| | Oxalyl chloride Basic information |
| | Oxalyl chloride Chemical Properties |
| Melting point | -10--8 °C (lit.) | | Boiling point | 62-65 °C (lit.) | | density | 1.5 g/mL at 20 °C (lit.) | | vapor density | 4.4 (vs air) | | vapor pressure | 150 mm Hg ( 20 °C) | | refractive index | n20/D 1.429(lit.) | | Fp | 176-178°C | | storage temp. | Store Cold | | solubility | Chloroform (Soluble), Ethyl Acetate | | form | Liquid | | color | APHA: 0-150 | | Odor | penetrating odor | | Water Solubility | reacts | | Decomposition | 176-178 ºC | | Sensitive | Moisture Sensitive | | Merck | 14,6914 | | BRN | 1361988 | | Exposure limits | ACGIH: TWA 50 ppm
OSHA: TWA 25 ppm; STEL 125 ppm
NIOSH: IDLH 2300 ppm | | Stability: | Stable. Incompatible with bases, alcohols, steel, oxidizing agents, alkali metals. Moisture sensitive. Reacts violently with water, liberating toxic gas. | | InChIKey | CTSLXHKWHWQRSH-UHFFFAOYSA-N | | CAS DataBase Reference | 79-37-8(CAS DataBase Reference) | | NIST Chemistry Reference | Oxalyl chloride(79-37-8) | | EPA Substance Registry System | Ethanedioyl dichloride (79-37-8) |
| | Oxalyl chloride Usage And Synthesis |
| Chemical Properties | colourless liquid with a pungent odour | | Uses | Oxalyl Chloride is used in the preparation of cardiolipin analogs which induce peroxidase activity by Cytochrome C. It is also used in the preparation of fluorescent indicators for cytosolic calcium. | | Production Methods | Oxalyl Chloride is produced by the reaction of anhydrous oxalic acid and phosphorus pentachloride. | | Preparation | Oxalyl chloride was first prepared in 1892 by the French chemist Adrien Fauconnier, who reacted diethyl oxalate with phosphorus pentachloride. Oxalyl chloride is also produced commercially from ethylene carbonate. Photochlorination gives the tetrachloride, which is subsequently degraded:
C2H4O2CO + 4 Cl2 → C2Cl4O2CO + 4 HCl
C2Cl4O2CO → C2O2Cl2 + COCl2 | | Application | Oxalyl chloride is used in organic synthesis. It may be used in the following processes:
Unncatalyzed reaction of silyl ketene acetals with oxalyl chloride yeilds symmetrical pulvinic acids.
Catalytic syntheses of N-heterocyclic ynones and ynediones by in situ activation of carboxylic acids with oxalyl chloride.
Oxalyl chloride was reportedly used in the first synthesis of dioxane tetraketone.
Preparation of Mosher′s acid chloride by reacting with Mosher′s acid in the presence of DMF.
Activation of dimethyl sulfoxide for use in the oxidation of long-chain alcohols to carbonyls.
Activation of α-keto carboxylic acids and N-heterocyclic carboxylic acids for alkynylation to form ynediones and N-heterocyclic ynones, respectively. | | Reactions | Oxalyl Chloride vigorously reacts with water, alcohols, and amines, and is employed for the synthesis of agrochemicals, pharmaceuticals, and fine chemicals. | | General Description | Oxalyl chloride is a commonly used chlorinating reagent that can be prepared by the reaction of oxalic acid and phosphorus pentachloride. | | Health Hazard | Oxalyl chloride is a corrosive respiratory irritant and lachrymator. The vapors will attack the skin, eyes and especially the mucous membranes of the nose and throat and respiratory system. This material should be used only in a well ventilated area. | | Fire Hazard | Extinguish with dry powder or carbon dioxide. Do not use water. Oxalyl chloride decomposes upon contact with water to produce toxic and corrosive fumes. When heated to decomposition, product emits toxic fumes. | | Chemical Reactivity | Product is sensitive to temperatures below -10° and above 40°C. It reacts vigorously with water and hydroxyl compounds. | | Safety Profile | Poison. Violently decomposed by water and alcohol. Severe irritant to skin, eyes, respiratory tract. Explodeson contact with dimethyl sulfoxide. Forms shock-sensitive explosive mixtures with potassium or with K-Na alloy. Will react with water or steam to | | Waste Disposal | Carefully mix acidic compound with dry sodium bicarbonate. Dilute slowly with water and wash down the drain with copious amounts of water. |
| | Oxalyl chloride Preparation Products And Raw materials |
| Raw materials | Phosphorus pentachloride-->Oxalic acid | | Preparation Products | 4-HO-DET-->2,6-Dichloropyridine-4-carboxaldehyde-->2-(2-NITROPHENYL)ACRYLALDEHYDE-->2,6-DICHLORO-4-ISOCYANATOPYRIDINE-->3-CARBETHOXY-4-HYDROXYCOUMARIN-->1,5-Diazabicyclo[4.3.0]non-5-ene-->1,3-BENZOTHIAZOLE-2-CARBONYL CHLORIDE-->Faropenem sodium hemipentahydrate-->2,6-Difluorobenzoyl isocyanate-->2-Nitrobenzoyl chloride-->4-AMINOBENZANILIDE-->4-Bromo-1-chloroisoquinoline-->2-(5-BENZYLOXY-1H-INDOL-3-YL)-ETHANOL-->4-Thiazolemethanamine, 2-amino-N,N-dimethyl--->2-CHLORO-4-METHYLPYRIMIDINE-5-CARBONYL CHLORIDE-->2-CHLORO-4-PHENYLPYRIMIDINE-5-CARBONYL CHLORIDE-->4-(chloromethyl)-2-thiazolamine-->Etodolac-->4-Propylbenzoic acid-->3-DIMETHYLAMINOBENZOYL CHLORIDE HYDROCHLORIDE-->1,3,5-TRIMETHYL-1H-PYRAZOLE-4-CARBOXYLIC ACID-->5-BROMOSALICYLAMIDE-->o-Anisoyl chloride-->Methyl 2-[5-(benzyloxy)-1H-indol-3-yl]-2-oxoacetate ,97%-->Epristeride-->Cinnamoyl chloride-->2-(5-BENZYLOXY-1H-INDOL-3-YL)-ETHYLAMINE-->5-BENZYLOXYINDOLE-3-GLYOXYLAMIDE-->4-Biphenylcarbonyl chloride-->O-TOLYL-ACETYL CHLORIDE-->4-Cyanobenzoyl chloride-->3,5-DIMETHYL-1H-PYRAZOLE-4-CARBOXYLIC ACID-->BENZOYL ISOCYANATE-->2-[5-(Benzyloxy)-1H-indol-3-yl]-2-oxoacetic acid ,97%-->1H-Pyrazole-4-carbonyl chloride, 1,3,5-trimethyl- (9CI)-->4-DIMETHYLAMINOBENZOYL CHLORIDE-->CHLOROACETYL ISOCYANATE-->2-Chlorobenzoyl isocyanate-->Zolpidem-->Alpidem |
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