69049-03-2

Basic information

• Product Name: 1-(2-chloroethyl)-4-ethyl-1,4-dihydro-5H-tetrazol-5-one
• Synonyms: 1-(2-chloroethyl)-4-ethyl-1,4-dihydro-5H-tetrazol-5-one;1-(2-Chloroethyl)-4-ethyl...;5H-Tetrazol-5-one, 1-(2-chloroethyl)-4-ethyl-1,4-dihydro-;1-(2-Chloroethyl)-4-ethyl-1H-tetrazol-5(4H)-one;1-(2-chloroethyl)-4-ethyl-4,5-dihydro-1H-1,2,3,4-tetrazol-5-one
• CAS NO: 69049-03-2
• Molecular Formula: C₅H₉ClN₄O
• Molecular Weight: 176.60416
• EINECS: 273-845-8
• Mol File: 69049-03-2.mol

Chemical Properties

• Boiling Point: 206.6°C at 760 mmHg
• Flash Point: 78.8°C
• Appearance: /
• Density: 1.45g/cm³
• Vapor Pressure: 0.235mmHg at 25°C
• Refractive Index: 1.615
• CAS DataBase Reference: 1-(2-chloroethyl)-4-ethyl-1,4-dihydro-5H-tetrazol-5-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-chloroethyl)-4-ethyl-1,4-dihydro-5H-tetrazol-5-one(69049-03-2)
• EPA Substance Registry System: 1-(2-chloroethyl)-4-ethyl-1,4-dihydro-5H-tetrazol-5-one(69049-03-2)

Safety Data

• Hazardous Substances Data: 69049-03-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(2-chloroethyl)-4-ethyl-1,4-dihydro-5H-tetrazol-5-one is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its chloroethyl group allows for a wide range of reactions with nucleophiles, facilitating the creation of diverse drug molecules. The tetrazole ring further enhances the compound's biological activity, making it a promising candidate for the development of new medications.
Used in Agrochemical Industry:
In the agrochemical sector, 1-(2-chloroethyl)-4-ethyl-1,4-dihydro-5H-tetrazol-5-one serves as an essential building block for the synthesis of various agrochemicals. Its versatility in organic synthesis enables the production of compounds with potential applications in crop protection, pest control, and other agricultural areas.
Used in Organic Synthesis:
1-(2-chloroethyl)-4-ethyl-1,4-dihydro-5H-tetrazol-5-one is utilized as a versatile intermediate in organic synthesis due to its reactivity with nucleophiles and the presence of the tetrazole ring. This allows chemists to create a variety of organic compounds with different functional groups and properties, expanding the scope of chemical research and development.
Overall, 1-(2-chloroethyl)-4-ethyl-1,4-dihydro-5H-tetrazol-5-one's unique structure and properties make it a valuable compound in various industries, particularly in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. Its potential for further research and development in these fields is promising, offering new opportunities for innovation and advancement.

InChI:InChI=1/C5H9ClN4O/c1-2-9-5(11)10(4-3-6)8-7-9/h2-4H2,1H3

Upstream product

• 107-04-0 1-Bromo-2-chloroethane 
• 69048-98-2 1-ethyl-1,4-dihydro-5H-tetrazol-5-one 
• 108-10-1 4-methyl-2-pentanone 
• 107-06-2 1,2-dichloro-ethane 

Downstream Products

• 104072-07-3 N-<1-<2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)ethyl>-4-piperidinyl>-N-phenylpropanamide 
• 69049-16-7 methyl 1-[2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)ethyl]-4-[(1-oxopropyl)phenylamino]-4-piperidinecarboxylate ethanedioate 
• 70879-28-6 N-{1-[2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)ethyl]-4-(methoxymethyl)-4-piperidinyl}-N-phenylpropanamide monohydrochloride monohydrate 
• 69049-15-6 alfentanil 
• 98244-83-8 1-ethyl-1,4-dihydro-4-<2-<4-<<1-(phenylmethyl)-1H-benzimidazol-2-yl>amino>-1-piperidinyl>ethyl>-5H-tetrazol-5-one 
• 101344-78-9 trans-1-<2-(4-ethyl-4,5-dihydro-1H-tetrazolyl)ethyl>-3-methyl-4-piperidine 
• 101344-78-9 cis-1-<2-(4-ethyl-4,5-dihydro-1H-tetrazolyl)ethyl>-3-methyl-4-piperidine 

Relevant articles and documents

Preparation method of alfentanil and sufentan and compounds used for preparation of sufentanil and alfentan

The invention discloses a preparation method of alfentanil and sufentan and compounds used for preparation of sufentanil and alfentan. Specifically, the method for preparation of a compound shown as formula V includes: carrying out BOC reaction on a compound shown as formula IV to obtain the compound shown as formula V in the specification. The method can conveniently, efficiently and safely prepare an intermediate product for synthesis of alfentanil and sufentan, i.e. the compound shown as formula V. And then, the compound shown as formula V can be effectively used for preparation of alfentanil and sufentan.

Synthetic 1,4-Disubstituted-1,4-dihydro-5H-tetrazol-5-one Derivatives of Fentanyl: Alfentanil (R 39209), a Potent, Extremely Short-Acting Narcotic Analgesic

The synthesis of a series of N-1,4-disubstituted-1,4-dihydro-5H-tetrazol-5-one piperidinyl derivatives of fentanyl (10), carfentanil (11), and sufentanil (12) is described.The 1-substituted tetrazolinones 2 were essentially prepared via the addition reaction of aluminum azide to isocyanates or acid chlorides in tetrahydrofuran.Alkylation of 2 under neutral or weakly basic conditions afforded almost exclusively the 1,4-disubstituted tetrazolinone isomer 3.N-Alkylation of the piperidine derivatives 4 with 3 in dimethylformamide yielded 9a-v.The morphinomimetic activity in rats, after intravenous injection of the compounds, was evaluated in the tail withdrawal reflex test.The fentanyl analogues 9a-c (R4 = H) are inactive at the measured dose of 2.5 or 10 mg/kg (iv).For the carfentanil analogues (R4 = COOCH3) maximal narcotic activity is found when R1 represents a lower alkyl group (9d-f) or a thienylethyl group (9n).The sufentanil analogues (R4 = CH2OCH3) show the same structure-activity relationship (SAR) profile as the carfentanil derivatives (R4 = COOCH3).The structural requirements for optimal activity are in good agreement with earlier observations in the series of 10-12.From the series the ethyl tetrazolinone derivative 9r, alfentanil (R 39209), was selected for clinical investigation.As an analgesic in rats, 9r is 140 times more potent then pethidine 15 and 72 times more potent than morphine 14.Alfentanil reaches its peak effect within 1 min after injection, and its duration of action is very short; at 2 times its MED50, 9r has a duration of action of 11 min.This duration is 30 min for 10 and 90 min for 14.Compared to 10, alfentanil 9r is about 4 times faster but 3 times shorter acting.Structurally, 9r shows most resemblance to sufentanil 12, since it differs only by substitution of a 4-ethyltetrazolinone ring for the thiophene ring.The considerable differences in their pharmacological profiles were explained in terms of marked variations in physicochemical and, hence, pharmacokinetic properties.

N-phenyl-N-(4-piperidinyl)amides

Novel compounds of the series of N-phenyl-N-(4-piperidinyl)amides having a (4,5-dihydro-4-R-5-oxo-1H-tetrazol-1-yl)alkyl or (4,5-dihydro-4-R-5-thioxo-1H-tetrazol-1-yl)alkyl substituent group in the 1-position of the piperidine nucleus, said compounds being useful as analgesic agents.