5-Methylthiophene-2-carboxaldehyde Chemical Properties

Melting point:

184-186 °C

Boiling point:

114 °C/25 mmHg (lit.)

Density 

1.17 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.583(lit.)

FEMA 

3209 | 5-METHYL-2-THIOPHENECARBOXALDEHYDE

Flash point:

190 °F

storage temp. 

2-8°C

solubility 

Soluble in ether and ethanol.

form 

Liquid

Specific Gravity

1.180

color 

Clear yellow to brown

Odor

at 0.10 % in dipropylene glycol. sweet almond cherry furfural woody acetophenone

Odor Type

fruity

biological source

synthetic

Sensitive 

Air Sensitive

JECFA Number

1050

BRN 

106896

InChIKey

VAUMDUIUEPIGHM-UHFFFAOYSA-N

LogP

1.48

CAS DataBase Reference

13679-70-4(CAS DataBase Reference)

NIST Chemistry Reference

5-Methyl-2-thiophenecarboxaldehyde(13679-70-4)

EPA Substance Registry System

2-Thiophenecarboxaldehyde, 5-methyl- (13679-70-4)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

23-24/25-36-26-7/9-37

WGK Germany 

3

F 

8

Hazard Note 

Irritant

TSCA 

T

HazardClass 

IRRITANT, AIR SENSITIVE

HS Code 

29349990

MSDS

• Language:English Provider:5-Methylthiophene-2-carboxaldehyde
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

5-Methylthiophene-2-carboxaldehyde Usage And Synthesis

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.

Definition

ChEBI: 5-Methyl-2-thiophenecarboxaldehyde is a member of thiophenes.

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.

Synthesis

GENERAL STEPS: A tetrahydrofuran (THF) solution of 0.99 M ethylmagnesium chloride (EtMgCl, 0.61 mL, 0.6 mmol) was cooled to 0°C under nitrogen protection, and dicyclohexylamine (0.01 mL, 0.05 mmol) and 2-methylthiophene (1a, 0.048 mL, 0.50 mmol) were slowly added dropwise. The reaction mixture was warmed to 60°C and stirred for 24 hours. Subsequently, 1.4 mL of THF and N,N-dimethylformamide (DMF, 0.5 mL, 6.46 mmol) were added sequentially and stirring was continued at 60°C for 1 hour. Upon completion of the reaction, the reaction was quenched with saturated aqueous ammonium chloride solution (1.0 mL) and the mixture was poured into a solvent mixture of ether/water to separate the organic and aqueous phases. The aqueous phase was extracted twice with ether, the organic layers were combined and dried with anhydrous sodium sulfate. The organic phase was concentrated under reduced pressure to obtain the crude product, which was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=20/1) to give 5-methyl-2-thiophenecarboxaldehyde (1a-CHO, 62.3 mg, colorless oil, 99% yield).

References

[1] Tetrahedron Letters, 2012, vol. 53, # 9, p. 1173 - 1176
[2] Dyes and Pigments, 2014, vol. 106, p. 154 - 160
[3] Patent: EP1555257, 2005, A1. Location in patent: Page/Page column 25-26
[4] Pharmaceutical Chemistry Journal, 1989, vol. 23, # 7, p. 592 - 596
[5] Khimiko-Farmatsevticheskii Zhurnal, 1989, vol. 23, # 7, p. 840 - 843

5-Methylthiophene-2-carboxaldehyde(13679-70-4)Related Product Information

• 5-Methyl-2-thiophenecarboxylic acid
• 5-METHYL-2-NITROANILINE
• 5-METHYL-2-THIOPHENESULFONYL CHLORIDE
• 5-Methylthiophene-2-carboxaldehyde
• 2-ACETYL-3-AMINO-5-PHENYLTHIOPHENE
• 1-(5-Methyl-2-thienyl)ethan-1-one
• 2,5-Thiophenedicarboxylic acid
• 2-[1-METHYL-3-(TRIFLUOROMETHYL)PYRAZOL-5-YL]-THIOPHENE-5-CARBOXALDEHYDE
• 2,2'-BITHIOPHENE-5-CARBOXALDEHYDE
• 5-Acetylthiophene-2-carboxylic acid
• 5-(2-PYRIDYL)THIOPHENE-2-CARBOXYLIC ACID
• Methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate
• 2-ACETYL-5-CYANOTHIOPHENE
• 2-Methyl-5-propionylthiophene
• 3-Methyl-2-thiophenecarboxaldehyde
• 5-(1,3,2-dioxaborinan-2-yl)-3-methylthiophene-2-carboxaldehyde
• Formaldehyde
• 2-Thiophenecarboxaldehyde