Chloressigsäureanhydrid

2-Chloroacetic anhydride · Monochloroacetic anhydride · CHLOROACETIC ACID ANHYDRIDE · MONOCHLOROACETIC ACID ANHYDRIDE · NSC 71207 · oroacetic anhydride · chloraceticanhydride · chloroacetylanhydride

https://huagongshe.com/de/chemical/10946

Molekülstruktur von Chloressigsäureanhydrid

Identifikatoren & physikalische Daten

CAS No.	541-88-8
Summenformel	C4H4Cl2O3
Durchschnittliche Molmasse	170,98 g/mol
Monoisotopische Masse	169,95374935 g/mol
SMILES	O=C(CCl)OC(=O)CCl
InChIKey	PNVPNXKRAUBJGW-UHFFFAOYSA-N
PubChem CID	10946
EC No.	208-794-2
DTXSID	DTXSID701014649
Lokaler Name	Chloressigsäureanhydrid

Chemische & physikalische Eigenschaften

XLogP	1,1
Polarare Oberfläche (TPSA)	43,4
H-Brücken-Donoren	0
H-Brücken-Akzeptoren	3
Frei drehbare Bindungen	4
Schwere Atome	9
Formalladung	0
Komplexität	109
Stoffklassen	Other Classes -> Acid Anhydrides, Other
SpringerMaterials Properties	Boiling point
Geruch	Pungent odor
Dichte	1.5494 @ 20 °C/4 °C1.449
Color/Form	PRISMS FROM BENZENEColorless to slightly yellow crystals
Löslichkeit	Freely sol in ether, chloroformslightly sol in benzenepractically insol in cold petroleum etherFreely soluble in ether, chloroform. Slightly soluble in benzene. Insoluble in cold ligroin
Siedepunkt	203 °C @ 760 mm Hg
Schmelzpunkt	46 °C51 °C
Dampfdruck	0.03 [mmHg]3.72X10-2 mm Hg @ 25 °C<0.75 mm Hg ( 20 °C)
Physical Description	Colorless to slightly yellow solid with a pungent odor[HSDB] White or off-white crystalline powder[MSDSonline]
Other Experimental Properties	Hydrolyzes with water to chloroacetic acid
Brechungsindex	1.4730 (estimate)
Flammpunkt	>230 °F
Lagerbedingungen	Hygroscopic, -20°C Freezer, Under inert atmosphere
Aggregatzustand	Crystals, Chunks or Low Melting Mass
Farbe	brown
Merck	14,2113
BRN	774533
Henry-Konstante	2.2×100 mol/(m3Pa) at 25℃, HSDB (2015)
Stabilität	Moisture Sensitive
InChI	1S/C4H4Cl2O3/c5-1-3(7)9-4(8)2-6/h1-2H2
InChIKey	PNVPNXKRAUBJGW-UHFFFAOYSA-N
SMILES	ClCC(=O)OC(=O)CCl
CAS Datenbank	541-88-8(CAS DataBase Reference)
EPA chemische Informationen	Acetic acid, chloro-, anhydride (541-88-8)

Sicherheit & Vorschriften

GHS-Einstufung	DangerH301+H311+H331 (67.5%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oralacute toxicity, dermalacute toxicity, inhalation]P260, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P333+P317, P361+P364, P362+P364, P363, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 154 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Regulatorische Informationen	Chemical: Acetic acid, chloro-, anhydrideStatus: Active Update: 06-02-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/12189Chloroacetic anhydride: Does not have an individual approval but may be used under an appropriate group standard
Gefahrenübersicht	A skin and eye irritantEmergency treatment: irritants[HSDB] Reacts with water evolving hydrochloric acidA corrosive substance that can cause injury to the skin, eyes, and respiratory tractCauses lacrimation and may cause edema and chemical pneumonitis after inhalation[MSDSonline]
Hazard Classes and Categories	Acute Tox. 3 (100%)
Skin, Eye, and Respiratory Irritations	IRRITATING TO SKIN & EYES, MODERATELY TOXIC BY INHALATION.
Entsorgungsverfahren	SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Preventive Measures	SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit 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.

Anwendungen & Verwendung

Verwenden

Chloroacetic anhydride has been used in the synthesis of 3,3-bis(sulfonato)-4,4-bis(chloroacetamido)azobenzene (BSBCA), a water-soluble, thiol-reactive and photo-switchable cross-linker, D,L-7-azatryptophan, 2-methyl-[3,4-di-O-acetyl-6-O-(chloroacetyl)-1,2-dideoxy-α-D-glucopyrano]-[2,1:4,5]-2-oxazoline.

Herstellung & Synthese

synthetische

chloroacetic anhydride Synthesis: Powdered s odium monochloroacetate(113.3g, 1.138 mol) was added slowly for a period of 15 min at room temperature (which slowly raises to 60°C) to a stirred solution of commercially available chloroaceyl chloride (127.5g, 1mol) in dry benzene (136mL) was refluxed for 9h. Salts were filtered off, the filtrate was cooled to room temperature, diluted with n-hexane and further cooled to 0°C. The solid separated was then filtered, washed with dry hexane and dried to yield chloroacetic anhydride as white crystalline compound in 60% yield (80g); mp=46-49°C [Lit. mp=46°C]. Alternatively, the benzene layer was directly subjected to high vacuum distillation.The product collected at 109-10°C at 10mm vacuum on cooling chloroacetic anhydride in lump form in 70 % yield (93g). It was observed that, the latter method gives anhydride in lump form while the former method gives in crystalline form.