13679-70-4

Basic information

• Product Name: 5-Methylthiophene-2-carboxaldehyde
• Synonyms: 5-Methyl-2-thiophenecarboxaldehyde, 98% 10ML;5-Methylthiophene-2-aldehyde 2-Formyl-5-methylthiophene;2-Formyl-5-methylthiophene, 5-Methyl-2-thenaldehyde;5-Methyl-2-thiophenecarboxaldehyde, 97+%;5 - Methyl - 2 - thiophene forMaldehyde;5-Methylthiophene-2-carbaldehyde for synthesis;2-Formyl-5-methylthiophene;2-Thiophenecarboxaldehyde, 5-methyl-
• CAS NO: 13679-70-4
• Molecular Formula: C₆H₆OS
• Molecular Weight: 126.18
• EINECS: 237-178-6
• Product Categories: Building Blocks;C1 to C6;C4 to C6;Carbonyl Compounds;Chemical Synthesis;Heterocyclic Building Blocks;Organic Building Blocks;Aromatic Aldehydes & Derivatives (substituted);Aldehydes;Thiophenes & Benzothiophenes;Thiophene&Benzothiophene;Heterocyclic Compounds;Thiophenes & Benzothiophenes;Building Blocks;Heterocyclic Building Blocks;Thiophenes;Alphabetical Listings;Flavors and Fragrances;M-N
• Mol File: 13679-70-4.mol
• Article Data: 24

Chemical Properties

• Melting Point: 184-186 °C
• Boiling Point: 114 °C25 mm Hg(lit.)
• Flash Point: 190 °F
• Appearance: Clear yellow to brown/Liquid
• Density: 1.17 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.127mmHg at 25°C
• Refractive Index: n20/D 1.583(lit.)
• Storage Temp.: 2-8°C
• Solubility: Soluble in ether and ethanol.
• Sensitive: Air Sensitive
• BRN: 106896
• CAS DataBase Reference: 5-Methylthiophene-2-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methylthiophene-2-carboxaldehyde(13679-70-4)
• EPA Substance Registry System: 5-Methylthiophene-2-carboxaldehyde(13679-70-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25-36-26-7/9-37
• WGK Germany: 3
• F: 8
• TSCA: T
• HazardClass: IRRITANT, AIR SENSITIVE
• Hazardous Substances Data: 13679-70-4(Hazardous Substances Data)

Usage

Description

May be synthesized from thiophene (or its derivatives) and formamide in the presence of POCl3; from N-(2-thenyl)formaldimines.

Chemical Properties

CLEAR YELLOW TO BROWN LIQUID

Occurrence

Reported found in French fried potato, roasted peanuts, tomato, wheat bread, raw chicken, cooked beef, pork liver, cognac, malt whiskey, coffee, popcorn, krill, shrimp and okra

Uses

5-Methylthiophene-2-carboxaldehyde is used as a food additive. It is an analytical reagent. The reagent has been synthesized and characterized using IR, 1H NMR and Mass spectral data.

Preparation

From thiophene (or its derivatives) and formamide in the presence of POCl3; from N-(2-thienyl)formaldimines.

Taste threshold values

Taste characteristics at 5 ppm: sweet, almond, fruity, heliotropine and nutty

General Description

5-Methyl-2-thiophenecarboxaldehyde can be obtained as a product from 2-thiophenecarboxaldehyde via metalation, and alkylation, followed by a series of reactions.

InChI:InChI=1/C6H6OS/c1-5-2-3-6(4-7)8-5/h2-4H,1H3

Upstream product

• 554-14-3 2-Methylthiophene 
• 68-12-2 N,N-dimethyl-formamide 
• 93-61-8 N-methyl-N-phenylformamide 
• 638-02-8 2,5-DIMETHYLTHIOPHENE 
• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 108-24-7 acetic anhydride 
• 75-44-5 phosgene 
• 107-06-2 1,2-dichloro-ethane 
• 96-43-5 2-thienyl chloride 
• 75-27-4 bromodichloromethane 
• 1918-79-2 2-methylthiophene-5-carboxylic acid 
• 3724-43-4 Vilsmeier reagent 
• 63826-59-5 5-methyl-2-thiophenemethanol 

Downstream Products

• 81020-67-9 3c-(5-methyl-[2]thienyl)-2-p-tolyl-acrylonitrile 
• 444117-63-9 2-(5-methyl-2-thienylmethylene)-1H-indene-1,3(2H)-dione 
• 80833-74-5 N-(5-methyl-2-thienylmethylidene)aniline 
• 403608-74-2 2-[2,3-diaza-4-(5-methyl-2-thienyl)buta-1,3-dienyl]-5-methylthiophene 
• 82230-49-7 5-methyl-2-<(methylamino)methyl>thiophene 
• 36634-72-7 (E)-1-(5-methylthien-2-yl)-2-phenylethene 

Relevant articles and documents

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Synthesis and biological evaluation of thiophene [3,2-b] pyrrole derivatives as potential anti-inflammatory agents

A series of thiophene [3,2-b] pyrrole derivatives were synthesized and evaluated their abilities to inhibit anti-inflammatory activity. In this series, substituent effects at the N-1, 2 and 5 positions of thiophene [3,2-b] pyrrole were examined. The results obtained are compared to those previously reported anti-inflammatory drugs like Tenidap sodium, Diclofenac sodium and Piroxicam. The results indicated the critical role of the group linked in the N-1 position and 2, 5 positions of thiophene [3,2-b] pyrrole with different functional groups.

Characteristic flavor formation of thermally processed N-(1-deoxy-α-D-ribulos-1-yl)-glycine: Decisive role of additional amino acids and promotional effect of glyoxal

The role of amino acids and α-dicarbonyls in the flavor formation of Amadori rearrangement product (ARP) during thermal processing was investigated. Comparisons of the volatile compounds and their concentrations when N-(1-deoxy-α-D-ribulos-1-yl)-glycine r

Preparation method of 5-methylthiophene-2-carboxaldehyde

The invention relates to a preparation method of 5-methylthiophene-2-carboxaldehyde. The method comprises the following steps: putting N, N-dimethylformamide into a container at about 10-15 DEG C, carrying out low-temperature treatment for 1-2 hours for later use, putting 2-methylthiophene into an environment with the pH value of 7-8.5 at normal temperature, performing treating for 1-4 hours for later use, and slowly dropwise adding the treated 2-methylthiophene into the container filled with N, N-dimethylformamide; performing heating to 45-60 DEG C, fully performing stirring, carrying out heat preservation reaction for 3-5 hours, and absorbing tail gas generated in the reaction process with sodium hydroxide. Briefly speaking, according to the technical scheme, an excellent optimization scheme is utilized, and the problems existing in preparation of 5-methylthiophene-2-carboxaldehyde are solved.

Palladium-catalyzed C-H formylation of electron-rich heteroarenes through radical dichloromethylation

A novel palladium-catalyzed C-H formylation of electron-rich N-, O-, and S-containing heteroarenes has been developed. The key to success is that the commercially available BrCHCl2 was used as a stoichiometric carbonyl source. Mechanistic investigations indicated that different from the known Reimer-Tiemann reaction, this net C-H formylation proceeded through an electrophilc radical-type path.