7,12-dihydro-7,12-dimethylbenzanthracene-7,12-diol
7,12-dimethyl-1,2-benzanthracene
Conditions | Yield |
---|---|
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 |
benz[a]anthracene-7,12-dione
methylmagnesium bromide
7,12-dimethyl-1,2-benzanthracene
Conditions | Yield |
---|---|
Reaktion ueber mehrere Stufen; |
7,12-dimethyl-7,12-dihydro-benz[a]anthracene
7,12-dimethyl-1,2-benzanthracene
Conditions | Yield |
---|---|
With sulfur at 200℃; | |
With sulfur at 210 - 220℃; |
7-iodomethyl-12-methylbenz[a]anthracene
7,12-dimethyl-1,2-benzanthracene
Conditions | Yield |
---|---|
With 1,4-dioxane; hydrogenchloride; tin(ll) chloride | |
With bisulfite solution Heating; Yield given; |
7-(12-Methylbenzanthryl)acetic acid
(E)-3-Ureido-but-2-enoic acid ethyl ester
7,12-dimethyl-1,2-benzanthracene
Conditions | Yield |
---|---|
at 180 - 185℃; |
7-(12-Methylbenzanthryl)acetic acid
7,12-dimethyl-1,2-benzanthracene
Conditions | Yield |
---|---|
With tin(IV) chloride at 110 - 120℃; | |
With zinc(II) chloride at 180 - 185℃; |
7,12-dimethoxy-7,12-dimethyl-7,12-dihydro-benz[a]anthracene
7,12-dimethyl-1,2-benzanthracene
Conditions | Yield |
---|---|
With sodium; benzene | |
With potassium; benzene |
7-bromo-12-methyl-benz[a]anthracene
methyl iodide
7,12-dimethyl-1,2-benzanthracene
Conditions | Yield |
---|---|
With n-butyllithium; diethyl ether; benzene |
diethyl ether
acetic acid-(12-methyl-benz[a]anthracen-7-yl ester)
methylmagnesium bromide
benzene
7,12-dimethyl-1,2-benzanthracene
Conditions | Yield |
---|---|
Reaktion ueber mehrere Stufen; |
7,12-epidioxy-7,12-dihydro-7,12-dimethylbenzanthracene
A
8,13-epoxy-8,13-dihydro-8,13-dimethyl-1a,7a-naphtho-8a,12a-benzoxepin
B
7,12-dihydro-7,12-dimethylbenzanthracene-7,12-diol
C
7,12-dimethyl-1,2-benzanthracene
Conditions | Yield |
---|---|
In chlorobenzene for 10h; Product distribution; Heating; other time, other solvent; |
hydrogenchloride
methanol
7,12-dimethyl-7,12-dihydro-benz[a]anthracen-7-ol
7,12-dimethyl-1,2-benzanthracene
7,12-dimethyl-1,2-benzanthracene
Conditions | Yield |
---|---|
With hydrogen iodide; acetic acid |
acetic acid-(12-methyl-benz[a]anthracen-7-yl ester)
7,12-dimethyl-1,2-benzanthracene
Conditions | Yield |
---|---|
With diethyl ether; benzene Reaktion ueber mehrere Stufen; |
12-methyltetraphen-7(12H)-one
7,12-dimethyl-1,2-benzanthracene
Conditions | Yield |
---|---|
With diethyl ether; benzene anschliessend mit wss. NH4Cl behandeln; |
7-(12-Methylbenzanthryl)acetic acid
tin(IV) chloride
7,12-dimethyl-1,2-benzanthracene
Conditions | Yield |
---|---|
at 110 - 120℃; |
diethyl ether
7,12-dimethoxy-7,12-dimethyl-7,12-dihydro-benz[a]anthracene
benzene
7,12-dimethyl-1,2-benzanthracene
diethyl ether
7,12-dimethoxy-7,12-dimethyl-7,12-dihydro-benz[a]anthracene
benzene
7,12-dimethyl-1,2-benzanthracene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: benzene; diethyl ether / Ambient temperature 2: 2TiCl2*LiAlH4 / tetrahydrofuran / 3 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: benzene; diethyl ether / 24 h / Ambient temperature 2: 57 percent aq. HI 3: 1 percent bisulfite solution / Heating View Scheme | |
Multi-step reaction with 2 steps 1: diethyl ether; benzene / Behandlung des nach der Hydrolyse erhaltenen Reaktionsprodukts mit wss. HI in Methanol 2: SnCl2; concentrated aqueous HCl; dioxane View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous HI 2: SnCl2; concentrated aqueous HCl; dioxane View Scheme | |
Multi-step reaction with 2 steps 1: aqueous HI 2: SnCl2; concentrated aqueous HCl; dioxane View Scheme |
7,12-dimethyl-1,2-benzanthracene
7,12-bis(bromomethyl)benz[a]anthracene
Conditions | Yield |
---|---|
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 3h; Inert atmosphere; Reflux; | 65.2% |
With carbon disulfide; bromine unter Kuehlung; |
7,12-dimethyl-1,2-benzanthracene
2'-Deoxyguanosine
A
2-Amino-7-(7-methyl-benzo[a]anthracen-12-ylmethyl)-1,7-dihydro-purin-6-one
B
2-Amino-8-(7-methyl-benzo[a]anthracen-12-ylmethyl)-1,7-dihydro-purin-6-one
C
2-Amino-7-(12-methyl-benzo[a]anthracen-7-ylmethyl)-1,7-dihydro-purin-6-one
D
2-Amino-9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-8-(7-methyl-benzo[a]anthracen-12-ylmethyl)-1,9-dihydro-purin-6-one
Conditions | Yield |
---|---|
With potassium perchlorate In N,N-dimethyl-formamide electrolysis; Further byproducts given; | A 55% B 10% C 12% D 13% |
7,12-dimethyl-1,2-benzanthracene
2'-deoxy-D-adenosine
A
7-(7-Methyl-benzo[a]anthracen-12-ylmethyl)-7H-purin-6-ylamine
B
3-(12-Methyl-benzo[a]anthracen-7-ylmethyl)-3H-purin-6-ylamine
Conditions | Yield |
---|---|
With potassium perchlorate In N,N-dimethyl-formamide electrolysis; | A 45% B 55% |
7,12-dimethyl-1,2-benzanthracene
trans-7,12-dihydro-7,12-dimethylbenzanthracene
cis-7,12-dihydro-7,12-dimethylbenzanthracene
Conditions | Yield |
---|---|
With hydrogen iodide In acetic acid for 0.25h; Heating; Title compound not separated from byproducts; | A 50% B 25% |
Conditions | Yield |
---|---|
In xylene under Ar; 7,12-dimethylbenz(a)anthracene added to p-xylene soln. of AgClO4 (molar ratio 1:1); stirred for 10 min; filtered; filtrate layered with n-hexane; sealed under Ar and wrapped with Al foil; stored at room temp. for 2 weeks; elem. anal.; | 49% |
7,12-dimethyl-1,2-benzanthracene
chromium(0) hexacarbonyl
(η6-7,12-dimethylbenz{a}anthracene)tricarbonylchromium
Conditions | Yield |
---|---|
In tetrahydrofuran; dibutyl ether refluxing under nitrogen for 7 h;; filtration; recrystn. from toluene-hexane at -78°C; purifn. by sublimation; elem. anal.; | 32% |
maleic anhydride
7,12-dimethyl-1,2-benzanthracene
7,12-dimethyl-7,12-dihydro-7,12-ethano-benz[a]anthracene-13,14-dicarboxylic acid-anhydride
Conditions | Yield |
---|---|
With benzene |
7,12-dimethyl-1,2-benzanthracene
7,12-bis-acetoxymethyl-benz[a]anthracene
Conditions | Yield |
---|---|
With lead(IV) acetate; acetic acid | |
Multi-step reaction with 2 steps 1: carbon disulfide; bromine / unter Kuehlung 2: potassium acetate View Scheme |
7,12-dimethyl-1,2-benzanthracene
7,12-epidioxy-7,12-dihydro-7,12-dimethylbenzanthracene
Conditions | Yield |
---|---|
With carbon disulfide mit Sauerstoff unter Belichtung; | |
With oxygen for 4h; Irradiation; |
7,12-dimethyl-1,2-benzanthracene
(+/-)-7,12-dimethylbenzanthracene-cis-5S,6R-dihydrodiol
Conditions | Yield |
---|---|
With pyridine; osmium(VIII) oxide; benzene Behandeln des Reaktionsprodukts in Dichlormethan mit wss. KOH und Mannit; | |
(i) OsO4, Py, benzene, (ii) mannitol, aq. NaOH, CH2Cl2; Multistep reaction; | |
With pyridine; osmium(VIII) oxide |
7,12-dimethyl-1,2-benzanthracene
A
7,12-dimethyl-5,6-dihydrobenzanthracene
B
8,9,10,11-tetrahydro-7,12-dimethylbenzanthracene
cis-7,12-dihydro-7,12-dimethylbenzanthracene
D
5,6,8,9,10,11-hexahydro-7,12-dimethylbenzanthracene
Conditions | Yield |
---|---|
With hydrogen; platinum(IV) oxide In ethyl acetate under 2585.7 Torr; for 22h; Ambient temperature; Title compound not separated from byproducts; | A 12 % Chromat. B 64 % Chromat. C 18 % Chromat. D 6 % Chromat. |
With hydrogen; platinum(IV) oxide In ethyl acetate under 2585.7 Torr; for 22h; Ambient temperature; | A 12 % Chromat. B 64 % Chromat. C 18 % Chromat. D 6 % Chromat. |
With hydrogen; platinum(IV) oxide; iron(II) chloride In hydrogenchloride under 1034.3 Torr; for 24h; Ambient temperature; Further byproducts given. Title compound not separated from byproducts; | A 11 % Chromat. B 6 % Chromat. C 15 % Chromat. D 62 % Chromat. |
With hydrogen; platinum(IV) oxide; iron(II) chloride In hydrogenchloride under 1034.3 Torr; for 24h; Ambient temperature; Further byproducts given; | A 11 % Chromat. B 6 % Chromat. C 15 % Chromat. D 62 % Chromat. |
7,12-dimethyl-1,2-benzanthracene
A
7,12-dimethyl-5,6-dihydrobenzanthracene
trans-7,12-dihydro-7,12-dimethylbenzanthracene
cis-7,12-dihydro-7,12-dimethylbenzanthracene
D
5,6,8,9,10,11-hexahydro-7,12-dimethylbenzanthracene
Conditions | Yield |
---|---|
With hydrogen; platinum(IV) oxide; iron(II) chloride In hydrogenchloride under 1034.3 Torr; for 24h; Ambient temperature; Further byproducts given; | A 11 % Chromat. B 6 % Chromat. C 15 % Chromat. D 62 % Chromat. |
7,12-dimethyl-1,2-benzanthracene
A
7,12-dimethyl-5,6-dihydrobenzanthracene
cis-7,12-dihydro-7,12-dimethylbenzanthracene
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethyl acetate under 1034.3 Torr; for 8h; Ambient temperature; | A 80 % Spectr. B 20 % Spectr. |
7,12-dimethyl-1,2-benzanthracene
A
8,9,10,11-tetrahydro-7,12-dimethylbenzanthracene
trans-7,12-dihydro-7,12-dimethylbenzanthracene
cis-7,12-dihydro-7,12-dimethylbenzanthracene
D
5,6,8,9,10,11-hexahydro-7,12-dimethylbenzanthracene
Conditions | Yield |
---|---|
With hydrogen; platinum(IV) oxide In acetic acid; ethyl acetate under 1551.4 Torr; for 22h; Further byproducts given; | A 10 % Chromat. B 10 % Chromat. C 19 % Chromat. D 55 % Chromat. |
7,12-dimethyl-1,2-benzanthracene
A
[3H]-7-Hydroxymethyl-12-methylbenz[a]anthracene
B
7,12-epidioxy-7,12-dihydro-7,12-dimethylbenzanthracene
Conditions | Yield |
---|---|
With oxygen In octane Product distribution; Irradiation; Oxidative degradation,initiated Co60 source(1-5 W/kg) ;other solvents;relative values k/ko (ko = benzo<a>pyrene)</a>; |
7,12-dimethyl-1,2-benzanthracene
cis-7,12-dihydro-7,12-dimethylbenzanthracene
Conditions | Yield |
---|---|
With hydrogen iodide In acetic acid for 1h; Heating; | 85 % Turnov. |
Multi-step reaction with 2 steps 1: 50 percent / HI / acetic acid / 0.25 h / Heating 2: HI / acetic acid / 1 h / Heating View Scheme |
7,12-dimethyl-1,2-benzanthracene
2'-Deoxyguanosine
A
7,12-dihydroxymethylbenz[a]anthracene
B
2-Amino-7-(7-methyl-benzo[a]anthracen-12-ylmethyl)-1,7-dihydro-purin-6-one
C
2-Amino-8-(7-methyl-benzo[a]anthracen-12-ylmethyl)-1,7-dihydro-purin-6-one
D
2-Amino-7-(12-methyl-benzo[a]anthracen-7-ylmethyl)-1,7-dihydro-purin-6-one
E
2-Amino-9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-8-(7-methyl-benzo[a]anthracen-12-ylmethyl)-1,9-dihydro-purin-6-one
Conditions | Yield |
---|---|
With potassium perchlorate In N,N-dimethyl-formamide Mechanism; other nucleosides; electrolysis; |
7,12-dimethyl-1,2-benzanthracene
trans-7,12-dihydro-7,12-dimethylbenzanthracene
Conditions | Yield |
---|---|
With ammonia; lithium |
Conditions | Yield |
---|---|
(i) NBS, (ii) aq. NaOH; Multistep reaction; |
7,12-dimethyl-1,2-benzanthracene
7,12-dimethyl-5,6-dihydrobenzanthracene
Conditions | Yield |
---|---|
With hydrogen; Pd/SrCO3 |
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.
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 .
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 ( |
Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.
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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