830-93-3

Basic information

• Product Name: 5-BROMOGRAMINE
• Synonyms: 5-BROMOGRAMINE;5-BROMO-3-DIMETHYLAMINOMETHYL-1H-INDOLE;5-BROMO-3-(DIMETHYLAMINOMETHYL)INDOLE;5-bromo-3-(dimethylamino)methyl-indol;5-bromogramine crystalline;[(5-Bromo-1H-indol-3-yl)methyl]dimethylamine;1H-Indole-3-MethanaMine, 5-broMo-N,N-diMethyl-
• CAS NO: 830-93-3
• Molecular Formula: C₁₁H₁₃BrN₂
• Molecular Weight: 253.14
• Product Categories: Heterocyclic Compounds;Halogenated Heterocycles;Heterocyclic Building Blocks;Indoles;IndolesBuilding Blocks;C11 to C27;Building Blocks;C11;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 830-93-3.mol
• Article Data: 19

Chemical Properties

• Melting Point: 149.5-150 °C
• Boiling Point: 346.9 °C at 760 mmHg
• Flash Point: 163.6 °C
• Appearance: White to off-white/Powder or Crystalline Powder
• Density: 1.449 g/cm³
• Vapor Pressure: 5.6E-05mmHg at 25°C
• Refractive Index: 1.655
• Storage Temp.: −20°C
• PKA: 16.04±0.30(Predicted)
• CAS DataBase Reference: 5-BROMOGRAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMOGRAMINE(830-93-3)
• EPA Substance Registry System: 5-BROMOGRAMINE(830-93-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• WGK Germany: 3
• RTECS: NL5170000
• Hazardous Substances Data: 830-93-3(Hazardous Substances Data)

Usage

General Description

5-Bromogramine is a chemical compound that belongs to the group of natural germacranolide sesquiterpenes. It is commonly found in the plant species Solidago graminea, also known as grass-leaved goldenrod. 5-Bromogramine has been found to exhibit various biological activities, including anti-inflammatory, anti-tumor, and anti-microbial properties. Studies have shown that it can inhibit the production of pro-inflammatory cytokines and downregulate the expression of inflammatory mediators. Additionally, it has been found to have cytotoxic effects on cancer cell lines and exhibit antimicrobial activity against various pathogens. Its diverse range of pharmacological activities makes 5-Bromogramine a promising candidate for further pharmaceutical development and research.

InChI:InChI=1/C11H13BrN2/c1-14(2)7-8-6-13-11-4-3-9(12)5-10(8)11/h3-6,13H,7H2,1-2H3

Upstream product

• 87-52-5 3-(Dimethylaminomethyl)indole 
• 10075-50-0 5-bromo-1H-indole 
• 50-00-0 formaldehyd 
• 124-40-3 dimethyl amine 
• 33797-51-2 eschenmoser's salt 
• 1177496-99-9 C₁₁H₁₁BrN₂O 

Downstream Products

• 152213-61-1 2-(6-bromo-1H-indol-3-yl)acetonitrile 
• 152213-63-3 (6-bromo-1H-indol-3-yl)acetic acid methyl ester 
• 152213-66-6 2-(6-bromo-1H-indol-3-yl)acetic acid 
• 117235-22-0 methyl 2-(5-bromo-1H-indole-3-yl)acetate 
• 40432-84-6 (5-bromo-1H-indol-3-yl)-acetic acid 
• 142273-20-9 kenpaullone 
• 877-03-2 5-bromo-1H-indole-3-carboxaldehyde 
• 1510820-49-1 diethyl 5’-bromo-2-methylenespiro[cyclohexane-1,3’-indol]-3-ene-5,5-dicarboxylate 
• 774-14-1 (5-bromo-1H-indol-3-yl)-acetonitrile 
• 6548-09-0 5-bromo-DL-tryptophan 
• 77216-22-9 1-[[2-(5-bromo-3-indolyl)-1,1-dimethylethyl]amino]-3-(2-methylphenoxy)-2-propanol 
• 833-04-5 5-bromo-α,α,2-trimethyl-1H-indole-3-ethanamine 

Relevant articles and documents

Rhodium-Catalyzed Stereoselective Cyclization of 3-Allenylindoles and N-Allenyltryptamines to Functionalized Vinylic Spiroindolenines

Herein, we report a highly enantio- and diastereoselective rhodium-catalyzed cyclization of N-allenyltryptamines and 3-allenylindoles to 6-membered spirocyclic indolenines. This allylic addition methodology offers the advantage of using a comparably cheap commercially available ligand with low loadings of an affordable rhodium precursor. The products can be converted into functionalized spirooxindoles and spiroindolines, which are regarded as important building blocks for the synthesis of a lot of natural products with biological activities.

Natural Products for Drug Discovery: Discovery of Gramines as Novel Agents against a Plant Virus

Plant viral diseases seriously affect crop yield and quality. The natural product gramine (1) and its simple structural analogues 2-35 were synthesized from indoles, amines, and aldehydes in one step. The antiviral effects of these alkaloids were evaluated systematically. Most of these compounds were found to have higher antiviral effects than commercial ribavirin for the first time. Especially compounds 22, 30, and 31 exhibited significantly higher effects than ningnanmycin, thereby emerging as novel antiviral leads for further optimization. The preliminary implementation indicated that these compounds likely inhibit the assembly of tobacco mosaic virus (TMV) by cross-linking TMV capsid protein. Gramine analogues were also found to have broad-spectrum fungicidal effects. Although gramine has been reported to have influence on germination and development of Erysiphe graminis, these compounds displayed no fungicidal effects against Blumeria graminis f. sp. tritici on wheat in our test. Some of these compounds also exhibited certain insecticidal activities.

Rhodium-Catalyzed Diastereo- And Enantioselective Tandem Spirocyclization/Reduction of 3-Allenylindoles: Access to Functionalized Vinylic Spiroindolines

A highly selective rhodium-catalyzed tandem spirocyclization/reduction of 3-allenylindoles is reported. By employing a Hantzsch ester as reductant, vinylic spiroindolines are obtained in excellent yields as well as diastereo- and enantioselectivity. In addition, the reaction's synthetic utility is highlighted by broad functional group compatibility and exemplified by a gram scale reaction with subsequent assorted transformations.