| Identification | More | [Name]
2,5-Dichlorothiophene | [CAS]
3172-52-9 | [Synonyms]
2,5-DICHLOROTHIOPHENE
2,6-DICHLOROTHIOPHENE
DICHLOROTHIOPHENE
2,5-dichloro-thiophen
thiophene,2,5-dichloro-
2,5-Dichlorothiophenene
2,5-Dichlorothiophene,97%
5-chloro-2-thienyl chloride | [EINECS(EC#)]
221-638-8 | [Molecular Formula]
C4H2Cl2S | [MDL Number]
MFCD00005423 | [Molecular Weight]
153.03 | [MOL File]
3172-52-9.mol |
| Safety Data | Back Directory | [Hazard Codes ]
T+,Xn | [Risk Statements ]
R40:Limited evidence of a carcinogenic effect.
R26/27/28:Very Toxic by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37:Wear suitable protective clothing and gloves .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
2929 | [WGK Germany ]
3 | [TSCA ]
T | [HazardClass ]
6.1 | [PackingGroup ]
II | [HS Code ]
29349990 | [Storage Class]
3 - Flammable liquids | [Hazard Classifications]
Flam. Liq. 3 |
| Hazard Information | Back Directory | [Chemical Properties]
clear colorless to slightly yellow liquid | [Uses]
2,5-Dichlorothiophene is mainly used as a pharmaceutical intermediate. It is used in the synthesis of 3,4-disubstituted thiophenes. | [Synthesis Reference(s)]
Tetrahedron, 52, p. 8863, 1996 DOI: 10.1016/0040-4020(96)00433-4 | [Synthesis]
The general procedure for the preparation of 2,5-dichlorothiophene is as follows:
1. 300 g of carbon tetrachloride and 84 g of thiophene were added to a 1000 mL three-necked flask, heated to reflux temperature and then 270 g of N-chlorotoluene diimide was slowly added.
2. After completion of the reaction, the reaction mixture was cooled to room temperature and filtered to remove insoluble impurities.
3. The filtrate was concentrated to recover carbon tetrachloride to give the remaining reaction mixture. 4.
4. the remaining reaction mixture was heated to 100 °C and subjected to reduced pressure distillation.
5. The 100 °C fraction was collected as the target product 2,5-dichlorothiophene in a yield of 145 g, 95% yield and 98.5% purity. | [References]
[1] Patent: CN105481827, 2016, A. Location in patent: Paragraph 0021; 0022
[2] Journal of Organic Chemistry, 1993, vol. 58, # 11, p. 3072 - 3075
[3] Tetrahedron, 1996, vol. 52, # 26, p. 8863 - 8866
[4] Journal of Chemical Crystallography, 2007, vol. 37, # 6, p. 387 - 398
[5] Patent: US2492644, 1947, |
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