3-methylbutyl nitrite

• ChemBase ID: 1389
• Molecular Formular: C5H11NO2
• Molecular Mass: 117.14634
• Monoisotopic Mass: 117.0789786
• SMILES: O(N=O)CCC(C)C
• Canonical SMILES: CC(CCON=O)C
• InChI: InChI=1S/C5H11NO2/c1-5(2)3-4-8-6-7/h5H,3-4H2,1-2H3
• InChIKey: OWFXIOWLTKNBAP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-methylbutyl nitrite
• IUPAC Traditional name: IPN; aspiral
• Brand Name: Aspiral; Vaporole
• Synonyms: Amyl nitrite; Isoamyl nitrite; 3-Methylbutanol nitrite; 3-Methylbutyl nitrite; Amilnitrit; Amilnitrite; Amyl nitrit; Amyl nitrite I; Amyl nitrosum; IPN; Isoamyl nitrite; Isopentyl nitrite; Nitramyl; Nitrous acid, 3-methylbutyl ester; Nitrous acid, isopentyl ester; Pentanoli nitris; Pentyl nitrite; Amyl Nitrite; Isopentyl nitrite; 亚硝戊酯; 亚硝酸异戊酯

Database IDs

• CAS Number: 110-46-3
• EC Number: 203-770-8
• MDL Number: MFCD00002057
• Beilstein Number: 969510
• Merck Index: 145123
• PubChem SID: 24896040; 160964849; 24849038; 24881347
• PubChem CID: 8053

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.1550164
• LogD (pH = 7.4): 2.1550164
• Log P: 2.1550164
• Molar Refractivity: 31.6262 cm^3
• Polarizability: 11.716929 Å^3
• Polar Surface Area: 38.66 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.87
• LOG S: -1.61
• Solubility (Water): 2.88e+00 g/l

PROPERTIES

Physical Property

• Boiling Point: 95-100°C; 99 °C(lit.)
• Flash Point: -20 °C; -20°C(-4°F); -4 °F
• Density: 0.872 g/mL at 25 °C(lit.); 0.875
• Refractive Index: 1.3870; n20/D 1.386(lit.); n20/D 1.387

Safety Information

• Storage Warning: Air & Light Sensitive
• RTECS: NT0187500
• European Hazard Symbols: Flammable (F); X; Harmful (Xn)
• UN Number: 1113; UN1113
• German water hazard class: 1
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11-20/22
• Safety Statements: 16; 16-24-46
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS06; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H302-H331; H225-H302-H332; H225-H331-H302
• GHS Precautionary statements: P210; P210-P241-P303+P361+P353-P321-P405-P501A; P210-P261-P311
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1113 3/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (GC); 96%; 97%, stab. with 0.2% anhyd. sodium carbonate
• Grade: purum
• Contains: ~2% sodium carbonate as stabilizer
• Linear Formula: (CH3)2CHCH2CH2ONO

DETAILS

DrugBank - DB01612

• Drug Groups: approved
• Description: Amyl Nitrite is an antihypertensive medicine. Amyl nitrite is employed medically to treat heart diseases such as angina and to treat cyanide poisoning. Like other alkyl nitrites, amyl nitrite is bioactive in mammals, being a vasodilator which is the basis of its use as a prescription medicine. As an inhalant, it also has psychoactive effect which has led to illegal drug use.
• Indication: For the rapid relief of angina pectoris.
• Pharmacology: Amyl nitrite, in common with other alkyl nitrites, is a potent vasodilator. It expands blood vessels, resulting in lowering of the blood pressure. Alkyl nitrite functions as a source of nitric oxide, which signals for relaxation of the involuntary muscles. Physical effects include decrease in blood pressure, headache, flushing of the face, increased heart rate, dizziness, and relaxation of involuntary muscles, especially the blood vessel walls and the anal sphincter. There are no withdrawal symptoms.
• Toxicity: Overdose symptoms include nausea, emesis (vomiting), hypotension, hypoventilation, dyspnea (shortness of breath), and syncope (fainting)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. The drug is metabolized rapidly, probably by hydrolytic denitration; approximately one-third of the inhaled amyl nitrite is excreted in the urine.
• Absorption: Amyl nitrite vapors are absorbed rapidly through the pulmonary alveoli, manifesting therapeutic effects within one minute after inhalation.
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - 150495

Packaging
100, 500 mL in glass bottle
5 mL in ampule

REFERENCES

• Widely used in non-aqueous nitrosation and diazotization reactions.
• For aromatic arylation as an alternative to the Gomberg reaction, see: J. Chem. Soc., 4257 (1962). For deamination of arylamines using THF as a hydrogen donor, see: J. Chem. Soc., Perkin 1, 541 (1973).
• For use in the generation of benzyne from anthranilic acid, see: J. Org. Chem., 38, 3462 (1973).
• ɑ-Amino esters are converted to ɑ-diazo esters: Tetrahedron, 31, 227 (1975).
• For other reactions of alkyl nitrites, see Isobutyl nitrite, L05259, and tert-Butyl nitrite, L16135.