2150-55-2

Basic information

• Product Name: 2-AMINO-4-THIAZOLINIC ACID
• Synonyms: 2-amino-4-carboxythiazoline;2-amino-4,5-dihydrothiazole-4-carboxylic acid;Dl-2-Amino-Thiazoline-4-Carboxylic Acid;2-AMINO-2-THIAZOLINE-4-ARBOXYLIC ACID;2-Imino-thiazolidine-4-carboxylic acid;2-amino-delta(2)-thiazoline-4-carboxylic acid;2-Aminothiazoline-4-carboxylic acid;rac 2-AMinothiazoline-4-carboxylic Acid
• CAS NO: 2150-55-2
• Molecular Formula: C₄H₆N₂O₂S
• Molecular Weight: 146.17
• EINECS: 218-433-0
• Product Categories: Amines;Heterocycles;Miscellaneous Reagents;Sulfur & Selenium Compounds
• Mol File: 2150-55-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 197-203°C (dec.)
• Boiling Point: 405.9 °C at 760 mmHg
• Flash Point: 199.3 °C
• Appearance: white powder
• Density: 1.85
• Vapor Pressure: 1E-07mmHg at 25°C
• Refractive Index: 1.78
• Storage Temp.: Store at 0-5°C
• Solubility: DMSO (Very Slightly, Heated), Methanol (Slightly, Heated), Water (Slightly, Heat
• PKA: 2.31±0.20(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 2-AMINO-4-THIAZOLINIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-4-THIAZOLINIC ACID(2150-55-2)
• EPA Substance Registry System: 2-AMINO-4-THIAZOLINIC ACID(2150-55-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-43
• Safety Statements: 36/37
• Hazardous Substances Data: 2150-55-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-4-THIAZOLINIC ACID is used as an intermediate in the manufacturing of L-tryptophan, an essential amino acid that plays a crucial role in various physiological processes, including the production of serotonin and melatonin. Its presence in the pharmaceutical industry is vital for the synthesis of medications targeting conditions such as depression, insomnia, and other mood disorders.
Used in Chemical Synthesis:
2-AMINO-4-THIAZOLINIC ACID serves as a key building block in the synthesis of various chemical compounds, particularly those involving the 1,3-thiazole ring system. Its unique structure allows for the development of novel molecules with potential applications in various fields, such as agrochemicals, dyes, and materials science.
Used in Research and Development:
Due to its versatile chemical properties, 2-AMINO-4-THIAZOLINIC ACID is utilized in research and development for the exploration of new chemical reactions, synthesis methods, and potential applications. Its ability to form various derivatives and complexes makes it an invaluable tool for scientists and researchers in the field of organic chemistry.

Synthesis Reference(s)

Synthetic Communications, 33, p. 1109, 2003 DOI: 10.1081/SCC-120017133

Air & Water Reactions

Slightly soluble in water.

Reactivity Profile

An organosulfide and amine derivative, carboxylic acid. Look at Reactive Groups 20 (organosulfides), 7 (amines), and 3 (carboxylic acids) may give indications about reactive tendencies.

Fire Hazard

Flash point data for 2-AMINO-4-THIAZOLINIC ACID are not available. 2-AMINO-4-THIAZOLINIC ACID is probably combustible.

InChI:InChI=1/C4H6N2O2S/c5-4-6-2(1-9-4)3(7)8/h2H,1H2,(H2,5,6)(H,7,8)

Upstream product

• 56-89-3 L-cystine 
• 57-06-7 N-allyl isothiocyanate 
• 565-64-0 2,3-dichloropropanoic acid 
• 17356-08-0 thiourea 
• 54598-78-6 3-carbamimidoylsulfanyl-2-chloro-propionic acid; hydrochloride 
• 56-89-3 cysteine disulfide 
• 151-50-8 potassium cyanide 

Downstream Products

• 20933-67-9 R(-)-2-thioxothiazolidine-4-carboxylic acid 
• 126004-93-1 N-carbamoyl-L-cysteine 
• 638-23-3 carbocisteine 
• 91138-50-0 3-benzoyl-2-imino-thiazolidine-4-carboxylic acid 

Relevant articles and documents

Synthesis method of DL-cysteine

The invention discloses a synthetic method of DLcysteine. The method comprises the following steps: by using acrylonitrile as a raw material, chlorinating to generate 2, 3dichloropropionitrile, hydrolyzing to generate corresponding acid, reacting the acid with thiourea to cyclize to generate 2-aminothiazoline-4-carboxylic acid, adding alkali sulfide to generate 2-mercaptothiazoline-4-carboxylic acid, and hydrolyzing to generate cysteine. The synthesis method provided by the invention has the advantages of short synthesis steps, mild preparation conditions, sufficient and cheap raw material sources and higher product yield.

One-pot synthesis of DL-2-Amino-2-thiazoline-4-carboxylic acid

DL-2-Amino-2-thiazoline-4-carboxylic acid was prepared in one-pot reaction from 2,3-dichloropropionic acid. Not only the procedure was simplified, but also the yield was increased from less than 63% recorded to 93%.

Oxidative Scission of the Disulfide Bond of Cystine and Polypeptides by the Action of Allyl Isothiocyanate

The interaction of allyl isothiocyanate (1) with L-cystine and polypeptides under mild conditions was studied in detail.The reaction mixtures composed of isothiocyanate and cystine were incubated at 40, 60 and 80 deg C, in which cystine completely decomposed after 120, 6 and 2 hr, respectively.Degradation products were isolated and identified as 2-allylamino-2-thiazoline-4-carboxylic acid (2), 2-amino-2-thiazoline-4-carboxylic acid (3) and 3(3H)-allyl-5,6-dihydro-5-amino-2(2H)-thioxo-1,3-thiazin-4-one (4).These products were formed through an oxidative acission of the disulfide bond in cystine by the electrophilic attack of allyl isothiocyanate; the products 2 and 4 seemed to be derived through alanyl N-allyldithiocarbamate and the product 3 through β-thiocyanoalanine.In addition, it was confirmed that a part of the disulfide bond in oxidized glutathione and insulin was also cleaved by isothiocyanate.