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The chemical compound ethyl nitrite is an alkyl nitrite. It may be prepared from ethanol Ethyl nitrite is the main ingredient in a traditional ethanol-based South African remedy for colds and flu known as Witdulsies and sold in pharmacies. It is known as a traditional Afrikaans remedy and may have Dutch roots, as the same remedy is apparently made by the Germano-Dutch Amish people in the USA. However FDA has blocked over-the-counter sales of this same remedy, known in the USA as sweet nitrite or sweet spirit of nitre since 1980 .

109-95-5

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109-95-5 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 109-95-5 differently. You can refer to the following data:
1. Ethyl nitrite has a characteristic ether-like odor.
2. Yellowish volatile liquid.Soluble in alcohol and ether; decomposes in water. Narcotic in high concentration.

Uses

Different sources of media describe the Uses of 109-95-5 differently. You can refer to the following data:
1. Organic reactions, synthetic flavoring.
2. Ethyl Nitrite is an S-nitrosylating agent that improve tissue oxygenation in humans and sheep at normoxia and at reduced fraction of inspired oxygen during microvasculature. Ethyl Nitrite is also used as a therapeutic gas utilized in neonatal Intensive Care Unit.

Preparation

From sodium nitrite in aqueous solution by displacing the acid with H2SO4 in the presence of ethyl alcohol; it forms azeotropic mixtures with isopentane (85%), amyl bromide (40%) and carbon disulfide (96%).

World Health Organization (WHO)

Ethyl nitrite was formerly available in over-the-counter preparations for use as a diaphoretic, a diuretic and an intestinal antispasmodic. In the 1970s its use was associated with cases of methaemoglobinaemia, some of which were fatal. This led to its withdrawal in 1980 by the United States Food and Drug Administration. WHO has no information regarding its current availability in pharmaceutical preparations.

General Description

A clear colorless to yellow liquid with a pleasant odor. Flammable over a wide range of vapor-air concentrations. Flash point -31°F. Less dense than water and insoluble in water. Vapors are heavier than air and narcotic in high concentrations. Produces toxic oxides of nitrogen during combustion.

Air & Water Reactions

Highly flammable. Vapors may ignite spontaneously and the reaction may reach explosive violence. Insoluble in water. Decomposes in water.

Reactivity Profile

ETHYL NITRITE is a powerful oxidizing agent. Highly dangerous in contact with acid or acid fumes. Dangerous when heated. Decomposes spontaneously at 194°F. Decomposed by light.

Hazard

Highly flammable, dangerous, explodes.

Health Hazard

Inhalation or ingestion causes headache, increased pulse rate, decreased blood pressure, and unconsciousness. Contact with liquid irritates eyes and skin.

Chemical Reactivity

Reactivity with Water: No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable if stored in a cool place and not exposed to strong light; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

Safety Profile

Poison by inhalation and ingestion. Narcotic in high concentrations. Lowers blood pressure. Methemoglobinemia has been reported. A very dangerous fire and severe explosion hazard when exposed to heat or flame. A powerful oxidizer. May explode when heated above 90℃. Highly dangerous when heated to decomposition or on contact with acid or acid fumes. To fight fire, use foam, CO2, dry chemical, or water spray. When heated to decomposition it emits toxic fumes of NOx. See also NITRITES and ETHERS.

Check Digit Verification of cas no

The CAS Registry Mumber 109-95-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 9 respectively; the second part has 2 digits, 9 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 109-95:
(5*1)+(4*0)+(3*9)+(2*9)+(1*5)=55
55 % 10 = 5
So 109-95-5 is a valid CAS Registry Number.
InChI:InChI=1/C4H10O.HNO2/c1-3-5-4-2;2-1-3/h3-4H2,1-2H3;(H,2,3)

109-95-5 Well-known Company Product Price

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  • TCI America

  • (E0152)  Ethyl Nitrite (ca. 15% in Ethanol, ca. 1.6mol/L)  

  • 109-95-5

  • 25mL

  • 250.00CNY

  • Detail
  • TCI America

  • (E0152)  Ethyl Nitrite (ca. 15% in Ethanol, ca. 1.6mol/L)  

  • 109-95-5

  • 500mL

  • 1,990.00CNY

  • Detail

109-95-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Ethyl nitrite

1.2 Other means of identification

Product number -
Other names Nitrous acid, ethyl ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:109-95-5 SDS

109-95-5Related news

Synthesis and structural identification of 5-amino-4-hydroxyiminopyrazoles and (E)-N1-aryl-3-aryl-4-[(substituted pyrazolyl)diazenyl] pyrazoles from 5-aminopyrazoles with Ethyl nitrite (cas 109-95-5) or sodium nitrite08/24/2019

5-Amino-4-hydroxyiminopyrazoles and (E)-N1-aryl-3-aryl-4-[(substitutedpyrazolyl)diazenyl]pyrazoles derivatives were conveniently synthesized as the corresponding products by reacting 5-aminopyrazoles with ethyl nitrite or sodium nitrite in ∼10% aqueous HCl solution. All of 5-amino-4-hydroxyimin...detailed

Original ContributionThe potent vasodilator Ethyl nitrite (cas 109-95-5) is formed upon reaction of nitrite and ethanol under gastric conditions08/23/2019

By acting as a bioreactor, affording chemical and mechanical conditions for the reaction between dietary components, the stomach may be a source of new bioactive molecules. Using gas chromatography-mass spectrometry we here demonstrate that, under acidic gastric conditions, ethyl nitrite is form...detailed

ArticleFormation of Ethyl nitrite (cas 109-95-5) in vivo after ethanol administration08/22/2019

The purpose of the current study was to ascertain whether ethyl nitrite could be detected in vitro from the reaction of ethanol with peroxynitrite, as well as after administration of ethanol to mice. Ethyl nitrite analyte was determined by using gas chromatography–mass spectrometry with headspa...detailed

Transformation of ethyl alcohol to Ethyl nitrite (cas 109-95-5) in acidified saliva: Possibility of its occurrence in the stomach08/20/2019

After taking alcoholic beverages, the ethanol is mixed with saliva and then gastric juice. As pH of gastric juice is around 2, the ethanol might be transformed to ethyl nitrite in the stomach by reacting with salivary nitrite. In this study, reactions between ethanol and nitrite in acidified sal...detailed

109-95-5Relevant academic research and scientific papers

Kinetic Study of Reactions of C2H5O and C2H5O2 with NO at 298 K and 0.55 - 2 torr

Daele, V.,Ray, A.,Vassalli, I.,Poulet, G.,Bras, G. Le

, p. 1121 - 1134 (1995)

The kinetics of C2H5O and C2H5O2 radicals with NO have been studied at 298 K using the discharge flow technique coupled to laser induced fluorescence (LIF) and mass spectrometry analysis.The temporal profiles of C2H5O were monitored by LIF.The rate constant for C2H5O + NO -> Products (2), measured in the presence of helium, has been found to be pressure dependent: k2 = (1.25 +/- 0.04) x 10-11, (1.66 +/- 0.06) x 10-11, (1.81 +/- 0.06) x 10-11 at P (He) = 0.55, 1 and 2 torr, respectively (units are cm3 molecule-1 s-1).The Lindemann-Hinshelwood analysis of these rate constant data and previous high pressure measurements indicates competition between association and disproportionation channels: C2H5O + NO + M -> C2H5ONO + M (2a), C2H5O + NO -> CH3CHO + HNO (2b).The following calculated average values were obtained for the low and high pressure limits of k2a and for k2b : k02a = (2.6 +/- 1.0) x 10-28 cm6 molecule-2 s-1, kinfinite2a = (3.1 +/- 0.8) x 10-11 cm3 molecule-1 s-1 and k2b ca. 8 x 10-12 cm3 molecule-1 s-1.The present value of k02a, obtained with He as the third body, is significantly lower than the value (2.0 +/- 1.0) x 10-27 cm6 molecule-2 s-1 recommended in air.The rate constant for the reaction C2H5O2 + NO -> C2H5O + NO2 (3) has been measured at 1 torr of He from the simulation of experimental C2H5O profiles.The value obtained for k3 = (8.2 +/- 1.6) x 10-12 cm3 molecule-1 s-1 is in good agreement with previous studies using complementary methods.

Synthesis and structure of dinitrosyl iron complexes with secondary thiolate bridging ligands [Fe2(μ-SCHR2)2(NO)4], R = Me, Ph

Davidovich,Gurzhiy,Sanina,Shchukarev,Garabadzhiu,Belyaev

, p. 197 - 201 (2015)

New dinitrosyl iron complexes of binuclear structure [Fe2(μ-SCHMe2)2(NO)4] and [Fe2(μ-SCHPh2)2(NO)4] were first synthesized employing new method from Fe(CO)5, corresponding thiol, and EtONO. Complexes structures were determined by XRD technique. DFT calculations were performed to probe the cis-conformer structures in gas and solution phases. NO donor ability of the complex with isopropyl thiolate ligand was studied.

Mechanism of Gas-Phase Nucleophilic Displacement Reaction of NO2(1-) with Ethyl Nitrate

Wlodek, S.,Wincel, H.

, p. 3435 - 3438 (1985)

A mechanism for the gas-phase nucleophilic displacement reaction, NO2(1-) + C2H5ONO2 --> NO3(1-) + C2H5ONO, has been postulated on the basis of the calculated stabilities of the (NO2(1-)*C2H5ONO2) complex.The potential-energy diagram for the reaction pathway is characterized by three minima.The relative yield of NO3(1-) in mixtures with various bath gases has been examined with high-pressure mass spectrometry.The results indicate that the efficiency of NO3(1-) production depends upon the nature of the third body.

Reaction of alcohol with NO2 on a Cleaned Glass Surface

Maeda, Yasuaki,Fujio, Yoshifumi,Munemori, Makoto

, p. 2127 - 2130 (1986)

Formation of alkyl nitrite from alcohol and NO2 was very fast on a Pyrex glass surface cleaned with chromic acid mixture.The reaction was practically zero order with respect to NO2.The rate constant was (1.7 +/- 0.08)*10E-18 cm3*molecule-1*s-1 for methyl nitrile formation and the apparent activation energy was -53.5 kJ*mol-1.

Rate Constants for the Reactions of CH3O and C2H5O with NO2 over a Range of Temperature and Total Pressure

Frost, Michael J.,Smith, Ian W. M.

, p. 1751 - 1756 (1990)

The kinetics of the reactions of CH3O and C2H5O radicals with NO2 have been studied using pulsed laser photolysis to create the radicals from the corresponding alkyl nitrite and by time-resolved, laser-induced fluorescence to observe the decay of the radical concentration.At 295 K, rate constants for CH3O+NO2 have been measured in the presence of Ar (6-100Torr), He(30-100 Torr) and CF4 (30-125 Torr).The association reaction to CH3ONO2 appears to predominate, and rate constants in the limit of low and high pressure are deduced: (k0/10E-29 cm6 molecule-2 s-1) =2.8+/-0.6(M=Ar); 1.6 +/- (M=He); 3.4+/-1.0(M=CF4), and (kinfinite/10E-11 cm3 molecule-1 s-1)=2.0+/-0.4, where the quoted errors correspond to two standard deviations.A limited number of measurements is also reported for this reaction at 390K.The rate of the reaction of C2H5O with NO2 at 295 K is found to be same in the presence of 15 and 100 Torr of Ar, and the measurements yield a rate constant: (kinfinite/10E-11 cm3 molecule-1 s-1) =2.8+/-0.3.

Flow analysis method for determining the concentration of methanol and ethanol in the gas phase using the nitrite formation reaction

Takenaka,Nguyen,Bandow,Maeda

, p. 5847 - 5851 (2000)

The emission sources of alcohols are significant from plants. The use of alcohol-fueled vehicles has increased. Due to the emission from these alcohol-fueled vehicles, the atmospheric alcohol concentrations are expected to be higher than that in the past from plant emission sources. A flow determination method for low molecular weight alcohols (methanol, ethanol) in the gas phase using the nitrite formation reaction, which was developed from an earlier method using a glass bottle was presented. The ambient air and NO2 (1000 ppm vol) were allowed to continuously flow in glass tube, which had been filled with 10 g of Pyrex glass beads. The flow rates of the ambient air and NO2 were 30 and 20 cc/min, respectively. The gas-phase alkyl nitrites produced by the dark reaction of atmospheric alcohols and NO2 on the Pyrex glass beads were analyzed by GC with an electron capture detector. The alcohol concentrations of the samples were computed using a calibrated conversion factor for each alcohol to its nitrite. The detection limits for the methanol and ethanol were 0.7 and 0.5 ppb vol, respectively. The method indicated significant improvement compared with the other methods for measuring ambient alcohol due to its high sensitivity, no required concentration process, and rather high yields of the alkyl nitrite from alcohol. It can be an automated analysis system for atmospheric alcohol.

Rate Constants for the Reactions of CH3O and C2H5O with NO over a Range of Temperature and Total Presuure

Frost, Michael J.,Smith, Ian W. M.

, p. 1757 - 1762 (1990)

The kinetics of the reactions of CH3O and C2H5O radicals with NO have been studied using pulsed laser photolysis to create the radicals from the corresponding alkyl nitrite and time-resolved, laser-induced fluorescence to observe the decay of the radical concentration.For the CH3O + NO reaction, rate constants have been determined at four temperatures between 296 and 573 K and over a range of total pressures up to 125 Torr using Ar and CF4 as diluent gases.The results clearly indicate competition between association to CH3ONO and reaction to H2CO + HNO.The experimental results are fitted well by an extended Lindemann-Hinshelwood mechanism, with values of the limiting high- and low-pressure rate constants of 3.6 (T/298)E-0.6*10E-11cm3 molecule-1s-1 and 1.35(T/298)E-3.8*10E-29 cm6 molecules-2s-1 (the latter being the value that the association rate constant would have in the absence of the rearrangment channel to CH3O + HNO).The rate constant for this last channel in the limit of low pressure is found to be almost independent of temperature and is fitted fairly well by 5.0(T/298)E-0.6*10E-12 cm3 molecule-1 s-1.The rate of the reaction between C2H5O and NO at 298K is found to be the same in the presence of 15 and 100 Torr of Ar, and the measurements yieled a rate constant of (4.4+/-0.4)*10E-11 cm3 molecule-1 s-1.

Temperature dependence of the near UV absorption spectra and photolysis products of ethyl nitrate

Zhu, Lei,Ding, Chuan-Fan

, p. 177 - 184 (1997)

The UV absorption cross sections for ethyl nitrate were measured as a function of temperature between 265 and 340 nm by using cavity ring-down spectroscopy.Absorption cross sections increased with temperature between 238 and 298 K.The variation with temperature was greater at longer wavelengths.Photodissociation product channels of ethyl nitrate at 308 nm were determined using an excimer laser and a cavity ring-down spectrometer.C2H5O + NO2 were the sole photofragmentation products with a quantum yield of 1.0+/-0.1, independent of temperature.Atmospheric implications are discussed.

Gas-phase Reaction of Hydroxyl Radicals with Alkyl Nitrite Vapors in H2O2+NO2+CO Mixtures

Audley, Gary J.,Baulch, Donald L.,Campbell, Ian M.,Waters, Des J.,Watling, Gillian

, p. 611 - 618 (1982)

The yields of CO2 from the chain reaction in H2O2+NO2+CO+alkyl nitrite mixtures, in wich OH is the chain carrier and alkyl nitrites induce a chain termination step, have been used to deduce rate constants (ks) for OH attack on alkyl nitrites (RONO) in the vapour phase at ambient temperatures.Values of ks/E9 dm3 mol-1 s-1 as a function of R were determined as follows: 0.71 +/-0.12 (CH3), 1.15+/-0.23 (C2H5), 1.56+/-0.32 (n-C3H7), 3.41+/-1.48 (n-C4H9), 3.89+/-0.58 (sec-C4H9), 3.47+/-0.52 (i-C4H9), 0.91+/-0.15 (t-C4H9), all based on ks=(1.63+/-0.16)E9 dm3 mol-1 s-1 for OH +n-butane.The small increase in ks from R=CH3 to t-4H9 is considered to support a recent postulate that both H-abstraction and NO-abstraction pathways are operative, at least for R=CH3.Under typical, sunlit urban atmosphere conditions it is deduced that OH attack on alkyl nitrites is a minor removal process compared to their photodissociative destruction.

α-Nitrohydrazones: Versatile intermediates for phosphonate derivatives formation from primary nitro compounds

El Ka?m,Grimaud,Jana,Tirla

, p. 2037 - 2038 (2002)

Primary nitro compounds can be easily converted into hydrazonophosphonate derivatives through coupling with aryldiazonium salts followed by an Arbuzov-type reaction with phosphite.

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