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17274-65-6

Basic Information
CAS No.: 17274-65-6
Name: 5-BROMO-N,N-DIMETHYLTRYPTAMINE
Article Data: 16
Molecular Structure:
Molecular Structure of 17274-65-6 (5-BROMO-N,N-DIMETHYLTRYPTAMINE)
Formula: C12H15BrN2
Molecular Weight: 267.168
Synonyms: 5-Bromo-N,N-dimethyltryptamine;2-(5-Bromo-1H-indol-3-yl)-N,N-dimethylethanamine;5-Bromo-N,N-dimethylaminoethyltryptamine;
EINECS: 1592732-453-0
Density: 1.397 g/cm3
Boiling Point: 382.6 °C at 760 mmHg
Flash Point: 185.2 °C
PSA: 19.03000
LogP: 3.03450
Synthetic route
19718-92-4

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

622-88-8

4-bromophenylhydrazine hydrochloride

17274-65-6

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

Conditions
ConditionsYield
With sulfuric acid for 2h; Heating;93%
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

B

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%
717139-78-1

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

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%
67-56-1

methanol

3610-42-2

5-bromotryptamine

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%
199658-93-0

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

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;
50-00-0

formaldehyd

3610-42-2

5-bromotryptamine

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%
10075-50-0

5-bromo-1H-indole

108-01-0

2-(N,N-dimethylamino)ethanol

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%
161202-91-1

1-hydroxy-N,N-dimethyltryptamine

A

61-50-7

N,N-dimethyltryptamine

B

17274-65-6

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

C

2-bromo-N,N-dimethyltryptamine

Conditions
ConditionsYield
With hydrogen bromide for 1h; Ambient temperature;A 11%
B 25%
C 2%
199658-93-0

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

A

61-50-7

N,N-dimethyltryptamine

B

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;
3610-42-2

5-bromotryptamine

74-88-4

methyl iodide

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.;
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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