Product Name

  • Name

    Indole-3-carbinol

  • EINECS 211-836-2
  • CAS No. 700-06-1
  • Article Data37
  • CAS DataBase
  • Density 1.272 g/cm3
  • Solubility
  • Melting Point 96-99 °C(lit.)
  • Formula C9H9NO
  • Boiling Point 360.6 °C at 760 mmHg
  • Molecular Weight 147.177
  • Flash Point 171.9 °C
  • Transport Information
  • Appearance Off-white powder
  • Safety 26-36
  • Risk Codes 36/38
  • Molecular Structure Molecular Structure of 700-06-1 (Indole-3-carbinol)
  • Hazard Symbols IrritantXi
  • Synonyms Indole-3-methanol(6CI,7CI,8CI);3-(Hydroxymethyl)indole;3-Indolylcarbinol;3-Indolylmethanol;Indinol;NSC 525801;Indole-3-methanol;
  • PSA 36.02000
  • LogP 1.66020

Synthetic 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%

Indole-3-carbinol Chemical Properties

Molecular Structure of Indole-3-methanol (CAS NO.700-06-1):

Molecular Formula: C9H9NO
Molecular Weight: 147.1739
IUPAC Name: 1H-Indol-3-ylmethanol
CAS NO: 700-06-1
Appearance:white to off white crystals
Melting point: 96-99 °C
Index of Refraction: 1.705
Molar Refractivity: 44.97 cm3
Molar Volume: 115.6 cm3
Surface Tension: 61.7 dyne/cm
Density: 1.272 g/cm3
Flash Point: 171.9 °C
Enthalpy of Vaporization: 63.98 kJ/mol
Boiling Point: 360.6 °C at 760 mmHg
Vapour Pressure: 7.89E-06 mmHg at 25°C
Classification Code: Anticarcinogenic agents; Antineoplastic Agents; Protective Agents; Reproductive Effect
Synonyms: 3-Hydroxymethylindole ; 3-Indolylcarbinol ; 5-21-03-00045 (Beilstein Handbook Reference) ; AI3-60090 ; BRN 0121323 ; CCRIS 3261 ; EINECS 211-836-2 ; Indinol ; Indole 3 carbinol ; Indole-3-carbinol ; NSC 525801 ; 1H-Indole-3-methanol (9CI)  
SMILES: OCc2c1ccccc1nc2
InChI: InChI=1/C9H9NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-5,10-11H,6H2
InChIKey: IVYPNXXAYMYVSP-UHFFFAOYAO
Std. InChI: InChI=1S/C9H9NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-5,10-11H,6H2
Std. InChIKey: IVYPNXXAYMYVSP-UHFFFAOYSA-N

Indole-3-carbinol Uses

  Indole-3-methanol (CAS NO.700-06-1) can prevent the development of estrogen-enhanced cancers including breast, endometrial and cervical cancers. It has be shown to inhibit carcinogenesis in several animal species, but it enhances tumor incidence if administered at a post-initiation stage.

Indole-3-carbinol Production

  Indole-3-methanol (CAS NO.700-06-1) naturally exists in vegetables such as cabbage, broccoli, brussels sprouts, and kale. It is also widely available in supplement form. In 1985,B Sundberg and his Co-worker did a study about "Identification and Quantification of Indole-3-methanol in Etiolated Seedlings of Scots Pine"(Pinus sylvestris L.). Indole-3-methanol did exist in buffer extract from etiolated seedlings of Pinus sylvestris L.And the stability of indole-3-methanol at different pH levels was investigated.

  As a metabolism of indole-3-acetic acid, Indole-3-methanol can be produced by the oxidation of indole-3-acetic acid catalyzed by two cytosolic basic isoperoxidases from Lupinus. This study has been done by A. Barceló in 1990. While indole-3-methanol is only a minor product of the oxidation of indole-3-acetic acid catalyzed by extracellular acidic isoperoxidases, it is the only product of the oxidation of indole-3-acetic acid catalyzed by two cytosolic basic isoperoxidases (EC 1.11.1.7) from lupin (Lupinus albus L.) hypocotyls. It can be produced by the breakdown of the glucosinolate glucobrassicin.

Indole-3-carbinol Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LDLo subcutaneous 500mg/kg (500mg/kg) BEHAVIORAL: COMA Food and Cosmetics Toxicology. Vol. 18, Pg. 159, 1980.

Indole-3-carbinol Safety Profile

Safty informations about Indole-3-methanol (CAS NO.700-06-1):
Hazard Codes:XiIrritant
Risk Statements:36/38
36/38 (Irritating to the eyes and skin)
Safety Statements:26-36
26 (In case of contact with eyes,rinse immediately with plenty of water and seek medical advice)
36 (Wear suitable protective clothing)
WGK Germany:3
RTECS:NL9483000
Hazard Note:Irritant
Moderately toxic by subcutaneous route. An experimental teratogen. When heated to decomposition it emits toxic fumes of NOx.

Indole-3-carbinol Specification

Handling and Storage
Handling: Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. 
Storage: Store in a tightly closed container. Store in a dry area. Keep refrigerated. (Store below 4oC/39oF.) 

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