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

Chemical Properties

Pale Beige Solid

Uses

Used in the manufacturing of L-tryptophan

Definition

ChEBI: A 1,3-thiazole that is 4,5-dihydro-1,3-thiazole which is substituted at positions 2 and 4 by an amino and a carboxy group, respectively.

Synthesis Reference(s)

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

General Description

White powder.

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

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

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.

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.