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2689-68-1

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2689-68-1 Usage

Chemical Properties

METHYL 4-OXOTETRAHYDROTHIOPHENE-3-CARBOXYLATE is White solid

Uses

METHYL 4-OXOTETRAHYDROTHIOPHENE-3-CARBOXYLATE is used in the preparation of a new class of neuroleptic agents.

Check Digit Verification of cas no

The CAS Registry Mumber 2689-68-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,6,8 and 9 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 2689-68:
(6*2)+(5*6)+(4*8)+(3*9)+(2*6)+(1*8)=121
121 % 10 = 1
So 2689-68-1 is a valid CAS Registry Number.
InChI:InChI=1/C6H8O3S/c1-9-6(8)4-2-10-3-5(4)7/h4H,2-3H2,1H3

2689-68-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name METHYL 4-OXOTETRAHYDROTHIOPHENE-3-CARBOXYLATE

1.2 Other means of identification

Product number -
Other names tetrahydro-4-oxo-3-thiophenecarboxylicacimethylester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2689-68-1 SDS

2689-68-1Synthetic route

C6H7O3S(1-)*Li(1+)

C6H7O3S(1-)*Li(1+)

methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

Conditions
ConditionsYield
With hydrogenchloride In water pH=Ca. 5;82%
3-Methoxycarbonylthiopropanoic acid methyl ester

3-Methoxycarbonylthiopropanoic acid methyl ester

methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

Conditions
ConditionsYield
With lithium methanolate; acetic acid In methanol; hexane; water81%
dimethyl-3-thiaadipate
7400-45-5

dimethyl-3-thiaadipate

methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

Conditions
ConditionsYield
With pyridine In toluene at 80℃; for 2.5h;80%
With lithium methanolate In methanol; toluene at 70 - 110℃;53.7%
Stage #1: dimethyl-3-thiaadipate With sodium methylate In tetrahydrofuran at 20℃; for 2.08333h; Reflux;
Stage #2: With hydrogenchloride In tetrahydrofuran; water
39%
Methyl thioglycolate
2365-48-2

Methyl thioglycolate

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

A

methyl tetrahydrothiophen-3-one-2-carboxylate
2689-69-2

methyl tetrahydrothiophen-3-one-2-carboxylate

B

methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

Conditions
ConditionsYield
With sodium hydride at -40℃; for 5h;A 57%
B 42%
With sodium hydride at -40℃; for 5h; Product distribution; var.: temp.: 0 degC;A 57%
B 42%
dimethyl-3-thiaadipate
7400-45-5

dimethyl-3-thiaadipate

A

methyl tetrahydrothiophen-3-one-2-carboxylate
2689-69-2

methyl tetrahydrothiophen-3-one-2-carboxylate

B

methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

Conditions
ConditionsYield
With sodium methylate In methanol for 0.666667h; Heating / reflux;A n/a
B 54%
With methanol; sodium for 0.666667h; Heating / reflux;A n/a
B 54%
With sodium methylate In diethyl ether for 3h; Heating;A 44%
B 18%
With lithium methanolate In toluene at 70 - 110℃; for 18.5h;A n/a
B 33%
With sodium hydride In 1,2-dimethoxyethane at -40℃; Inert atmosphere;
acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

Conditions
ConditionsYield
Stage #1: Methyl thioglycolate With sodium methylate In methanol at 20℃; for 3h;
Stage #2: acrylic acid methyl ester In dimethyl sulfoxide at 0 - 20℃; for 18h; Michael addition; Dieckmann cyclization;
Stage #3: With hydrogenchloride In water; dimethyl sulfoxide
48%
dimethyl thiodiglycolate
16002-29-2

dimethyl thiodiglycolate

methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; mineral oil for 5h; Reflux;35%
3-butoxycarbonylmethylsulfanyl-propionic acid methyl ester

3-butoxycarbonylmethylsulfanyl-propionic acid methyl ester

A

methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

B

3-oxo-tetrahydro-thiophene-2-carboxylic acid butyl ester

3-oxo-tetrahydro-thiophene-2-carboxylic acid butyl ester

Conditions
ConditionsYield
With sodium; benzene
methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

4-hydroxyimino-tetrahydro-thiophene-3-carboxylic acid methyl ester
58230-46-9

4-hydroxyimino-tetrahydro-thiophene-3-carboxylic acid methyl ester

Conditions
ConditionsYield
With hydroxylamine hydrochloride; barium carbonate In methanol Heating / reflux;98%
With hydroxylamine hydrochloride; barium carbonate In methanol for 12h; Reflux;98%
methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

methyl 2,5-dihydro-4-methoxythiophene-3-carboxylate
22097-91-2

methyl 2,5-dihydro-4-methoxythiophene-3-carboxylate

Conditions
ConditionsYield
97%
methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

toluene-4-sulfonic acid hydrazide
1576-35-8

toluene-4-sulfonic acid hydrazide

methyl 2,5-dihydro-4-(N'-tosylhydrazino)thiophene-3-carboxylate
152507-80-7

methyl 2,5-dihydro-4-(N'-tosylhydrazino)thiophene-3-carboxylate

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 0.5h; Ambient temperature;95%
methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

3-methylthio-5-methylamino-1H-1,2,4-triazole
99492-88-3

3-methylthio-5-methylamino-1H-1,2,4-triazole

2-methylthio-9-methyl-5,7-dihydrothieno<3,4-e>-1,2,4-triazolo<1,5-a>pyrimidin-8(9H)-one
119699-86-4

2-methylthio-9-methyl-5,7-dihydrothieno<3,4-e>-1,2,4-triazolo<1,5-a>pyrimidin-8(9H)-one

Conditions
ConditionsYield
at 160℃; for 0.0833333h;93%
methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

methyl 4-aminothiophene-3-carboxylate
69363-85-5

methyl 4-aminothiophene-3-carboxylate

Conditions
ConditionsYield
With hydroxylamine hydrochloride In methanol for 1h; Reflux;93%
methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

α-bromoacetophenone
70-11-1

α-bromoacetophenone

methyl 4-oxo-3-(2-oxo-2-phenylethyl)tetrahydrothiophene-3-carboxylate

methyl 4-oxo-3-(2-oxo-2-phenylethyl)tetrahydrothiophene-3-carboxylate

Conditions
ConditionsYield
With potassium carbonate In acetone at 65℃; for 1h;92%
methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

methyl 2,5-dihydro-4-(p-toluenesulfonato)thiophene-3-carboxylate
67525-75-1

methyl 2,5-dihydro-4-(p-toluenesulfonato)thiophene-3-carboxylate

Conditions
ConditionsYield
With 4-methyl-morpholine In dichloromethane for 1.5h; Cooling with ice;88.5%
With 4-methyl-morpholine In dichloromethane at 10℃; for 1.5h;85%
methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

methyl vinyl ketone
78-94-4

methyl vinyl ketone

methyl 4-oxo-3-(3-oxobutyl)tetrahydrothiophene-3-carboxylate
85696-91-9

methyl 4-oxo-3-(3-oxobutyl)tetrahydrothiophene-3-carboxylate

Conditions
ConditionsYield
Stage #1: methyl 4-oxotetrahydrothiophene-3-carboxylate With iron(III) chloride hexahydrate In dichloromethane at 23℃; for 0.0833333h;
Stage #2: methyl vinyl ketone In dichloromethane at 20℃; for 48h; Michael Addition;
88%
With triphenylphosphine In acetonitrile for 5h; Ambient temperature;73%
methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

3-(2-aminoanilino)-4-(carbomethoxy)-2,5-dihydrothiophene
61325-23-3

3-(2-aminoanilino)-4-(carbomethoxy)-2,5-dihydrothiophene

Conditions
ConditionsYield
With acetic acid In ethanol for 4h; Heating;86%
methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

4-nitrobenzyl halide

4-nitrobenzyl halide

3-(4-Nitro-benzyl)-4-oxo-tetrahydro-thiophene-3-carboxylic acid methyl ester
84782-87-6

3-(4-Nitro-benzyl)-4-oxo-tetrahydro-thiophene-3-carboxylic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In acetone Heating;86%
methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

p-NO2C6H4CH2-halide

p-NO2C6H4CH2-halide

3-(4-Nitro-benzyl)-4-oxo-tetrahydro-thiophene-3-carboxylic acid methyl ester
84782-87-6

3-(4-Nitro-benzyl)-4-oxo-tetrahydro-thiophene-3-carboxylic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In acetone Heating;86%
methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

4-hydroxythiophene-3-carboxylic acid methyl ester
65369-21-3

4-hydroxythiophene-3-carboxylic acid methyl ester

Conditions
ConditionsYield
With dihydrogen peroxide In methanol for 2h;85%
methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

EtOCOCH2-halide

EtOCOCH2-halide

3-Ethoxycarbonylmethyl-4-oxo-tetrahydro-thiophene-3-carboxylic acid methyl ester
84790-04-5

3-Ethoxycarbonylmethyl-4-oxo-tetrahydro-thiophene-3-carboxylic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In acetone Heating;85%
methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

2-ethylisothiourea hydrobromide
1071-37-0

2-ethylisothiourea hydrobromide

5H,7H-2-ethylthiodihydrothieno<3,4-d>pyrimidin-4-one
5719-20-0

5H,7H-2-ethylthiodihydrothieno<3,4-d>pyrimidin-4-one

Conditions
ConditionsYield
With sodium carbonate In water at 25℃; for 18h; Darkness;84.6%
With sodium carbonate for 12h; Ambient temperature;83%
With sodium carbonate In water at 20℃; Darkness;
methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

4-methoxy-2-nitroaniline
96-96-8

4-methoxy-2-nitroaniline

4-(4-Methoxy-2-nitro-phenylamino)-2,5-dihydro-thiophene-3-carboxylic acid methyl ester

4-(4-Methoxy-2-nitro-phenylamino)-2,5-dihydro-thiophene-3-carboxylic acid methyl ester

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In toluene for 4h; Heating;84%
methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

4-(tert-Butyl-dimethyl-silanyloxy)-2,5-dihydro-thiophene-3-carboxylic acid methyl ester
146496-36-8

4-(tert-Butyl-dimethyl-silanyloxy)-2,5-dihydro-thiophene-3-carboxylic acid methyl ester

Conditions
ConditionsYield
With triethylamine82%
methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

CH2=CHCH2-halide

CH2=CHCH2-halide

methyl 3-allyl-4-oxotetrahydrothiophene-3-carboxylate
84782-86-5

methyl 3-allyl-4-oxotetrahydrothiophene-3-carboxylate

Conditions
ConditionsYield
With potassium carbonate In acetone Heating;81%
methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

4-ethoxycarbonyl-3-methyl-1-phenylaminocarbonyl-1,2-diaza-1,3-butadiene

4-ethoxycarbonyl-3-methyl-1-phenylaminocarbonyl-1,2-diaza-1,3-butadiene

3-ethyl 3a-methyl 1-[(anilinocarbonyl)amino]-6a-hydroxy-2-methyl-6,6a-dihydro-1H-thieno[3,4-b]pyrrole-3,3a(4H)-dicarboxylate
1311296-62-4

3-ethyl 3a-methyl 1-[(anilinocarbonyl)amino]-6a-hydroxy-2-methyl-6,6a-dihydro-1H-thieno[3,4-b]pyrrole-3,3a(4H)-dicarboxylate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 20℃; for 5.5h;81%
methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

benzyl halide

benzyl halide

methyl 3-benzyl-4-oxotetrahydrothiophene-3-carboxylate
84782-84-3

methyl 3-benzyl-4-oxotetrahydrothiophene-3-carboxylate

Conditions
ConditionsYield
With potassium carbonate In acetone Heating;80%
methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

PhCH2-halide

PhCH2-halide

methyl 3-benzyl-4-oxotetrahydrothiophene-3-carboxylate
84782-84-3

methyl 3-benzyl-4-oxotetrahydrothiophene-3-carboxylate

Conditions
ConditionsYield
With potassium carbonate In acetone Heating;80%
sodium cyanide
773837-37-9

sodium cyanide

methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

3-cyano-3-hydroxy-tetrahydrothiophene-4-carboxylic acid methyl ester
155251-30-2

3-cyano-3-hydroxy-tetrahydrothiophene-4-carboxylic acid methyl ester

Conditions
ConditionsYield
With sodium hydrogensulfite In methanol; water at 20℃; for 16h; pH=7 - 8; Time;80%
Stage #1: sodium cyanide With sodium hydrogensulfite In water Cooling with ice;
Stage #2: methyl 4-oxotetrahydrothiophene-3-carboxylate In methanol; water at 20℃; for 16h;
methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

5-amino-1-(2-amino-4-trifluoromethylphenyl)-3-methylthio-1H-1,2,4-triazole
88722-50-3

5-amino-1-(2-amino-4-trifluoromethylphenyl)-3-methylthio-1H-1,2,4-triazole

4,5-dihydro-2-methylthio-8-trifluoromethyl-1,2,4-triazolo<1,5-a>-1,3,5-benzotriazepin-5(6H)-one
120929-95-5

4,5-dihydro-2-methylthio-8-trifluoromethyl-1,2,4-triazolo<1,5-a>-1,3,5-benzotriazepin-5(6H)-one

Conditions
ConditionsYield
for 3h; Product distribution; Mechanism; Heating;79%
for 3h; Heating;79%
methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

HCCCH2-halide

HCCCH2-halide

methyl 4-oxo-3-(propargyl)tetrahydrothiophene-3-carboxylate
84782-85-4

methyl 4-oxo-3-(propargyl)tetrahydrothiophene-3-carboxylate

Conditions
ConditionsYield
With potassium carbonate In acetone Heating;79%
methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

EtOCOCH=C(OEt)CH2-halide

EtOCOCH=C(OEt)CH2-halide

3-((Z)-2-Ethoxy-3-ethoxycarbonyl-allyl)-4-oxo-tetrahydro-thiophene-3-carboxylic acid methyl ester
84782-88-7

3-((Z)-2-Ethoxy-3-ethoxycarbonyl-allyl)-4-oxo-tetrahydro-thiophene-3-carboxylic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In acetone Heating;79%
methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

prop-2-enyl halide

prop-2-enyl halide

methyl 3-allyl-4-oxotetrahydrothiophene-3-carboxylate
84782-86-5

methyl 3-allyl-4-oxotetrahydrothiophene-3-carboxylate

Conditions
ConditionsYield
With potassium carbonate In acetone Heating;78%
methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

ethoxycarbonylmethyl halide

ethoxycarbonylmethyl halide

3-Ethoxycarbonylmethyl-4-oxo-tetrahydro-thiophene-3-carboxylic acid methyl ester
84790-04-5

3-Ethoxycarbonylmethyl-4-oxo-tetrahydro-thiophene-3-carboxylic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In acetone Heating;78%

2689-68-1Relevant articles and documents

-

Hromatka et al.

, p. 1520,1525 (1973)

-

HALOGENATED-HETEROARYL AND OTHER HETEROCYCLIC KINASE INHIBITORS, AND USES THEREOF

-

Paragraph 0598; 0636; 0640-0642, (2021/11/04)

The invention relates to kinase inhibitors, in particular inhibitors of protein kinases including the SIK-family CSF1R, ABL/BCR-ABL, SRC, HCK, PDGFR, KIT and/or their mutants. Although structurally similar to dasatinib, the kinase inhibitors of the invention are distinctive; possessing a particular class of halogenated heteroaryls. Such kinase inhibitors can display one or more certain properties distinct to dasatinib and other structurally similar kinase inhibitors. The kinase inhibitors of the invention or pharmaceutical compositions comprising them may be used in the treatment of a disorder or condition, such as a proliferative disorder, for example, a leukaemia or solid tumour. In particular, these and other structurally similar kinase inhibitors may be used in the treatment of a proliferative disorder - such as a mixed phenotype acute leukaemia (MPAL) - characterised by (inter-alia) the presence of MEF2C protein, a human chromosomal translocation at 11q23, and/or a KMT2A fusion oncoprotein. The kinase inhibitors or pharmaceutical compositions disclosed herein may be used topically to modulate skin pigmentation in a subject, for example to impart UV protection and reduce skin cancer risk.

The novel method to synthesis of cantharidin intermediate

Tan, Chunbin,Liu, Xiaoling,Du, Hongfei

, p. 271 - 276 (2019/07/31)

Sulfur-containing dehydrocantharidin(SD) was yielded (76% to 96%) by Diels-Alder reaction in an ionic-liquid system under ordinary pressure and temperature. We explored the influences of different ionic-liquid types, reaction temperatures, and reaction times in this reaction. We found that the optimal reaction temperature was about 35°C, the reaction time was 20 h, and the most suitable ionic liquid was 1-butyl-3-methylimidazolium tetrafluoroborate. Furthermore, in the recycling process of ionic liquid, we found that CH3CN was the most suitable extraction solvent. We explored four steps in the synthetic route to SD and achieved a good yield of 38% in total. We envisage that this process could be further developed at an industrial scale for the synthesis of Cantharidin and is destined to be an environmentally friendly way to solve the lack of cantharis as a natural resource.

SEMICONDUCTING POLYMERS AND TERNARY BLENDS THEREOF

-

Paragraph 0084; 0089, (2016/08/17)

Semiconducting photovoltaic polymers and compositions are disclosed. The polymers and compositions exhibit increased power conversion efficiency in solar cells and other applications.

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