3-Acetyl-2,5-dichlorothiophene supplier

Name
3-Acetyl-2,5-dichlorothiophene
EINECS 252-893-3
CAS No. 36157-40-1
Article Data10
CAS DataBase
Density 1.452 g/cm³
Solubility
Melting Point 37-40 °C(lit.)
Formula C₆H₄Cl₂OS
Boiling Point 233.9 °C at 760 mmHg
Molecular Weight 195.069
Flash Point 95.3 °C
Transport Information
Appearance white to light yellow crystal powder
Safety 26-36-36/37/39-22-36/37
Risk Codes 20/21/22-36/37/38
Molecular Structure
Hazard Symbols Xn,Xi
Synonyms 1-(2,5-Dichloro-3-thienyl)ethanone;1-(2,5-Dichlorothiophen-3-yl)ethanone;2,5-Dichloro-3-acetylthiophene;2,5-Dichloro-3-thienyl methyl ketone;
PSA 45.31000
LogP 3.25750

Synthetic route

: 3172-52-9
2,5-diclorothiophene

: 75-36-5
acetyl chloride

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

Conditions

Conditions	Yield
With aluminum (III) chloride In carbon disulfide at 20℃; for 25h; Friedel-Crafts Acylation;	90%
With aluminum (III) chloride In carbon disulfide at 20℃;	76.7%
With aluminium trichloride In chloroform at 20℃; for 5h;	52%

: 61170-81-8
1-methyl-4-chlorobutenal

: 16911-84-5
thioacetyl chloride

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

Conditions

Conditions	Yield
Stage #1: 1-methyl-4-chlorobutenal With sodium hydrogencarbonate In acetone at -15 - 10℃; for 1h; Stage #2: thioacetyl chloride In acetone at 75℃; for 4h; Solvent; Temperature; Reagent/catalyst;	117.6 g

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

: 59160-46-2
2-bromo-1-(2,5-dichlorothien-3-yl)ethanone

Conditions

Conditions	Yield
	100%
With bromine; acetic acid at 15 - 25℃;	85%

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: 166196-79-8
1-(2,5-dichloro-3-thienyl)-3-(dimethylamino)prop-2-en-1-one

Conditions

Conditions	Yield
Reflux;	100%

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

: 100-44-7
benzyl chloride

: 160982-09-2
3-Acetyl-2-(phenylmethyl)thio-5-chlorothiophene

Conditions

Conditions	Yield
Stage #1: benzyl chloride With thiourea In ethanol; water for 2h; Reflux; Large scale; Stage #2: 3-acetyl-2,5-dichlorothiophene With sodium hydroxide In ethanol; water for 3h; Reflux; Large scale; regioselective reaction;	97%
With sodium hydroxide; sodium hypochlorite; thiourea In ethanol; water

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

: 73568-29-3
2-chloro-6-methoxyquinolin-3-carboxaldehyde

: 1253278-28-2
(2E)-3-(2-chloro-6-methoxyquinolin-3-yl)-1-(2,5-dichlorothien-3-yl)prop-2-en-1-one

Conditions

Conditions	Yield
With sodium hydroxide In methanol; water at 20℃; for 2h; Claisen Schmidt condensation;	96%
With sodium hydroxide In ethanol; water

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

: 1245550-94-0
C6H4ClO4S2(1-)*Na(1+)

Conditions

Conditions	Yield
With sodium sulfite In ethanol at 25 - 110℃; Reflux;	95.5%
With sodium sulfite In ethanol; water at 25 - 110℃; Reflux;	95.5%

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

: 613-45-6
2,4-Dimethoxybenzaldehyde

: (E)-1-(2,5-dichlorothiophen-3-yl)-3-(2,4-dimethoxyphenyl)prop-2-en-1-one

Conditions

Conditions	Yield
With potassium hydroxide In methanol at 20℃; for 10h; Claisen-Schmidt Condensation;	95%

: 110-91-8
morpholine

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

: 210098-03-6
3-acetyl-5-chloro-2-(4-morpholino)thiophene

Conditions

Conditions	Yield
	94%

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

: 34841-06-0
3-bromo-4-methoxybenzylaldehyde

: (E)-3-(3-bromo-4-methoxyphenyl)-1-(2,5-dichlorothiophen-3-yl)prop-2-en-1-one

Conditions

Conditions	Yield
With potassium hydroxide In methanol at 20℃; for 10h; Claisen-Schmidt Condensation;	94%

: 121-32-4
4-hydroxy-3-ethoxybenzaldehyde

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

: 105-56-6
ethyl 2-cyanoacetate

: 6-(2,5-dichlorothiophen-3-yl)-1,2-dihydro-4-(3-ethoxy-4-hydroxyphenyl)-2-oxopyridine-3-carbonitrile

Conditions

Conditions	Yield
With ammonium acetate; potassium hydroxide In ethanol for 6h; Reflux;	92%

...Expand

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

: 58119-67-8
1-(5-Chlor-3-thienyl)-ethanon

Conditions

Conditions	Yield
With zinc In water; acetic acid for 2.5h; Heating;	91%

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

: (R)-1-(2,5-dichlorothiophen-3-yl)ethan-1-ol

Conditions

Conditions	Yield
With (S)-2-[(1,3,2-dioxaborolan-2-yloxy)diphenylmethyl]pyrrolidine; dimethylsulfide borane complex In tetrahydrofuran at 25℃; for 2h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	91%

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

: 104-55-2
3-phenyl-propenal

: C15H10Cl2OS

Conditions

Conditions	Yield
With sodium hydroxide In ethanol Claisen-Schmidt condensation;	88%

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

: 100-39-0
benzyl bromide

: 160982-09-2
3-Acetyl-2-(phenylmethyl)thio-5-chlorothiophene

Conditions

Conditions	Yield
With sodium hydroxide; thiourea In tetrahydrofuran; water	88%
With sodium hydroxide; thiourea In tetrahydrofuran; water	88%

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

: 459-57-4
4-fluorobenzaldehyde

: 105-56-6
ethyl 2-cyanoacetate

: 6-(2,5-dichlorothiophen-3-yl)-4-(4-fluorophenyl)-1,2-dihydro-2-oxopyridine-3-carbonitrile

Conditions

Conditions	Yield
With ammonium acetate; potassium hydroxide In ethanol for 6h; Reflux;	88%

...Expand

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

: 123-11-5
4-methoxy-benzaldehyde

: (E)-1-(2,5-dichlorothiophen-3-yl)-3-(4-methoxy)prop-2-en-1-one

Conditions

Conditions	Yield
With sodium hydroxide In ethanol Claisen-Schmidt condensation;	86%
With potassium hydroxide In methanol Claisen-Schmidt Condensation;
With sodium methylate In methanol

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

: 104-88-1
4-chlorobenzaldehyde

: C13H7Cl3OS

Conditions

Conditions	Yield
With sodium hydroxide In ethanol Claisen-Schmidt condensation;	86%
With sodium methylate In methanol

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

: 939-97-9
4-tert-Butylbenzaldehyde

: 105-56-6
ethyl 2-cyanoacetate

: 4-(4-tert-butylphenyl)-6-(2,5-dichlorothiophen-3-yl)-1,2-dihydro-2-oxopyridine-3-carbonitrile

Conditions

Conditions	Yield
With ammonium acetate; potassium hydroxide In ethanol for 6h; Reflux;	86%

...Expand

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

: 25434-84-8
5-chloro-3-phenyl-1H-indole-2-carboxyhydrazide

: 1504554-95-3
C21H14Cl3N3OS

Conditions

Conditions	Yield
In methanol Reflux;	85%

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

: 99-61-6
3-nitro-benzaldehyde

: C13H7Cl2NO3S

Conditions

Conditions	Yield
With sodium hydroxide In ethanol Claisen-Schmidt condensation;	84%
With sodium methylate In methanol

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

: 105-56-6
ethyl 2-cyanoacetate

: 613-45-6
2,4-Dimethoxybenzaldehyde

: 6-(2,5-dichlorothiophen-3-yl)-1,2-dihydro-4-(2,4-dimethoxyphenyl)-2-oxopyridine-3-carbonitrile

Conditions

Conditions	Yield
With ammonium acetate; potassium hydroxide In ethanol for 6h; Reflux;	84%

...Expand

: 4701-17-1
5-bromo-2-thiophencarboxaldehyde

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

: (E)-3-(5-bromothiophen-2-yl)-1-(2,5-dichlorothiophen-3-yl)-2-propen-1-one

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃;	83.6%

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

: 100-52-7
benzaldehyde

: C13H8Cl2OS

Conditions

Conditions	Yield
With sodium hydroxide In ethanol Claisen-Schmidt condensation;	83%
With sodium methylate In methanol

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

: 642-31-9
9-anthracene aldehyde

: (E)-3-(anthracen-9-yl)-1-(2,5-dichlorothiophen-3-yl)prop-2-en-1-one

Conditions

Conditions	Yield
With potassium hydroxide In methanol at 20℃; for 10h; Claisen-Schmidt Condensation;	83%

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

: 105-56-6
ethyl 2-cyanoacetate

: 100-10-7
4-dimethylamino-benzaldehyde

: 6-(2,5-dichlorothiophen-3-yl)-4-[4-(dimethylamino)-phenyl]-1,2-dihydro-2-oxopyridine-3-carbonitrile

Conditions

Conditions	Yield
With ammonium acetate; potassium hydroxide In ethanol for 6h; Reflux;	82%

...Expand

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

: 34841-06-0
3-bromo-4-methoxybenzylaldehyde

: 105-56-6
ethyl 2-cyanoacetate

: 4-(3-bromo-4-methoxyphenyl)-6-(2,5-dichlorothiophen-3-yl)-1,2-dihydro-2-oxopyridine-3-carbonitrile

Conditions

Conditions	Yield
With ammonium acetate; potassium hydroxide In ethanol for 6h; Reflux;	82%

...Expand

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

: 104-87-0
4-methyl-benzaldehyde

: C14H10Cl2OS

Conditions

Conditions	Yield
With sodium hydroxide In ethanol Claisen-Schmidt condensation;	81%

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

: 70070-24-5
5-bromo-3-phenylindole-2-carboxyhydrazide

: 1504554-96-4
C21H14BrCl2N3OS

Conditions

Conditions	Yield
In methanol Reflux;	80%

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

: 2973-77-5
3,5-dibromo-4-hydroxybenzaldehyde

: (E)-3-(3,5-dibromo-4-hydroxyphenyl)-1-(2,5-dichlorothiophen-3-yl)prop-2-en-1-one

Conditions

Conditions	Yield
With potassium hydroxide In methanol at 20℃; for 10h; Claisen-Schmidt Condensation;	80%

: 36157-40-1
3-acetyl-2,5-dichlorothiophene

: 105-56-6
ethyl 2-cyanoacetate

: 122-03-2
(4-isopropylbenzaldehyde)

: 6-(2,5-dichlorothiophen-3-yl)-1,2-dihydro-4-(4-isopropylphenyl)-2-oxopyridine-3-carbonitrile

Conditions

Conditions	Yield
With ammonium acetate; potassium hydroxide In ethanol for 6h; Reflux;	79%

...Expand

3-Acetyl-2,5-dichlorothiophene Specification

The 3-Acetyl-2,5-dichlorothiophene is an organic compound with the formula C₆H₄Cl₂OS. The IUPAC name of this chemical is 1-(2,5-dichlorothiophen-3-yl)ethanone. With the CAS registry number 36157-40-1, it is also named as Ethanone, 1-(2,5-dichloro-3-thienyl)-. The product's categories are Sulphur Derivatives; Heterocycles series; Thiophene & Benzothiophene; Miscellaneous. Besides, it is a white to light yellow crystal powder, which should be stored in closed cool and dry place. It is an important fine organic intermediate which widely used in the fields of medicine and chemical industry.

Physical properties about 3-Acetyl-2,5-dichlorothiophene are: (1)ACD/LogP: 2.82; (2)ACD/LogD (pH 5.5): 2.82; (3)ACD/LogD (pH 7.4): 2.82; (4)ACD/BCF (pH 5.5): 82.38; (5)ACD/BCF (pH 7.4): 82.38; (6)ACD/KOC (pH 5.5): 818.41; (7)ACD/KOC (pH 7.4): 818.41; (8)#H bond acceptors: 1; (9)#Freely Rotating Bonds: 1; (10)Polar Surface Area: 45.31 Å²; (11)Index of Refraction: 1.575; (12)Molar Refractivity: 44.45 cm³; (13)Molar Volume: 134.3 cm³; (14)Polarizability: 17.62×10^-24cm³; (15)Surface Tension: 44.6 dyne/cm; (16)Density: 1.452 g/cm³; (17)Flash Point: 95.3 °C; (18)Enthalpy of Vaporization: 47.07 kJ/mol; (19)Boiling Point: 233.9 °C at 760 mmHg; (20)Vapour Pressure: 0.0543 mmHg at 25°C.

Preparation: this chemical can be prepared by 2,5-dichloro-thiophene and acetyl chloride. This reaction will need reagent aluminium chloride and petroleum ether.

Uses of 3-Acetyl-2,5-dichlorothiophene: it can be used to produce 1-(5-chloro-thiophen-3-yl)-ethanone by heating. It will need reagent Zn and solvent H₂O, acetic acid with reaction time of 2.5 hours. The yield is about 91%.

When you are using this chemical, please be cautious about it as the following:
It is harmful by inhalation, in contact with skin and if swallowed. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin and do not breathe dust.

You can still convert the following datas into molecular structure:
(1)SMILES: Clc1sc(Cl)c(C(=O)C)c1
(2)InChI: InChI=1/C6H4Cl2OS/c1-3(9)4-2-5(7)10-6(4)8/h2H,1H3
(3)InChIKey: GYFDNIRENHZKGR-UHFFFAOYAT
(4)Std. InChI: InChI=1S/C6H4Cl2OS/c1-3(9)4-2-5(7)10-6(4)8/h2H,1H3
(5)Std. InChIKey: GYFDNIRENHZKGR-UHFFFAOYSA-N

Product Name

3-Acetyl-2,5-dichlorothiophene

Synthetic route

3-Acetyl-2,5-dichlorothiophene Specification

Related Products

Hot Products