Benzyl 2-(Hydroxymethyl)-1-Indolinecarboxylate

Base Information

• Chemical Name: Benzyl 2-(Hydroxymethyl)-1-Indolinecarboxylate
• CAS No.: 135829-04-8
• Molecular Formula: C17H17NO3
• Molecular Weight: 283.327
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID70380048
• ChEMBL ID: CHEMBL4591196
• Mol file: 135829-04-8.mol

Synonyms:135829-04-8;Benzyl 2-(Hydroxymethyl)-1-Indolinecarboxylate;benzyl 2-(hydroxymethyl)indoline-1-carboxylate;benzyl 2-(hydroxymethyl)-2,3-dihydroindole-1-carboxylate;benzyl 2-(hydroxymethyl)-2,3-dihydro-1H-indole-1-carboxylate;Oprea1_002982;SCHEMBL5763420;CHEMBL4591196;DTXSID70380048;QSMOQTIGILELKY-UHFFFAOYSA-N;MFCD02682013;1-Benzyloxycarbonylindoline-2-methanol;AKOS015902299;SB64265;MS-22135;CS-0361201;FT-0622792;(+/-) 1-Benzyloxycarbonyl-2-hydroxymethylindoline;EN300-12615282;W-205476;BENZYL2-(HYDROXYMETHYL)-1-INDOLINECARBOXYLATE;1H-Indole-1-carboxylicacid,2,3-dihydro-2-(hydroxymethyl)-,phenylmethyl ester

Chemical Property of Benzyl 2-(Hydroxymethyl)-1-Indolinecarboxylate

Chemical Property:

• Vapor Pressure: 5.75E-09mmHg at 25°C
• Melting Point: 67 °C
• Refractive Index: 1.615
• Boiling Point: 452.2 °C at 760 mmHg
• Flash Point: 227.3 °C
• PSA: 49.77000
• Density: 1.251 g/cm³
• LogP: 2.81180
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 283.12084340
• Heavy Atom Count: 21
• Complexity: 354

Purity/Quality:

98%min ^*data from raw suppliers

Benzyl2-(Hydroxymethyl)-1-Indolinecarboxylate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(N(C2=CC=CC=C21)C(=O)OCC3=CC=CC=C3)CO

Technology Process of Benzyl 2-(Hydroxymethyl)-1-Indolinecarboxylate

There total 5 articles about Benzyl 2-(Hydroxymethyl)-1-Indolinecarboxylate 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: 83.0%

methyl (+/-)-1-benzyloxycarbonyl-indoline-2-carboxylate (135829-03-7) → benzyl 2-(Hydroxymethyl)-1-indolinecarboxylate (135829-04-8)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; at 20 ℃; for 5h;

Reference yield:

2,3-Dihydro-1H-indol-2-ylmethanol (27640-31-9,27640-33-1,77122-21-5,138969-57-0) + phenyl chloroformate (1885-14-9) → benzyl 2-(Hydroxymethyl)-1-indolinecarboxylate (135829-04-8)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water;

Reference yield:

indolin-2-yl carboxylic acid (16851-56-2,78348-24-0) → benzyl 2-(Hydroxymethyl)-1-indolinecarboxylate (135829-04-8)

Guidance literature:

Multi-step reaction with 3 steps

1: thionyl chloride / 24 h / 20 °C / Cooling with ice

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 24 h / 20 °C

3: sodium tetrahydroborate; calcium chloride / tetrahydrofuran; methanol / 2 h / 20 °C

With sodium tetrahydroborate; thionyl chloride; N-ethyl-N,N-diisopropylamine; calcium chloride; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ol5002158

upstream raw materials:

methyl (+/-)-1-benzyloxycarbonyl-indoline-2-carboxylate

2,3-Dihydro-1H-indol-2-ylmethanol

phenyl chloroformate

indolin-2-yl carboxylic acid

Downstream raw materials:

N-(benzyloxycarbonyl)indoline-2-carbaldehyde

Refernces

• 1、 -. "BICYCLIC UNSATURATED TERTIARY AMINE COMPOUND". Page/Page column 81. . Retrieved 2010/02/11.
• 2、 -. "Heterocycle carboxamides as antiviral agents". . . Retrieved 2008/06/13.