Isoamyl nitrite

Base Information

• Chemical Name: Isoamyl nitrite
• CAS No.: 110-46-3
• Molecular Formula: C5H11NO2
• Molecular Weight: 117.148
• Hs Code.: 29209090
• European Community (EC) Number: 203-770-8
• ICSC Number: 1012
• NSC Number: 7903
• UN Number: 1993,1113
• UNII: 5N0U5TUC9Z
• DSSTox Substance ID: DTXSID9025455
• Nikkaji Number: J5.092J
• Wikipedia: Amyl_nitrite
• Wikidata: Q27888090
• NCI Thesaurus Code: C87283
• Metabolomics Workbench ID: 37764
• ChEMBL ID: CHEMBL1535371
• Mol file: 110-46-3.mol

Synonyms:Isopentylalcohol, nitrite (8CI);3-Methylbutanol nitrite;3-Methylbutyl nitrite;Amylnitrite;Aspiral;NSC 7903;Nitramyl;Nitrous acid, isopentyl ester;Pentyl nitrite;Vaporole;

Chemical Property of Isoamyl nitrite

Chemical Property:

• Appearance/Colour: yellow liquid
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: n20/D 1.386(lit.)
• Boiling Point: 99.1 °C at 760 mmHg
• Flash Point: 10 °C
• PSA: 38.66000
• Density: 0.98 g/cm³
• LogP: 1.73050
• Storage Temp.: 2-8°C
• Sensitive.: Air & Light Sensitive
• Water Solubility.: <0.01 g/100 mL at 18℃
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 117.078978594
• Heavy Atom Count: 8
• Complexity: 63.4
• Transport DOT Label: Flammable Liquid

Purity/Quality:

97% ^*data from raw suppliers

Isopentyl Nitrite ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn
• Hazard Codes: F,Xn
• Statements: 11-20/22
• Safety Statements: 16-24-46

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CCON=O
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance may cause effects on the blood and cardiovascular system. This may result in cardiac disorders and the formation of methaemoglobin. The effects may be delayed. Medical observation is indicated.
• Uses: It is used in synthesizing perfumes, drugs and diazo compounds. It can be used as an oxidizing agent, solvent. Isobutyl nitrite ester is a drug that is the the fastest short-acting nitrates vasodilator. It is also used as hydrocyanic acid and its salts poisoning antidote.Vasodilators, for the treatment of angina pectoris, also it is used for cyanide poisoning; it is used in synthesizing perfumes, drugs and diazo compounds. It can be used as an oxidizing agent, solvent. Vasodilator. Isoamyl nitrite is a light yellow, transparent liquid with a pleasant, fragrant, fruity odor. Amyl nitrite was introduced to medicine in 1859 and has been under considerable pharmacological investigation since that time. Its major use was for treating angina pectoris through its vasodilative effect on the coronary arteries. However, this effect is transient, and nitroglycerin and longer acting nitrates have largely replaced it. Amyl nitrite has been most helpful in clarifying the differential diagnosis of murmurs. For example, left ventricular outflowobstruction increases followingamyl nitrite administration. Mitral regurgitation decreases following amyl nitrite as does the apical diastolic rumble of mitral stenosis. The Austin–Flint rumble decreases followingamyl nitrite as does a ventricular septal defect and acyanotic tetralogy of Fallot. Pulmonic stenosis increases as does isolated valvular pulmonary stenosis following amyl nitrite. Isoamyl nitrite has also been reportedly used for inhalation abuse. The symptoms following inhalation of large doses by humans are flushing of the face, pulsatile headache, disturbing tachycardia, cyanosis (methemoglobinemia), weakness, confusion, restlessness, faintness, and collapse, particularly if the individual is standing. The symptoms are usually of short duration. Industrial intoxication has not been reported. Isopentyl nitrite is used in the conversion of 2,6-disubstituted phenols to diphenoquinones and aminophenols to quinone diazides. It acts as an oxidant and nitrosating agent. It finds application in aromatic arylation, deamination of arylamines using tetrahydrofuran as a hydrogen donor. It is also useful for the preparation of benzyne using anthranilic acid. It is an antihypertensive and vasodilator to treat heart diseases such as angina and an antidote for cyanide poisoning. Further, it is used as a solvent and cleaning agent for a printed circuit board. In addition to this, it is considered to be a replacement for freon.
• Production method: It is derived from isoamyl alcohol and sodium nitrite. According to the actual production situation, it may have a different method of operation. 1. The reaction takes place in the reaction tube, in synthetic aqueous solution of sodium nitrite, isoamyl alcohol, hydrochloric acid, respectively, are put into the high slot. First sodium nitrite solution and hydrochloric acid solution are dropped at the same rate into the synthesis pipe, when the chlorine gas bubbles in the pipe,isoamyl alcohol is slowly dropped from the top of the pipe, that is in the pipeline synthetic crude. Washed, dried, fractionated to get the products. 2. The reaction is carried out in a reaction tank of sodium nitrite, isoamyl alcohol and water are added to the reaction pot, stirring, cooling to 5 ℃, solution of hydrochloric acid is dropped. At 5 ℃ insulation for 1h, after standing hours to remove the water layer, acetate layer is washed with water, then washed with sodium carbonate solution, and then washed with water. After removing the layer of water, it is dehydrated with anhydrous sodium carbonate, filtered. The filtrate is distilled, collecting 97-99 ℃ distillate, to get isoamyl nitrite.
• Description: Amyl nitrite had been used clinically as early as 1867, when the Scottish physician Sir Thomas Brunton used it as a vasodilator as treatment for angina pectoris in his patients. In the late 1880s, a protective effect on cyanide toxicity in canines was noted when amyl nitrite was inhaled postexposure. Amyl nitrite has been used clinically in a multicomponent cyanide antidote kit and is also a recreational drug of abuse (‘poppers’).

Technology Process of Isoamyl nitrite

There total 12 articles about Isoamyl nitrite which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

→ 3,5-Bis-(trifluoromethyl)aniline (328-74-5) + isopentyl nitrite (110-46-3)

Guidance literature:

Reference yield: 96.4%

→ isopentyl nitrite (110-46-3)

Guidance literature:

Reference yield: 96.0%

i-Amyl alcohol (123-51-3) → isopentyl nitrite (110-46-3)

Guidance literature:

With hydrogenchloride; sodium nitrite; In water; at 0 ℃; for 0.0555556h; Temperature; Large scale;

upstream raw materials:

i-Amyl alcohol

methyl nitrite

((isopentyloxy)methyl)benzene

i-pentyl bromide

Downstream raw materials:

1-phenylazo-acetaldehyde-oxime

(phenylazo)benzaldoxime

phenylazo-p-anisoylaldoxime

bianthrone

Refernces

• 1、 Zhong, Yifei,Raulli, Robert E.,Abtout, Samir,Authier, Simon,Ascah, Alexis,Lambert, Daniel,Gutierrez, Gloria,Cantú, Norma L.,Gutierrez, Nadean,Cabell, Larry,McDonough, Joe,Cakouros, Kelly C.,Gurman, Pablo,Savransky, Vladimir,Barry, John. "RETRACTED ARTICLE: Proof of concept efficacy study of intranasal stabilized isoamyl nitrite (SIAN) in rhesus monkeys against acute cyanide poisoning". . . Retrieved 2021.
• 2、 -. "Method for recycling byproducts in synthesis of diphenyl sulfide compound". Paragraph 0115-0120. . Retrieved 2021/03/30.
• 3、 -. "Method and device for continuously preparing alkyl nitrite through channelization". Paragraph 0031-0034; 0039-0052. . Retrieved 2019/07/04.