Rubiadin supplier | CasNO.117-02-2

Name
1,3-DIHYDROXY-2-METHYLANTHRAQUINONE
EINECS
CAS No. 117-02-2
Article Data21
CAS DataBase
Density 1.476 g/cm³
Solubility
Melting Point 290℃
Formula C₁₅H₁₀O₄
Boiling Point 527.1 °C at 760 mmHg
Molecular Weight 254.242
Flash Point 286.6 °C
Transport Information
Appearance
Safety
Risk Codes 22
Molecular Structure
Hazard Symbols Xn
Synonyms Anthraquinone,1,3-dihydroxy-2-methyl- (7CI,8CI);Rubiadin (6CI);1,3-Dihydroxy-2-methylanthraquinone;C.I. 75350;Rubiadine;
PSA 74.60000
LogP 2.18160

Synthetic route

: 85-44-9
phthalic anhydride

: 608-25-3
2-methylbenzene-1,3-diol

: 117-02-2
rubiadin

Conditions

Conditions	Yield
With aluminum (III) chloride; sodium chloride at 165 - 175℃; for 1h; Friedel-Crafts Acylation;	65%
With aluminum (III) chloride; sodium chloride at 130 - 170℃; for 0.75h;	64%
With aluminum (III) chloride; sodium chloride at 165 - 170℃; for 0.75h; Friedel-Crafts Acylation;	40%
With aluminum (III) chloride; sodium chloride
With aluminum (III) chloride Microwave irradiation;

: 22170-88-3
1,3-dimethoxy-2-methylanthraquinone

: 117-02-2
rubiadin

Conditions

Conditions	Yield
With hydrogen bromide; acetic acid

: 22170-89-4
1-hydroxy-3-methoxy-2-methyl-9,10-anthraquinone

: 117-02-2
rubiadin

Conditions

Conditions	Yield
With aluminium trichloride at 200℃; durch langsames Erhitzen;
With hydrogen bromide; acetic acid

: 7460-43-7
rubiadin-1-methyl ether

: 117-02-2
rubiadin

Conditions

Conditions	Yield
With sulfuric acid at 150℃; durch kurzes Erhitzen (10 min);

: 28026-96-2
3,5-dihydroxy-4-methylbenzoic acid

: 65-85-0
benzoic acid

: 117-02-2
rubiadin

Conditions

Conditions	Yield
With sulfuric acid at 120℃;
With sulfuric acid at 110 - 120℃;

: 1010-60-2
2-chloro-1,4-naphthoquinone

: 122305-38-8
(Z)-1-Ethoxy-2-methyl-1,3-bis-trimethylsilanyloxy-buta-1,3-diene

: 117-02-2
rubiadin

Conditions

Conditions	Yield
With hydrogenchloride 1.) benzene, r.t., 20-72 h; 2.) THF, r.t., 1-3 h; 3.) reflux, 1-5 h; Multistep reaction;

rubiadin-1-methyl ether: rubiadin-1-methyl ether

: 117-02-2
rubiadin

Conditions

Conditions	Yield
With hydrogenchloride at 140 - 150℃;

: 623-11-0
1-methyl-4-nitrosobenzene

: 7485-42-9
1,2,4-trihydroxy-3-methyl-anthraquinone

SnCl2: SnCl2

: 117-02-2
rubiadin

...Expand

: 6971-52-4
3-methoxy-2-methylphenol

: 117-02-2
rubiadin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 2: aluminium chloride; carbon disulfide 3: fuming sulfuric acid 4: AlCl3 / 200 °C / durch langsames Erhitzen View Scheme

: 5673-07-4
2,6-dimethoxytoluene

: 117-02-2
rubiadin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: aluminium chloride; carbon disulfide 2: fuming sulfuric acid 3: AlCl3 / 200 °C / durch langsames Erhitzen View Scheme

: 4837-88-1
6-methoxy-2-nitrotoluene

: 117-02-2
rubiadin

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: tin; aqueous hydrochloric acid 2: aqueous H2SO4 / Diazotization 4: aluminium chloride; carbon disulfide 5: fuming sulfuric acid 6: AlCl3 / 200 °C / durch langsames Erhitzen View Scheme

: 2-(2,4-dimethoxy-3-methyl-benzoyl)-benzoic acid

: 117-02-2
rubiadin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: fuming sulfuric acid 2: AlCl3 / 200 °C / durch langsames Erhitzen View Scheme

: 19500-02-8
2-methyl-3-methoxyaniline

: 117-02-2
rubiadin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: aqueous H2SO4 / Diazotization 3: aluminium chloride; carbon disulfide 4: fuming sulfuric acid 5: AlCl3 / 200 °C / durch langsames Erhitzen View Scheme

: 18018-09-2
1,3-dichloro-2-methyl-anthraquinone

: 117-02-2
rubiadin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: aqueous HBr; acetic acid View Scheme

: 117-02-2
rubiadin

: 77-78-1
dimethyl sulfate

: 22170-88-3
1,3-dimethoxy-2-methylanthraquinone

Conditions

Conditions	Yield
With potassium carbonate In acetone for 22h; Reflux;	100%
With potassium carbonate; acetone

: 117-02-2
rubiadin

: 108-24-7
acetic anhydride

: 10383-64-9
3-acetoxy-1-hydroxy-2-methylanthraquinone

Conditions

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 20h;	100%
With potassium carbonate In acetone

: 52162-55-7, 69256-45-7, 61826-14-0
2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride

: 117-02-2
rubiadin

: C34H30O7

Conditions

Conditions	Yield
Stage #1: rubiadin With sodium hydride In acetonitrile; mineral oil at 0℃; for 0.166667h; Stage #2: 2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride at 20℃; for 0.333333h;	93%

: 117-02-2
rubiadin

: 100914-52-1
4-bromo-1,3-dihydroxy-2-methylanthraquinone

Conditions

Conditions	Yield
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 24h; Reflux;	60%
With bromine; sodium acetate; acetic acid

: 4887-24-5
triacetoxyborane

: 117-02-2
rubiadin

: 3-acetoxy-1-diacetoxyboranyloxy-2-methyl-anthraquinone

Conditions

Conditions	Yield
With acetic anhydride

: 117-02-2
rubiadin

: 572-09-8
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

: 904795-74-0
1-hydroxy-2-methyl-3-(tetra-O-acetyl-β-D-glucopyranosyloxy)-anthraquinone

Conditions

Conditions	Yield
With sodium hydroxide; acetone

: 117-02-2
rubiadin

: 572-09-8
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

: 2-methyl-1,3-bis-(tetra-O-acetyl-β-D-glucopyranosyloxy)-anthraquinone

Conditions

Conditions	Yield
With quinoline; silver(l) oxide

: 117-02-2
rubiadin

: 7460-43-7
rubiadin-1-methyl ether

Conditions

Conditions	Yield
(methylation);

: 117-02-2
rubiadin

: 108-24-7
acetic anhydride

: 7416-31-1
rubiadin diacetate

Conditions

Conditions	Yield
With pyridine
With potassium carbonate

: 117-02-2
rubiadin

: 57186-30-8
3-β-D-glucopyranosyloxy-1-hydroxy-2-methyl-anthraquinone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: acetone; aq. NaOH solution 2: methanol; aq. NaOH solution View Scheme

: 117-02-2
rubiadin

: 1-methoxy-2-methyl-3-(tetra-O-acetyl-β-D-glucopyranosyloxy)-anthraquinone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: acetone; aq. NaOH solution 2: acetone; silver oxide View Scheme

: 117-02-2
rubiadin

: 1-acetoxy-2-methyl-3-(tetra-O-acetyl-β-D-glucopyranosyloxy)-anthraquinone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: acetone; aq. NaOH solution 2: pyridine View Scheme

: 117-02-2
rubiadin

: 2324-25-6
3-acetoxy-1-methoxy-2-methylanthraquinone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 20 h / 20 °C 2: potassium carbonate / acetone / 22 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / acetone 2: potassium carbonate; dimethyl sulfate / acetone / 22 h / Reflux View Scheme

: 117-02-2
rubiadin

: 63965-55-9
1-methoxy-3-acetoxy-2-bromomethyl-1-methoxyathraquinone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / acetone / 20 h / 20 °C 2: potassium carbonate / acetone / 22 h / Reflux 3: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 24 h / Reflux View Scheme
Multi-step reaction with 3 steps 1: potassium carbonate / acetone 2: potassium carbonate; dimethyl sulfate / acetone / 22 h / Reflux 3: N-Bromosuccinimide / tetrachloromethane / 30 h / Reflux View Scheme

: 117-02-2
rubiadin

: 63965-57-1
2-ethoxymethyl-3-hydroxy-1-methoxyanthracene-9,10-dione

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium carbonate / acetone / 20 h / 20 °C 2: potassium carbonate / acetone / 22 h / Reflux 3: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 24 h / Reflux 4: sodium hydroxide / water / 24 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetone 2.1: potassium carbonate; dimethyl sulfate / acetone / 22 h / Reflux 3.1: N-Bromosuccinimide / tetrachloromethane / 30 h / Reflux 4.1: sodium hydroxide; water / ethanol 4.2: Reflux View Scheme

Rubiadin Specification

The 9,10-Anthracenedione,1,3-dihydroxy-2-methyl- is an organic compound with the formula C₁₅H₁₀O₄. The IUPAC name of this chemical is 1,3-dihydroxy-2-methylanthracene-9,10-dione. With the CAS registry number 117-02-2, it is also named as 1,3-Dihydroxy-2-methyl-9,10-anthracenedione. The product's categories are Anthraquinones, Hydroquinones and Quinones.

Physical properties about 9,10-Anthracenedione,1,3-dihydroxy-2-methyl- are: (1)ACD/LogP: 4.44; (2)ACD/LogD (pH 5.5): 4.42; (3)ACD/LogD (pH 7.4): 3.91; (4)ACD/BCF (pH 5.5): 1348.54; (5)ACD/BCF (pH 7.4): 416.01; (6)ACD/KOC (pH 5.5): 6005.77; (7)ACD/KOC (pH 7.4): 1852.72; (8)#H bond acceptors: 4; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 2; (11)Polar Surface Area: 52.6 Å²; (12)Index of Refraction: 1.709; (13)Molar Refractivity: 67.25 cm³; (14)Molar Volume: 172.2 cm³; (15)Polarizability: 26.66×10^-24cm³; (16)Surface Tension: 73.1 dyne/cm; (17)Density: 1.476 g/cm³; (18)Flash Point: 286.6 °C; (19)Enthalpy of Vaporization: 83.17 kJ/mol; (20)Boiling Point: 527.1 °C at 760 mmHg; (21)Vapour Pressure: 1E-11 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C2c1ccccc1C(=O)c3c2cc(O)c(c3O)C
(2)InChI: InChI=1/C15H10O4/c1-7-11(16)6-10-12(13(7)17)15(19)9-5-3-2-4-8(9)14(10)18/h2-6,16-17H,1H3
(3)InChIKey: IRZTUXPRIUZXMP-UHFFFAOYAQ
(4)Std. InChI: InChI=1S/C15H10O4/c1-7-11(16)6-10-12(13(7)17)15(19)9-5-3-2-4-8(9)14(10)18/h2-6,16-17H,1H3
(5)Std. InChIKey: IRZTUXPRIUZXMP-UHFFFAOYSA-N

Product Name

1,3-DIHYDROXY-2-METHYLANTHRAQUINONE

Synthetic route

Rubiadin Specification

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