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Home> Encyclopedia >Pharmaceutical Intermediates>Organic Intermediate>Organic Intermediates
Methoxyammonium chloride structure
Methoxyammonium chloride structure

Methoxyammonium chloride

Iupac Name:O-methylhydroxylamine;hydrochloride
CAS No.: 593-56-6
Molecular Weight:47.0565
Modify Date.: 2022-11-29 07:12
Introduction: antineoplastic, hydroxymethyltransferase inhibitor View more+
1. Names and Identifiers
1.1 Name
Methoxyammonium chloride
1.2 Synonyms

(aminooxy)methane hydrochloride (Aminooxy)methane hydrochloride (1:1) EINECS 209-798-7 Hydroxylamine, O-methyl-, hydrochloride Hydroxylamine, O-methyl-, hydrochloride (1:1) MAH methane, (aminooxy)-, hydrochloride Methane, (aminooxy)-, hydrochloride (1:1) METHOXYAMINE HCL Methoxyamine hydrochloride methoxy-amine hydrochloride Methoxyamine Hydrochloride, O-Methylhydroxylamine hydrochloride, Methoxylamine hydrochloride Methoxyamine, hydrochloride Methoxylamine hydrochloride methyloxyammoniumchloride METHYOXYAMINE HCL MFCD00012951 MOX REAGENT N-methoxyamine hydrochloride O-Methoxyamine HCl O-methyl hydroxylamine hydrochloride O-METHYLHYDROXYAMINE HYDROCHLORIDE O-METHYLHYDROXYLAMINE HCL O-METHYLHYDROXYLAMINE HYDROCHLORIDE O-METHYLHYDROXYLAMMONIUM CHLORIDE O-methyl-hydroxylammonium chloride

1.3 CAS No.
593-56-6
1.4 CID
521874
1.5 EINECS(EC#)
209-798-7
1.6 Molecular Formula
CH6ClNO (isomer)
1.7 Inchi
InChI=1S/CH5NO.ClH/c1-3-2;/h2H2,1H3;1H
1.8 InChkey
XNXVOSBNFZWHBV-UHFFFAOYSA-N
1.9 Canonical Smiles
CON.Cl
1.10 Isomers Smiles
CON.Cl
2. Properties
2.1 Density
0.854
2.1 Melting point
148-153℃
2.1 Boiling point
105-110°C
2.1 Refractive index
n20/D 1.4021
2.1 Flash Point
°C
2.1 Precise Quality
83.01380
2.1 PSA
35.25000
2.1 logP
1.00880
2.1 Solubility
alcohol: soluble(lit.)
2.2 Appearance
O-methylhydroxylamine hydrochloride appears as off-white crystals. (NTP, 1992)
2.3 Storage
Hygroscopic. Ambient temperatures.
2.4 Chemical Properties
White to very faintly yellow crystalline powder
2.5 Color/Form
MOBILE LIQUID
2.6 Water Solubility
H2O: soluble
2.7 Stability
Stable under normal temperatures and pressures.
2.8 StorageTemp
Sealed in dry,Room Temperature
3. Use and Manufacturing
3.1 General Description
Off-white crystals.
3.2 Methods of Manufacturing
After 500 mg of hydroxyphthalimide (Aldrich) was dissolved in 5 ml of dimethylformamide under argon flow, 0.2 ml of iodinated methane (Aldrich) was added, and 0.5 ml of 1, 8-diazabicyclo[5.4.0]undec-7-ene (Aldrich) was slowly added. After the mixture was stirred at 60° C. for 2 hours, the temperature was again lowered to room temperature, and then the reaction was stopped by adding a 2 N hydrochloric acid solution. The reaction liquid was diluted by adding 20 ml of ethyl acetate, followed by drying over magnesium sulfate and filtration. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography using a mixture eluent of ethyl acetate/hexane (1:5) and then dried to obtain 407 mg of a compound (yield: 75percent). The compound was dissolved in 5 ml of dichloromethane, and 0.11 ml of methyl hydrazine (TCI) was slowly added at 0° C. After the reaction liquid was stirred at room temperature for 2 hours, the temperature was again lowered to 0° C. The generated solid was then filtered out, and 1 ml of a 4 M hydrochloric acid dioxane solution (Aldrich) was added to the residual filtrate, followed by filtration and drying, to obtain 173 mg of a solid (yield: 90percent). 10 mg of the obtained solid and 54 mg of SAC-0906 obtained as obtained above were dissolved in 1 ml of pyridine (Aldrich) under argon flow, followed by stirring at 80° C. for 4 hours. After the temperature was lowered to room temperature, the reaction liquid was acidified by adding a 2 N hydrochloric acid solution, followed by extraction with 20 ml of diethyl ether, drying over magnesium sulfate, and filtration. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography using a mixed eluent of ethyl acetate/hexane (1:5) to obtain the target compound SAC-1012 (48 mg, yield: 85percent).
3.3 Purification Methods
Crystallise the hydrochloride from absolute EtOH or EtOH by addition of diethyl ether. [Kovach et al. J Am Chem Soc 107 7360 1985, Beilstein 1 IV 1252.] Methoxyammonium chloride Preparation Products And Raw materials Preparation Products
3.4 Usage
antineoplastic, hydroxymethyltransferase inhibitor
4. Safety and Handling
4.1 Symbol
GHS05, GHS09
4.1 Hazard Codes
Xi
4.1 Signal Word
Danger
4.1 Risk Statements
R36/37/38
4.1 Safety Statements
S24/25
4.1 Packing Group
III
4.1 Fire Hazard
Flash point data for Methoxyammonium chloride are not available. Methoxyammonium chloride is probably combustible.
4.2 Hazard Class
8
4.2 Hazard Declaration
H314-H400
4.2 RIDADR
UN 3261
4.2 Caution Statement
P273-P280-P305 + P351 + P338-P310
4.2 WGK Germany
3
4.2 RTECS
NC3980000
4.2 Protective Equipment and Clothing
...CORROSIVE TO SKIN & HIGHLY IRRITANT TO EYES & MUCOUS MEMBRANES... /HYDROXYLAMINE/
4.3 Report
Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.
Safety Profile

Mutation data reported. When heated to decomposition it emits very toxic fumes of HCl, NH3 and NOx. See also AMINES.
Safety Information of METHYLOXYLAMMONIUM CHLORIDE(593-56-6).
Hazard Codes:C,Xi,N
Risk Statements:34-36/37/38-50-43-20/21/22
Safety Statements:3-24-26-36/37/39-45-61-24/25-27
RIDADR:UN 3265 8/PG 2
WGK Germany:3
RTECS:NC3980000
F:3-10
Hazard Note:Corrosive/Hygroscopic
HazardClass:8
PackingGroup:III
?

4.4 Skin, Eye, and Respiratory Irritations
...CORROSIVE TO SKIN & HIGHLY IRRITANT TO EYES & MUCOUS MEMBRANES... /HYDROXYLAMINE/
4.5 Safety

Mutation data reported. When heated to decomposition it emits very toxic fumes of HCl, NH3 and NOx. See also AMINES.
Safety Information of METHYLOXYLAMMONIUM CHLORIDE(593-56-6).
Hazard Codes:C,Xi,N
Risk Statements:34-36/37/38-50-43-20/21/22
Safety Statements:3-24-26-36/37/39-45-61-24/25-27
RIDADR:UN 3265 8/PG 2
WGK Germany:3
RTECS:NC3980000
F:3-10
Hazard Note:Corrosive/Hygroscopic
HazardClass:8
PackingGroup:III
?

4.6 Sensitive
Hygroscopic
4.7 Specification

Stability and Reactivity of METHYLOXYLAMMONIUM CHLORIDE(593-56-6).
Chemical Stability: Hygroscopic: absorbs moisture or water from the air.?
Conditions to Avoid: Incompatible materials, exposure to moist air or water.?
Incompatibilities with Other Materials Exposure to moist air or water, strong bases, acid chlorides, acid anhydrides.?
Hazardous Decomposition Products Hydrogen chloride, nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, nitrogen.?
Hazardous Polymerization Has not been reported.?
First Aid Measures of METHYLOXYLAMMONIUM CHLORIDE(593-56-6).
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin: Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.?
Ingestion: Do not induce vomiting. Get medical aid immediately.?
Inhalation: Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.?
Notes to Physician: Treat symptomatically and supportively.?
Handling and Storage of METHYLOXYLAMMONIUM CHLORIDE(593-56-6).
Handling: Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Do not ingest or inhale. Use only in a chemical fume hood.?
Storage: Store in a cool, dry place. Store in a tightly closed container. Corrosives area.?
?

4.8 Toxicity
1. ???

oms-bcs 900?mmol/L

??? DKBSAS ?? Doklady Biological Sciences (English Translation). 257 (1981),154.
2. ???

msc-ham:lng 2?g/L

??? SOGEBZ ?? Soviet Genetics. Translation of GNKAA5. 11 (1975),475.
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Acute toxicity - Dermal, Category 4

Skin irritation, Category 2

Skin sensitization, Category 1

Eye irritation, Category 2

Carcinogenicity, Category 2

Specific target organ toxicity \u2013 repeated exposure, Category 1

Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H302 Harmful if swallowed

H312 Harmful in contact with skin

H315 Causes skin irritation

H317 May cause an allergic skin reaction

H318 Causes serious eye damage

H351 Suspected of causing cancer

H372 Causes damage to organs through prolonged or repeated exposure

H400 Very toxic to aquatic life

H412 Harmful to aquatic life with long lasting effects

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.

P272 Contaminated work clothing should not be allowed out of the workplace.

P201 Obtain special instructions before use.

P202 Do not handle until all safety precautions have been read and understood.

P260 Do not breathe dust/fume/gas/mist/vapours/spray.

P273 Avoid release to the environment.

Response

P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell.

P330 Rinse mouth.

P302+P352 IF ON SKIN: Wash with plenty of water/...

P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.

P321 Specific treatment (see ... on this label).

P362+P364 Take off contaminated clothing and wash it before reuse.

P332+P313 If skin irritation occurs: Get medical advice/attention.

P333+P313 If skin irritation or rash occurs: Get medical advice/attention.

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P337+P313 If eye irritation persists: Get medical advice/attention.

P308+P313 IF exposed or concerned: Get medical advice/ attention.

P314 Get medical advice/attention if you feel unwell.

P391 Collect spillage.

Storage

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

9. Other Information
9.0 Merck
14,5989
9.1 BRN
3589723
9.2 Methoxyamine hydrochloride
Methoxyamine hydrochloride (also known as O-methylhydroxylamine hydrochloride; Methoxyamine; Methoxyamine hydrochloride (OMHA), is an important medicine, pesticide intermediates. Its major applications are as follows:
  • it can be used for color photography and film printing.
  • it is used as a reducing agent in organic synthesis industry for preparation of oximes.
  • the field of medicine: it can be used for the synthesis of second-generation cephalosporins antibiotics cefuroxime (ester), neopropene, norethindine and hydroxyurea.
  • the field of pesticides: the synthesis of new efficient, low-toxicity bactericidal metominostrobin.
  • It is mainly produced by sodium nitrite method in our country.
The similar compound of methoxyamine hydrochloride, the ethoxylamine hydrochloride is mainly used for the production of herbicides, oxycarbazone, diltiazem and other herbicides.
9.3 Application
  • Used as a methoxyamine reagent, also used in the production of the side chain of Cefuroxime and other new drugs
  • Used for pesticide synthesis.
  • Use for pharmaceuticals production
  • Used for the preparation of O-methyloxime together with aldehydes or ketones.
9.4 Chemical Properties
White to very faintly yellow crystalline powder
9.5 Uses
antineoplastic, hydroxymethyltransferase inhibitor
9.6 Uses
Methoxylamine is a methoxime derivative used as internal standard for Prostaglandin assays by gas chromatography-mass spectrometry
9.7 General Description
Off-white crystals.
9.8 Air & Water Reactions
Water soluble.
9.9 Reactivity Profile
In aqueous solution, Methoxyammonium chloride behaves as an acid. Materials in this group are generally soluble in water. The resulting solutions contain moderate concentrations of hydrogen ions and have pH's of less than 7.0. They react as acids to neutralize bases. These neutralizations generate heat, but less or far less than is generated by neutralization of inorganic acids, inorganic oxoacids, and carboxylic acid. They usually do not react as either oxidizing agents or reducing agents but such behavior is not impossible. Many of these compounds catalyze organic reactions.
9.10 Fire Hazard
Flash point data for Methoxyammonium chloride are not available. Methoxyammonium chloride is probably combustible.
9.11 Purification Methods
Crystallise the hydrochloride from absolute EtOH or EtOH by addition of diethyl ether. [Kovach et al. J Am Chem Soc 107 7360 1985, Beilstein 1 IV 1252.]
9.12 Storage Conditions
After 500 mg of hydroxyphthalimide (Aldrich) was dissolved in 5 ml of dimethylformamide under argon flow, 0.2 ml of iodinated methane (Aldrich) was added, and 0.5 ml of 1, 8-diazabicyclo[5.4.0]undec-7-ene (Aldrich) was slowly added. After the mixture was stirred at 60° C. for 2 hours, the temperature was again lowered to room temperature, and then the reaction was stopped by adding a 2 N hydrochloric acid solution. The reaction liquid was diluted by adding 20 ml of ethyl acetate, followed by drying over magnesium sulfate and filtration. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography using a mixture eluent of ethyl acetate/hexane (1:5) and then dried to obtain 407 mg of a compound (yield: 75percent). The compound was dissolved in 5 ml of dichloromethane, and 0.11 ml of methyl hydrazine (TCI) was slowly added at 0° C. After the reaction liquid was stirred at room temperature for 2 hours, the temperature was again lowered to 0° C. The generated solid was then filtered out, and 1 ml of a 4 M hydrochloric acid dioxane solution (Aldrich) was added to the residual filtrate, followed by filtration and drying, to obtain 173 mg of a solid (yield: 90percent). 10 mg of the obtained solid and 54 mg of SAC-0906 obtained as obtained above were dissolved in 1 ml of pyridine (Aldrich) under argon flow, followed by stirring at 80° C. for 4 hours. After the temperature was lowered to room temperature, the reaction liquid was acidified by adding a 2 N hydrochloric acid solution, followed by extraction with 20 ml of diethyl ether, drying over magnesium sulfate, and filtration. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography using a mixed eluent of ethyl acetate/hexane (1:5) to obtain the target compound SAC-1012 (48 mg, yield: 85percent).
9.13 Reactive Group
Ethers
9.14 Fire Hazards
Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
9.15 Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)
9.16 Personal Protective Equipment
MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. Splash proof safety goggles should be worn while handling this chemical. Alternatively, a full face respirator, equipped as above, may be used to provide simultaneous eye and respiratory protection. (NTP, 1992)
9.17 First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. Corrosive chemicals will destroy the membranes of the mouth, throat, and esophagus and, in addition, have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. Transport the victim IMMEDIATELY to a hospital. (NTP, 1992)
9.18 Usage
Methoxylamine hydrochloride is used as a reagent in the preparation of O-methyl oximes from aldehydes. It is orally bioavailable small molecule inhibitor with potential adjuvant activity. It is also used as internal standard for prostaglandin assays by gas chromatography-mass spectrometry.
9.19 Usage
Methoxyamine hydrochloride was used as a reagent in the preparation of O-methyl oximes and also used in the synthesis of O-methyl oximes from aldehydes2 or ketones. It is also applied as an internal standard for Prostaglandin assays by gas chromatography-mass spectrometry.
9.20 Manufacturing Info
Hydroxylamine, O-methyl-, hydrochloride (1:1): ACTIVE
10. Computational chemical data
  • Molecular Weight: 47.0565g/mol
  • Molecular Formula: CH6ClNO
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 83.0137915
  • Monoisotopic Mass: 83.0137915
  • Complexity: 4.8
  • Rotatable Bond Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 2
  • Topological Polar Surface Area: 35.2
  • Heavy Atom Count: 4
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 2
  • CACTVS Substructure Key Fingerprint: AAADcYACIAAEAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAEgAUAAAAAAAAAAICAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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