3-Allyl-1H-indole

Base Information

• Chemical Name: 3-Allyl-1H-indole
• CAS No.: 16886-09-2
• Molecular Formula: C11H11 N
• Molecular Weight: 157.215
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID00484023
• Nikkaji Number: J266.793B
• Wikidata: Q82321973
• Mol file: 16886-09-2.mol

Synonyms:3-Allyl-1H-indole;16886-09-2;3-Allylindole;3-(prop-2-en-1-yl)-1h-indole;3-prop-2-enyl-1H-indole;3-(2-PROPENYL)INDOLE;MFCD08361736;1H-Indole, 3-(2-propen-1-yl)-;1H-indole, 3-(2-propenyl)-;SCHEMBL547396;SCHEMBL10109110;UWJLKFQVYFDQEQ-UHFFFAOYSA-;DTXSID00484023;UWJLKFQVYFDQEQ-UHFFFAOYSA-N;AKOS006291114;PB41189;AS-31205;SY023431;CS-0051669;EN300-1830122;A882145;InChI=1/C11H11N/c1-2-5-9-8-12-11-7-4-3-6-10(9)11/h2-4,6-8,12H,1,5H2

Chemical Property of 3-Allyl-1H-indole

Chemical Property:

• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.636
• Boiling Point: 297.9°Cat760mmHg
• Flash Point: 127.6°C
• PSA: 15.79000
• Density: 1.074g/cm³
• LogP: 2.89640
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 157.089149355
• Heavy Atom Count: 12
• Complexity: 164

Purity/Quality:

NLT 98% ^*data from raw suppliers

3-(Prop-2-en-1-yl)-1H-indole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCC1=CNC2=CC=CC=C21

Technology Process of 3-Allyl-1H-indole

There total 44 articles about 3-Allyl-1H-indole 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%

indole (120-72-9) + allyl alcohol (107-18-6) → 3-allylindole (16886-09-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethyl borane; In tetrahydrofuran; at 70 ℃; for 12h; Inert atmosphere;

DOI:10.1002/chem.201203435

Reference yield: 88.0%

indole (120-72-9) + allyl bromide (106-95-6) → 3-allylindole (16886-09-2)

Guidance literature:

With sodium perborate; In water; at 20 ℃; for 7.5h; Green chemistry;

DOI:10.1080/00397911.2014.963874

Reference yield: 78.0%

indole (120-72-9) + allyl bromide (106-95-6) → 1-allylindole (16886-08-1) + 3-allylindole (16886-09-2)

Guidance literature:

With potassium tert-butylate; 18-crown-6 ether; In diethyl ether; for 1h; Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1021/jo01304a006

upstream raw materials:

indole

Allyl acetate

allyl alcohol

allyl bromide

Downstream raw materials:

3-indol-3-yl-propane-1,2-diol

3-allyl-1-benzyl-1H-indole

Refernces

• 1、 Kulkarni, Mukund G.,Davawala, Saryu I.,Dhondge, Attrimuni P.,Gaikwad, Dnyaneshwar D.,Borhade, Ajit S.,Chavhan, Sanjay W.. "An efficient two-step synthesis of 3-allylindoles". . p. 1003 - 1005. Retrieved 2006.
• 2、 Kimura, Masanari,Futamata, Makoto,Mukai, Ryutaro,Tamaru, Yoshinao. "Pd-catalyzed C3-selective allylation of indoles with allyl alcohols promoted by triethylborane". . p. 4592 - 4593. Retrieved 2005.
• 3、 Dhankher, Persis,Benhamou, Laure,Sheppard, Tom D.. "Rapid Assembly of Functionalised Spirocyclic Indolines by Palladium-Catalysed Dearomatising Diallylation of Indoles with Allyl Acetate". . p. 13375 - 13381. Retrieved 2014.
• 4、 Inada et al.. "-". . p. 833. Retrieved 1976.
• 5、 Nguyen, Vu T.,Nguyen, Viet D.,Haug, Graham C.,Dang, Hang T.,Jin, Shengfei,Li, Zhiliang,Flores-Hansen, Carsten,Benavides, Brenda S.,Arman, Hadi D.,Larionov, Oleg V.. "Alkene synthesis by photocatalytic chemoenzymatically compatible dehydrodecarboxylation of carboxylic acids and biomass". . p. 9485 - 9498. Retrieved 2019/10/11.
• 6、 Kerkovius, Jeff K.,Kerr, Michael A.. "Total Synthesis of Isodihydrokoumine, (19 Z)-Taberpsychine, and (4 R)-Isodihydroukoumine N4-Oxide". supporting information. p. 8415 - 8419. Retrieved 2018/07/05.