3-Bromo-2,5-dimethoxybenzyl Alcohol

Base Information

• Chemical Name: 3-Bromo-2,5-dimethoxybenzyl Alcohol
• CAS No.: 196302-51-9
• Molecular Formula: C9H11BrO3
• Molecular Weight: 247.089
• DSSTox Substance ID: DTXSID20436549
• Mol file: 196302-51-9.mol

Synonyms:3-Bromo-2,5-dimethoxybenzyl Alcohol;196302-51-9;SCHEMBL3927720;DTXSID20436549;JTYYNNSRXWOIEE-UHFFFAOYSA-N;(3-Bromo-2,5-dimethoxy-phenyl)-methanol;(3-Bromo-2,5-dimethyoxy-phenyl)-methanol

Chemical Property of 3-Bromo-2,5-dimethoxybenzyl Alcohol

Chemical Property:

• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 245.98916
• Heavy Atom Count: 13
• Complexity: 154

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=C(C(=C1)Br)OC)CO

Technology Process of 3-Bromo-2,5-dimethoxybenzyl Alcohol

There total 5 articles about 3-Bromo-2,5-dimethoxybenzyl Alcohol 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: 100.0%

3-bromo-2,5-dimethoxybenzaldehyde (68216-65-9) → (3-Bromo-2,5-dimethoxy-phenyl)-methanol (196302-51-9)

Guidance literature:

With borane-THF; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1021/ol036284k

Reference yield:

2,5-dimethoxy-3-bromobenzoic acid (100940-12-3) → (3-Bromo-2,5-dimethoxy-phenyl)-methanol (196302-51-9)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1055/s-2007-984520

Reference yield:

2-hydroxy-5-methoxybenzaldehyde (672-13-9) → (3-Bromo-2,5-dimethoxy-phenyl)-methanol (196302-51-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / AcONa; Br₂ / acetic acid / 1 h / 20 °C

2: 99 percent / K₂CO₃ / dimethylformamide / 24 h / 20 °C

3: 100 percent / BH₃*THF / tetrahydrofuran / 1 h / 0 °C

With borane-THF; bromine; sodium acetate; potassium carbonate; In tetrahydrofuran; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/ol036284k

upstream raw materials:

3-bromo-2,5-dimethoxybenzaldehyde

2,5-dimethoxy-3-bromobenzoic acid

2-hydroxy-5-methoxybenzaldehyde

3-Bromo-2-hydroxy-5-methoxy-benzaldehyde

Downstream raw materials:

[1(1RS,3Z,5R,6S,7S),3R]-N-{3-[1-benzenesulfonyl-7,9-bis(tert-butyl-dimethylsilyloxy)-4,6-dimethyl-5-triisopropylsilyloxy-non-3-enyl]-2,5-dimethoxy-phenyl}-4-(tert-butyldimethylsilyloxy)-3-methoxy-butyramide

[1(3Z,5R,6S,7S),3R]-N-{3-[7,9-bis(tert-butyl-dimethylsilyloxy)-4,6-dimethyl-5-triisopropylsilyloxy-non-3-enyl]-2,5-dimethoxy-phenyl}-4-(tert-butyldimethylsilyloxy)-3-methoxy-N-(2,2,2-trichloroethoxymethyl)-butyramide

[1(3Z,5R,6S,7S),3R]-N-{3-[7,9-bis(tert-butyl-dimethylsilyloxy)-4,6-dimethyl-5-triisopropylsilyloxy-non-3-enyl]-2,5-dimethoxy-phenyl}-4-(tert-butyldimethylsilyloxy)-3-methoxy-butyramide

[1(3Z,5R,6S,7S),3R]-N-{3-[7-(tert-butyl-dimethylsilyloxy)-9-hydroxy-4,6-dimethyl-5-triisopropylsilyloxy-non-3-enyl]-2,5-dimethoxy-phenyl}-4-hydroxy-3-methoxy-N-(2,2,2-trichloroethoxymethyl)-butyramide

Refernces

• 1、 Bernardo, Paul H.,Fitriyanto, Wuri,Chai, Christina L. L.. "Palladium-mediated synthesis of calothrixin B". . p. 1935 - 1939. Retrieved 2008/03/28.
• 2、 Evano, Gwilherm,Schaus, Jennifer V.,Panek, James S.. "A Convergent Synthesis of the Macrocyclic Core of Cytotrienins: Application of RCM for Macrocyclization". . p. 525 - 528. Retrieved 2007/10/03.