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Basic Information
CAS No.: 6609-64-9
Name: 2-Chloro-1,3,2-dioxaphospholane-2-oxide
Article Data: 27
Molecular Structure:
Molecular Structure of 6609-64-9 (2-Chloro-1,3,2-dioxaphospholane-2-oxide)
Formula: C2H4ClO3P
Molecular Weight: 142.479
Synonyms: Ethylenephosphorochloridate (6CI,7CI);Phosphorochloridic acid, cyclic ethylene ester(8CI);2-Chloro-2-oxido-1,3,2-dioxaphospholane;2-Chloro-2-oxo-1,3,2-dioxaphospholane;Cyclic ethylene phosphorochloridate;Ethylene chlorophosphate;
EINECS: 229-560-6
Density: 1.52 g/cm3
Melting Point: 12-14 °C
Boiling Point: 96.7 °C at 760 mmHg
Flash Point: >230 °F
Solubility: Miscible with water and chloroform.
Appearance: clear colourless liquid
Hazard Symbols: CorrosiveC
Risk Codes: 14-34
Safety: 8-25-26-27-36/37/39-45
Transport Information: UN 3265 8/PG 2
PSA: 45.34000
LogP: 1.38010
Synthetic route
107-21-1

ethylene glycol

6609-64-9

2-Chloro-2-oxo-1,3,2-dioxaphospholane

Conditions
ConditionsYield
With trichlorophosphate In dichloromethane at 0℃; for 14h;92%
Stage #1: ethylene glycol In dichloromethane at 0℃; for 0.5h;
Stage #2: With trichlorophosphate In dichloromethane at 0℃; for 14h;
92%
With potassium hydroxide; silica gel; trichlorophosphate 1.) reflux; 2.) rt., 3 h; Yield given. Multistep reaction;
822-39-9

2-chloro-1,3,2-dioxaphospholan

6609-64-9

2-Chloro-2-oxo-1,3,2-dioxaphospholane

Conditions
ConditionsYield
With oxygen In benzene at 50℃; for 24h; Inert atmosphere;86.3%
With oxygen In toluene at 20℃; for 24h; Solvent;75.57%
With oxygen In toluene59%
822-39-9

2-chloro-1,3,2-dioxaphospholan

A

poly(D,L-lactide-co-ethylene methyl phosphate)

poly(D,L-lactide-co-ethylene methyl phosphate)

B

6609-64-9

2-Chloro-2-oxo-1,3,2-dioxaphospholane

Conditions
ConditionsYield
A n/a
B 85%
1315103-53-7

4,8,14,18,23,26,28,31,32-nonamethoxy-35-hydroxypillar[5]arene

822-39-9

2-chloro-1,3,2-dioxaphospholan

A

C46H51O12P

B

6609-64-9

2-Chloro-2-oxo-1,3,2-dioxaphospholane

Conditions
ConditionsYield
In para-xylene at 100℃; for 12h; Inert atmosphere;
7381-30-8

2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane

6609-64-9

2-Chloro-2-oxo-1,3,2-dioxaphospholane

Conditions
ConditionsYield
With trichlorophosphate In water; toluene at 60 - 80℃; for 10h; Solvent; Temperature;111.2 g
96960-92-8

1-O-hexadecyl-2-O-methyl-sn-glycerol

6609-64-9

2-Chloro-2-oxo-1,3,2-dioxaphospholane

111248-00-1

2-(1-hexadecyl-2-methyl-sn-glycerol)-2-oxo-1,3,2-dioxaphospholane

Conditions
ConditionsYield
With triethylamine In benzene for 2h; Ambient temperature;100%
With triethylamine In benzene
With triethylamine In benzene for 2h; Ambient temperature;
81206-32-8

2-heptadecyl-4-(hydroxymethyl)-2-oxazoline

6609-64-9

2-Chloro-2-oxo-1,3,2-dioxaphospholane

81206-33-9

(R)-2-Heptadecyl-4-(2-oxo-2λ5-[1,3,2]dioxaphospholan-2-yloxymethyl)-4,5-dihydro-oxazole

Conditions
ConditionsYield
With triethylamine In benzene for 2h; Ambient temperature;100%
82936-52-5

1-Octadecyl-2-acetamido-sn-glycerol

6609-64-9

2-Chloro-2-oxo-1,3,2-dioxaphospholane

82936-53-6

2-(1-Octadecyl-2-acetamido-2-deoxy-sn-glycero)-2-oxo-1,3,2-dioxaphospholane

Conditions
ConditionsYield
With triethylamine In benzene100%
dmap; triethylamine In benzene
6609-64-9

2-Chloro-2-oxo-1,3,2-dioxaphospholane

818-61-1

2-hydroxyethyl acrylate

150205-71-3

acrylic acid 2-(2-oxo-2Ι5-[1,3,2]dioxaphospholan-2-yloxy)-ethyl ester

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at -30 - 40℃;100%
Stage #1: 2-hydroxyethyl acrylate With triethylamine In tetrahydrofuran at -20℃; for 0.25h; Inert atmosphere;
Stage #2: 2-Chloro-2-oxo-1,3,2-dioxaphospholane In tetrahydrofuran at -20℃; Inert atmosphere;
70%
With triethylamine In acetonitrile at -20℃; for 0.5h; Inert atmosphere;
764-48-7

2-hydroxyethyl vinyl ether

6609-64-9

2-Chloro-2-oxo-1,3,2-dioxaphospholane

2-ethylene glycol vinyl ether-1,3,2-dioxaphospholane 2-oxide

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at -20 - 20℃; for 2h;100%
With triethylamine In dichloromethane at 4℃; for 12h;76%
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Specification

The 2-Chloro-1,3,2-dioxaphospholane-2-oxide, with its CAS registry number 6609-64-9, has the chemical formula of C2H4ClO3P. For being a kind of clear colourless liquid, its product categories are including Biochemistry; Nucleosides, Nucleotides & Related Reagents; Phosphorylating and Phosphorothioating Agents; Phosphorylation; Protecting Agents, Phosphorylating Agents & Condensing Agents; Synthetic Organic Chemistry. 

The physical properties of 2-Chloro-1,3,2-dioxaphospholane-2-oxide are as below: (1)#H bond acceptors: 3; (2)#H bond donors: 0; (3)#Freely Rotating Bonds: 0; (4)Polar Surface Area: 45.34; (5)Index of Refraction: 1.434; (6)Molar Refractivity: 24.31 cm3; (7)Molar Volume: 93.2 cm3; (8)Polarizability: 9.63×10-24 cm3; (9)Surface Tension: 37.9 dyne/cm; (10)Density: 1.52 g/cm3; (11)Enthalpy of Vaporization: 32.23 kJ/mol; (12)Boiling Point: 96.7 °C at 760 mmHg; (13)Vapour Pressure: 49.3 mmHg at 25°C; (14)Exact Mass: 141.958658; (15)MonoIsotopic Mass: 141.958658; (16)Topological Polar Surface Area: 35.5; (17)Heavy Atom Count: 7; (18)Complexity: 104.

Production method of this chemical: 2-chloro-[1,3,2]dioxaphospholane could react to produce 2-Chloro-1,3,2-dioxaphospholane-2-oxide. This chemical could happen in the presence of the reagent of dinitrogen tetraoxide.

Use of this chemical: 2-Chloro-1,3,2-dioxaphospholane-2-oxide could react with methanol to produce 2-methoxy-[1,3,2]dioxaphospholane 2-oxide. This reaction could happen in the presence of reagent of triethylamine and the solvent of CH2Cl2, and it needs 2 hours to react.

When you are dealing with this chemical, you should be very careful. This is corrosive which may destroy living tissue on contact, and it may react violently with water and then could cause burns. Due to the above hazard information, you should wear suitable protective clothing, gloves and eye/face protection while using. Then try to avoid contacting with eyes. If in case of contact with eyes, rinse immediately with plenty of water and seek medical advice, and if in case of accident or if you feel unwell seek medical advice immediately (show the label where possible). Besides, take off immediately all contaminated clothing after contacting. When store it, you should keep this container dry.

In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: C1COP(=O)(O1)Cl
(2)InChI: InChI=1S/C2H4ClO3P/c3-7(4)5-1-2-6-7/h1-2H2
(3)InChIKey: SBMUNILHNJLMBF-UHFFFAOYSA-N