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700-06-1

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700-06-1 Usage

Chemical Properties

Indole-3-carbinol is an off-white powder. It is soluble in organic solvents such as benzene, ethanol, DMSO, and dimethyl formamide (DMF), which should be purged with an inert gas. The solubility of Indole-3-carbinol in ethanol and DMF is approximately 10 mg/ml and approximately 3 mg/ml in DMSO. Indole-3-carbinol is an unstable compound that undergoes rapid oligomerization in acid pH environments, like the stomach.

Occurrence

Indole-3-carbinol is produced by members of the family Cruciferae, and particularly members of the genus Brassica (e.g., cabbage, radishes, cauliflower, broccoli, Brussels sprouts, and daikon).

Uses

Indole-3-carbinol has been used for encapsulation with poly-lactic-co-glycolic acid (PLGA), to study its in-vitro anti-cancerogenic effects on breast adenocarcinoma epithelial (MCF7), colon adenocarcinoma epithelial (Caco2), prostate carcinoma epithelial (PC3) cells. It has also been used as a cytochrome P4501A (CYP1A) inducer.

Definition

ChEBI: Indole-3-carbinol is an indolyl alcohol carrying a hydroxymethyl group at position 3. It is a constituent of the cruciferous vegetables and had anticancer activity.

Preparation

Using indole, phosphorus oxychloride and N,N-dimethylformamide as raw materials, indole-3-carbaldehyde was synthesized by Vilsmeier-Haack reaction with a yield of 87.1%.

Application

Indole-3-carbinol (I3C) is a secondary plant metabolite of 3-methylindole produced in Brassica family vegetables. It is an inhibitor of Amyloid-beta deposition and Inhibits cancinogenesis at the initiation stage. Indole-3-carbinol is used in cancer prevention, specifically for breast, cervical and colon cancers. It has also been widely used to address lupus.

Synthesis Reference(s)

Canadian Journal of Chemistry, 31, p. 775, 1953 DOI: 10.1139/v53-106The Journal of Organic Chemistry, 61, p. 1493, 1996 DOI: 10.1021/jo951219c

General Description

Indole-3-carbinol is a novel secondary plant metabolite produced in cruciferous vegetables, such as cabbage, cauliflower and brussels sprouts.

Biochem/physiol Actions

Inhibits cancinogenesis at the initiation stage. Has be shown to inhibit carcinogenesis in several animal species, but it enhances tumor incidence if administered at a post-initiation stage. Found in cruciferous vegetables.

Anticancer Research

I3C is a bioactive compound majorly found in Brassica vegetables including broccoli,cauliflower, and collard greens. I3C and its derivative diindolylmethane (DIM)have been investigated for cancer prevention and treatment of breast, prostate, andovarian cancers. I3C partially modulates the tyrosine kinase/PI3K/Akt signalingpathway which leads to the prevention of lung adenocarcinoma which is induced byusing tobacco carcinogen in A/J mice. DIM transduces signaling via aryl hydrocarbon(Ah) receptor, NF-κB/Wnt/Akt/mTOR signaling pathways, cell cycle arrest,modulated cytochrome P450 enzymes, and altered angiogenetic and invasive,metastatic, and epigenetic behavior of cancer cells. Combination of DIM and I3Cinduces Nrf2-mediated phase II drug metabolizing genes (GSTm2, UGT1A1, andNQO1) and antioxidant genes (HO-1, SOD-1) (Weng et al. 2008; 2012).

Check Digit Verification of cas no

The CAS Registry Mumber 700-06-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,0 and 0 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 700-06:
(5*7)+(4*0)+(3*0)+(2*0)+(1*6)=41
41 % 10 = 1
So 700-06-1 is a valid CAS Registry Number.
InChI:InChI=1/C9H9NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-5,10-11H,6H2

700-06-1 Well-known Company Product Price

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  • Detail
  • TCI America

  • (I0496)  3-Indolemethanol  >95.0%(N)

  • 700-06-1

  • 5g

  • 470.00CNY

  • Detail
  • TCI America

  • (I0496)  3-Indolemethanol  >95.0%(N)

  • 700-06-1

  • 25g

  • 1,460.00CNY

  • Detail
  • Alfa Aesar

  • (L15762)  3-Indolemethanol, 97%   

  • 700-06-1

  • 1g

  • 181.0CNY

  • Detail
  • Alfa Aesar

  • (L15762)  3-Indolemethanol, 97%   

  • 700-06-1

  • 5g

  • 572.0CNY

  • Detail

700-06-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name indole-3-methanol

1.2 Other means of identification

Product number -
Other names INDOLE-3-METHANOL

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:700-06-1 SDS

700-06-1Synthetic route

indole
120-72-9

indole

formaldehyd
50-00-0

formaldehyd

indole-3-carbinol
700-06-1

indole-3-carbinol

Conditions
ConditionsYield
With sodium methylate for 8h; Heating;100%
With methanol; sodium hydrogencarbonate
With sodium methylate
Indole-3-carboxaldehyde
487-89-8

Indole-3-carboxaldehyde

indole-3-carbinol
700-06-1

indole-3-carbinol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 0℃; for 1h;100%
With formic acid In ethanol at 80℃; for 12h; Catalytic behavior;91%
With ammonia; calcium In tetrahydrofuran at -33℃; for 2h; other reagents: lithium, sodium, liq. ammonia;80%
3-methoxycarbonylindole
942-24-5

3-methoxycarbonylindole

indole-3-carbinol
700-06-1

indole-3-carbinol

Conditions
ConditionsYield
Stage #1: 3-methoxycarbonylindole With pentadec-3-en-2-one; trimethylsilyl trifluoromethanesulfonate; triphenylphosphine In dichloromethane at -78 - 0℃; for 1h; Inert atmosphere;
Stage #2: With diisobutylaluminium hydride In hexane; dichloromethane at -78℃; Inert atmosphere;
Stage #3: With potassium carbonate In methanol; hexane; dichloromethane at 20℃; for 0.5h; Inert atmosphere;
84%
Indole-3-carboxaldehyde
487-89-8

Indole-3-carboxaldehyde

dimethyl amine
124-40-3

dimethyl amine

A

indole-3-carbinol
700-06-1

indole-3-carbinol

B

3-(Dimethylaminomethyl)indole
87-52-5

3-(Dimethylaminomethyl)indole

Conditions
ConditionsYield
With sodium tetrahydroborate; water In methanol at 55 - 60℃; for 2.5h;A 25%
B 74%
Indole-3-carboxaldehyde
487-89-8

Indole-3-carboxaldehyde

A

indole-3-carbinol
700-06-1

indole-3-carbinol

B

3-aminomethylindole
22259-53-6

3-aminomethylindole

C

bis(indol-3-ylmethyl)amine
93742-14-4

bis(indol-3-ylmethyl)amine

Conditions
ConditionsYield
With ammonium hydroxide; sodium tetrahydroborate In methanol at 14 - 18℃; for 20h;A 72%
B 9%
C 13%
Indole-3-carboxaldehyde
487-89-8

Indole-3-carboxaldehyde

A

indole-3-carbinol
700-06-1

indole-3-carbinol

B

N-((1H-indol-3-yl)methyl)formamide

N-((1H-indol-3-yl)methyl)formamide

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 20℃; for 1.5h; Leukardt-Wallach Amination;A 30%
B 49%
indole-3-acetic acid
87-51-4

indole-3-acetic acid

A

3-Methylindole
83-34-1

3-Methylindole

B

Indole-3-carboxaldehyde
487-89-8

Indole-3-carboxaldehyde

C

indole-3-carbinol
700-06-1

indole-3-carbinol

D

3-(3-methylindol-1-yl)methylindole
59027-01-9

3-(3-methylindol-1-yl)methylindole

Conditions
ConditionsYield
With 1,3,6,8-tetra-n-butylpyrimido<5,4-g>pteridine-2,4,5,7(1H,3H,6H,8H)-tetrone 10-oxide In acetonitrile for 0.0833333h; Irradiation;A 14%
B 36%
C 12%
D 8%
With 1,3,6,8-tetra-n-butylpyrimido<5,4-g>pteridine-2,4,5,7(1H,3H,6H,8H)-tetrone 10-oxide In acetonitrile for 0.166667h; Product distribution; Ambient temperature; Irradiation; depends on time and wavelength of irradiation and ratio of reacted compounds;
1,3,5-Trioxan
110-88-3

1,3,5-Trioxan

indole
120-72-9

indole

methanol
67-56-1

methanol

sodium methylate
124-41-4

sodium methylate

indole-3-carbinol
700-06-1

indole-3-carbinol

1-(1H-indol-3-yl)-N,N-dimethylmethanamine oxide
17206-03-0

1-(1H-indol-3-yl)-N,N-dimethylmethanamine oxide

indole-3-carbinol
700-06-1

indole-3-carbinol

Conditions
ConditionsYield
With sodium hydroxide; diethyl ether; water
(3-indolylmethyl)trimethylammonium iodide
5457-31-8

(3-indolylmethyl)trimethylammonium iodide

indole-3-carbinol
700-06-1

indole-3-carbinol

Conditions
ConditionsYield
With sodium hydroxide; diethyl ether; water
indole-3-acetic acid
87-51-4

indole-3-acetic acid

A

Indole-3-carboxaldehyde
487-89-8

Indole-3-carboxaldehyde

B

indole-3-carbinol
700-06-1

indole-3-carbinol

C

3-methylideneoxindole
1861-29-6

3-methylideneoxindole

D

2-oxindole-3-methanol
2005-90-5

2-oxindole-3-methanol

Conditions
ConditionsYield
With oxygen In water horseradish peroxidase;
glucobrassicin

glucobrassicin

A

indole-3-carbinol
700-06-1

indole-3-carbinol

B

indole-3-acetonitrile
771-51-7

indole-3-acetonitrile

C

3,3'-diindolylmethane
1968-05-4

3,3'-diindolylmethane

Conditions
ConditionsYield
With myrosinase In water at 37℃; for 4h; Mechanism;
With myrosinase In water for 40h; Mechanism; low water system;
glucobrassicin

glucobrassicin

A

indole-3-carbinol
700-06-1

indole-3-carbinol

B

indole-3-acetonitrile
771-51-7

indole-3-acetonitrile

C

3,3'-diindolylmethane
1968-05-4

3,3'-diindolylmethane

Conditions
ConditionsYield
With myrosinase In water at 37℃; for 4h; Product distribution; other solvent, other substrates;
indole-3-acetic acid
87-51-4

indole-3-acetic acid

A

Indole-3-carboxaldehyde
487-89-8

Indole-3-carboxaldehyde

B

indole-3-carbinol
700-06-1

indole-3-carbinol

C

1H-indol-3-ylmethyl radical

1H-indol-3-ylmethyl radical

D

C10H7NO2(1-)

C10H7NO2(1-)

E

C10H9NO2(1+)

C10H9NO2(1+)

Conditions
ConditionsYield
With phosphate buffer; potassium bromide; dinitrogen monoxide In water at 20℃; Rate constant; Product distribution; Irradiation; effect of pH on the rate, effect of oxygen on the decay, effect of glutathione on the oxidation;
indole-3-acetic acid
87-51-4

indole-3-acetic acid

A

Indole-3-carboxaldehyde
487-89-8

Indole-3-carboxaldehyde

B

indole-3-carbinol
700-06-1

indole-3-carbinol

C

scatole hydroperoxide

scatole hydroperoxide

Conditions
ConditionsYield
With cationic peanut peroxidase; oxygen In acetate buffer at 25℃; pH=5.0; Kinetics; Product distribution; Further Variations:; Reagents; Oxidation;
3-Methylindole
83-34-1

3-Methylindole

indole-3-carbinol
700-06-1

indole-3-carbinol

Conditions
ConditionsYield
With phosphate buffer; goat lung microsomes (cytochrome 450); NADPH at 37℃; for 0.0333333h; pH=7.4; Enzyme kinetics; Oxidation;
methanol
67-56-1

methanol

Indole-3-carboxaldehyde
487-89-8

Indole-3-carboxaldehyde

sodium borate

sodium borate

indole-3-carbinol
700-06-1

indole-3-carbinol

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

(3-indolylmethyl)trimethylammonium iodide

aqueous NaOH

aqueous NaOH

A

indole-3-carbinol
700-06-1

indole-3-carbinol

B

bis-indol-3-ylmethyl ether

bis-indol-3-ylmethyl ether

C

(1-indol-3-ylmethyl-indol-3-ylmethyl)-trimethyl-ammonium; iodide

(1-indol-3-ylmethyl-indol-3-ylmethyl)-trimethyl-ammonium; iodide

aqueous indol-3-ylmethyl-trimethyl-ammonium-methyl sulfate

aqueous indol-3-ylmethyl-trimethyl-ammonium-methyl sulfate

A

indole-3-carbinol
700-06-1

indole-3-carbinol

B

(1-indol-3-ylmethyl-indol-3-ylmethyl)-trimethyl-ammonium; methyl sulfate

(1-indol-3-ylmethyl-indol-3-ylmethyl)-trimethyl-ammonium; methyl sulfate

Conditions
ConditionsYield
With sodium hydroxide
indole-3-acetic acid
87-51-4

indole-3-acetic acid

A

indole-3-carbinol
700-06-1

indole-3-carbinol

B

3-methylideneoxindole
1861-29-6

3-methylideneoxindole

Conditions
ConditionsYield
With horseradish peroxidase In ethanol; water at 37℃; for 2h; Kinetics;
With horseradish peroxidase In ethanol; water at 37℃; for 2h;
indolyl-3-methyl thioacetate
86204-54-8

indolyl-3-methyl thioacetate

A

indole-3-carbinol
700-06-1

indole-3-carbinol

B

diindolyl-3,3'-methylsulfide
86204-61-7

diindolyl-3,3'-methylsulfide

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran at 20℃;
3-(Dimethylaminomethyl)indole
87-52-5

3-(Dimethylaminomethyl)indole

indole-3-carbinol
700-06-1

indole-3-carbinol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ethanol; aqueous H2O2
2: water; NaOH-solution; diethyl ether
View Scheme
indole
120-72-9

indole

formaldehyd
50-00-0

formaldehyd

A

indole-3-carbinol
700-06-1

indole-3-carbinol

B

1-hydroxymethyl-1H-indole
5031-11-8

1-hydroxymethyl-1H-indole

Conditions
ConditionsYield
With calcium oxide at 65℃; neat (no solvent);
brussalexin A

brussalexin A

indole-3-carbinol
700-06-1

indole-3-carbinol

Conditions
ConditionsYield
With water for 72h;
N-methyl-S-(3-indolylmethyl)carbamodithioate
1395069-51-8

N-methyl-S-(3-indolylmethyl)carbamodithioate

indole-3-carbinol
700-06-1

indole-3-carbinol

Conditions
ConditionsYield
With water
indol-3ylmethanethiol
86204-60-6

indol-3ylmethanethiol

indole-3-carbinol
700-06-1

indole-3-carbinol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 0.33 h / 20 °C
2: water
View Scheme
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 0.33 h / 20 °C
2: water / 72 h
View Scheme
indolyl-3-methyl thioacetate
86204-54-8

indolyl-3-methyl thioacetate

indole-3-carbinol
700-06-1

indole-3-carbinol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrazine hydrate / tetrahydrofuran / 0.75 h / 80 °C
2: triethylamine / dichloromethane / 0.33 h / 20 °C
3: water
View Scheme
Multi-step reaction with 3 steps
1: hydrazine hydrate / tetrahydrofuran / 0.75 h / 80 °C
2: triethylamine / dichloromethane / 0.33 h / 20 °C
3: water / 72 h
View Scheme
phenylhydrazine
100-63-0

phenylhydrazine

indole-3-carbinol
700-06-1

indole-3-carbinol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: toluene-4-sulfonic acid / 20 h / Reflux
2.1: sodium hydroxide / ethanol / 40 °C
2.2: 0.42 h / 250 °C / Microwave irradiation
View Scheme
indole-3-carbinol
700-06-1

indole-3-carbinol

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

t-butyl 3-hydroxymethylindole-1-carboxylate
96551-22-3

t-butyl 3-hydroxymethylindole-1-carboxylate

Conditions
ConditionsYield
With dmap In acetonitrile at 25℃; for 16h;100%
With dmap; triethylamine In dichloromethane at 20℃; for 1h;15%
indole-3-carbinol
700-06-1

indole-3-carbinol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

3-(((tert-butyldimethylsilyl)oxy)methyl)-1H-indole

3-(((tert-butyldimethylsilyl)oxy)methyl)-1H-indole

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 0.5h;100%
indole-3-carbinol
700-06-1

indole-3-carbinol

Indole-3-carboxaldehyde
487-89-8

Indole-3-carboxaldehyde

Conditions
ConditionsYield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide for 8h; Ambient temperature;98%
With 1,3,6,8-tetra-n-butylpyrimido<5,4-g>pteridine-2,4,5,7(1H,3H,6H,8H)-tetrone 10-oxide In acetonitrile for 0.0333333h; Irradiation;90%
With LACTIC ACID; dihydrogen peroxide at 30℃; for 7h;87%
indole-3-carbinol
700-06-1

indole-3-carbinol

2-Mercaptobenzothiazole
149-30-4

2-Mercaptobenzothiazole

2-[(1H-indol-3-yl)methylthio]benzo[d]thiazole
87549-67-5

2-[(1H-indol-3-yl)methylthio]benzo[d]thiazole

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 6.25h; Mitsunobu reaction;96%
indole-3-carbinol
700-06-1

indole-3-carbinol

methyl iodide
74-88-4

methyl iodide

N,O-dimethylindole
1067241-18-2

N,O-dimethylindole

Conditions
ConditionsYield
Stage #1: indole-3-carbinol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 4h;
Stage #2: methyl iodide In N,N-dimethyl-formamide at 0 - 20℃;
95%
indole-3-carbinol
700-06-1

indole-3-carbinol

4-nitrobenzenediazonium tetrafluoroborate
456-27-9

4-nitrobenzenediazonium tetrafluoroborate

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

3-(4-nitro-phenylazo)-indole

Conditions
ConditionsYield
In ethanol; water94%
indole-3-carbinol
700-06-1

indole-3-carbinol

tert-butyl((1-methoxy-2-methylprop-1-en-1-yl)oxy)dimethylsilane
89337-62-2

tert-butyl((1-methoxy-2-methylprop-1-en-1-yl)oxy)dimethylsilane

methyl 3-(1H-indol-3-yl)-2,2-dimethylpropanoate

methyl 3-(1H-indol-3-yl)-2,2-dimethylpropanoate

Conditions
ConditionsYield
With magnesium bis(trifluoromethane solfonyl)imide In dichloromethane for 0.5h; Ambient temperature;93%
carbon disulfide
75-15-0

carbon disulfide

indole-3-carbinol
700-06-1

indole-3-carbinol

methyl iodide
74-88-4

methyl iodide

dithiocarbonic acid O-(1H-indol-3-ylmethyl) ester S-methyl ester

dithiocarbonic acid O-(1H-indol-3-ylmethyl) ester S-methyl ester

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 0℃; for 0.25h;93%
indole-3-carbinol
700-06-1

indole-3-carbinol

β-naphthol
135-19-3

β-naphthol

malononitrile
109-77-3

malononitrile

2-amino-4-(1H-indol-3-yl)-4H-benzo[g]chromene-3-carbonitrile

2-amino-4-(1H-indol-3-yl)-4H-benzo[g]chromene-3-carbonitrile

Conditions
ConditionsYield
With dimethyl sulfoxide; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 20℃; for 5h;92%
indole-3-carbinol
700-06-1

indole-3-carbinol

malononitrile
109-77-3

malononitrile

recorcinol
108-46-3

recorcinol

2-amino-7-hydroxy-4-(1H-indol-3-yl)-4H-chromene-3-carbonitrile

2-amino-7-hydroxy-4-(1H-indol-3-yl)-4H-chromene-3-carbonitrile

Conditions
ConditionsYield
With dimethyl sulfoxide; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 20℃; for 5h;92%
indole-3-carbinol
700-06-1

indole-3-carbinol

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

2-(1H-indol-3-yl)benzo[d]thiazole
31224-76-7

2-(1H-indol-3-yl)benzo[d]thiazole

Conditions
ConditionsYield
With tetrabutyl phosphonium bromide In water at 80℃; for 2h; Catalytic behavior;92%
indole-3-carbinol
700-06-1

indole-3-carbinol

4-methyl-1,2-diaminobenzene
496-72-0

4-methyl-1,2-diaminobenzene

2-(1H-indole-3-yl)-5-methyl-1H-benzimidazole
940704-02-9

2-(1H-indole-3-yl)-5-methyl-1H-benzimidazole

Conditions
ConditionsYield
With tetrabutyl phosphonium bromide In water at 80℃; for 3.5h; Catalytic behavior;90%
indole-3-carbinol
700-06-1

indole-3-carbinol

phenyl(2-(prop-2-yn-1-ylamino)phenyl)methanone

phenyl(2-(prop-2-yn-1-ylamino)phenyl)methanone

C41H31N3O

C41H31N3O

Conditions
ConditionsYield
With sodium hydroxide In N,N-dimethyl-formamide at 25℃; for 3h; Green chemistry;87%
2-methyl-1H-indole
95-20-5

2-methyl-1H-indole

indole-3-carbinol
700-06-1

indole-3-carbinol

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

(4-methoxyphenyl)(2-methyl-3-indolyl)methane

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In ethanol at 20℃; for 2.5h; ultrasonic irradiation;86%
indole-3-carbinol
700-06-1

indole-3-carbinol

4-hydroxy[1]benzopyran-2-one
1076-38-6

4-hydroxy[1]benzopyran-2-one

malononitrile
109-77-3

malononitrile

2-amino-4-(1H-indol-3-yl)-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile

2-amino-4-(1H-indol-3-yl)-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile

Conditions
ConditionsYield
With dimethyl sulfoxide; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 20℃; for 5.5h;86%
indole-3-carbinol
700-06-1

indole-3-carbinol

Bis-dimethylamino-aethoxyphosphin
3402-24-2

Bis-dimethylamino-aethoxyphosphin

1-[(dimethylamino)(ethoxy)phosphoryl]-3-[(dimethylamino)(ethoxy)phosphoryloxymethyl]indole

1-[(dimethylamino)(ethoxy)phosphoryl]-3-[(dimethylamino)(ethoxy)phosphoryloxymethyl]indole

Conditions
ConditionsYield
With air85.3%
morpholine
110-91-8

morpholine

indole-3-carbinol
700-06-1

indole-3-carbinol

4-((1H-indol-3-yl)methyl)morpholine
5379-88-4

4-((1H-indol-3-yl)methyl)morpholine

Conditions
ConditionsYield
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In toluene for 24h; Heating;85%
With 1,1'-bis(diphenylphosphino)ferrocene; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In toluene at 20℃; Inert atmosphere; Reflux; Molecular sieve;85%
With ethanol; sodium ethanolate
indole-3-carbinol
700-06-1

indole-3-carbinol

indole-3-acetic acid
87-51-4

indole-3-acetic acid

A

3-(methoxymethyl)-1H-indole
78440-76-3

3-(methoxymethyl)-1H-indole

B

2-(1H-indol-3-ylmethyl)-1H-indole-3-acetic acid
68232-56-4

2-(1H-indol-3-ylmethyl)-1H-indole-3-acetic acid

Conditions
ConditionsYield
In methanol; waterA 6%
B 85%
indole-3-carbinol
700-06-1

indole-3-carbinol

triethyl phosphite
122-52-1

triethyl phosphite

diethyl ((1H-indol-3-yl)methyl)phosphonate
17053-23-5

diethyl ((1H-indol-3-yl)methyl)phosphonate

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide at 120℃; for 24h; Inert atmosphere;83%
With tetra-(n-butyl)ammonium iodide In neat (no solvent) at 125℃; for 24h; Michaelis-Arbuzov Synthesis; Inert atmosphere; Schlenk technique; Sealed tube; Green chemistry;83%
2-pyrrolidinon
616-45-5

2-pyrrolidinon

indole-3-carbinol
700-06-1

indole-3-carbinol

C13H12N2O2

C13H12N2O2

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine; 9-azanoradamantane N-oxyl; oxygen; copper(l) chloride In tetrahydrofuran at 23℃; for 24h; Molecular sieve;81%
indole-3-carbinol
700-06-1

indole-3-carbinol

2-naphthaleneacetonitrile
7498-57-9

2-naphthaleneacetonitrile

3-(1H-indol-3-yl)-2-(naphthalen-2-yl)propanenitrile

3-(1H-indol-3-yl)-2-(naphthalen-2-yl)propanenitrile

Conditions
ConditionsYield
With [(bis(2-dicyclohexylphosphinoethyl)amine)Fe(CO)Br2]; sodium triethylborohydride; sodium hydroxide In toluene at 130℃; for 6h; Glovebox; Sealed tube; Inert atmosphere; Flow reactor; High pressure;81%
indole-3-carbinol
700-06-1

indole-3-carbinol

Bis-dimethylamino-aethoxyphosphin
3402-24-2

Bis-dimethylamino-aethoxyphosphin

1-[(dimethylamino)(ethoxy)phosphino]-3-[(dimethylamino)(ethoxy)phosphinoxymethyl]indole

1-[(dimethylamino)(ethoxy)phosphino]-3-[(dimethylamino)(ethoxy)phosphinoxymethyl]indole

Conditions
ConditionsYield
80.3%
indole-3-carbinol
700-06-1

indole-3-carbinol

A

2-(indol-3-ylmethyl)-3,3'-methylenediindole
138250-72-3

2-(indol-3-ylmethyl)-3,3'-methylenediindole

B

(1H-indol-3-yl)-(1H-indol-2-yl)-methane
114648-66-7

(1H-indol-3-yl)-(1H-indol-2-yl)-methane

Conditions
ConditionsYield
With pH 5 buffer In methanolA 10%
B 80%
With pH 5 buffer In methanolA 10 % Chromat.
B 80 % Chromat.
3-Methylindole
83-34-1

3-Methylindole

indole-3-carbinol
700-06-1

indole-3-carbinol

2-[(1H-indol-3-yl)methyl]-3-methyl-1H-indole
70423-69-7

2-[(1H-indol-3-yl)methyl]-3-methyl-1H-indole

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In ethanol at 20℃; for 2.5h; ultrasonic irradiation;80%
indole-3-carbinol
700-06-1

indole-3-carbinol

2-chloro-3-(chloromethyl)-1H-indole

2-chloro-3-(chloromethyl)-1H-indole

Conditions
ConditionsYield
With 1,3-dichloro-5,5-dimethylhydantoin In ethyl acetate at 20℃;80%
indole-3-carbinol
700-06-1

indole-3-carbinol

p-toluidine
106-49-0

p-toluidine

N-((1H-indol-3-yl)methyl)-4-methylbenzeneamine

N-((1H-indol-3-yl)methyl)-4-methylbenzeneamine

Conditions
ConditionsYield
With [Co(PCPMe-iPr)Cl]; potassium tert-butylate In toluene at 80℃; for 16h; Inert atmosphere; Green chemistry;79%
With trans-[Fe(N,N’-bis(diisopropylphosphino)-N''-dimethyl-2,4,6-triamino-1,3,5-triazine)(CO)Br2]; potassium tert-butylate In toluene at 80℃; for 16h; Inert atmosphere;73%
indole-3-carbinol
700-06-1

indole-3-carbinol

3,3'-diindolylmethane
1968-05-4

3,3'-diindolylmethane

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

700-06-1Relevant articles and documents

-

Clerin,Bruice

, p. 5571 (1974)

-

Chemoselective transfer hydrogenation of aromatic and heterocyclic aldehydes by green chemically prepared cobalt oxide nanoparticles

Krishnaveni,Lakshmi,Kaveri,Kadirvelu

, (2020/09/16)

A new surfactant (quercetin) assisted hydrothermal method is used for the preparation of phase pure cobalt oxide (Co3O4) nanoparticles (Nps). The quercetin acted well as surfactant in producing size controlled Nps. The produced Nps were extensively characterized by various techniques to reveal its chemical composition, structure, morphology, size and thermal behavior. The main objective of the study is to employ the prepared material as heterogeneous catalyst for hydrogenation of therapeutically important aldehydes. The capability of the catalyst is appear to be good, since the yield of alcohols from structurally different aldehydes is adequate with short period of time. Also the catalyst is recyclable, stable, no need of addition of ligands for activation and environmentally benign.

Facile Installation of 2-Reverse Prenyl Functionality into Indoles by a Tandem N-Alkylation-Aza-Cope Rearrangement Reaction and Its Application in Synthesis

Chen, Xiaobei,Fan, Huaqiang,Zhang, Shilei,Yu, Chenguang,Wang, Wei

supporting information, p. 716 - 723 (2016/01/12)

An unprecedented tandem N-alkylation-ionic aza-Cope (or Claisen) rearrangement-hydrolysis reaction of readily available indolyl bromides with enamines is described. Due to the complicated nature of the two processes, an operationally simple N-alkylation and subsequent microwave-irradiated ionic aza-Cope rearrangement-hydrolysis process has been uncovered. The tandem reaction serves as a powerful approach to the preparation of synthetically and biologically important, but challenging, 2-reverse quaternary-centered prenylated indoles with high efficiency. Notably, unusual nonaromatic 3-methylene-2,3-dihydro-1H-indole architectures, instead of aromatic indoles, are produced. Furthermore, the aza-Cope rearrangement reaction proceeds highly regioselectively to give the quaternary-centered reverse prenyl functionality, which often produces a mixture of two regioisomers by reported methods. The synthetic value of the resulting nonaromatic 3-methylene-2,3-dihydro-1Hindole architectures has been demonstrated as versatile building blocks in the efficient synthesis of structurally diverse 2-reverse prenylated indoles, such as indolines, indolefused sultams and lactams, and the natural product bruceolline D.

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