constituent of synfuel(1).

FORMED FROM INCOMPLETE COMBUSTION OF ORGANIC MATERIALS (EG, REFUSE BURNING, OPERATION OF MOTOR VEHICLES, INDUST PROCESSES)

Environmental Bioconcentration · 1 item

A bioconcentration factor (BCF) of 3141 has been estimated for 2-anthracenamine using a linear regression equation based on a measured water solubility of 0.056 mg/l at 25 °C(1,2,SRC). This BCF value suggests that 2-anthracenamine bioaccumulates significantly in aquatic organisms(SRC).

Volatilization from Water/Soil · 1 item

The Henry's Law constant for 2-anthracenamine has been estimated to be 3.0X10-7 atm-cu m/mol at 25 °C by combining a measured Henry's Law Constant for anthracene of 7.2X10-4 atm-cu m/mole at 25 °C(1) with an estimation method based on structural bond contributions to intrinsic hydrophilic character(2,SRC). Given this value of Henry's Law constant and the relatively high Koc (15904 to 94276(4)) of 2-anthracenamine, it appears as though volatilization would not be a significant removal process from soil or water(3,SRC). This is apparent from the result of an EXAMS run for a model pond in which the effects of adsorption were considered. In this case, the volatilization half-life was determined to be 98 years(5,SRC).

Non-Human Toxicity Excerpts · 2 items

IN MICE, SC INJECTIONS (EVIDENCE LESS CONVINCING) INDUCED TUMORS IN LIVER; IN RATS, TOPICAL ADMIN (TESTED IN MORE THAN 1 INSTITUTE) INDUCED LOCAL TUMORS & TUMORS IN BREAST, SC INJECTIONS INDUCED SKIN TUMORS; IN HAMSTERS, TOPICAL ADMIN (TESTED IN MORE THAN 1 INSTITUTE) INDUCED LOCAL TUMORS. /FROM TABLE/

2-Aminoanthracene was tested for the induction of sex linked recessive lethal mutations in Drosophila melanogaster using a standard protocol approved by the National Toxicology Program. Canton-S wild type males were dosed with concentrations of 2-aminoanthracene that resulted in approximately 30% mortality. Following treatment, males were mated individually to Basc virgin females to produce 3 broods for analysis. 2-Aminoanthracene was positive at a dose of 1,000 ppm when administered to males by feeding.

Environmental Abiotic Degradation · 1 item

The half-life for reaction of 2-anthracenamine vapor with photochemically generated hydroxyl radicals in air has been estimated to be 1.8 hours based on an estimated reaction rate constant of 2.2X10-10 cu cm/molecules-sec at 25 °C(1,SRC) and average ambient hydroxyl radical concentration of 5.0X10+5 molecules/cu cm(2). Polyaromatic hydrocarbons, in general, absorb UV light in the environmentally significant range (wavelengths greater than 290 nm) and are susceptible to direct photolysis in the environment(3). The occurrence of an amino group on the anthracene structure, is predicted to cause 2-anthracenamine to photolyze faster than anthracene which has an estimated near-surface photolysis half-life (latitude 40 deg N, midday, midsummer) of 4.5 days in water(3,SRC). 2-Anthracenamine contains no hydrolyzable functional groups, and therefore, is not expected to undergo hydrolysis in the environment(4,5,SRC).

Probable Routes of Human ExposureNIOSH (NOES Survey 1981-1983) has statistically estimated that 198 workers are exposed to 2-anthracenamine in the USA(1).
Environmental Fate/Exposure Summary · 1 item

2-Anthracenamine has been identified as a constituent of synthetic fuel. If released to soil, 2-anthracenamine is expected to be immobilized by strong adsorption to the soil and it would probably photolyze on soil surfaces. Volatilization and hydrolysis are not expected to be environmentally relevant fate processes in either soil or water. Insufficient data are available to predict the significance of biodegradation. If released to water, 2-anthracenamine may adsorb strongly to suspended solids and sediments, bioaccumulate significantly in aquatic organisms, or photolyze in near-surface waters (estimated midday, midsummer half-life less than 4.5 days). If released to the atmosphere, 2-anthracenamine is expected to exist in both vapor and particulate form. This compound may react with photochemically generated hydroxyl radicals (estimated vapor phase half-life 1.8 hours), it may undergo direct photolysis, or it may be subject to dry deposition. Adsorption onto particulate matter may retard direct photolysis and reaction with hydroxyl radicals. (SRC)

Regulatory information

Clean Water Act RequirementsToxic pollutant designated pursuant to section 307(a)(1) of the Clean Water Act and is subject to effluent limitations. /Polynuclear aromatic hydrocarbons/

Safety data

wgk
3
rtecs
CA9275000
hs_code
29214990
Toxicity
mmo-sat 6 nmol/plate BBRCA9 89,259,79
risk_code
36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
safety_code
26-24/25
Hazard statements
H315-H319-H335
Precautionary statements
P261-P264-P271-P280-P302+P352-P305+P351+P338
Hazardous Substances Data
613-13-8(Hazardous Substances Data)

DefinitionChEBI: Anthracen-2-amine is an anthracenamine.