4-Bromogramine

Base Information

• Chemical Name: 4-Bromogramine
• CAS No.: 64258-88-4
• Molecular Formula: C11H13BrN2
• Molecular Weight: 253.14
• Hs Code.: 2933990090
• Mol file: 64258-88-4.mol

Synonyms:3-dimethylaminobenzoyl isothiocyanate;3-dimethylaminomethyl-4-bromoindole;Benzoyl isothiocyanate,3-(dimethylamino);

Chemical Property of 4-Bromogramine

Chemical Property:

• Melting Point: 146-147 °C(Solv: methanol (67-56-1))
• Boiling Point: 346.9±27.0 °C(Predicted)
• PKA: 16.07±0.30(Predicted)
• PSA: 19.03000
• Density: 1.449±0.06 g/cm3(Predicted)
• LogP: 2.99200

Purity/Quality:

98%Min ^*data from raw suppliers

4-Bromogramine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Bromogramine

There total 8 articles about 4-Bromogramine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

(4-bromo-1-triisopropylsilyl-1H-indol-3-ylmethyl)-dimethylamine (146886-59-1) → 1-(4-bromo-1H-indol-3-yl)-N,N-dimethylmethanamine (64258-88-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 4h;

DOI:10.1021/jo981723s

Reference yield: 97.0%

4-bromo-1H-indole (52488-36-5) + formaldehyd (50-00-0,30525-89-4,61233-19-0) + dimethyl amine (124-40-3) → 1-(4-bromo-1H-indol-3-yl)-N,N-dimethylmethanamine (64258-88-4)

Guidance literature:

With acetic acid; In water; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.bmcl.2021.128205

Reference yield:

1-(N-triisopropylsilyl-1H-indol-3-yl)-N,N-dimethylmethanamine (146886-51-3) → 1-(4-bromo-1H-indol-3-yl)-N,N-dimethylmethanamine (64258-88-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: t-BuLi / diethyl ether; pentane / 1 h / 0 °C

1.2: 56 percent / BrCH₂CH₂Br

2.1: TBAF / tetrahydrofuran / 0.17 h / 20 °C

With tetrabutyl ammonium fluoride; tert.-butyl lithium; In tetrahydrofuran; diethyl ether; pentane;

DOI:10.1021/ol017310m

upstream raw materials:

4-bromo-1H-indole

formaldehyd

dimethyl amine

(4-bromo-1-triisopropylsilyl-1H-indol-3-ylmethyl)-dimethylamine

Downstream raw materials:

2-(4-bromo-1H-indol-3-yl)acetonitrile

dl-4-bromotryptophan

N-benzylrugulovasines A and B

4-bromo-3-[2-(2,5-dihydro-4-methyl-5-oxo-2-furanyl)-2-[methyl(phenylmethyl)amino]ethyl]-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester

Refernces

• 1、 Chauder, Brian,Larkin, Andrew,Snieckus, Victor. "Rapid route to 3,4-substituted indoles via a directed ortho metalation-retro-Mannich sequence.". . p. 815 - 817. Retrieved 2007/10/03.
• 2、 Martin,Liras. "Novel applications of vinylogous Mannich reactions. Total synthesis of rugulovasines A and B". . p. 10450 - 10451. Retrieved 2007/10/02.