57658-36-3

Basic information

• Product Name: 5-Mercapto-1H-tetrazole-1-acetic acid
• Synonyms: MTAA;5-MERCAPTOTETRAZOLE-1-ACETIC ACID;5-MERCAPTOTETRAZOLYLACETIC ACID SODIUM SALT;5-MERCAPTO-1H-TETRAZOLE-1-ACETIC ACID;2,5-dihydro-5-thioxo-1H-tetrazol-1-acetic acid;MTAA:5- MERCAPTO-1H- TETRAZOLE –1-ACETIC ACID;1-Carboxymethyl-5-mercapto-1,2,3,4-tetrazole;(5-Mercapto-1H-tetrazol-1-yl)acetic acid
• CAS NO: 57658-36-3
• Molecular Formula: C₃H₄N₄O₂S
• Molecular Weight: 160.15
• EINECS: 260-884-0
• Product Categories: Organic acids
• Mol File: 57658-36-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 179-180 °C (decomp)
• Boiling Point: 284.7 °C at 760 mmHg
• Flash Point: 126 °C
• Appearance: /
• Density: 1.99 g/cm³
• Vapor Pressure: 0.000761mmHg at 25°C
• Refractive Index: 1.852
• PKA: 3.31±0.10(Predicted)
• CAS DataBase Reference: 5-Mercapto-1H-tetrazole-1-acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Mercapto-1H-tetrazole-1-acetic acid(57658-36-3)
• EPA Substance Registry System: 5-Mercapto-1H-tetrazole-1-acetic acid(57658-36-3)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-63
• Safety Statements: 22-36/37
• Hazardous Substances Data: 57658-36-3(Hazardous Substances Data)

Usage

Description

5-Mercapto-1H-tetrazole-1-acetic acid, also known as 5-Mercapto-1-tetrazolylacetic Acid, is an organic compound characterized by its unique chemical structure that features a thiol group and a tetrazole ring. 5-Mercapto-1H-tetrazole-1-acetic acid is known for its versatile properties and potential applications in various fields due to its ability to form stable complexes with metal ions and its role as an intermediate in the synthesis of certain pharmaceuticals.

Uses

Used in Pharmaceutical Industry:
5-Mercapto-1H-tetrazole-1-acetic acid is used as an intermediate in the synthesis of Ceforanide (C242930), a cephalosporin-based antibiotic. It plays a crucial role in the production of this antibiotic, which is widely utilized in the sterilization of various medical procedures to prevent infections and ensure patient safety.
Used in Nanotechnology:
5-Mercapto-1H-tetrazole-1-acetic acid is employed as a novel capping ligand for the stabilization of metal nanoparticles in water. Its ability to form stable complexes with metal ions makes it an ideal candidate for this application, as it can help prevent the aggregation of nanoparticles and enhance their stability in aqueous solutions. This property is particularly useful in the development of metal nanoparticles for various applications, such as drug delivery, imaging, and sensing.

InChI:InChI=1/C3H4N4O2S/c8-2(9)1-7-3(10)4-5-6-7/h1H2,(H,8,9)(H,4,6,10)

Synthetic route

N,N-dimethyl-2-(5-thioxo-4,5-dihydro-tetrazol-1-yl)-acetamide (61197-32-8) → (5-thioxo-4,5-dihydro-tetrazol-1-yl)-acetic acid (57658-36-3)

Conditions	Yield
With sodium hydroxide

(5-thioxo-4,5-dihydro-tetrazol-1-yl)-acetic acid (57658-36-3) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → C6H12N4O2SSi (81589-11-9)

Conditions	Yield
With <(C6H5O)PO>2NH In 1,2-dichloro-ethane for 1h; Heating;	98.5%

(5-thioxo-4,5-dihydro-tetrazol-1-yl)-acetic acid (57658-36-3) → 2-(5-sulfanyl-1H-1,2,3,4-tetrazol-1-yl)acetic acid disodium salt

Conditions	Yield
With sodium hydroxide In water at 90℃; for 2h;	90%

t-Butyl 3-chloromethyl-7α-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate-5,5-dioxide + (5-thioxo-4,5-dihydro-tetrazol-1-yl)-acetic acid (57658-36-3) → t-Butyl 7α-methoxy-3[[(1-carboxymethyl-tetrazol-5-yl)-thio[methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate-5,5-dioxide + t-Butyl 7α-methoxy-3[[(1-carboxymethyl-tetrazol-5-yl)-thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate-5,5-dioxide

Conditions	Yield
With sodium hydrogencarbonate; ethyl acetate In water; acetone	A 73% B n/a

manganese(II) perchlorate hexahydrate + (5-thioxo-4,5-dihydro-tetrazol-1-yl)-acetic acid (57658-36-3) → Mn(5-mercapto-1H-tetrazole-1-acetic acid (1-))2(H2O)2

Conditions	Yield
With Et3N In water tetrazole-compd. dissolved in H2O, Mn-compd. in H2O added dropwise, pH ajusted to 4.0 with Et3N, stirred at 80°C for 2 h, cooled; filtered, filtrate evaporated at room temp. for 2 months, elem. anal.;	73%

water (7732-18-5) + (5-thioxo-4,5-dihydro-tetrazol-1-yl)-acetic acid (57658-36-3) + zinc(II) oxide → Zn(5-mercapto-1H-tetrazole-1-acetic acid (2-))(H2O)

Conditions	Yield
In water tetrazole-compd. dissolved in H2O, ZnO added, stirred at 90°C for3 h, cooled; filtered, filtrate evaporated at room temp. for 3 months, elem. anal.;	70%

water (7732-18-5) + (5-thioxo-4,5-dihydro-tetrazol-1-yl)-acetic acid (57658-36-3) + cadmium(II) oxide → Cd(5-mercapto-1H-tetrazole-1-acetic acid (2-))(H2O)

Conditions	Yield
In water tetrazole-compd. dissolved in H2O, CdO added, stirred at 90°C for3 h, cooled; filtered, filtrate evaporated at room temp. for 3 months, elem. anal.;	68%

cobalt(II) chloride hexahydrate + (5-thioxo-4,5-dihydro-tetrazol-1-yl)-acetic acid (57658-36-3) → Co(5-mercapto-1H-tetrazole-1-acetic acid (1-))2(H2O)2

Conditions	Yield
With Et3N In tetrahydrofuran; water Co-compd. in H2O added dropwise to tetrazole-compd. in THF, pH ajusted to 4.0 with Et3N, stirred at 80°C for 2 h, cooled; filtered, filtrate evaporated at room temp. for 2 months, elem. anal.;	66%

2-chloro-4,6-dimethylpyrimidine (4472-44-0) + (5-thioxo-4,5-dihydro-tetrazol-1-yl)-acetic acid (57658-36-3) → 2-{5-[(4,6-dimethylpyrimidin-2-yl)sulfanyl]-1H-tetrazol-1-yl}acetic acid

Conditions	Yield
With triethylamine In acetonitrile for 4h; Reflux;	66%

(5-thioxo-4,5-dihydro-tetrazol-1-yl)-acetic acid (57658-36-3) + sodium 7-(2-thienylacetamido)-2β-methyl-3-acetoxymethylceph-3-em-4-carboxylate (80366-38-7) → disodium 7-(2-thienylacetamido)-2β-methyl-3-(1-carborxymethyl-1H-tetrazol-5-yl)thiomethylceph-3-em-4-carboxylate (80366-41-2)

Conditions	Yield
With phosphate buffer; sodium hydrogencarbonate In water at 50℃; for 6h;	20%

2β-chloromethyl-2α-methylpenam-3α-carboxylic acid p-nitrobenzyl ester + (5-thioxo-4,5-dihydro-tetrazol-1-yl)-acetic acid (57658-36-3) + diazodiphenylmethane (908093-98-1) → p-nitrobenzyl 2β-(1-diphenylmethoxycarbonylmethyl-5-tetrazolylthio)methyl-2α-methylpenam-3α-carboxylate

Conditions	Yield
With sodium bicarbonate In dichloromethane; water; acetone	14%

(5-thioxo-4,5-dihydro-tetrazol-1-yl)-acetic acid (57658-36-3) + (6R)-3-acetoxymethyl-7t-[2-(3-methyl-5-nitro-3H-imidazol-4-ylsulfanyl)-acetylamino]-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid; sodium salt (72248-77-2) → (6R)-3-(1-carboxymethyl-1H-tetrazol-5-ylsulfanylmethyl)-7t-[2-(3-methyl-5-nitro-3H-imidazol-4-ylsulfanyl)-acetylamino]-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (72193-28-3)

Conditions	Yield
With sodium hydroxide

(5-thioxo-4,5-dihydro-tetrazol-1-yl)-acetic acid (57658-36-3) + 7-Aminocephalosporanic acid (957-68-6) → 3-<<<1H-1-(carboxymethyl)tetrazol-5-yl>thio>methyl>cephem (59118-46-6)

Conditions	Yield
With sodium carbonate

1,1-dimethylethyl 3-(chloromethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate 5,5-dioxide (95672-05-2) + (5-thioxo-4,5-dihydro-tetrazol-1-yl)-acetic acid (57658-36-3) → 1,1-dimethylethyl 3-({[1-(carboxymethyl)tetrazol-5-yl]thio}methyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 5,5-dioxide (116536-10-8)

Conditions	Yield
With sodium hydrogencarbonate In water; acetone

(6R,7R)-trimethylsilyl 7-(trimethylsilyl)amino-3-iodomethylceph-3-em-4-carboxylate (106134-67-2) + (5-thioxo-4,5-dihydro-tetrazol-1-yl)-acetic acid (57658-36-3) → 3-<<<1H-1-(carboxymethyl)tetrazol-5-yl>thio>methyl>cephem (59118-46-6)

Conditions	Yield
With pyridine; methanol 1.) freon TF, CH2Cl2, from 0 to 5 deg C, 30 min, 2.) from 0 to 5 deg, 10 min; Yield given. Multistep reaction;

(5-thioxo-4,5-dihydro-tetrazol-1-yl)-acetic acid (57658-36-3) + (6R,7R)-Trimethylsilyl 7-[((Trimethylsilyl)oxy)carbonyl]-amino-3-iodomethylceph-3-em-4-carboxylate (111389-99-2) → 3-<<<1H-1-(carboxymethyl)tetrazol-5-yl>thio>methyl>cephem (59118-46-6)

Conditions	Yield
With pyridine; methanol 1.) CH2Cl2, 2.) from 0 to 5 deg C, 15 min; Yield given. Multistep reaction;

Upstream product

• 61197-32-8 N,N-dimethyl-2-(5-thioxo-4,5-dihydro-tetrazol-1-yl)-acetamide 
• 56-40-6 glycine 
• 74-88-4 methyl iodide 

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