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541508

Sigma-Aldrich

2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide

95%

Synonym(s):

2,2-Dimethyltrimethylene phosphorochloridate, 2-Chloro-2-oxo-5,5-dimethyl-1,3,2-dioxaphosphorinane, 2-Chloro-5,5-dimethyl-1,3,2λ5-dioxaphosphinan-2-one, 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphinane 2-oxide, 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinan-2-one, 2-Chloro-5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinane, 2-Chloro-5,5-dimethyl-2-oxodioxaphosphorinane, 5,5-Dimethyl-2-chloro-2-oxo-1,3,2-dioxaphosphorinane

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About This Item

Empirical Formula (Hill Notation):
C5H10ClO3P
CAS Number:
4090-55-5
Molecular Weight:
184.56
EC Number:
223-831-2
MDL number:
MFCD03425416
UNSPSC Code:
12352100
PubChem Substance ID:
24878541
NACRES:
NA.22

Assay

95%

mp

97-102 °C (lit.)

SMILES string

CC1(C)COP(Cl)(=O)OC1

InChI

1S/C5H10ClO3P/c1-5(2)3-8-10(6,7)9-4-5/h3-4H2,1-2H3

InChI key

VZMUCIBBVMLEKC-UHFFFAOYSA-N

General description

2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide is also referred to as 5,5-dimethyl-2-oxo-2-chloro-1,3,2-dioxaphosphinane (DMOCP). It can be prepared by reacting phosphorous oxychloride (in dry toluene) with 2,2-dimethyl-1,3-propane diol and triethyl amine.

Application

2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide may be used in the synthesis of 5,5-dimethyl-2-oxido-[1,3,2]-dioxaphosphorinane-2-yl-amino carboxylates and cyclic diguanosine monophosphate (c-di-GMP).

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis and antimicrobial activity of 5, 5'-dimethyl-2-oxido-[1, 3, 2]-dioxaphos-phorinane-2-yl-amino carboxylates.
Babu BH, et al.
Chemistry (Weinheim An Der Bergstrasse, Germany), 19(3), 256-260 (2008)
Jiří Fukal et al.
Physical chemistry chemical physics : PCCP, 19(47), 31830-31841 (2017-11-25)
A benchmark for structural interpretation of the
Barbara L Gaffney et al.
Current protocols in nucleic acid chemistry, Chapter 14, Unit 14-Unit 14 (2012-03-08)
The bacterial signaling molecule, cyclic diguanosine monophosphate (c-di-GMP), plays a key role in controlling biofilm formation and pathogenic virulence, among many other functions. It has widespread consequences for human health, and current research is actively exploring its molecular mechanisms. The

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