4-Bromo-5-methylthiophene-2-carbaldehyde

Base Information

• Chemical Name: 4-Bromo-5-methylthiophene-2-carbaldehyde
• CAS No.: 29421-75-8
• Molecular Formula: C6H5BrOS
• Molecular Weight: 205.075
• Hs Code.: 2934999090
• European Community (EC) Number: 835-763-6
• DSSTox Substance ID: DTXSID90573834
• Nikkaji Number: J1.544.028G
• Wikidata: Q82462672
• Mol file: 29421-75-8.mol

Synonyms:4-bromo-5-methylthiophene-2-carbaldehyde;29421-75-8;4-bromo-5-methyl-2-thiophenecarbaldehyde;4-Bromo-5-methylthiophene-2-carboxaldehyde;MFCD01118659;2-Thiophenecarboxaldehyde,4-bromo-5-methyl-;4-bromo-5-methyl-2-thiophenecarboxaldehyde;SCHEMBL1199234;DTXSID90573834;NXBRLTKLAXZRPO-UHFFFAOYSA-N;GEO-00516;AKOS005167018;SB66994;AS-48010;SY083098;4-bromo-5-methyl-thiophene-2-carbaldehyde;3-bromo-2-methyl-5-thiophenecarboxyaldehyde;CS-0061189;EN300-155217;F17533;A819910;AN-584/11663464;W-200286;Z1269128772

Chemical Property of 4-Bromo-5-methylthiophene-2-carbaldehyde

Chemical Property:

• Boiling Point: 266.767 °C at 760 mmHg
• Flash Point: 115.137 °C
• PSA: 45.31000
• Density: 1.667 g/cm³
• LogP: 2.63150
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 203.92445
• Heavy Atom Count: 9
• Complexity: 118

Purity/Quality:

99.3% ^*data from raw suppliers

4-bromo-5-methylthiophene-2-carbaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=C(S1)C=O)Br

Technology Process of 4-Bromo-5-methylthiophene-2-carbaldehyde

There total 3 articles about 4-Bromo-5-methylthiophene-2-carbaldehyde 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%

5-methylthiophene-2-carboxaldehyde (13679-70-4) → 3-bromo-2-methyl-5-thiophenecarboxyaldehyde (29421-75-8)

Guidance literature:

With bromine; In acetic acid; at 0 - 20 ℃; Darkness;

DOI:10.1002/anie.201306183

Reference yield: 84.0%

3,5-dibromo-2-methylthiophene (29421-73-6) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 3-bromo-2-methyl-5-thiophenecarboxyaldehyde (29421-75-8)

Guidance literature:

3,5-dibromo-2-methylthiophene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h; Inert atmosphere;

N,N-dimethyl-formamide; In tetrahydrofuran; hexane; at -78 - 0 ℃; Inert atmosphere;

DOI:10.1021/jacs.8b02982

Reference yield:

2-Methylthiophene (554-14-3) → 3-bromo-2-methyl-5-thiophenecarboxyaldehyde (29421-75-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N-Bromosuccinimide; acetic acid

2.1: n-butyllithium / hexane; tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere

2.2: -78 - 0 °C / Inert atmosphere

With N-Bromosuccinimide; n-butyllithium; acetic acid; In tetrahydrofuran; hexane;

DOI:10.1021/jacs.8b02982

upstream raw materials:

5-methylthiophene-2-carboxaldehyde

3,5-dibromo-2-methylthiophene

N,N-dimethyl-formamide

2-Methylthiophene

Downstream raw materials:

3-(4-bromo-5-methyl-thien-2-yl)-2-cyanoacrylic acid

3-[4-(4-aminophenyl)-5-methyl-thien-2-yl]-2-cyanoacrylic acid

N-(2,6-diisopropylphenyl)-N'-{4-[2-methyl-5-(cyanoacrylic acid)-3-thienyl]-phenyl}-1,7-bis(6-undecanoxy)perylene-3,4,9,10-tetracarboxylic diimide

5-methyl-4-bromo-2-thiopheneformaldehyde diethyl acetal

Refernces

• 1、 Yokoyama, Yasushi,Hosoda, Naoya,Osano, Yasuko T.,Sasaki, Chizuko. "Absolute stereochemistry and CD spectra of resolved enantiomers of the colored form of a photochromic dithienylethene". . p. 1093 - 1094. Retrieved 1998.
• 2、 Kolmar, Theresa,Büllmann, Simon M.,Sarter, Christopher,H?fer, Katharina,J?schke, Andres. "Development of High-Performance Pyrimidine Nucleoside and Oligonucleotide Diarylethene Photoswitches". supporting information. p. 8164 - 8173. Retrieved 2021/03/08.
• 3、 Singh, Ashish,Verma, Parul,Samanta, Debabrata,Dey, Anupam,Dey, Jyotirmoy,Maji, Tapas Kumar. "Stabilization of ultra-small gold nanoparticles in a photochromic organic cage: modulating photocatalytic CO2reduction by tuning light irradiation". supporting information. p. 5780 - 5786. Retrieved 2021/03/16.