2-Chloro-1,3,2-dioxaphospholane supplier

Name
2-Chloro-1,3,2-dioxaphospholane
EINECS 212-499-4
CAS No. 822-39-9
Article Data38
CAS DataBase
Density 1.422
Solubility
Melting Point -28oC
Formula C2H4 Cl O2 P
Boiling Point 117.4 °C at 760 mmHg 62 oC (20 mmHg)
Molecular Weight 126.479
Flash Point 86 ºC
Transport Information UN 3264
Appearance clear colorless to slightly yellow liquid
Safety S25;S8
Risk Codes R14;R34
Molecular Structure
Hazard Symbols
Synonyms Ethylenephosphorochloridite (6CI,7CI); Phosphorochloridous acid, cyclic ethylene ester(8CI); Ethylene glycol, cyclic phosphorochloridite (8CI);2-Chloro-1,3,2-dioxaphospholane; Cyclic O,O-ethylene phosphorochloridite;Cyclic ethylene chlorophosphite; Cyclic ethylene phosphorochloridite; Ethylenechlorophosphite; Ethylene glycol chlorophosphite
PSA 32.05000
LogP 1.49890

Synthetic route

: 107-21-1
ethylene glycol

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

Conditions

Conditions	Yield
With phosphorus trichloride In dichloromethane at 0℃; for 14h;	92%
With phosphorus trichloride In dichloromethane at 20℃; for 0.5h; Inert atmosphere;	74.7%
With phosphorus trichloride In dichloromethane at 20℃; for 3h; Inert atmosphere;	67%

: 107-21-1
ethylene glycol

A: 37445-80-0
1,1,6,6-tetrachloro-2,5-dioxa-1,6-diphosphahexane

B: 822-39-9
2-chloro-1,3,2-dioxaphospholan

Conditions

Conditions	Yield
With triethylamine; phosphorus trichloride at 45℃; Reagent/catalyst;	A 51.7% B n/a
With phosphorus trichloride anfangs unter Luehlung,dann bei 60-70grad;

: 18882-67-2
2-methyl-[1,3,2]dioxarsolane

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

Conditions

Conditions	Yield
With phosphorus trichloride In benzene

: 110-86-1
pyridine

: 60-29-7
diethyl ether

: 107-21-1
ethylene glycol

: 7719-12-2, 52843-90-0
phosphorus trichloride

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

...Expand

: 75-09-2
dichloromethane

: 107-21-1
ethylene glycol

: 7719-12-2, 52843-90-0
phosphorus trichloride

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

...Expand

: 60-29-7
diethyl ether

: 107-21-1
ethylene glycol

: 121-69-7
N,N-dimethyl-aniline

: 7719-12-2, 52843-90-0
phosphorus trichloride

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

...Expand

: 107-21-1
ethylene glycol

: 7719-12-2, 52843-90-0
phosphorus trichloride

A: 37445-80-0
1,1,6,6-tetrachloro-2,5-dioxa-1,6-diphosphahexane

B: 822-39-9
2-chloro-1,3,2-dioxaphospholan

Conditions

Conditions	Yield
anfangs unter Kuehlung, dann bei 60-70grad;

...Expand

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: 85741-80-6
2-azido-1,3,2-dioxaphospholane

Conditions

Conditions	Yield
With trimethylsilylazide at 0 - 5℃; for 3h;	100%
With (C2H5)3N*NH3

: 88070-48-8
N-methylbenzamide

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: ethylene benzoylmethyphosphoramidite

Conditions

Conditions	Yield
In diethyl ether Ambient temperature;	97%

: 127472-90-6
2,3-Di(stearoyloxy)-1-propanthiol

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: 134152-76-4
2-(2,3-Distearoyloxypropyl)-1,3,2-dioxaphospholan-2-sulfid

Conditions

Conditions	Yield
With triethylamine In benzene for 3h; Ambient temperature;	96%

: lithium 2-(diphenylphosphanyl)pyrrolide

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: 2-diphenylphosphino-1-(1,3,2-dioxaphospholane)pyrrole

Conditions

Conditions	Yield
In diethyl ether at 23℃; for 25h; Glovebox; Inert atmosphere;	96%

: 67-56-1
methanol

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: 3741-36-4
methoxy-2 dioxaphospholane-1,3,2

Conditions

Conditions	Yield
Stage #1: methanol In dichloromethane at 20℃; for 0.5h; Stage #2: 2-chloro-1,3,2-dioxaphospholan In dichloromethane at 0 - 20℃; for 12h;	95%
With pyridine
With 2,3-Dimethylaniline
With triethylamine

: 64-17-5
ethanol

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: 695-11-4
2-Ethoxy-1,3,2-dioxaphospholan

Conditions

Conditions	Yield
Stage #1: ethanol In dichloromethane at 20℃; for 0.5h; Stage #2: 2-chloro-1,3,2-dioxaphospholan In dichloromethane at 0 - 20℃; for 12h;	95%
With triethylamine

: 7042-60-6
2,2,2-trichloro-1-(2-oxo-1-aza-1-cyclopentyl)ethanol

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: ethylene 2,2,2-trichloro-1-(2-oxo-1-aza-1-cyclopentyl)ethyl phosphite

Conditions

Conditions	Yield
With triethylamine In benzene at 0℃;	95%

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: 927-74-2
1-butyn-4-ol

: 2-(3-butynyloxy)-1,3,2-dioxaphospholane

Conditions

Conditions	Yield
Stage #1: 3-Butyn-1-ol In dichloromethane at 20℃; for 0.5h; Stage #2: 2-chloro-1,3,2-dioxaphospholan In dichloromethane at 0 - 20℃; for 12h;	95%

: 400-32-8
1,1,1-trifluoro-2,4-pentanediol

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: C9H15F3O6P2

Conditions

Conditions	Yield
In dichloromethane at 0 - 20℃; for 8h;	95%

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: 57044-25-4
(R)-oxiranemethanol

: (R)-2-(oxiran-2-ylmethoxy)-1,3,2-dioxaphospholane

Conditions

Conditions	Yield
With triethylamine In diethyl ether at 0 - 20℃; for 3h; Reagent/catalyst; Solvent;	94.8%

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: 107-18-6
allyl alcohol

: 53969-10-1
2-allyloxy-1,3,2-dioxaphospholane

Conditions

Conditions	Yield
Stage #1: allyl alcohol In dichloromethane at 20℃; for 0.5h; Stage #2: 2-chloro-1,3,2-dioxaphospholan In dichloromethane at 0 - 20℃; for 12h;	94%
With pyridine; diethyl ether
With triethylamine

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: 108-95-2
phenol

: 1077-05-0
2-phenoxy-[1,3,2]dioxaphospholane

Conditions

Conditions	Yield
Stage #1: phenol In dichloromethane at 20℃; for 0.5h; Stage #2: 2-chloro-1,3,2-dioxaphospholan In dichloromethane at 0 - 20℃; for 13.5h;	94%
With triethylamine
With triethylamine In hexane

: 90-15-3
α-naphthol

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: 110232-62-7
2-(1-naphthalenoxy)-1,3,2-dioxaphospholane

Conditions

Conditions	Yield
Stage #1: α-naphthol In dichloromethane at 20℃; for 0.5h; Stage #2: 2-chloro-1,3,2-dioxaphospholan In dichloromethane at 0 - 20℃; for 12h;	94%
With triethylamine In benzene

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: 108-18-9
diisopropylamine

: 28623-31-6
2-Diisopropylamino-1,3,2-dioxaphospholane

Conditions

Conditions	Yield
In dichloromethane Cooling with ice; Inert atmosphere;	94%
In dichloromethane at 20℃; for 16h; Amination;	93%
In diethyl ether at 0℃;

: 770-37-6
2-(N-benzylidenamino)ethanol

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: 2-(benzylideneamino)ethyl ethylene phosphite

Conditions

Conditions	Yield
With triethylamine In diethyl ether at 20℃;	94%

: 767-00-0
4-cyanophenol

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: 2-(4-cyanophenoxy)-1,3,2-dioxaphospholane

Conditions

Conditions	Yield
Stage #1: 4-cyanophenol In dichloromethane at 20℃; for 0.5h; Stage #2: 2-chloro-1,3,2-dioxaphospholan In dichloromethane at 0 - 20℃; for 12h;	94%

: 627-27-0
homoalylic alcohol

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: 2-(but-3-en-1-yloxy)-1,3,2-dioxaphospholane

Conditions

Conditions	Yield
Stage #1: homoalylic alcohol In dichloromethane at 20℃; for 0.5h; Stage #2: 2-chloro-1,3,2-dioxaphospholan In dichloromethane at 0 - 20℃; for 12h;	94%

: 7057-80-9
pentafluoroethyl alcohol

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: 2-(1,1,2,2,2-pentafluoroethoxy)-1,3,2-dioxaphospholane

Conditions

Conditions	Yield
Stage #1: pentafluoroethyl alcohol In dichloromethane at 20℃; for 0.5h; Stage #2: 2-chloro-1,3,2-dioxaphospholan In dichloromethane at 0 - 20℃; for 12h;	94%

: 920-66-1
1,1,1,3',3',3'-hexafluoro-propanol

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: 85762-88-5
2-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)-1,3,2-dioxaphospholane

Conditions

Conditions	Yield
Stage #1: 1,1,1,3',3',3'-hexafluoro-propanol In dichloromethane at 20℃; for 0.5h; Stage #2: 2-chloro-1,3,2-dioxaphospholan In dichloromethane at 0 - 20℃; for 12h;	94%

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: 135-19-3
β-naphthol

: 2-(2-naphthalenoxy)-1,3,2-dioxaphospholane

Conditions

Conditions	Yield
Stage #1: β-naphthol In dichloromethane at 20℃; for 0.5h; Stage #2: 2-chloro-1,3,2-dioxaphospholan In dichloromethane at 0 - 20℃; for 12h;	94%

: 2163-42-0
2-methyl-1.3-propanediol

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: C8H16O6P2

Conditions

Conditions	Yield
In dichloromethane at 0 - 20℃; for 12h;	94%

: 24892-49-7, 139687-48-2
2,4-dimethylpentane-2,4-diol

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: C11H22O6P2

Conditions

Conditions	Yield
In dichloromethane at 0 - 20℃; for 12h;	94%

: 57-55-6
propylene glycol

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: 92304-17-1
2,2'-(1-methyl-ethane-1,2-diyldioxy)-bis-[1,3,2]dioxaphospholane

Conditions

Conditions	Yield
In dichloromethane at 0 - 20℃; for 12h;	93%
With triethylamine

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: 504-63-2
trimethyleneglycol

: 92304-16-0
2,2'-propane-1,3-diyldioxy-bis-[1,3,2]dioxaphospholane

Conditions

Conditions	Yield
In dichloromethane at 0 - 20℃; for 12h;	93%
With triethylamine

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: 431-03-8
dimethylglyoxal

: 76266-23-4
2-(β-Chloroaethoxi)-2-oxo-4,5-dimethyl-1,3,2λ5-dioxaphospholen

Conditions

Conditions	Yield
Mechanism;	93%
In neat (no solvent) at 80℃;	93%

: 106-44-5
p-cresol

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: 857367-49-8
2-(4-methylphenoxy)-1,3,2-dioxaphospholane

Conditions

Conditions	Yield
Stage #1: p-cresol In dichloromethane at 20℃; for 0.5h; Stage #2: 2-chloro-1,3,2-dioxaphospholan In dichloromethane at 0 - 20℃; for 12h;	93%
With pyridine In chloroform-d1

: 367-12-4
2-fluorophenol

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: 2-(2-fluorophenoxy)-1,3,2-dioxaphospholane

Conditions

Conditions	Yield
Stage #1: 2-fluorophenol In dichloromethane at 20℃; for 0.5h; Stage #2: 2-chloro-1,3,2-dioxaphospholan In dichloromethane at 0 - 20℃; for 12h;	93%

: 371-41-5
4-Fluorophenol

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: 2-(4-fluorophenoxy)-1,3,2-dioxaphospholane

Conditions

Conditions	Yield
Stage #1: 4-Fluorophenol In dichloromethane at 20℃; for 0.5h; Stage #2: 2-chloro-1,3,2-dioxaphospholan In dichloromethane at 0 - 20℃; for 12h;	93%

: 372-20-3
3-fluorophenol

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: 2-(3-fluorophenoxy)-1,3,2-dioxaphospholane

Conditions

Conditions	Yield
Stage #1: 3-fluorophenol In dichloromethane at 20℃; for 0.5h; Stage #2: 2-chloro-1,3,2-dioxaphospholan In dichloromethane at 0 - 20℃; for 12h;	93%

: 444-30-4
2-(trifluoromethyl)phenol

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: 2-(2-trifluoromethylphenoxy)-1,3,2-dioxaphospholane

Conditions

Conditions	Yield
Stage #1: 2-(trifluoromethyl)phenol In dichloromethane at 20℃; for 0.5h; Stage #2: 2-chloro-1,3,2-dioxaphospholan In dichloromethane at 0 - 20℃; for 12h;	93%

2-Chloro-1,3,2-dioxaphospholane Chemical Properties

IUPAC Name: 2-Chloro-1,3,2-dioxaphospholane
Synonyms of 1,3,2-Dioxaphospholane,2-chloro- (CAS NO.822-39-9): 2-Chloro-1,3,2-dioxaphospholane ; Ethylene chlorophosphite ; Ethylene glycol chlorophosphite
CAS NO: 822-39-9
Molecular Formula: C₂H₄ClO₂P
Molecular Weight: 126.48
Molecular Structure:
EINECS: 212-499-4
H bond acceptors: 2
H bond donors: 0
Freely Rotating Bonds: 0
Polar Surface Area: 32.05 Å²
Flash Point: 24.8 °C
Enthalpy of Vaporization: 34.09 kJ/mol
Boiling Point: 117.4 °C at 760 mmHg
Vapour Pressure: 20.8 mmHg at 25°C
Storage temp: 2-8°C
Sensitive: Moisture Sensitive
Appearance: Clear Colourless Oil
SMILES: ClP1OCCO1
InChI: InChI=1/C2H4ClO2P/c3-6-4-1-2-5-6/h1-2H2
InChIKey: OLSFRDLMFAOSIA-UHFFFAOYAF
Std. InChI: InChI=1S/C2H4ClO2P/c3-6-4-1-2-5-6/h1-2H2
Std. InChIKey: OLSFRDLMFAOSIA-UHFFFAOYSA-N
Product Categories of 1,3,2-Dioxaphospholane,2-chloro- (CAS NO.822-39-9): Biochemistry;Nucleosides, Nucleotides & Related Reagents;Phosphorylating and Phosphorothioating Agents;Phosphorylation;Protecting Agents, Phosphorylating Agents & Condensing Agents;Synthetic Organic Chemistry;Phosphorylating and Phosphitylating Agents

2-Chloro-1,3,2-dioxaphospholane Uses

1,3,2-Dioxaphospholane,2-chloro- (CAS NO.822-39-9) is used as highly reactive cyclic phosphitylating reagent which provides fast coupling rates, and hydrolytic cleavage occurs more readily than with acyclic analogs.

2-Chloro-1,3,2-dioxaphospholane Safety Profile

Hazard Codes: Corrosive C
Risk Statements: 14-34-37
R14 : Reacts violently with water.
R34: Causes burns.
R37: Irritating to respiratory system
Safety Statements: 8-25-26-36/37/39-45
S8: Keep container dry.
S25: Avoid contact with eyes.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
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 the label whenever possible.)
RIDADR: UN 3264 8/PG 2
WGK Germany: 3
F: 1-10
HazardClass: 8
PackingGroup: II

2-Chloro-1,3,2-dioxaphospholane Specification

General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Water Reactive. Combustible liquid.
Extinguishing Media: Do NOT use water directly on fire. Use foam, dry chemical, or carbon dioxide.
Handling: Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage: Keep 1,3,2-Dioxaphospholane,2-chloro- (CAS NO.822-39-9) away from sources of ignition. Store in a cool, dry place. Store in a tightly closed container. Keep under a nitrogen blanket. Keep refrigerated. (Store below 4°C/39°F.)

Product Name

2-Chloro-1,3,2-dioxaphospholane

Synthetic route

2-Chloro-1,3,2-dioxaphospholane Chemical Properties

2-Chloro-1,3,2-dioxaphospholane Uses

2-Chloro-1,3,2-dioxaphospholane Safety Profile

2-Chloro-1,3,2-dioxaphospholane Specification

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