Mandelonitrile
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Mandelonitrile
structure -
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CAS No:
532-28-5
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Formula:
C8H7NO
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Chemical Name:
Mandelonitrile
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Synonyms:
Benzeneacetonitrile,α-hydroxy-;Mandelonitrile;α-Hydroxybenzeneacetonitrile;Phenylglycolonitrile;Mandelic acid nitrile;α-Cyanobenzyl alcohol;Benzaldehyde,cyanohydrin;α-Hydroxyphenylacetonitrile;2-Hydroxy-2-phenylacetonitrile;dl-Mandelonitrile;(±)-Mandelonitrile;(±)-α-Mandelonitrile;NSC 77668;α-Hydroxybenzyl cyanide;Alpha-hydroxy phenylacetonitrile;613-88-7
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CAS No:
Description
reddish-brown liquid
Reddish-brown to dark red-brown liquid. (NTP, 1992)|Solid
Reddish-brown to dark red-brown liquid. (NTP, 1992)|Mandelonitrile is a cyanohydrin that is phenylacetonitrile in which one of the methylene hydrogens is replaced by a hydroxy group.
Characteristics
44
0.83
Yellow to brown Liquid
1.1165 at 68° F (NTP, 1992)
-10 °C
98-102 °C @ Press: 12-14 Torr
207 °F
1.568
alcohol: freely soluble
Store below +30°C.
Subcutaneous-mouse LDL0 1.16 mg/kg
Flammable; emits toxic hydrogen cyanide and nitrogen oxide gas when heated
128.9 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]
This compound is sensitive to moisture. (NTP, 1992). Insoluble in water.
Alcohols and Polyols
Nitriles, such as ALPHA-HYDROXYBENZENEACETONITRILE, may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids.
Safety Information
III
6.1
UN 3276 6.1/PG 3
3
23/24/25-41
22-26-36/37/39-45-24/25
OO8400000
T
Treasury is ventilated, low temperature and dry; stored and transported separately from oxidants, acids and food
Stable, but moisture sensitive. Combustible. Incompatible with strong oxidizing agents.
P261-P280-P301 + P310-P305 + P351 + P338-P311
H301 + H311 + H331-H318
This chemical is combustible. (NTP, 1992)
Fires involving this compound should be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)
SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing 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 keep this material in a tightly closed container under an inert atmosphere, and store it at refrigerated temperatures. STORE AWAY FROM SOURCES OF IGNITION. (NTP, 1992)
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 a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate 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)
Drug Information
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016)
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. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. 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: 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. Generally, the induction of vomiting is NOT recommended outside of a physician's care due to the risk of aspirating the chemical into the victim's lungs. However, if the victim is conscious and not convulsing and if medical help is not readily available, consider the risk of inducing vomiting because of the high toxicity of the chemical ingested. Ipecac syrup or salt water may be used in such an emergency. 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. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
mandelonitrile
Mandelonitrile Use and Manufacturing
It is derived from the addition of benzaldehyde and sodium cyanide. Dissolve sodium cyanide in water, stir and cool, add dropwise benzaldehyde at -5 to 5°C, add hydrochloric acid after the addition, keep the temperature at about 10°C, and let it stand. Separate the oil layer and wash with water to obtain the finished product.
It is one of the active ingredients in Laetrile (vitamin B17) medicine.
Benzeneacetonitrile, .alpha.-hydroxy-: ACTIVE
Computed Properties
Molecular Weight:133.15
XLogP3:1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:133.052763847
Monoisotopic Mass:133.052763847
Topological Polar Surface Area:44
Heavy Atom Count:10
Complexity:141
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Pharmacological action not clearly described
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