| Identification | More | [Name]
Methyl chloroformate | [CAS]
79-22-1 | [Synonyms]
Carbonochloridic acid methyl ester
CHLOROFORMIC ACID METHYL ESTER
MCF
METHOXYCARBONYL CHLORIDE
METHYL CHLOROCARBONATE
METHYL CHLOROFORMATE
Carbonochlorididicacidmethylester
Chlorameisensaeure methylester
chlorameisensaeuremethylester
Chlorocarbonate de methyle
chlorocarbonatedemethyle
chlorocarbonatedemethyle(french)
Chlorocarbonic acid, methyl ester
chlorocarbonicacidmethylester
Chloroformiate de methyle
chloroformiatedemethyle
chloroformiatedemethyle(french)
chloro-formicacimethylester
Formic acid, chloro-, methyl ester
k-stoff | [EINECS(EC#)]
201-187-3 | [Molecular Formula]
C2H3ClO2 | [MDL Number]
MFCD00000639 | [Molecular Weight]
94.5 | [MOL File]
79-22-1.mol |
| Chemical Properties | Back Directory | [Appearance]
Methyl chloroformate is a colorless liquid
with an unpleasant, acrid odor. This is a highly corrosive
and flammable material. | [Melting point ]
-61°C | [Boiling point ]
70-72 °C(lit.) | [density ]
1.223 g/mL at 25 °C(lit.)
| [vapor density ]
3.26 (vs air)
| [vapor pressure ]
4.8 psi ( 20 °C)
| [refractive index ]
n20/D 1.387(lit.)
| [Fp ]
64 °F
| [storage temp. ]
Store at 0-5°C | [solubility ]
Chloroform, Ethyl Acetate | [form ]
Liquid | [color ]
Clear colorless to light yellow | [Odor]
Acrid. | [Water Solubility ]
hydrolysis | [Merck ]
13,6071 | [Dielectric constant]
12.9 | [Stability:]
Moisture Sensitive | [CAS DataBase Reference]
79-22-1(CAS DataBase Reference) | [NIST Chemistry Reference]
Carbonochloridic acid, methyl ester(79-22-1) | [EPA Substance Registry System]
79-22-1(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
F,T+ | [Risk Statements ]
R11:Highly Flammable.
R21/22:Harmful in contact with skin and if swallowed .
R26:Very Toxic by inhalation.
R34:Causes burns. | [Safety Statements ]
S14:Keep away from ... (incompatible materials to be indicated by the manufacturer) .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S63:In case of accident by inhalation, remove casualty to fresh air and keep at rest.
S46:If swallowed, seek medical advice immediately and show this container or label .
S39:Wear eye/face protection .
S36/37:Wear suitable protective clothing and gloves . | [RIDADR ]
UN 1238 6.1/PG 1
| [WGK Germany ]
2
| [RTECS ]
FG3675000
| [F ]
10-19-21 | [Autoignition Temperature]
485 °C | [HazardClass ]
6.1(a) | [PackingGroup ]
I | [HS Code ]
29151300 | [Safety Profile]
Poison by ingestion,
inhalation, and intraperitoneal routes.
Moderately toxic by skin contact. Human
systemic effects by inhalation: conjunctiva
irritation and respiratory effects. Corrosive
to skin, eyes, and mucous membranes. Very
dangerous fire hazard when exposed to heat
sources, sparks, flame, or oxidzers. Reacts
with water or steam to produce toxic and
corrosive fumes. When heated to
decomposition it emits toxic fumes of Cl-,
methyl chloroformate, and phosgene. | [Hazardous Substances Data]
79-22-1(Hazardous Substances Data) |
| Hazard Information | Back Directory | [General Description]
A colorless liquid with a pungent odor. Flash point 54°F. Corrosive to metals and tissue. Vapors heavier than air. Very toxic by inhalation. Used to make other chemicals and insecticides. | [Reactivity Profile]
METHYL CHLOROFORMATE(79-22-1) is incompatible with water, strong oxidizing agents, alcohols, bases (including amines). Decomposes slowly in water to yield methanol, HCl, and CO2; reaction can be hazardous if water is hot. Attacks many metals especially in humid atmosphere [Handling Chemicals Safely 1980. p. 476]. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291]. | [Air & Water Reactions]
Highly flammable. Gives off hydrochloric acid fumes in contact with moist air. Slightly soluble in water and decomposed by water to hydrochloric acid with evolution of heat. | [Hazard]
Flammable, dangerous fire risk. Highly corrosive and irritant to skin and eyes. | [Health Hazard]
Methyl chloroformate is highly toxic upon inhalation and upon ingestion. A concentration of 1 mg/liter (190 ppm) has been lethal in 10 minutes. It is corrosive and irritating to skin. | [Potential Exposure]
Used in synthesis of pharmaceuticals;
herbicides, plastics and other organic chemicals; as a solvent in the photographic industry; as a chemical intermediate in the production of other chemicals. In WWI it was
used as military tear-producing warfare agent. | [Fire Hazard]
This chemical is very dangerous when exposed to heat sources, sparks, flame, or oxidizers. METHYL CHLOROFORMATE will react with water or steam to produce toxic and corrosive fumes. Vapors may travel to a source of ignition and flash back. Withdraw immediately in case of rising sound from venting safety device or any discoloration of tank due to fire. Toxic fumes of phosgene are produced when the material is heated to decomposition. Heat or steam should be avoided. | [First aid]
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
30 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if
heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get medical attention. If victim is conscious, administer water or
milk. Do not induce vomiting. Medical observation is
recommended for 24 to 48 hours after breathing overexposure, as pulmonary edema may be delayed. As first aid for
pulmonary edema, a doctor or authorized paramedic may
consider administering a drug or other inhalation therapy. | [Shipping]
UN1238 Methyl chloroformate, Hazard class:
6.1; Labels: 6.1-Poison Inhalation Hazard, 3-Flammable
liquid, 8-Corrosive material Inhalation Hazard Zone A | [Incompatibilities]
May form explosive mixture with air.
Violent reaction with alkali metals; ethers. Incompatible
with strong acids; strong bases; alcohols, oxidizers,
dimethylsulfoxide; dimethyl formamide. Contact with water
or moisture produces corrosive and poisonous hydrogen
chloride gas, methanol and carbon monoxide. Corrodes
metals in the presence of moisture. Attacks some plastics,
rubber and coatings. | [Description]
Methyl chloroformate is a colorless liquidwith an unpleasant, acrid odor. This is a highly corrosiveandflammablematerial. Molecular weight = 94.50;Specific gravity (H2O:1)= 1.22; Boiling point= 71℃;Freezing/Melting point=- -61℃; Flash point= 17℃;Autoignition temperature = 504℃. Flammability Limits:LEL= 6.7%; UEL = unknown.Hazard Identification(based on NFPA-704 M Rating System): Health 1,Flammability 3, Reactivity 1. Slightly soluble in water. | [Chemical Properties]
Methyl chloroformate is a colorless liquid with an unpleasant, acrid odor. This is a highly corrosive and flammable material. Decomposed by hot water; stable to cold water. Soluble in methanol alcohol, ether, and benzene. | [Waste Disposal]
Consult with environmental
regulatory agencies for guidance on acceptable disposal
practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform to EPA regulations
governing storage, transportation, treatment, and waste
disposal | [Uses]
Chloroformic Acid Methyl Ester is used in the synthesis of a new class of potent Cdk4 inhibitors in the treatment of cancer. Also used in the synthesis of Phorboxazole B. | [Application]
Methyl chloroformate (MCF) is generally used for the derivatization of functional groups such as carboxylic acids, amines, and phenols.
MCF can also be used:
To activate 3-acylpyridines for nucleophilic addition with alkynyltin reagents to form 2,3-disubstituted 1,2-dihydropyridines.
Chloroesterification of terminal alkynes to form β-chloro-α,β-unsaturated esters.
As an electrophilic reagent to mediate the reaction of pyridine with lithium dialkyl- or diarylcuprates to form 4-substituted 1,4-dihydropyridine derivatives.
To convert nitronates into methoxycarbonyl nitronates. | [Production Methods]
Prepared from phosgene and methyl alcohol. | [Flammability and Explosibility]
Flammable | [Chemical Reactivity]
Reactivity with Water: Reacts slowly, evolving hydrogen chloride (hydrochloric acid). Reaction can be hazardous if water is hot; Reactivity with Common Materials: Corrodes rubber; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Flush with water, rinse with sodium bicarbonate or lime solution; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent. | [Synthesis]
Methyl chloroformate prepared by reacting methyl alcohol with phosgene.
A side product (methyl carbonate) could be formed if the temperature is not kept rather low and phosgene is not used in excess:
To a reaction flask fitted with a dropping-funnel, a tube to introduce the gaseous phosgene and an exit tube a 10 ml of methyl chloroformate is placed. The reaction flask is cooled to 0° C and the current of phosgene containing no chlorine is bubbled in. About one-third of reaction flask is filled with methanol from the dropping-funnel all at once. When the phosgene gas is no longer being absorbed additional portion of a fresh methanol is added to the reaction mixture. As soon as the reaction is complete, methyl chloroformate is transferred to a separatory funnel containing cold water. The heavier layer which separates from the aqueous layer is washed twice with cold water, dried over calcium chloride and fractionally distilled. The fraction passing over between 69-72 °C is collected. The yield of methyl chloroformate is about 70% of theory.
The war gases chemistry and analysis, by M. Sartory, 102, 1939. | [storage]
Color Code—Red: Flammability Hazard: Store ina flammable liquid storage area or approved cabinet awayfrom ignition sources and corrosive and reactive materials.Prior to working with methyl chloroformate you should betrained on its proper handling and storage. Before enteringconfined space where this chemical may be present, checkto make sure that an explosive concentration does not exist.Store in tightly closed containers in a cool, well-ventilatedarea away from all forms of moisture, oxidizers, strongacids, strong bases. See incompatibilities for other materialsto avoid. Where possible, automatically pump liquid fromdrums or other storage containers to process containers.Drums must be equipped with self-closing valves, pressurevacuum bungs, and flame arresters. Use only nonsparkingtools and equipment, especially when opening and closingcontainers of this chemical. Wherever this chemical is used,handled, manufactured, or stored, use explosion-proof electrical equipment and fittings. |
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