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Aldoxime

HCID 7863
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Basic information

CAS
107-29-9
Standard SMILES
CC=NO
InChIKey
FZENGILVLUJGJX-UHFFFAOYSA-N
Molecular formula
C2H5NO
Average molar mass
59.07 g/mol
Monoisotopic mass
59.03711378

Overview

Acetaldehyde oxime appears as a colorless liquid with a pungent odor. Has two crystalline modifications, one melting at 12 °C and the other at 46.5 °C.

Names & identifiers

Preferred name
Aldoxime
IUPAC
N-ethylidenehydroxylamine
English name
Acetaldoxime
Molecular formula
C2H5NO
Molecular weight
59.07

Names & synonyms

ACETALDEHYDE OXIME107-29-9Acetaldehyde, oximeDTXSID2020004USAF AM-5AI3-52258ME6U10SD7DCHEBI:28465NSC-4974RefChem:915385CHEBI:22307DTXCID901474392
Show more names
(E)-acetaldehyde oxiMeAAOAAXEthanal oximeusafam-5ACETALDOXIME
203-479-6AldoximeEthylidenehydroxylamineHydroiminoethaneN-ethylidenehydroxylamineAcetaldoxime,syn & anti(1E)-Ethanal oxime #acetoaldoxime

Database identifiers

CAS
107-29-9
PubChem CID
7863
DTXSID
DTXSID2020004
EC Number
203-479-6

Properties

Computed structural propertiesFilling in

XLogP
-0.1
Topological polar surface area
32.6 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
4
Formal charge
0
Complexity
25.2

Experimental & physicochemical properties

Chemical Classes · 2 items

Nitrogen Compounds -> Oximes

Flammable agents - 3rd degree

SpringerMaterials PropertiesBoiling point
LogP · 2 items

log Kow = -0.13

-0.13

Density0.9656 at 20 °C/4 °C
Color/Form · 2 items

Needles

Two crystalline modifications, alpha-form and beta-form

Solubility · 3 items

Very soluble in water

Very soluble in alcohol, ether

Miscible with ethanol, ether

Flash PointFlash point < 22 °C
Boiling Point115 °C
DecompositionWhen heated to decomposition it emits toxic fumes of /nitrogen oxides/.

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H226 (99.5%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P303+P361+P353, P304+P340, P305+P351+P338, P317, P319, P330, P337+P317, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 219 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 5 items

Chemical: Acetaldehyde, oxime

Acetaldehyde, oxime is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Acetaldehyde, oxime are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 20-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/5292

Acetaldehyde, oxime: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelFlammable Liquid
Fire Hazards · 2 items

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Health Hazards · 2 items

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:

Chemistry & industry

Uses & manufacturing

Uses · 2 items

Used as an intermediate in chemical synthesis; [HSDB]

It is the intermediate of synthetizing pesticides methom, thiodicarb and alanycarb; it can also be used in organic synthesis.

U.S. Production · 5 items

2023: 250,000 - <550,000 lb

Acetaldehyde oxime is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#4138]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Acetaldehyde, oxime. Aggregated National Production Volume: 1 to < 10 million pounds.

Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Acetaldehyde, oxime. National Production Volume: 10,566,000 lb/yr.

Consumer UsesSolvent
Industry UsesSolvent
Methods of ManufacturingDonaruma; United States of America patent 2763686 (1956 to du Pont).
General Manufacturing Information · 2 items

Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing

Acetaldehyde, oxime: ACTIVE

Applications · 3 items

UsesPesticide intermediate, synthesis of pesticides “Methomyl”, “Thiodicarb”, etc.; organic synthesis intermediate. When melted, excellent solvent for many inorganic and organic compounds, organic synthesis, stabilizer, plasticizer, alcohol denaturant. Creation of acylamide through the aldehyde oxime one-pot method. With the presence of catalyst InCl3, acetaldehyde oxime replaces water and reacts with nitrile water to create acylamide at a high yield.

Related reactions

62 records
New reaction record
HRID 17781 reaction equation
HRID 17781As reactantuspto-grants-2010_06
HRID 56060 reaction equation
HRID 56060As reactantuspto-grants-2016_09
HRID 97415 reaction equation
HRID 97415As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 162101 reaction equation
HRID 162101As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 193123 reaction equation
HRID 193123As reactantTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 278942 reaction equation
HRID 278942As reactantuspto-grants-2002_03
HRID 391420 reaction equation
HRID 391420As reactantuspto-grants-2013_02
HRID 450472 reaction equation
HRID 450472As reactantuspto-grants-2013_07
Page 1 of 8

Compound notes

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Melting Point · 2 items

45 °C

Two crystalline modifications with melting point of 12 °C for beta-form and 46.5 °C for alpha-form

Odor ThresholdOdor Threshold Low: 1.0 [ppm]
Vapor Pressure · 2 items

7.71 [mmHg]

9.9 mm Hg at 25 °C /Extrapolated to super-cooled liquid/; 5.0 mm Hg at 25 °C /Extrapolated to solid/

Physicochemical properties

Melting point
44 · 44-46 °C
Boiling point
115 °C · 115 °C(lit.)
Density
0.98 g/mL · 0.98 g/mL at 25 °C
vapor pressure
13 hPa · 13 hPa (25 °C)
refractive index
20 · n20/D 1.426(lit.)
Flash point
135 °F · 135 °F
storage temp.
2 · 2-8°C
solubility
185 g/l · 185g/l
pka
11.82 · 11.82±0.10(Predicted)
form
Low Melting Solid or Liquid
color
White or clear
explosive limit
4.2 · 4.2-50%(V)
Water Solubility
soluble
Merck
14 · 14,42
BRN
1209252 · 1209252
Henry's Law Constant
1.7 · 1.7×100 mol/(m3Pa) at 25℃, HSDB (2015)
Dielectric constant
3.4 · 3.4(20℃)
InChI
1S/C2H5NO/c1-2-3-4/h2,4H,1H3/b3-2+
InChIKey
FZENGILVLUJGJX-NSCUHMNNSA-N
SMILES
C\C=N\O
LogP
-0.13 · -0.13
CAS DataBase Reference
107 · 107-29-9(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
6 U10SD7D · ME6U10SD7D
NIST Chemistry Reference
Acetaldoxime(107-29-9)
EPA Substance Registry System
Acetaldehyde, oxime (107-29-9)
UNSPSC Code
12352126 · 12352126
NACRES
22 · NA.22
Symbol(GHS)
2 · GHS02,GHS06
Signal word
Danger
Hazard statements
311 · H311+H331-H315-H319-H226
Precautionary statements
501 · P501-P240-P261-P210-P233-P243-P241-P242-P271-P264-P280-P370+P378-P337+P313-P305+P351+P338-P361+P364-P303+P361+P353-P332+P313-P304+P340+P311-P403+P233-P403+P235-P405
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes
Xi,Xn
Risk Statements
36 · 36/37/38-20/21/22-10-36-20/22
Safety Statements
26 · 26-36-24/25-16
RIDADR
2332 · UN 2332
WGK Germany
3 · 3
RTECS
2975000 · AB2975000
Autoignition Temperature
380 °C · 380 °C
TSCA
TSCA listed
HazardClass
3 · 3
PackingGroup
III
HS Code
29280090 · 29280090
Storage Class
3 · 3 - Flammable liquids
Hazard Classifications
3 InhalationAcute · Acute Tox. 3 InhalationAcute Tox. 4 OralAquatic Chronic 3Eye Irrit. 2Flam. Liq. 3
Hazardous Substances Data
107 · 107-29-9(Hazardous Substances Data)
Toxicity
50 orally · LD50 orally in Rabbit: 740 mg/kg
REACH Registrations
Active
Limited Quantities
5 L · 5.0 L (1.3 gallons) (liquid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)

· May cause toxic effects if inhaled or absorbed through skin.

Hazards Summary · 1 item

Emergency treatment: Irritants; [HSDB] May form explosive peroxides with air; [CAMEO] Not irritating or sensitizing to guinea pig skin; Expected to induce methemoglobinemia based on studies of related oximes; Likely inhibits acetaldehyde dehydrogenase in the liver; No evidence of mutagenicity; [IUCLID] May form explosive mixtures with air; An irritant; [Alfa Aesar MSDS]

DOT ID and Guide2332 129
Reactive GroupOximes
Reactivity AlertsHighly Flammable
Reactivity Profile · 1 item

ACETALDEHYDE OXIME may explode or decompose violently during distillation if samples have been previously been exposed to the air, which causes formation of peroxides of various types. Reacts as both a weak acid and as a weak base. Gives acetaldehyde and a hydroxylammonium salt if heated with aqueous acid. A nickel-catalyzed aldoxime rearrangement to an amide went out of control when a different solvent was employed [J. Loss Prev., 1993, 6(2), 69].

DOT Emergency Guidelines · 5 items

/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Health: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering.

/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection.

For more DOT Emergency Guidelines (Complete) data for ACETALDEHYDE OXIME (8 total), please visit the HSDB record page.

DOT Hazard Classification · 4 items

Acetaldehyde oxime

UN2332

Class 3 Flammable and combustible liquid (49 eCFR § 173.120)

PG III: the degree of danger presented by the material is minor

Air and Water ReactionsHighly flammable. Easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Very soluble in water.

Safety & protection

Fire FightingExcerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
Accidental Release Measures · 2 items

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 2 items

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:

General First Aid:

Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Fire Fighting Procedures · 2 items

Use water spray to cool unopened containers.

Suitable extinguishing media: For small (incipient) fires, use media such as "alcohol" foam, dry chemical, or carbon dioxide. For large fires, apply water from as far as possible. Use very large quantities (flooding) of water applied as a mist or spray; solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Special protective equipment for firefighters Wear self contained breathing apparatus for fire fighting if necessary.

Storage Conditions · 1 item

Conditions for safe storage Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Recommended storage temperature: 2 - 8 °C

Cleanup Methods · 1 item

Personal precautions: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations

Nonfire Spill ResponseExcerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
Disposal Methods · 3 items

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material.

Contaminated packaging: Dispose of as unused product.

Preventive Measures · 3 items

Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.

Precautions for safe handling: Avoid contact with skin and eyes. Avoid inhalation of vapour or mist. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Isolation and Evacuation · 2 items

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:

Immediate precautionary measure

Personal Protective Equipment (PPE) · 2 items

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:

Personal protective equipment: Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU). Hand protection: Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. Eye protection: Face shield and safety glasses Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin and body protection: Complete suit protecting against chemicals, Flame retardant antistatic protective clothing, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.

Toxicology

Interactions · 1 item

/Acetaldehyde oxime/ probably inhibits acetaldehyde dehydrogenase in the liver. Ethyl alcohol use after excessive exposure to this substance may result in high acetaldehyde concentrations giving rise to headache, red face, nausea, vomiting, sweating and rapid pulse 9the so called antabuse effect).

Ecotoxicity Values · 1 item

LC50; Species: Pimephales promelas (Fathead Minnow) age 31 day, length 17.1 mm, weight 0.071 g; Conditions: freshwater, flow through, 24.4 °C, pH 7.4, hardness 45.6 mg/L CaCO3, alkalinity 39.2 mg/L CaCO3, dissolved oxygen 7.2 mg/L; Concentration: 76000 ug/L for 96 hr (95% confidence interval: 68300-84500 ug/L) /95% purity/

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 40(SRC), determined from a structure estimation method(2), indicates that acetaldehyde oxime is expected to have very high mobility in soil(SRC). Volatilization of acetaldehyde oxime from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.9X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(2). Acetaldehyde oxime is expected to volatilize from dry soil surfaces(SRC) based upon an extrapolated vapor pressure of 5 mm Hg at 25 °C(3). A single biological screening study has noted that two microbes isolated from soil are able to grow on acetaldehyde oxime as a sole carbon source(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 40(SRC), determined from a structure estimation method(2), indicates that acetaldehyde oxime is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 5.9X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 117 hours and 38 days, respectively(SRC). According to a classification scheme(4), an estimated BCF of 3(SRC), from its log Kow of -0.13(5) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low. Acetaldehyde oxime does not absorb at wavelengths >290 nm(6) and, therefore, is not expected to be susceptible to direct photolysis by sunlight in water(SRC). Insufficient data are available to predict the importance of hydrolysis in environmental waters(SRC). A single biological screening study has noted that two microbes isolated from soil are able to grow on acetaldehyde oxime as a sole carbon source(7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), acetaldehyde oxime, which has an extrapolated solid-phase vapor pressure of 5.0 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase acetaldehyde oxime is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 7.6 days(SRC), calculated from its measured rate constant of 2.2X10-12 cu cm/molecule-sec at 25 °C(3). Acetaldehyde oxime does not absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
Ongoing Test Status · 1 item

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from, as of July 17, 2013: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=107-29-9]

Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc of acetaldehyde oxime can be estimated to be 40(SRC). According to a classification scheme(2), this estimated Koc value suggests that acetaldehyde oxime is expected to have very high mobility in soil.

TSCA Test Submissions · 1 item

The mutagenicity of acetaldehyde oxime (AAO) was evaluated in Salmonella tester strains TA98, TA100, TA1535, TA1537, and TA1538, in the presence of added metabolic activation by Aroclor-induced rat liver S9 fraction. AAO, in 50% aqueous solutions, was tested for mutagenicity at concentrations ranging from 5-5000 ug/plate using the plate incorporation method. AAO did not cause a positive response in any of the bacterial tester strains with metabolic activation.

Artificial Pollution Sources · 1 item

Acetaldehyde oxime's production and use as an intermediate in the synthesis of the pesticides methom, thiodicarb and alanycarb and in other organic synthesis(1) may result in its release to the environment through various waste streams(SRC).

Environmental BiodegradationPURE CULTURE: Acetaldehyde oxime was able to be used as a sole carbon source for the growth of one bacteria isolate and one fungi isolate obtained from a silty clay loam soil(1).
Environmental Bioconcentration · 1 item

An estimated BCF of 3 was calculated in fish for acetaldehyde oxime(SRC), using a log Kow of -0.13(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil · 1 item

The Henry's Law constant for acetaldehyde oxime is estimated as 5.9X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that acetaldehyde oxime is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 117 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 38 days(SRC). Acetaldehyde oxime's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Acetaldehyde oxime is expected to volatilize from dry soil surfaces(SRC) based upon a solid-phase extrapolated vapor pressure of 5 mm Hg at 25 °C(3).

Non-Human Toxicity Excerpts · 5 items

/LABORATORY ANIMALS: Acute Exposure/ Primary irritation studied on the skin of guinea pigs: slightly irritating.

/LABORATORY ANIMALS: Acute Exposure/ Guinea pig maximization test: Non sensitizing.

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ One-generation reproductive toxicity studies have been conducted on the following three oximes: acetaldehyde oxime, aldecarb oxime, and methyl isobutyl ketoxime. ... Rats were exposed to the test material for 10 weeks prior to mating and 2 weeks of mating. Males were killed following mating, and females were continuously exposed through gestation and lactation. For methyl isobutyl ketoxime, the F1 generation was exposed from weaning until approximately 7 weeks of age to include when the vaginal opening occurred in females or when balanopreputial separation occurred in males. With the exception of an increased number of stillbirths in the aldecarb oxime high-dose-group animals, no adverse effects were observed in any of the reproductive or litter parameters or in the F1 pups. Toxicity to the F0 animals included signs of hemolytic anemia, along with compensatory extramedullary hematopoiesis and hemosiderosis of the spleen. This occurred for all three test materials. For acetaldehyde oxime, the no-observed-adverse-effect level (NOAEL) for the F0 generation was considered to be less than 5 mg/kg/day, based on decreased mean corpuscular hemoglobin concentration values and histological changes in the spleen. The NOAEL for the F1 generation and reproductive toxicity was considered to be 50 mg/kg/day, the highest dose tested. For aldecarb oxime, the NOAEL for parental toxicity was considered to be less than 5 mg/kg/day, based on the histological changes observed in the livers of females in all groups. The NOAEL for reproductive toxicity and the F1 generation was considered to be 25 mg/kg/day, based on the higher number of stillborn pups in the high-dose group. For methyl isobutyl ketoxime, the NOAEL for parental toxicity was considered to be 30 mg/kg/day, based on the histological effects on the spleen. The NOAEL for the F1 generation and reproductive toxicity was 100 mg/kg/day, the highest dose tested.

/GENOTOXICITY/ The mutagenicity of 6 oxime compounds was evaluated in the Salmonella plate incorporation assay and mouse lymphoma L5178Y TK +/- assay. All of the oximes were mutagenic in the mouse lymphoma assay in the absence of exogenous metabolic activation. Acetaldehyde oxime was also mutagenic in the presence of S9 activation. In contrast to these results, a positive response was noted only for 2-(hydroxyimino)-N-phenyl-acetamide oxime in strain TA1535 in the absence of activation in the Salmonella/microsome test.

For more Non-Human Toxicity Excerpts (Complete) data for ACETALDEHYDE OXIME (6 total), please visit the HSDB record page.

Safety data

PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
rtecs
AB2975000
ridadr
UN 2332
hs_code
29280090
Toxicity
LD50 orally in Rabbit: 740 mg/kg
risk_code
36/37/38-20/21/22-10-36-20/22
Signal word
Danger
Symbol(GHS)
GHS02,GHS06
hazard_code
Xi,Xn
safety_code
26-36-24/25-16
hazard_class
3
Storage Class
3 - Flammable liquids
packing_group
III
Hazard statements
H311+H331-H315-H319-H226
Limited Quantities
5.0 L (1.3 gallons) (liquid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
REACH Registrations
Active
Hazard Classifications
Acute Tox. 3 InhalationAcute Tox. 4 OralAquatic Chronic 3Eye Irrit. 2Flam. Liq. 3
Autoignition Temperature
380 °C
Precautionary statements
P501-P240-P261-P210-P233-P243-P241-P242-P271-P264-P280-P370+P378-P337+P313-P305+P351+P338-P361+P364-P303+P361+P353-P332+P313-P304+P340+P311-P403+P233-P403+P235-P405
Hazardous Substances Data
107-29-9(Hazardous Substances Data)

UsesAcetaldoxime is used as an oxygen scavenger in boiler water. It is also used as an intermediate in chemical synthesis and pharmaceuticals. It is involved in the rearrangement reaction to prepare acetamide by using nickel(II) acetate as a catalyst. It acts as a precursor to prepare heterocyclic compound such as spiroisoxazoline. Further, it is used to prepare alkylated(Z)-oximes by deprotonation followed by reaction with benzyl bromide.

General DescriptionA colorless liquid with a pungent odor. Density 0.966 g / cm3. Flash point 75°F. Boiling point 235°F. Has two crystalline modifications, one melting at 12°C and the other at 46.5°C.

Preparation methods · 2 items

PreparationWith suitable precautions, to a solution of 325 gm (4.68 moles) of hy­droxylamine hydrochloride in 300 ml of water mixed with a solution of 255 gm (2.55 moles) of sodium carbonate in 600 ml of water, cooled in an ice-salt mixture, is added dropwise, with stirring, a solution of 200 gm (4.55 moles) of acetaldehyde in 100 ml of water. After standing overnight, the solution is saturated with sodium chloride and the product is separated by repeated extractions with ether. The combined ether extracts are dried over calcium chloride, filtered, and distilled to afford 215 gm (80%), b.p. 112-114°C (760 mm Hg). Because many aldehydes are not very water soluble, this reaction may be carried out either with vigorous stirring or by adding sufficient alcohol to make the reaction mixture homogeneous. When the product has to be purified by distillation, it has been recommended that the flask be im­mersed into an oil bath maintained at a constant temperature above the anticipated boiling point of the product rather than warming the product and oil bath up to the boiling range from room temperature. By this technique heptaldoxime, b.p. 103-107°C (66 mm Hg), m.p. 53-55°C, cy­clohexanone oxime, b.p. 100-105°C (10-12 mm Hg), m.p. 87-88°C; and methyl ethyl ketoxime, b.p. 150-155°C, have been prepared. The treatment of a carbonyl compound with a hydroxylamine salt, with or without a solvent (or water), and with a neutralization step of the hydroxylamine salt using a simple base may be considered as a general preparative procedure.

PreparationAcetaldehyde oxime is produced through the reaction between hydroxylamine and acetaldehyde aqueous solution. The reaction equation is as follows: CH3CHO+NH2OH•HCl+NaOH→CH3CH=NOH+NaCl+H2O In current industrial production, high levels of crystalline hydroxylamine sulfate are widely used as raw material, made into a 20%~50% aqueous solution and combined with acetaldehyde to create acetaldehyde oxime. The reaction equation is as follows: CH3CHO+(NH2OH)2•H2SO4→CH3CH=NOH In the aforementioned addition of acetaldehyde into hydroxylamine sulfate aqueous solution, the reaction occurs for 2 hours in 40~50℃ temperature. After it is cooled, inorganic salts are removed to achieve a clear aqueous solution of approximately 50% acetaldehyde oxime. Through inspection, it is revealed that there are very few impurities in addition to acetaldehyde and water in the solution, and the yield of acetaldehyde oxime is above 90% (as hydroxylamine sulfate). Extraction and refinement of this solution can yield a product of over 90% acetaldehyde oxime.

Upstream & downstream products

Upstream raw materials

Hydroxylamine sulfateAcetaldehyde aqueous solutionAcetic acid hydroxyammonium saltEthylidene diacetateAcetohydroxamic acidHydroxylamineEthanol

Downstream products

Chloroacetaldehyde oximeMethomylMethylthio acetaldoximeThiophene-2-ethylamineThiodicarb3'-BroMo-5'-(trifluoroMethyl)acetophenone, 97%CB5083Ethyl 1-(4-chlorophenyl)-5-methyl-1H-1,2,4-triazole-3-carboxylate2-Propanone, 1-(5-isoxazolyl)- (9CI)

Additional notes

DefinitionThe –CH:NOH radical resulting from reactions between aldehydes and hydroxylamine or by the oxidation of primary amines by persulfuric acid.