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7,12-Dimethylbenz[a]anthracene

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Name

7,12-Dimethylbenz[a]anthracene

EINECS 200-359-5
CAS No. 57-97-6 Density 1.142 g/cm3
PSA 0.00000 LogP 5.76300
Solubility N/A Melting Point 122-123 °C(lit.)
Formula C20H16 Boiling Point 463.5 °C at 760 mmHg
Molecular Weight 256.347 Flash Point 227.3 °C
Transport Information N/A Appearance Yellow powder
Safety 45-53-36/37 Risk Codes 22-45
Molecular Structure Molecular Structure of 57-97-6 (7,12-DIMETHYLBENZ[A]ANTHRACENE) Hazard Symbols ToxicT;HarmfulXn
Synonyms

7,12-Dimethylbenz[a]anthracene;9,10-Dimethyl-1,2-benz[a]anthracene;9,10-Dimethyl-1,2-benzanthracene;DMBA;DMBAn;NSC408823;

Article Data 19

7,12-Dimethylbenz[a]anthracene Synthetic route

2518-00-5

7,12-dihydro-7,12-dimethylbenzanthracene-7,12-diol

57-97-6

7,12-dimethyl-1,2-benzanthracene

Conditions
ConditionsYield
With hydrogenchloride; acetic acid; tin(ll) chloride
With 2TiCl2*LiAlH4 In tetrahydrofuran for 3h; Heating; Yield given;
Multi-step reaction with 2 steps
1: 57 percent aq. HI
2: 1 percent bisulfite solution / Heating
View Scheme
Multi-step reaction with 2 steps
1: methanol; sulfuric acid
2: potassium; benzene
View Scheme
2498-66-0

benz[a]anthracene-7,12-dione

75-16-1

methylmagnesium bromide

57-97-6

7,12-dimethyl-1,2-benzanthracene

Conditions
ConditionsYield
Reaktion ueber mehrere Stufen;
35281-31-3

7,12-dimethyl-7,12-dihydro-benz[a]anthracene

57-97-6

7,12-dimethyl-1,2-benzanthracene

Conditions
ConditionsYield
With sulfur at 200℃;
With sulfur at 210 - 220℃;
27018-50-4

7-iodomethyl-12-methylbenz[a]anthracene

57-97-6

7,12-dimethyl-1,2-benzanthracene

Conditions
ConditionsYield
With 1,4-dioxane; hydrogenchloride; tin(ll) chloride
With bisulfite solution Heating; Yield given;
63020-22-4

7-(12-Methylbenzanthryl)acetic acid

5435-44-9, 22243-66-9

(E)-3-Ureido-but-2-enoic acid ethyl ester

57-97-6

7,12-dimethyl-1,2-benzanthracene

Conditions
ConditionsYield
at 180 - 185℃;
63020-22-4

7-(12-Methylbenzanthryl)acetic acid

57-97-6

7,12-dimethyl-1,2-benzanthracene

Conditions
ConditionsYield
With tin(IV) chloride at 110 - 120℃;
With zinc(II) chloride at 180 - 185℃;
63018-76-8

7,12-dimethoxy-7,12-dimethyl-7,12-dihydro-benz[a]anthracene

57-97-6

7,12-dimethyl-1,2-benzanthracene

Conditions
ConditionsYield
With sodium; benzene
With potassium; benzene
81830-40-2

7-bromo-12-methyl-benz[a]anthracene

74-88-4

methyl iodide

57-97-6

7,12-dimethyl-1,2-benzanthracene

Conditions
ConditionsYield
With n-butyllithium; diethyl ether; benzene
60-29-7

diethyl ether

17526-35-1

acetic acid-(12-methyl-benz[a]anthracen-7-yl ester)

75-16-1

methylmagnesium bromide

71-43-2

benzene

57-97-6

7,12-dimethyl-1,2-benzanthracene

Conditions
ConditionsYield
Reaktion ueber mehrere Stufen;
2518-01-6

7,12-epidioxy-7,12-dihydro-7,12-dimethylbenzanthracene

A

65273-21-4

8,13-epoxy-8,13-dihydro-8,13-dimethyl-1a,7a-naphtho-8a,12a-benzoxepin

B

2518-00-5

7,12-dihydro-7,12-dimethylbenzanthracene-7,12-diol

C

57-97-6

7,12-dimethyl-1,2-benzanthracene

Conditions
ConditionsYield
In chlorobenzene for 10h; Product distribution; Heating; other time, other solvent;

7,12-Dimethylbenz[a]anthracene Chemical Properties

IUPAC Name: 7,12-dimethylbenzo[b]phenanthrene
Molecular Formula: C20H16
Molecular Weight: 256.36g/mol
Chemical Properties: yellow powder
Density: 1.142 g/cm3
EINECS: 200-359-5
Liansport Information: UN 3077 9/PG 3
Melting Point: 122-123°C(lit.)
Boiling Point: 463.5 °C at 760 mmHg 
Flash Point: 227.3 °C 
storage temperature: 2-8°C
Freely Rotating Bonds: 0 
Polar Surface Area: 0 Å2 
Index of Refraction: 1.728 
Molar Refractivity: 89.43 cm3 
Molar Volume: 224.3 cm3 
Polarizability: 35.45× 10-24cm3 
Surface Tension: 49.1 dyne/cm  
Enthalpy of Vaporization: 69.69 kJ/mol 
Vapour Pressure: 2.51E-08 mmHg at 25°C
Solubility: insoluble in water
Sensitivity: incompatible with strong oxidizing agents  
   The chemical synonyms of Dimethylbenzanthracene (57-97-6) are DMBA ; 7,12-Dimethylbenzanthracene ; Dimethylbenz[a]anthracene ; Dimethylbenzanthrene ; Dimethylbenzanthracene ; 7,12-Dimethyltetraphene ; ETHYL ACETATE ; 9,10-Dimethyl-1,2-benzanthracene .Product categories of  Dimethylbenzanthracene (57-97-6) are Organics ; Aromatics Compounds ; Aromatics ; Mutagenesis Research Chemicals ; Alpha Sort ; D ; DAlphabetic ; DID - DIN ; Volatiles/ Semivolatiles .The molecular structure of Dimethylbenzanthracene (57-97-6) is.

7,12-Dimethylbenz[a]anthracene Uses

It is a highly potent carcinogen that is activated by microsomal enzymes to a diol epoxide metabolite that binds covalently to DNA in mammalian cells, leading ultimately to tumor induction .

7,12-Dimethylbenz[a]anthracene Toxicity Data With Reference

1.    

skn-mus 64 µg MLD

    CALEDQ    Cancer Letters (Shannon, Ireland). 4 (1978),333.
2.    

dnd-hmn:emb 220 nmol/L

    MUREAV    Mutation Research. 89 (1981),95.
3.    

dni-hmn:lvr 1 mmol/L

    VOONAW    Voprosy Onkologii. Problems of Onkology. 28 (11)(1982),53.
4.    

otr-mus:emb 300 µg/L

    PMRSDJ    Progress in Mutation Research. 5 (1985),659.
5.    

orl-rat TDLo:37,500 µg/kg (female 14-20D post):ETA,TER

    CRNGDP    Carcinogenesis. 3 (1978),413.
6.    

ipr-rat TDLo:24 mg/kg (20D preg):ETA,TER

    CCSUDL    Carcinogenesis-A Comprehensive Survey 3 (1978),413.
7.    

ivn-rat TDLo:15 mg/kg (21D preg):ETA,TER

    JNCIAM    Journal of the National Cancer Institute. 52 (1974),1365.
8.    

ivn-rat TDLo:15 mg/kg (21D preg):ETA,TER

    NEOLA4    Neoplasma. 23 (1976),285.
9.    

imp-rat TDLo:11 µg/kg:ETA,TER

    NISFAY    Nippon Sanka Fujinka Gakkai Zasshi. Journal of Japanese Obstetrics and Gynecology. 34 (1982),1853.
10.    

ipc-rat TDLo:1250 µg/kg:ETA,TER

    GANNA2    Gann. Japanese Journal of Cancer Research. 62 (

7,12-Dimethylbenz[a]anthracene Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

7,12-Dimethylbenz[a]anthracene Safety Profile

Suspected carcinogen with experimental carcinogenic, neoplastigenic, tumorigenic, and teratogenic data. A transplacental carcinogen. Poison by ingestion, intravenous, subcutaneous, intraperitoneal, and intratracheal routes. Other experimental reproductive effects. Human mutation data reported. A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

 

Hazard Codes:  C,T,N,Xn,F
C:  Corrosive
T:  Toxic
N:  Dangerous for the environment
Xn: Harmful
F:  Highly Flammable  
Risk Statements:  45-22-67-65-50/53-38-11-39/23/24/25-23/24/25
45:  May cause cancer
22:  Harmful if swallowed
65:  Harmful: May cause lung damage if swallowed 
67:  Vapors may cause drowsiness and dizziness 
11:  Highly Flammable 
23/24/25:  Toxic by inhalation, in contact with skin and if swallowed
39/23/24/25:  Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed 
50/53:  Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment 
38:  Irritating to the skin 
Safety Statements:  53-36/37-45-62-61-60
45:  In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible)
53:  Avoid exposure - obtain special instructions before use
60:  This material and/or its container must be disposed of as hazardous waste 
61:  Avoid release to the environment. Refer to special instructions safety data sheet 
62:  If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label 
36/37:  Wear suitable protective clothing and gloves 
F  10-13-23
F 10:  Keep under argon
F 13:  Malodorous
F 23:  Sensitive to air
HazardClass: 6.1(b)

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