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195995

Sigma-Aldrich

2-Thiopheneacetyl chloride

98%

Synonym(s):

2-Thienylacetyl chloride

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About This Item

Empirical Formula (Hill Notation):
C6H5ClOS
CAS Number:
39098-97-0
Molecular Weight:
160.62
Beilstein/REAXYS Number:
114547
EC Number:
254-290-0
MDL number:
MFCD00005456
UNSPSC Code:
12352100
PubChem Substance ID:
24851729
NACRES:
NA.22

vapor pressure

4 mmHg ( 83 °C)

Quality Level

200

assay

98%

form

liquid

refractive index

n20/D 1.551 (lit.)

bp

105-106 °C/22 mmHg (lit.)
130-135 °C/90 mmHg (lit.)

density

1.303 g/mL at 25 °C (lit.)

functional group

acyl chloride

storage temp.

2-8°C

SMILES string

ClC(=O)Cc1cccs1

InChI

1S/C6H5ClOS/c7-6(8)4-5-2-1-3-9-5/h1-3H,4H2

InChI key

AJYXPNIENRLELY-UHFFFAOYSA-N

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Application

2-Thiopheneacetyl chloride was used in the synthesis of:
  • (S)-ethyl-1-(2-thiopheneacetyl)-3-piperidinecarboxylate, nipecotate-containing immunopotentiator
  • 5-fluorouracil-cephalosporin prodrug
  • series of new N,N′-di(thiopheneacetyl)diamines derivatives
  • 6-β-(thiophen-2′-yl)acetamidomorphine

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

215.6 °F - closed cup

flash_point_c

102 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCBG1818V
1392663V
1382002V
1392664V
1393366V

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Sigma-Aldrich

127442

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Development of an efficient synthesis for a nipecotate-containing immunopotentiator.
Moher ED, et al.
Organic Process Research & Development, 8(4), 593-596 (2004)
Synthesis and Biological Evaluation of N, N'-di (thiopheneacetyl) diamines Series as Antitubercular Agents.
Nora de Souza MV, et al.
Phosphorus, Sulfur, and Silicon and the Related Elements, 183(12), 2990-2997 (2008)
James M Macdougall et al.
Bioorganic & medicinal chemistry, 12(22), 5983-5990 (2004-10-23)
A series of 6-beta-arylamidomorphines was synthesized and biologically evaluated. Various aryl substituents were introduced into the arylamidomorphines to examine substituent structure-activity relationships. Competition binding assays showed that compounds 10a-h bound to the mu opioid receptor with high affinity (0.2-0.6 nM).
Ryan M Phelan et al.
Bioorganic & medicinal chemistry letters, 19(4), 1261-1263 (2009-01-27)
An efficient synthesis of a 5-fluorouracil-cephalosporin prodrug is described for use against colorectal and other cancers in antibody and gene-directed therapies. The compound shows stability in aqueous media until specifically activated by beta-lactamase (betaL). The kinetic parameters of the 5-fluorouracil-cephalosporin
Radoslaw Laufer et al.
Bioorganic & medicinal chemistry, 22(17), 4968-4997 (2014-07-22)
TTK kinase was identified by in-house siRNA screen and pursued as a tractable, novel target for cancer treatment. A screening campaign and systematic optimization, supported by computer modeling led to an indazole core with key sulfamoylphenyl and acetamido moieties at

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