3-Thiophenemalonic acid

Base Information

• Chemical Name: 3-Thiophenemalonic acid
• CAS No.: 21080-92-2
• Molecular Formula: C7H6O4S
• Molecular Weight: 186.188
• Hs Code.: 29309090
• European Community (EC) Number: 244-198-9
• UNII: KK6MPZ6HAH
• DSSTox Substance ID: DTXSID9066675
• Nikkaji Number: J225.393C
• Wikidata: Q72508865
• ChEMBL ID: CHEMBL3360550
• Mol file: 21080-92-2.mol

Synonyms:3-Thiophenemalonic acid;21080-92-2;3-Thienylmalonic acid;2-(thiophen-3-yl)malonic acid;2-thiophen-3-ylpropanedioic acid;Propanedioic acid, 3-thienyl-;3-Thienylpropanedioic acid;(3-Thienyl)malonic acid;Thiophene-3-malonic acid;2-(thiophen-3-yl)propanedioic acid;KK6MPZ6HAH;Propanedioic acid, 2-(3-thienyl)-;2-(3-Thienyl)malonic acid;CHEMBL3360550;MFCD00005469;3-Thiophene malonic acid;3-Thiophenemalonicacid;3-thiophenemalonic;UNII-KK6MPZ6HAH;BIDD:GT0437;SCHEMBL162736;2-(3-Thienyl)malonic acid #;3-Thiophenemalonic acid, 97%;3-Thiophenemalonic acid, 98%;DTXSID9066675;GCOOGCQWQFRJEK-UHFFFAOYSA-;BCP11989;EINECS 244-198-9;BDBM50038338;AKOS015856697;AC-4339;AS-11843;SY015822;3-THIENYLMALONIC ACID [EP IMPURITY];FT-0616410;T1354;F11220;A912337;SR-01000944735;SR-01000944735-1;W-107575;5-(trifluoromethyl)benzo[b]thiophene-2-carboxylic?acid

Chemical Property of 3-Thiophenemalonic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 5.23E-07mmHg at 25°C
• Melting Point: 139 °C (dec.)(lit.)
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 396.775 °C at 760 mmHg
• PKA: 2.73±0.10(Predicted)
• Flash Point: 193.763 °C
• PSA: 102.84000
• Density: 1.574 g/cm³
• LogP: 1.00090
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 185.99867984
• Heavy Atom Count: 12
• Complexity: 190

Purity/Quality:

99% ^*data from raw suppliers

3-Thiophenemalonic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

Useful:

• Canonical SMILES: C1=CSC=C1C(C(=O)O)C(=O)O
• Uses: 3-Thiophenemalonic Acid (Ticarcillin EP Impurity C) is an intermediate used to synthesize temocillin. It is also used to prepare malonate-based inhibitors of mammalian serine racemase.

Technology Process of 3-Thiophenemalonic acid

There total 4 articles about 3-Thiophenemalonic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.6%

Methyl 2-cyano-2-(3-thienyl)acetate (81344-59-4) → 2-(thiophen-3-yl)malonic acid (21080-92-2)

Guidance literature:

With water; sodium hydroxide; at 25 - 30 ℃;

Reference yield:

diethyl 2-(thiophen-3-yl)malonate (37784-67-1) → 2-(thiophen-3-yl)malonic acid (21080-92-2)

Guidance literature:

With lithium hydroxide; In methanol; water; at 25 ℃; for 2h;

DOI:10.1002/cbic.201800734

Reference yield:

cyano-dihydrothiophen-3-ylidene-acetic acid methyl ester (40548-04-7) → 2-(thiophen-3-yl)malonic acid (21080-92-2)

Guidance literature:

Multi-step reaction with 3 steps

1: sulfuryl dichloride / dichloromethane / 25 °C

2: pyridine / 20 - 30 °C

3: sodium hydroxide; water / 25 - 30 °C

With pyridine; sulfuryl dichloride; water; sodium hydroxide; In dichloromethane;

upstream raw materials:

cyano-dihydrothiophen-3-ylidene-acetic acid methyl ester

Methyl 2-cyano-2-(3-thienyl)acetate

diethyl 2-(thiophen-3-yl)malonate

Downstream raw materials:

diethyl 2-(thiophen-3-yl)malonate

2,2-dimethyl-5-(thiophen-3-yl)-1,3-dioxane-4,6-dione

ticarcillin disodium

5-nitro-3-thiophenemalonic acid

Refernces

• 1、 -. "Preparation method of ticarcillin sodium key intermediate, namely 2-(3-thienyl) malonic acid". . . Retrieved 2018/04/03.
• 2、 -. "Chemical process". . . Retrieved 2008/06/13.