13250-85-6

Usage

General Description

2,3-bis(hydroxymethyl)thiophene is a chemical compound with the molecular formula C6H8O2S. It is a colorless to light yellow liquid with a strong and pleasant odor. 2,3-bis(hydroxymethyl)thiophene is used as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. It is also utilized as a building block in the production of polymers and as a cross-linking agent in the manufacture of coatings and adhesives. 2,3-bis(hydroxymethyl)thiophene is flammable and should be handled with care, avoiding contact with skin and eyes and keeping it away from sources of ignition.

Upstream product

• 1451-95-2 thiophene-2,3-dicarboxylic acid 
• 527-72-0 2-thiophenylcarboxylic acid 
• 124-38-9 carbon dioxide 
• 88-13-1 3-Thiophene carboxylic acid 

Downstream Products

• 113615-91-1 6-Phenyl-4,4a,5,7,7a,8-hexahydrothieno<2,3-e>isoindole-5,7-dione 

Relevant academic research and scientific papers

Versatile synthesis of 3,4-b diheteropentalenes

We describe a new route for the synthesis of thieno[3,4-b]thiophene, alkyl derivatives thereof, seleno[3,4-b]thiophene, and thieno[3,4-b]furan made from inexpensive starting materials, such as thiophene-2-carboxylic acid and furan-2-carboxylic acid. Such fused heterocycles are of great interest for low band gap organic semiconductors and applications including OLEDs, organic photovoltaic cells, and electrochromics.

Synthesis of mono- and bisadducts of thieno-o-quinodimethane with c 60 for efficient polymer solar cells

A series of mono- and bisadducts of thieno-o-quinodimethane with C 60 (TOQC) was efficiently prepared through the Diels-Alder reaction of pristine or solubilizing side-chain-substituted 2,3-bis(chloromethyl) thiophene with C60. The pristine TOQC bisadduct (bis-TOQC) shows much higher performance than the side-chain-substituted TOQC bisadducts in polymer solar cells, while the situation is inverse for the TOQC monoadducts. The best power conversion efficiency of 5.1% was achieved from the bis-TOQC:P3HT solar cells under simulated AM1.5G irradiation (86 mW/cm2).

A synthesis of two novel benzo[f]ninhydrin analogs: 6-methoxybenzo[f]ninhydrin and thieno[f]ninhydrin

Improved methodology for the synthesis of benzo[f]ninhydrin (1) is described. The generality of this approach is illustrated with the synthesis of two novel analogs, 6-methoxybenzo[f]ninhydrin (3) and thieno[f]ninhydrin (4).

Thiophene bioisosteres of GluN2B selective NMDA receptor antagonists: Synthesis and pharmacological evaluation of [7]annuleno[b]thiophen-6-amines

Thiophene bioisosteres of potent GluN2B receptor negative allosteric modulators were prepared and evaluated pharmacologically. The five-step synthesis of 4,5,7,8-tetrahydro[7]annuleno[b]thiophen-6-one (10) was considerably improved by carboxylation of thiophene-3-carboxylic acid (8) in the first reaction step. Reductive amination and alkylation led to three homologous series of secondary and tertiary phenylalkylamines 5, 11 and 12. Metalation, reaction with 1-formylpiperidine and subsequent reduction provided hydroxymethyl derivatives 15 and 16, which had been designed as bioisosteres of phenols. 2-Bromo derivatives 18 were obtained by bromination of ketone 10 with NBS and subsequent reductive amination. High GluN2B affinity was achieved with [7]annuleno[b]thiophenes bearing a 3-phenylpropylamino or 4-phenylbutylamino moiety (e.g. 5c: Ki = 5.9 nM; 11d: Ki = 9.0 nM). Tertiary ethylamines 12 showed lower GluN2B affinity than tertiary methylamines 11 or secondary amines 5 (e.g. 5c: Ki = 5.9 nM; 11c: Ki = 6.0; 12c: Ki = 51 nM). A Br-atom or a hydroxymethyl moiety in 2-position were less tolerated by the GluN2B receptor. Very similar relationships between the structure and GluN2B affinity and structure and σ affinity, in particular σ2 affinity, were detected. A slight preference for the ifenprodil binding site of GluN2B receptors over σ1 and σ2 receptors was found for methylamines 11c (≈2-fold) and 11d (≈1.5–2-fold) as well as for bromo derivative 18c (≈3-fold).

IDO/TDO Inhibitor

A compound of formula (I) given below or a pharmaceutically acceptable salt of the compound is useful as an IDO/TDO inhibitor. Thus, the compound of formula (I) or the pharmaceutically acceptable salt of the compound can be used as, for example, a therapeutic agent for a disease or a disorder selected from tumor, infectious disease, neurodegenerative disorder, cataract, organ transplant rejection, autoimmune disease, postoperative cognitive impairment, and disease related to women's reproductive health [in the following formula (I), ring A represents an aromatic ring, an aliphatic ring, a heterocyclic ring, or a condensed ring of two or more rings selected from an aromatic ring, an aliphatic ring and a heterocyclic ring; X, R1 and R2 represent a substituent on a ring atom constituting ring A; m represents an integer of 0 to 6; X represents, for example, a halogen atom; and R1 and R2 are the same or different and are selected from, for example, the group consisting of groups of formula (a) or formula (b); and in the following formula (a) and formula (b), Y is selected from the group consisting of O, S, and Se, Z is selected from the group consisting of O, S, and Se, n represents an integer of 1 to 8, r represents an integer of 1 to 8, s represents an integer of 1 to 8, R4 represents, for example, —C(═NH)—HN2, and R6 represents, for example, a substituted or unsubstituted aryl group].

Synthesis of thieno[3,4-b]thiophene, thieno[3,4-b]furan, related compounds and their derivatives and use thereof

Inexpensive and facile methods of preparing fused heterocycles such as thieno[3,4-b]thiophene, thieno[3,4-b]furan, related compounds, and their derivatives are disclosed. Also disclosed are regioregular polymers prepared from the fused heterocycles.

SYNTHESIS OF THIENO[3,4-b]THIOPHENE, THIENO[3,4-b]FURAN, RELATED COMPOUNDS AND THEIR DERIVATIVES AND USE THEREOF

Inexpensive and facile methods of preparing fused heterocycles such as thieno[3,4-b]thiophene, thieno[3,4-b]furan, related compounds, and their derivatives are disclosed. Also disclosed are regioregular polymers prepared from the fused heterocycles.

Stereoselective synthesis of thiophenedimethyl- and benzenedimethyl- α,α′-bridged bis(glycines)

Conformationally constrained cystine analogues have been synthesized which have an all-carbon backbone-chain as a bridge between the α,α′-positions in two glycine units. An aromatic ring consisting of a 1,2-disubstituted benzene or a 2,3- and 2,5-disubstituted thiophene has been inserted into the bridge. Chiral auxiliaries were used to effect stereoselective syntheses of the (S,S)-bis(amino acids). The latter were further derivatized as Fmoc-derivatives suitable for peptide syntheses. The product 2,3-bis[(2A,5S)-(2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-pyrazinyl)methyl]-5- methylthiophene has been subjected to X-ray analysis. Acta Chemica Scandinavica 1997.

2,3 DIMETHYLENE-2,3-DIHYDROTHIOPHENE: THE THIOPHENE ANALOGUE OF ORTHO-XYLYLENE

The hitherto unknown 2,3-dimethylene-2,3-dihydrothiophene (the thiophene analogue of ortho-xylylene) and a substituted derivative have been prepared in solution and trapped as Diels-Alder adducts in good to excellent yields.