3,3'-Diindolylmethane supplier

Name
3,3'-Diindolylmethane
EINECS 100-201-5
CAS No. 1968-05-4
Article Data105
CAS DataBase
Density 1.271 g/cm³
Solubility
Melting Point 167 °C
Formula C₁₇H₁₄N₂
Boiling Point 504.8 °C at 760 mmHg
Molecular Weight 246.312
Flash Point 232.5 °C
Transport Information
Appearance
Safety 22-24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Indole,3,3'-methylenedi- (6CI,7CI,8CI);3,3'-Bisindolylmethane;3,3'-Methylenebis-1H-indole;Arundine;Bis(1H-indol-3-yl)methane;Bis(3-indolyl)methane;HB 236;DIINDOLYMETHANE;
PSA 31.58000
LogP 4.24000

Synthetic route

: 120-72-9
indole

: 50-00-0
formaldehyd

: 1968-05-4
3,3'-diindolylmethane

Conditions

Conditions	Yield
With acetic acid In water at 90℃; for 5h;	98%
With 4,4'-(propane-1,3-diyl)bis(1-methyl-1,4-diazabicyclo-[2.2.2]octane-1,4-diium) tetra-hydrogensulfate In water at 20℃; for 2h; Green chemistry;	98%
In water at 100℃; for 0.333333h; Temperature; Time; Microwave irradiation;	98%

: 120-72-9
indole

: ethanolic ethoxymethanol

: 1968-05-4
3,3'-diindolylmethane

Conditions

Conditions	Yield
With iron(III) sulphate monohydrate In ethanol at 20℃; for 10h;	96%

: 120-72-9
indole

: 100-97-0
hexamethylenetetramine

: 1968-05-4
3,3'-diindolylmethane

Conditions

Conditions	Yield
Stage #1: indole; hexamethylenetetramine With indium(III) chloride In isopropyl alcohol at 20℃; for 8h; Stage #2: With water In isopropyl alcohol at 80℃; for 0.5h;	92%
With indium(III) chloride In isopropyl alcohol at 80℃; for 8h;	92%
Stage #1: indole; hexamethylenetetramine With [bmim]BF4 at 60℃; for 5h; Stage #2: With water at 80℃; for 0.5h; Further stages.;	78%

: 120-72-9
indole

: 109-87-5
Dimethoxymethane

: 1968-05-4
3,3'-diindolylmethane

Conditions

Conditions	Yield
With povidone-phosphotungstic acid catalyst In dichloromethane at 25℃; for 1h; Friedel-Crafts Alkylation; Inert atmosphere;	92%

: 120-72-9
indole

: 5457-31-8
(3-indolylmethyl)trimethylammonium iodide

: 1968-05-4
3,3'-diindolylmethane

Conditions

Conditions	Yield
In water at 80℃; Sealed tube; Green chemistry; regioselective reaction;	92%

: 60122-38-5
indol-3-ylmethylthio-β-propionic acid

: 1968-05-4
3,3'-diindolylmethane

Conditions

Conditions	Yield
With sodium hydroxide for 2h; Heating;	90%

: 60122-35-2
indol-3-ylmethylthioacetic acid

: 1968-05-4
3,3'-diindolylmethane

Conditions

Conditions	Yield
With sodium hydroxide for 2h; Heating;	90%
Multi-step reaction with 2 steps 1: 74 percent / sodium hydroxide / H2O / 0.75 h / 70 - 80 °C 2: 90 percent / aq.sodium hydroxide (50percent) / 2 h / Heating View Scheme

: 120-72-9
indole

: 67-56-1
methanol

: 1968-05-4
3,3'-diindolylmethane

Conditions

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; potassium tert-butylate at 150℃; for 12h; Reagent/catalyst; Concentration; Inert atmosphere; Schlenk technique;	86%
With sodium perchlorate; 2,6-di-O-methyl-β-cyclodextrin In water Ambient temperature; electrolysis;	74%
With sodium triflate at 80℃; for 24h; Reagent/catalyst; Temperature; Concentration;	70%
With C37H36Cl2NPRuS2; potassium hydroxide In toluene at 135℃; for 18h; Inert atmosphere;	68%

: 120-72-9
indole

: 6000-43-7
2-aminoethanoic acid hydrochloride

: 1968-05-4
3,3'-diindolylmethane

Conditions

Conditions	Yield
With phosphotungstic acid 44-hydrate; alloxan monohydrate In N,N-dimethyl-formamide at 110℃;	86%

: 456-27-9
4-nitrobenzenediazonium tetrafluoroborate

: 114648-74-7
3-((1H-indol-3-yl)methyl)-1,2-dimethyl-1H-indole

A: 1968-05-4
3,3'-diindolylmethane

B: 53330-79-3
3-(4-nitro-phenylazo)-indole

C: 1,2-dimethyl-3-(p-nitrophenylazo)indole

Conditions

Conditions	Yield
In ethanol; water	A 34% B 83% C 85%

...Expand

: 456-27-9
4-nitrobenzenediazonium tetrafluoroborate

: 22546-09-4
(4-methoxyphenyl)(2-methyl-3-indolyl)methane

A: 1968-05-4
3,3'-diindolylmethane

B: 53330-79-3
3-(4-nitro-phenylazo)-indole

C: 52547-70-3
2-methylindole-3-azo-(4'-nitrobenzene)

Conditions

Conditions	Yield
In water	A 26% B n/a C 80%

...Expand

: 456-27-9
4-nitrobenzenediazonium tetrafluoroborate

: 22546-09-4
(4-methoxyphenyl)(2-methyl-3-indolyl)methane

A: 1968-05-4
3,3'-diindolylmethane

B: 52547-70-3
2-methylindole-3-azo-(4'-nitrobenzene)

Conditions

Conditions	Yield
In water	A 26% B 80%

...Expand

: 120-72-9
indole

: 31899-46-4
3-((methylthio))methyl-1H-indole

: 1968-05-4
3,3'-diindolylmethane

Conditions

Conditions	Yield
With copper diacetate In 1,4-dioxane at 80℃; for 2h;	80%

: 120-72-9
indole

: 127-19-5
N,N-dimethyl acetamide

: 1968-05-4
3,3'-diindolylmethane

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; copper(II) ferrite at 140℃; for 4h; Temperature; Reagent/catalyst;	80%

: 120-72-9
indole

: C15H21NO6S

A: 1968-05-4
3,3'-diindolylmethane

B: C17H22N2O4

Conditions

Conditions	Yield
With potassium fluoride; C46H34I4O6 In toluene at 70℃; for 10h; Catalytic behavior; Temperature; Friedel-Crafts Alkylation; Schlenk technique; enantioselective reaction;	A n/a B 79%

...Expand

: 700-06-1
indole-3-carbinol

: 1968-05-4
3,3'-diindolylmethane

Conditions

Conditions	Yield
With sodium hydroxide for 1h; Heating;	77%
With sodium hydroxide In water for 1h; Heating / reflux;	77%
With potato dextrose agar for 6h;	45%

: 1373922-48-5
3,3'-methylenebis(7-bromo-1H-indole)

: 1968-05-4
3,3'-diindolylmethane

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene at 130℃; for 16h; Inert atmosphere;	75%

: 120-72-9
indole

: 50-00-0
formaldehyd

: 769-42-6
1,3-dimethylbarbituric acid

A: 1968-05-4
3,3'-diindolylmethane

B: 33297-14-2
5-indol-3-ylmethyl-1,3-dimethyl-pyrimidine-2,4,6-trione

Conditions

Conditions	Yield
at 100℃; for 0.416667h;	A 10% B 74%

...Expand

: 120-72-9
indole

: 87-51-4
indole-3-acetic acid

: 1968-05-4
3,3'-diindolylmethane

Conditions

Conditions	Yield
With copper(II) acetate monohydrate In acetonitrile at 115℃; for 2h; Sealed tube; regioselective reaction;	74%

: 120-72-9
indole

: C19H12F6N2O3

: 1968-05-4
3,3'-diindolylmethane

Conditions

Conditions	Yield
With iron(II) triflate; 1,10-Phenanthroline In dichloromethane at 20℃; for 5h; Curtius Rearrangement;	72%

: 14558-49-7
tetrahydro-1,3-oxazine

: 120-72-9
indole

: 1968-05-4
3,3'-diindolylmethane

Conditions

Conditions	Yield
With acetic acid In acetonitrile for 3h; Heating;	70%
With acetic acid In acetonitrile for 3h; Heating;	70%

: 114648-68-9
3-indol-3-ylmethylene-3H-indol-3-ium perchlorate

: 1968-05-4
3,3'-diindolylmethane

Conditions

Conditions	Yield
With sodium hydroxide; sodium tetrahydroborate In methanol; water for 0.166667h;	70%

: 120-72-9
indole

: 109-82-0
methyleneaminoacetonitrile

A: 1968-05-4
3,3'-diindolylmethane

B: [bis-(1H-indol-3-ylmethyl)-amino]-acetonitrile

Conditions

Conditions	Yield
With dysprosium(III) trifluoromethanesulfonate In ethanol for 24h; Ambient temperature;	A 18% B 68%

...Expand

: 120-72-9
indole

: 110-18-9
N,N,N,N,-tetramethylethylenediamine

: 1968-05-4
3,3'-diindolylmethane

Conditions

Conditions	Yield
With copper diacetate; palladium diacetate at 70℃; for 12h; Neat (no solvent);	62%

: 120-72-9
indole

: 92487-21-3
N'-((1H-indol-3-yl)methylene)-4-methylbenzenesulfonohydrazide

: 1968-05-4
3,3'-diindolylmethane

Conditions

Conditions	Yield
With copper(l) iodide; caesium carbonate In 1,4-dioxane at 110℃; Catalytic behavior; Reagent/catalyst; Solvent; Sealed tube; Inert atmosphere; regioselective reaction;	61%

: 120-72-9
indole

: 20503-92-8
3-phenyl-oxazolidine

: 1968-05-4
3,3'-diindolylmethane

Conditions

Conditions	Yield
With acetic acid In acetonitrile for 4h; Heating;	55%
With acetic acid In acetonitrile for 12h; Ambient temperature;	55%

: 120-72-9
indole

: 50-00-0
formaldehyd

: 141-97-9
ethyl acetoacetate

A: ethyl 2-((1H-indol-3-yl)methyl)-3-oxo-3-phenylpropanoate

B: 1968-05-4
3,3'-diindolylmethane

Conditions

Conditions	Yield
In water at 60℃; for 20h;	A 54% B 11%

...Expand

: 120-72-9
indole

: 64-18-6
formic acid

: 1968-05-4
3,3'-diindolylmethane

Conditions

Conditions	Yield
With triethylsilane; tris(pentafluorophenyl)borate In neat (no solvent) at 20℃; for 4h;	54%

: 120-72-9
indole

: 487-89-8
Indole-3-carboxaldehyde

: 1968-05-4
3,3'-diindolylmethane

Conditions

Conditions	Yield
Stage #1: Indole-3-carboxaldehyde With toluene-4-sulfonic acid hydrazide In 1,4-dioxane at 60℃; Stage #2: indole With copper(l) iodide; caesium carbonate at 110℃; regioselective reaction;	53%

: 120-72-9
indole

: 50-00-0
formaldehyd

A: 858232-12-9
1-[1-(1H-indol-3-yl)methyl]-1H-indole

B: 1968-05-4
3,3'-diindolylmethane

Conditions

Conditions	Yield
With acetic acid In water at 50 - 90℃; for 3 - 20h;	A 2.1% B 45%
With calcium oxide In neat (no solvent) at 100℃; for 3h; Reagent/catalyst; Mannich Aminomethylation; stereoselective reaction;	A 25 %Chromat. B 65 %Chromat.

...Expand

: 24424-99-5
di-tert-butyl dicarbonate

: 1968-05-4
3,3'-diindolylmethane

: 666752-28-9
3,3'-methylenebis(1H-indole-1-carboxylic acid) 1,1'-bis(1,1-dimethylethyl) ester

Conditions

Conditions	Yield
With dmap In tetrahydrofuran	95%
dmap In tetrahydrofuran	95%

: 1968-05-4
3,3'-diindolylmethane

: 456-27-9
4-nitrobenzenediazonium tetrafluoroborate

: 53330-79-3
3-(4-nitro-phenylazo)-indole

Conditions

Conditions	Yield
In ethanol; water at 20℃; for 3h;	92%

: 1084795-22-1
propargyl carbonate

: 1968-05-4
3,3'-diindolylmethane

: bis(1-(buta-1,3-dien-2-yl)-1H-indol-3-yl)methane

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane at 70℃; for 4h; Schlenk technique; Inert atmosphere;	85%

: 1968-05-4
3,3'-diindolylmethane

: 385806-28-0
6-bromo-9-[2,3,5-tris-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-ribofuranosyl]purine

: C73H118N10O8Si6

Conditions

Conditions	Yield
With caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; palladium diacetate In toluene Heating;	82%

: 1968-05-4
3,3'-diindolylmethane

: 122-51-0
orthoformic acid triethyl ester

: 6336-32-9
5H,11H-indolo[3,2-b]carbazole

Conditions

Conditions	Yield
With sulfuric acid In methanol for 0.0833333h; Heating;	80%
With sulfuric acid In methanol for 5h; Reflux;	73%
With sulfuric acid In methanol for 5h; Reflux;	73%
With sulfuric acid In methanol for 1.05h; Reflux;	69.9%

: 1968-05-4
3,3'-diindolylmethane

: 80352-42-7
1-(4-bromophenyl)-2,2-dihydroxyethanone

: C33H20Br2N2O4

Conditions

Conditions	Yield
With copper(II) acetate monohydrate; acetic acid In toluene at 100℃; regioselective reaction;	76%

: 7078-98-0
2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone

: 1968-05-4
3,3'-diindolylmethane

: C38H40N2O

Conditions

Conditions	Yield
With phosphoric acid In water at 100℃; for 9h; Inert atmosphere; Schlenk technique;	76%

: 1968-05-4
3,3'-diindolylmethane

: 58028-74-3
2-pyrrolidin-1-ylbenzaldehyde

: 15-((1H-indol-3-yl)methyl)-1,2,3,15b-tetrahydro-9H-benzo[5,6]pyrrolo[2',1':3,4][1,4]diazepino[1,2-a]indole

Conditions

Conditions	Yield
With 1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; sodium sulfate In dichloromethane at 80℃; for 24h; Sealed tube; regioselective reaction;	71%

3,3'-Diindolylmethane Specification

The 3,3'-Diindolylmethane, with the CAS registry number 1968-05-4, has systematic name of 3,3'-methanediylbis(1H-indole). And its IUPAC name is 3-(1H-indol-3-ylmethyl)-1H-indole. Being a kind of white crystalline powder, it could be used as the pharmaceutical intermediates and could be used to treat Recurring Respiratory Papillomatosis currently. Besides, its product categories are including Indoles and derivatives; IndoleDerivative; Indoline & Oxindole; Indoles; Simple Indoles. When you are using this chemical, you should be careful. Do not breathe dust and try to avoid contacting with skin and eyes.

The characteristics of this chemical are as below: (1)ACD/LogP: 4.06; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.06; (4)ACD/LogD (pH 7.4): 4.06; (5)ACD/BCF (pH 5.5): 711.3; (6)ACD/BCF (pH 7.4): 711.32; (7)ACD/KOC (pH 5.5): 3829.12; (8)ACD/KOC (pH 7.4): 3829.21; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 9.86; (13)Index of Refraction: 1.765; (14)Molar Refractivity: 80.11 cm³; (15)Molar Volume: 193.7 cm³; (16)Polarizability: 31.76 ×10^-24 cm³; (17)Surface Tension: 62.7 dyne/cm; (18)Density: 1.271 g/cm3; (19)Flash Point: 232.5 °C; (20)Enthalpy of Vaporization: 74.5 kJ/mol; (21)Boiling Point: 504.8 °C at 760 mmHg; (22)Vapour Pressure: 8.07E-10 mmHg at 25°C; (23)Exact Mass: 246.115698; (24)MonoIsotopic Mass: 246.115698; (25)Topological Polar Surface Area: 31.6; (26)Heavy Atom Count: 19; (27)Complexity: 286.

In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CC3=CNC4=CC=CC=C43
(2)InChI: InChI=1S/C17H14N2/c1-3-7-16-14(5-1)12(10-18-16)9-13-11-19-17-8-4-2-6-15(13)17/h1-8,10-11,18-19H,9H2
(3)InChIKey: VFTRKSBEFQDZKX-UHFFFAOYSA-N

Product Name

3,3'-Diindolylmethane

Synthetic route

3,3'-Diindolylmethane Specification

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