84501-67-7

Basic information

• Product Name: 1-(2-bromoethyl)-4-ethyl-1,4-dihydro-5H-tetrazol-5-one
• Synonyms: 1-(2-bromoethyl)-4-ethyl-1,4-dihydro-5H-tetrazol-5-one;Einecs 282-986-4;5H-Tetrazol-5-one, 1-(2-broMoethyl)-4-ethyl-1,4-dihydro-;EOS-60376
• CAS NO: 84501-67-7
• Molecular Formula: C₅H₉BrN₄O
• Molecular Weight: 221.05516
• EINECS: 282-986-4
• Product Categories: Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 84501-67-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 223℃
• Flash Point: 89°(192°F)
• Appearance: Colorless/Liquid
• Density: 1.777
• Vapor Pressure: 0.0969mmHg at 25°C
• Refractive Index: 1.5070
• Solubility: Chloroform, Dichloromethane
• CAS DataBase Reference: 1-(2-bromoethyl)-4-ethyl-1,4-dihydro-5H-tetrazol-5-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-bromoethyl)-4-ethyl-1,4-dihydro-5H-tetrazol-5-one(84501-67-7)
• EPA Substance Registry System: 1-(2-bromoethyl)-4-ethyl-1,4-dihydro-5H-tetrazol-5-one(84501-67-7)

Safety Data

• Hazardous Substances Data: 84501-67-7(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Liquid

Uses

Intermediate in the preparation of Alfentanil.

InChI:InChI=1/C5H9BrN4O/c1-2-9-5(11)10(4-3-6)8-7-9/h2-4H2,1H3

Upstream product

• 106-93-4 ethylene dibromide 
• 69048-98-2 1-ethyl-1,4-dihydro-5H-tetrazol-5-one 

Downstream Products

• 101345-06-6 N-{(3R,4R)-1-[2-(4-Ethyl-5-oxo-4,5-dihydro-tetrazol-1-yl)-ethyl]-3-methyl-piperidin-4-yl}-N-(2-fluoro-phenyl)-2-methoxy-propionamide 
• 120657-07-0 N-{1-[2-(4-Ethyl-5-oxo-4,5-dihydro-tetrazol-1-yl)-ethyl]-4-phenyl-piperidin-4-yl}-N-phenyl-propionamide 
• 120072-14-2 N-{1-[2-(4-Ethyl-5-oxo-4,5-dihydro-tetrazol-1-yl)-ethyl]-4-thiazol-2-yl-piperidin-4-yl}-N-phenyl-propionamide 
• 121879-92-3 1-[2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)ethyl]-4-(2-pyridyl)-4-(N-phenylpropionamido)piperidine 
• 120071-99-0 N-[1-[2-(4-Ethyl-5-oxo-4,5-dihydro-tetrazol-1-yl)-ethyl]-4-(4-methyl-thiazol-2-yl)-piperidin-4-yl]-N-phenyl-propionamide 
• 120656-74-8 1-[2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)ethyl]-4-phenyl-4-[N-(2-fluorophenyl)propionamido]piperidine 
• 120656-81-7 N-(2-Chloro-phenyl)-N-{1-[2-(4-ethyl-5-oxo-4,5-dihydro-tetrazol-1-yl)-ethyl]-4-phenyl-piperidin-4-yl}-propionamide 
• 120072-22-2 N-{4-(4,5-Dimethyl-thiazol-2-yl)-1-[2-(4-ethyl-5-oxo-4,5-dihydro-tetrazol-1-yl)-ethyl]-piperidin-4-yl}-N-phenyl-propionamide 
• 121879-94-5 1-[2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)ethyl]-4-(2-pyridyl)-4-[N-(2-fluorophenyl)propionamido]piperidine 
• 120072-16-4 N-{1-[2-(4-Ethyl-5-oxo-4,5-dihydro-tetrazol-1-yl)-ethyl]-4-thiazol-2-yl-piperidin-4-yl}-N-(2-fluoro-phenyl)-propionamide 
• 120072-01-7 N-[1-[2-(4-Ethyl-5-oxo-4,5-dihydro-tetrazol-1-yl)-ethyl]-4-(4-methyl-thiazol-2-yl)-piperidin-4-yl]-N-(2-fluoro-phenyl)-propionamide 
• 69049-06-5 alfentanil hydrochloride 
• 71195-58-9 alfentanil 

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.