7404-50-4

Basic information

• Product Name: (AMIDINOTHIO)ACETIC ACID
• Synonyms: [(aminoiminomethyl)thio]acetic acid;(AMIDINOTHIO)ACETIC ACID PURUM;s-(carboxymethyl)isothiourea
• CAS NO: 7404-50-4
• Molecular Formula: C₃H₆N₂O₂S
• Molecular Weight: 134.15694
• EINECS: 231-010-5
• Product Categories: Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfur Compounds;Thioureas
• Mol File: 7404-50-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: ~234 °C (dec.)
• Boiling Point: 307.9 °C at 760 mmHg
• Flash Point: 140 °C
• Appearance: /
• Density: 1.61 g/cm³
• CAS DataBase Reference: (AMIDINOTHIO)ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (AMIDINOTHIO)ACETIC ACID(7404-50-4)
• EPA Substance Registry System: (AMIDINOTHIO)ACETIC ACID(7404-50-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39
• WGK Germany: 3
• Hazardous Substances Data: 7404-50-4(Hazardous Substances Data)

Usage

General Description

(Amidinothio)acetic acid is a chemical compound with the formula RC(NH)N(H)CS2HCO2H, where R is a variable group. It is a derivative of amino acids and is mainly used as a chelating agent in the textile and paper industries. The compound has the ability to bind metal ions, making it useful in water treatment and in preventing metal ions from interfering with certain chemical processes. Additionally, it has potential applications in pharmaceuticals, as it can be used in the synthesis of certain drugs. Despite its usefulness, (amidinothio)acetic acid can be hazardous if not handled properly, and should therefore be used with caution in industrial and laboratory settings.

InChI:InChI=1/C3H6N2O2S/c4-3(5)8-1-2(6)7/h1H2,(H3,4,5)(H,6,7)

Upstream product

• 3926-62-3 sodium monochloroacetic acid 
• 17356-08-0 thiourea 
• 79-11-8 chloroacetic acid 
• 79-08-3 bromoacetic acid 
• 7732-18-5 water 

Downstream Products

• 556-90-1 pseudothiohydantoin 
• 352-97-6 guanidineacetic acid 
• 6020-87-7 creatine monohydrate powder 
• 556-90-1 pseudothiohydantoin 

Relevant articles and documents

Study of the structure of (carbamimidoylsulfanyl)acetic ("pseudothiohydantoic") acid by XRD and PM6 methods

It was shown by the method of powder X-ray diffraction analysis that in the crystalline state the product of the reaction of thiourea with chloroacetic acid in water, (carbamimidoylsulfanyl)acetic acid, existed in the zwitter-ion tautomeric form. The structure consists of virtually planar infi nite layers normal to the c axis of the unit cell which are bound by van der Waals interactions. The layers are formed by infi nite rows elongated along the b axis of the unit cell consisting of materially planar zwitter-ionic molecules linked by strong bifurcated hydrogen bonds. The results of quantum-chemical calculations by PM6 method are in agreement with the XRD results: whereas an isolated molecule exists in nonzwitter-ionic tautomeric form, in the crystal only the zwitterionic tautomer is present.

Synthesis of (aminoiminomethyl)thioacetic acid and some of its esters

The aim of this paper was to find the simplest method for the synthesis of (aminoiminomethyl)thioacetic acid and some of its esters ( methyl- and ethyl-) in order to test them biologically as potential plant growth regulators.

Reactions of Thiourea with Chloro- and Bromoacetic Acids

The reaction of chloroacetic acid with thiourea represents an SN2 substitution of chlorine by sulphur atom and is about two orders of magnitude slower than that of bromoacetic acid.Chloroacetate ion reacts slower than chloroacetic acid by only about 30percent.The acid catalyzed splitting off of hydroxyl group from the formed tetrahedral intermediate is rate-limiting in the cyclization of the S-carboxylatomethyleneisothiouronium salt, formation of the intermediate being rate-limiting below pH 2.