Chloromethyl pivalate

HCID 87885
NotesReactions
Substructure searchFind similar structures

Basic information

CAS
18997-19-8
Standard SMILES
CC(C)(C)C(=O)OCCl
InChIKey
GGRHYQCXXYLUTL-UHFFFAOYSA-N
Molecular formula
C6H11ClO2
Average molar mass
150.6 g/mol
Monoisotopic mass
150.04475727

Names & identifiers

Preferred name
Chloromethyl pivalate
IUPAC
chloromethyl 2,2-dimethylpropanoate
English name
Chloromethyl pivalate
Molecular formula
C6H11ClO2
Molecular weight
150.6

Names & synonyms

Chloromethyl pivalate18997-19-8chloromethyl 2,2-dimethylpropanoatePivaloyloxymethyl chloridePropanoic acid, 2,2-dimethyl-, chloromethyl esterChloromethyl Trimethylacetate2,2-Dimethylpropionic Acid Chloromethyl EsterZQU16YZ6MFchloromethyl 2,2-dimethylpropionateEINECS 242-735-1DTXSID1066445GGRHYQCXXYLUTL-UHFFFAOYSA-
Show more names
POM-CLCMPVAdefovir Impurity 13hloromethyl pivalatechloromethylepivalateCHLOROMETHYL PIVARATEPivaloxymethylchlorde
((TERT-BUTYLCARBONYL)OXY)METHYL CHLORIDE(2,2-DIMETHYL-1-OXOPROPOXY)METHYL CHLORIDE.ALPHA.,.ALPHA.-DIMETHYLPROPIONYLOXYMETHYL CHLORIDERefChem:575896DTXCID6035992Propanoic acid, 2,2dimethyl, chloromethyl esterALPHA,ALPHA-DIMETHYLPROPIONYLOXYMETHYL CHLORIDE242-735-1

Database identifiers

CAS
18997-19-8
PubChem CID
87885
DTXSID
DTXSID1066445
UNII
ZQU16YZ6MF
EC Number
242-735-1
Nikkaji
J26.281A

Properties

Computed structural properties

XLogP
2.2
Topological polar surface area
26.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
3
Heavy atoms
9

Experimental & physicochemical properties

Chemical ClassesToxic Gases & Vapors -> Other Toxic Gases & Vapors
Physical DescriptionColorless to very faintly yellow clear liquid; [Acros Organics MSDS]

Physicochemical properties

Melting point
-40 °C · <-40°C
Boiling point
146 · 146-148 °C (lit.)
Density
1.045 g/mL · 1.045 g/mL at 25 °C (lit.)
refractive index
20 · n20/D 1.417(lit.)
Flash point
104 °F · 104 °F
storage temp.
2 · Inert atmosphere,2-8°C

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P363, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 52 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 3 items

Chemical: Propanoic acid, 2,2-dimethyl-, chloromethyl ester

Status: Active Update: 22-02-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/23716

Propanoic acid, 2,2-dimethyl-, chloromethyl ester: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Hazards SummaryAn irritant and lachrymator; May cause CNS depression; [Acros Organics MSDS] See Diphosgene and Chloromethyl methyl ether.
Hazard Classes and CategoriesFlam. Liq. 3 (100%)

Toxicology

Adverse EffectsLacrimator (Lachrymator) - A substance that irritates the eyes and induces the flow of tears.

Safety data

PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
ridadr
UN 3272 3/PG 3
hs_code
29159000
risk_code
10-20/21/22-36/37/38

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationPropanoic acid, 2,2-dimethyl-, chloromethyl ester: ACTIVE
Applications · 3 items

DescriptionChloromethyl pivalate (CP) is an electrolyte solvent used in novel lithium-oxygen (Li-O2) batteries. As the structure of CP does not contain any α-H atoms, CP-based electrolytes exhibit excellent chemical stability in both superoxide radical solutions and the actual Li-O2 battery environment, effectively resisting the corrosive effects of superoxide radicals. Furthermore, even without the use of a catalyst in the cathode of the Li-O2 battery, the battery demonstrates high specific capacity and good cycling stability[6].

UsesChloromethyl pivalate was used in the synthesis of pivaloyloxy methyl ester of ofloxacin as prodrug. It was used as the reagent during the synthesis of an isoindoline-annulated, tricyclic sultam library via microwave-assisted, continuous-flow organic synthesis.

General DescriptionChloromethyl pivalate reacts with sodium salt of sulbactam to yield sulbactam pivoxil. It undergoes acylation reaction with 9-(2-phosphonylmethoxyethyl)adenine (PMEA) to yield bis(pivaloyloxymethyl) PMEA.

Upstream & downstream products

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
河北立业化学制品有限公司0310-6697998 13930001710 · [email protected]

Related reactions

364 records
New reaction record

Compound notes

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