2-Mercaptoacetamide

Base Information

• Chemical Name: 2-Mercaptoacetamide
• CAS No.: 758-08-7
• Molecular Formula: C2H5 N O S
• Molecular Weight: 91.1338
• Hs Code.: 2930909899
• European Community (EC) Number: 633-285-0
• NSC Number: 524366
• UNII: 512243B4TP
• DSSTox Substance ID: DTXSID30226711
• Nikkaji Number: J659.450F
• Wikidata: Q27260845
• Mol file: 758-08-7.mol

Synonyms:2-Mercaptoacetamide;758-08-7;2-sulfanylacetamide;Mercaptoacetamide;Thioglycolamide;Acetamide, 2-mercapto-;thiolacetamide;Acetamide, 2-mercapto-(6CI,7CI,8CI,9CI);Thioglycolamide (crude);USAF HA-3;.alpha.-Mercaptoacetamide;NSC 524366;BRN 1209321;UNII-512243B4TP;MFCD00068159;512243B4TP;NSC-524366;4-03-00-00624 (Beilstein Handbook Reference);C2H5NOS;a-Mercaptoacetamide;alpha-Mercaptoacetamide;DTXSID30226711;NSC524366;AKOS006229961;LS-9809;MS-22227;Acetamide,2-mercapto-(6ci,7ci,8ci,9ci);CS-0094728;FT-0612754;EN300-25459;Q27260845

Chemical Property of 2-Mercaptoacetamide

Chemical Property:

• Vapor Pressure: 0.00405mmHg at 25°C
• Melting Point: 157.5-158.5 °C
• Boiling Point: 279.3°C at 760 mmHg
• PKA: 8.34±0.10(Predicted)
• Flash Point: 12
• PSA: 81.89000
• Density: 1.192g/cm³
• LogP: 0.10180
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 91.00918496
• Heavy Atom Count: 5
• Complexity: 44.9

Purity/Quality:

97% ^*data from raw suppliers

2-Mercaptoacetamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,F,T
• Hazard Codes: C,F,T
• Statements: 11-20/21/22
• Safety Statements: 16-26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C(=O)N)S
• General Description: 2-Mercaptoacetamide is a small-molecule inhibitor that targets the zinc-dependent metalloprotease activity of botulinum neurotoxin serotype A (BoNT/A), effectively blocking its ability to cleave proteins involved in neurotransmitter release. Key structural features, such as the sulfur atom in the mercaptoacetamide group and electron-withdrawing substituents on the phenyl ring (e.g., chlorine or trifluoromethyl), enhance its inhibitory potency. Analogs like 4-chloro and 4-trifluoromethyl derivatives exhibit low micromolar activity and improved cellular efficacy compared to hydroxamic acid inhibitors, making them promising candidates for therapeutic development against botulism.

Technology Process of 2-Mercaptoacetamide

There total 11 articles about 2-Mercaptoacetamide 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: 100.0%

Methyl thioglycolate (2365-48-2) → Thioglycolamide (758-08-7)

Guidance literature:

With ammonia; In methanol; at 20 ℃; for 14h; Inert atmosphere;

DOI:10.1002/jlcr.3398

Reference yield: 90.0%

Chloroacetamide (79-07-2) → Thioglycolamide (758-08-7)

Guidance literature:

With hydrosulfide exchange resin (from Amberlite IRA-400); triethylamine hydrochloride; In methanol; for 1h; Ambient temperature;

DOI:10.1055/s-1995-3929

Reference yield:

Chloroacetamide (79-07-2) → Thioglycolamide (758-08-7) + thiodiglcollic acid bis-amide (14618-65-6)

Guidance literature:

With ethanol; hydrogen sulfide; ammonia;

upstream raw materials:

2-methoxyethyl 2-mercaptoacetate

Methyl thioglycolate

ethyl 2-sulfanylacetate

Chloroacetamide

Downstream raw materials:

4,5,6,7-tetrahydro-cyclopenta[1,4]thiazin-3-one

2,2-diphenyl-thiazolidin-4-one

[(4-amino-phenyl)-arsanediyldimercapto]-di-acetic acid diamide

4-oxothiazolidine

Refernces

Botulinum neurotoxin serotype A inhibitors: Small-molecule mercaptoacetamide analogs

10.1016/j.bmc.2009.03.013

This research aims to develop small-molecule inhibitors against botulinum neurotoxin serotype A (BoNT/A), a highly toxic substance that causes botulism and poses a significant threat due to its potential use in bioterrorism. The study focuses on designing mercaptoacetamide analogs that can inhibit the zinc-dependent metalloprotease activity of BoNT/A, which is responsible for cleaving proteins involved in neurotransmitter release, leading to paralysis. The researchers synthesized a series of 2-mercaptoacetamide analogs based on a 5-amino-3-phenylpyrazole scaffold and investigated their structure–activity relationships. Key findings include the critical role of the sulfur atom in the mercaptoacetamide for inhibitory activity and the influence of substituents on the phenyl ring, with electron-withdrawing groups like chlorine and trifluoromethyl showing enhanced potency. The most active analogs, such as 12a (4-chloro) and 12d (4-trifluoromethyl), demonstrated low micromolar inhibitory activity against BoNT/A. These mercaptoacetamide inhibitors not only showed equipotency with previously reported hydroxamic acid inhibitors but also exhibited better cellular activity, suggesting they could prevent SNARE cleavage in neuronal cells without pre-incubation with the toxin. The study concludes that these novel mercaptoacetamide-based inhibitors are promising lead structures for further development into therapeutic agents against botulinum intoxication.