Product Name

  • Name

    5-BROMO-N,N-DIMETHYLTRYPTAMINE

  • EINECS 1592732-453-0
  • CAS No. 17274-65-6
  • Article Data16
  • CAS DataBase
  • Density 1.397 g/cm3
  • Solubility
  • Melting Point
  • Formula C12H15BrN2
  • Boiling Point 382.6 °C at 760 mmHg
  • Molecular Weight 267.168
  • Flash Point 185.2 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 17274-65-6 (5-BROMO-N,N-DIMETHYLTRYPTAMINE)
  • Hazard Symbols
  • Synonyms 5-Bromo-N,N-dimethyltryptamine;2-(5-Bromo-1H-indol-3-yl)-N,N-dimethylethanamine;5-Bromo-N,N-dimethylaminoethyltryptamine;
  • PSA 19.03000
  • LogP 3.03450

Synthetic route

4-(N,N-dimethylamino)butyraldehyde dimethyl acetal
19718-92-4

4-(N,N-dimethylamino)butyraldehyde dimethyl acetal

4-bromophenylhydrazine hydrochloride
622-88-8

4-bromophenylhydrazine hydrochloride

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions
ConditionsYield
With sulfuric acid for 2h; Heating;93%
2-(5-bromo-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-N,N-dimethyl-acetamide
717139-78-1

2-(5-bromo-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-N,N-dimethyl-acetamide

A

4-amino-2-(2-amino-5-bromo-phenyl)-4-dimethyl-butan-1-ol

4-amino-2-(2-amino-5-bromo-phenyl)-4-dimethyl-butan-1-ol

B

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions
ConditionsYield
Stage #1: 2-(5-bromo-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-N,N-dimethyl-acetamide With sodium tetrahydroborate; boron trifluoride diethyl etherate In 1,2-dimethoxyethane at 25 - 27℃; for 12h;
Stage #2: With 4 N NAOH In 1,2-dimethoxyethane at 80℃; for 0.5h;
Stage #3: With 1,2-diaza-bicyclo[2.2.2]octane In 1,2-dimethoxyethane for 2h;		A n/a
B 85%
2-(5-bromo-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-N,N-dimethyl-acetamide
717139-78-1

2-(5-bromo-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-N,N-dimethyl-acetamide

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions
ConditionsYield
Stage #1: 2-(5-bromo-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-N,N-dimethyl-acetamide With sodium tetrahydroborate; boron trifluoride diethyl etherate In 1,2-dimethoxyethane at -15 - 20℃;
Stage #2: With 1,4-diaza-bicyclo[2.2.2]octane for 2h; Heating / reflux;
Stage #3: With manganese(IV) oxide; sodium hydroxide; water more than 3 stages;		85%
methanol
67-56-1

methanol

5-bromotryptamine
3610-42-2

5-bromotryptamine

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions
ConditionsYield
With formaldehyd; nitrogen; sodium cyanoborohydride; acetic acid at 0 - 20℃; for 24h;84%
2-(5-bromo-1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide
199658-93-0

2-(5-bromo-1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; hexane; ethyl acetate75%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Heating / reflux;
formaldehyd
50-00-0

formaldehyd

5-bromotryptamine
3610-42-2

5-bromotryptamine

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions
ConditionsYield
With sodium acetate; sodium cyanoborohydride In methanol at 0 - 25℃; for 5h;70.4%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

2-(N,N-dimethylamino)ethanol
108-01-0

2-(N,N-dimethylamino)ethanol

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions
ConditionsYield
With C37H36Cl2NPRuS2; caesium carbonate at 135℃; for 24h; Inert atmosphere; Sealed tube;40%
1-hydroxy-N,N-dimethyltryptamine
161202-91-1

1-hydroxy-N,N-dimethyltryptamine

A

N,N-dimethyltryptamine
61-50-7

N,N-dimethyltryptamine

B

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

C

2-bromo-N,N-dimethyltryptamine

2-bromo-N,N-dimethyltryptamine

Conditions
ConditionsYield
With hydrogen bromide for 1h; Ambient temperature;A 11%
B 25%
C 2%
...Expand
2-(5-bromo-1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide
199658-93-0

2-(5-bromo-1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide

A

N,N-dimethyltryptamine
61-50-7

N,N-dimethyltryptamine

B

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions
ConditionsYield
With lithium aluminium tetrahydride In 1,4-dioxane for 3h; Heating;
5-bromotryptamine
3610-42-2

5-bromotryptamine

methyl iodide
74-88-4

methyl iodide

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions
ConditionsYield
Stage #1: 5-bromotryptamine With vinylsulfonylmethyl polystyrene In N,N-dimethyl-formamide
Stage #2: methyl iodide In N,N-dimethyl-formamide
Stage #3: With N-ethyl-N,N-diisopropylamine In dichloromethane Hoffman elimination; Further stages.;
indole
120-72-9

indole

(+-)-indolin-3-ol

(+-)-indolin-3-ol

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 87 percent
2: 70 percent / LiAlH4
3: 92 percent / triethylsilane, CF3COOH
4: 55 percent / Na2WO4*2H2O, 30percent H2O2 / methanol; H2O
5: 25 percent / 47percent aq. HBr / 1 h / Ambient temperature
View Scheme
N,N-dimethyltryptamine
61-50-7

N,N-dimethyltryptamine

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 92 percent / triethylsilane, CF3COOH
2: 55 percent / Na2WO4*2H2O, 30percent H2O2 / methanol; H2O
3: 25 percent / 47percent aq. HBr / 1 h / Ambient temperature
View Scheme
2-(1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide
29095-44-1

2-(1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 70 percent / LiAlH4
2: 92 percent / triethylsilane, CF3COOH
3: 55 percent / Na2WO4*2H2O, 30percent H2O2 / methanol; H2O
4: 25 percent / 47percent aq. HBr / 1 h / Ambient temperature
View Scheme
2-(dihydroindol-3-yl)-N,N-dimethylethylamine
38662-17-8, 79867-87-1

2-(dihydroindol-3-yl)-N,N-dimethylethylamine

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 55 percent / Na2WO4*2H2O, 30percent H2O2 / methanol; H2O
2: 25 percent / 47percent aq. HBr / 1 h / Ambient temperature
View Scheme
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: diethyl ether / 0 °C
2: H2O / 0.5 h
3: LiAlH4 / dioxane / 3 h / Heating
View Scheme
2-(5-bromo-1H-indol-3-yl)-2-oxoacetyl chloride
63843-81-2

2-(5-bromo-1H-indol-3-yl)-2-oxoacetyl chloride

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2O / 0.5 h
2: LiAlH4 / dioxane / 3 h / Heating
View Scheme
4,4-diethoxy-N,N-dimethyl-1-butanamine
1116-77-4

4,4-diethoxy-N,N-dimethyl-1-butanamine

4-bromophenylhydrazine hydrochloride
622-88-8

4-bromophenylhydrazine hydrochloride

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions
ConditionsYield
Stage #1: 4,4-diethoxy-N,N-dimethyl-1-butanamine; 4-bromophenylhydrazine hydrochloride With acetic acid In water for 4h; Fischer Indole Synthesis; Reflux;
Stage #2: With sodium hydrogencarbonate In water pH=8 - 9;
formaldehyd
50-00-0

formaldehyd

2-(5-bromo-1H-indol-3-yl)ethanamine hydrochloride
81868-12-4

2-(5-bromo-1H-indol-3-yl)ethanamine hydrochloride

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions
ConditionsYield
With sodium methylate; sodium cyanoborohydride; acetic acid In methanol; water at 20℃;
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

N,N-dimethyltryptamine
61-50-7

N,N-dimethyltryptamine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol for 18h;100%
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-3-fluoro-2-oxoindole
1294480-65-1

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-3-fluoro-2-oxoindole

Conditions
ConditionsYield
With aluminum (III) chloride; Selectfluor In methanol; acetonitrile at 0 - 20℃; for 0.5h;95%
1-(methylsulfonyl)-pyrrolidine
51599-68-9

1-(methylsulfonyl)-pyrrolidine

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

almotriptan
154323-57-6

almotriptan

Conditions
ConditionsYield
With nickel dichloride; lithium tert-butoxide; nixantphos In tetrahydrofuran at 0 - 80℃; for 13h; Reagent/catalyst; Inert atmosphere;92%
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

methyl iodide
74-88-4

methyl iodide

5-bromo-N,N,N-trimethyltryptamine

5-bromo-N,N,N-trimethyltryptamine

Conditions
ConditionsYield
In chloroform at 0 - 20℃;88%
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

N,N-dimethyl 2-(5-cyano-1H-indol-3-yl)ethylamine
17380-42-6

N,N-dimethyl 2-(5-cyano-1H-indol-3-yl)ethylamine

Conditions
ConditionsYield
With 1,1'-bis(diphenylphosphino)ferrocene; zink cyanide; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In DMF (N,N-dimethyl-formamide) at 110℃; for 21h;84%
dicyanozinc
557-21-1

dicyanozinc

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

N,N-dimethyl 2-(5-cyano-1H-indol-3-yl)ethylamine
17380-42-6

N,N-dimethyl 2-(5-cyano-1H-indol-3-yl)ethylamine

Conditions
ConditionsYield
1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) In DMF (N,N-dimethyl-formamide); chloroform at 110℃; for 21h; Product distribution / selectivity;84%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; zinc In hexanes; N,N-dimethyl-formamide at 20 - 60℃; for 0.75h;37.6%
methanolic ammonia

methanolic ammonia

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

benzoyl chloride
98-88-4

benzoyl chloride

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole
208464-42-0

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole

Conditions
ConditionsYield
With dmap In dichloromethane; triethylamine84%
...Expand
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

benzoyl chloride
98-88-4

benzoyl chloride

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole
208464-42-0

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole

Conditions
ConditionsYield
With triethylamine; dmap In dichloromethane at 20℃; for 20h;84%
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

3-[2-(Dimethylamino)ethyl]-1H-indole-5-carboxaldehyde
152673-51-3

3-[2-(Dimethylamino)ethyl]-1H-indole-5-carboxaldehyde

Conditions
ConditionsYield
With tert.-butyl lithium In DMF (N,N-dimethyl-formamide); hexane at -75 - -30℃; for 1.33333h;81.8%
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

[2-(1-benzyl-5-bromo-1H-indol-3-yl)-ethyl]-dimethyl-amine

[2-(1-benzyl-5-bromo-1H-indol-3-yl)-ethyl]-dimethyl-amine

Conditions
ConditionsYield
With sodium hydride; benzyl chloride In DMF (N,N-dimethyl-formamide)76.6%
Benzyl propargyl ether
4039-82-1

Benzyl propargyl ether

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

{2-[5-(3-benzyloxy-prop-1-ynyl)-1H-indol-3-yl]-ethyl}-dimethyl-amine
717139-86-1

{2-[5-(3-benzyloxy-prop-1-ynyl)-1H-indol-3-yl]-ethyl}-dimethyl-amine

Conditions
ConditionsYield
With piperidine; tri-tert-butyl phosphine; copper(I) iodide; dichloro bis(acetonitrile) palladium(II) In hexane at 50℃; for 20h;75%
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

5-amino-3-(2-dimethylaminoethyl)-1H-indol
99505-03-0

5-amino-3-(2-dimethylaminoethyl)-1H-indol

Conditions
ConditionsYield
Stage #1: 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole With tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran at 20℃; for 0.0833333h;
Stage #2: With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 21h; Heating / reflux;
Stage #3: With hydrogenchloride; sodium hydroxide; water more than 3 stages;		74.1%
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

C12H15BrN2O
1310827-05-4

C12H15BrN2O

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In chloroform at 0℃; for 0.166667h; Inert atmosphere;73%
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

C17H24N2OS
208464-59-9

C17H24N2OS

Conditions
ConditionsYield
34%
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

3-[2-(N,N-Dimethylamino)ethyl]-5-(4-hydroxytetrahydropyran-4-yl)-1H-indole

3-[2-(N,N-Dimethylamino)ethyl]-5-(4-hydroxytetrahydropyran-4-yl)-1H-indole

Conditions
ConditionsYield
30%
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

5-(1-Aza-1-methyl-4-hydroxycyclohex-4-yl)-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

5-(1-Aza-1-methyl-4-hydroxycyclohex-4-yl)-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions
ConditionsYield
With tert.-butyl lithium; potassium hydride In tetrahydrofuran20%
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole
17274-65-6

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

3-(2-dimethylamino-ethyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3-dihydro-indol-2-one

3-(2-dimethylamino-ethyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3-dihydro-indol-2-one

Conditions
ConditionsYield
Stage #1: 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole With tert.-butyl lithium In diethyl ether; pentane at -78 - -30℃; for 1.25h;
Stage #2: With 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In diethyl ether; pentane at -30 - -25℃; for 0.5h;
Stage #3: In diethyl ether; chloroform; water; pentane at 20℃; for 1.5h;		15.3%

1H-Indole-3-ethanamine,5-bromo-N,N-dimethyl- Specification

The 1H-Indole-3-ethanamine,5-bromo-N,N-dimethyl-, with the CAS registry number 17274-65-6, is also known as 5-Bromo-N,N-dimethyltryptamine. This chemical's molecular formula is C12H15BrN2 and molecular weight is 267.16. What's more, its systematic name is 2-(5-bromo-1H-indol-3-yl)-N,N-dimethylethanamine.

Physical properties of 1H-Indole-3-ethanamine,5-bromo-N,N-dimethyl- are: (1)ACD/LogP: 2.92; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 7.4): 1.1; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1.47; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 13.92; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 3; (11)olar Surface Area: 19.03 Å2; (12)Index of Refraction: 1.638; (13)Molar Refractivity: 68.75 cm3; (14)Molar Volume: 191.1 cm3; (15)Polarizability: 27.25×10-24cm3; (16)Surface Tension: 47.9 dyne/cm; (17)Density: 1.397 g/cm3; (18)Flash Point: 185.2 °C E; (19)nthalpy of Vaporization: 63.1 kJ/mol; (20)Boiling Point: 382.6 °C at 760 mmHg; (21)Vapour Pressure: 4.67E-06 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: CN(C)CCc2cnc1ccc(Br)cc12
(2)Std. InChI: InChI=1S/C12H15BrN2/c1-15(2)6-5-9-8-14-12-4-3-10(13)7-11(9)12/h3-4,7-8,14H,5-6H2,1-2H3
(3)Std. InChIKey: ATEYZYQLBQUZJE-UHFFFAOYSA-N

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