140-40-9

Basic information

• Product Name: 2-ACETAMIDO-5-NITROTHIAZOLE
• Synonyms: AKOS AU36-M376;2-ACETYLAMINO-5-NITROTHIAZOLE;2-ACETAMINO-5-NITROTHIAZOLE;2-ACETAMIDO-5-NITROTHIAZOLE;N-(5-NITRO-2-THIAZOLYL)ACETAMIDE;2-acetamido-5-nitro-thiazol;5-Nitro-2-acetamidothiazole;5-Nitro-2-acetilaminotiazolo
• CAS NO: 140-40-9
• Molecular Formula: C₅H₅N₃O₃S
• Molecular Weight: 187.18
• EINECS: 205-414-7
• Product Categories: CORT SOL
• Mol File: 140-40-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 263°C (dec.)
• Boiling Point: 303.8°Cat760mmHg
• Flash Point: 137.5°C
• Appearance: /solid
• Density: 1.546 (estimate)
• Vapor Pressure: 0.000911mmHg at 25°C
• Refractive Index: 1.6560 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 8.78±0.50(Predicted)
• Merck: 14,410
• BRN: 167361
• CAS DataBase Reference: 2-ACETAMIDO-5-NITROTHIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ACETAMIDO-5-NITROTHIAZOLE(140-40-9)
• EPA Substance Registry System: 2-ACETAMIDO-5-NITROTHIAZOLE(140-40-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-36/37-24/25
• RTECS: XJ1570000
• Hazardous Substances Data: 140-40-9(Hazardous Substances Data)

Usage

Chemical Properties

Yellow-brown solid

Uses

Different sources of media describe the Uses of 140-40-9 differently. You can refer to the following data:
1. antiinflammatory, glucocorticoid
2. Nithiamide is a drug for chemotherapy. A protistocide drug with antibacterial activity.

Safety Profile

Poison by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of SO, and NOx,.

Purification Methods

Recrystallise acinitrazole from EtOH or AcOH. [Hurd & Wehrmeister J Am Chem Soc 71 4007 1949, Beilstein 27 III/IV 4676.]

InChI:InChI=1/C5H5N3O3S/c1-3(9)7-5-6-2-4(12-5)8(10)11/h2H,1H3,(H,6,7,9)

Synthetic route

2-amino-5-nitro-1,3-thiazole (121-66-4) + acetic anhydride (108-24-7) → Nitazole (140-40-9)

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	91%

2-acetamidothiazole (2719-23-5) + ethyl nitrate (625-58-1) → Nitazole (140-40-9)

Conditions	Yield
With sulfuric acid; potassium nitrate

2-acetamidothiazole (2719-23-5) → Nitazole (140-40-9)

Conditions	Yield
With sulfuric acid; nitric acid
With nitric acid; acetic anhydride
With ammonium nitrate; sulfuric acid at 20 - 30℃; for 2.5h; Yield given;

2-amino-5-nitro-1,3-thiazole (121-66-4) → Nitazole (140-40-9)

Conditions	Yield
With acetic anhydride
With pyridine
With sulfuric acid

2-acetamido-5-bromothiazole (7336-54-1) → Nitazole (140-40-9)

Conditions	Yield
With nitric acid; acetic anhydride; acetic acid

acetic anhydride (108-24-7) + thiazol-2-ylamine; nitrate (57530-25-3) → Nitazole (140-40-9)

Conditions	Yield
(i) Na2CO3, CCl4, (ii) H2SO4; Multistep reaction;

Nitazole (140-40-9) → 2-amino-5-nitro-1,3-thiazole (121-66-4)

Conditions	Yield
With hydrogenchloride

Nitazole (140-40-9) + 2-bromo-propionic acid amide (5875-25-2) → 2-(2-acetylimino-5-nitro-thiazol-3-yl)-propionamide (23599-21-5)

Conditions	Yield
With sodium hydride; N,N-dimethyl-formamide

Nitazole (140-40-9) + 2-Bromo-N-(n-octyl)acetamide (5326-97-6) → 2-(2-acetylimino-5-nitro-thiazol-3-yl)-N-octyl-acetamide (38922-42-8)

Conditions	Yield
With sodium hydride; N,N-dimethyl-formamide

Nitazole (140-40-9) + ethyl bromoacetate (105-36-2) → N-acetyl-N-(5-nitro-thiazol-2-yl)-glycine ethyl ester (38922-43-9) + (2-acetylimino-5-nitro-thiazol-3-yl)-acetic acid ethyl ester (23599-22-6)

Conditions	Yield
With sodium hydride; N,N-dimethyl-formamide

Nitazole (140-40-9) + 4-bromobutanenitrile (5332-06-9) → N-(3-cyano-propyl)-N-(5-nitro-thiazol-2-yl)-acetamide (39020-59-2) + 4-(2-acetylimino-5-nitro-thiazol-3-yl)-butyronitrile (38922-53-1)

Conditions	Yield
With sodium hydride; N,N-dimethyl-formamide

Nitazole (140-40-9) → N-(3-cyano-propyl)-N-(5-nitro-thiazol-2-yl)-acetamide (39020-59-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaH, DMF 2: aq. HCl View Scheme

Nitazole (140-40-9) → 4-[acetyl-(5-nitro-thiazol-2-yl)-amino]-butyramide (38922-63-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaH, DMF 2: aq. HCl View Scheme
Multi-step reaction with 3 steps 1: NaH, DMF 2: aq. HCl 3: aq. HCl View Scheme

Nitazole (140-40-9) → 4-(2-acetylimino-5-nitro-thiazol-3-yl)-butyramide (38922-54-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaH, DMF 2: aq. HCl View Scheme

Upstream product

• 2719-23-5 2-acetamidothiazole 
• 625-58-1 ethyl nitrate 
• 121-66-4 2-amino-5-nitro-1,3-thiazole 
• 7336-54-1 2-acetamido-5-bromothiazole 
• 108-24-7 acetic anhydride 
• 57530-25-3 thiazol-2-ylamine; nitrate 

Downstream Products

• 121-66-4 2-amino-5-nitro-1,3-thiazole 

Relevant articles and documents

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