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ChemicalBook--->CAS DataBase List--->18997-19-8

18997-19-8

18997-19-8 Structure

18997-19-8 Structure
IdentificationMore
[Name]

Chloromethyl pivalate
[CAS]

18997-19-8
[Synonyms]

2,2-DIMETHYLPROPIONIC ACID CHLOROMETHYL ESTER
CHLOROMETHYL 2,2-DIMETHYLPROPIONATE
CHLOROMETHYL PIVALATE
CHLOROMETHYL PIVARATE
CHLOROMETHYL TRIMETHYLACETATE
CMPV
PIVALIC ACID CHLOROMETHYL ESTER
PIVALOYLOXYMETHYL CHLORIDE
POM
POM-CL
TRIMETHYLACETIC ACID CHLOROMETHYL ESTER
2,2-dimethyl-propanoicacichloromethylester
Pivaloxymethylchlorde
Chloromethyl pivalate, 99+%
Propanoic acid, 2,2-dimethyl-, chloromethyl ester
CHLORO METHYL PIVILATE
2,2-Dimethylpropanoic acid chloromethyl ester
Chloromethyl Pivalate [Amino-Protecting Agent]
Pivaloyloxymethyl chloride, POM-Cl
(2,2-Dimethyl-1-oxopropoxy)methyl chloride
[EINECS(EC#)]

242-735-1
[Molecular Formula]

C6H11ClO2
[MDL Number]

MFCD00000884
[Molecular Weight]

150.6
[MOL File]

18997-19-8.mol
Chemical PropertiesBack Directory
[Appearance]

Clear colorless to slightly yellow liquid
[Melting point ]

<-40°C
[Boiling point ]

146-148 °C (lit.)
[density ]

1.045 g/mL at 25 °C(lit.)
[refractive index ]

n20/D 1.417(lit.)
[Fp ]

104 °F
[storage temp. ]

Flammables area
[solubility ]

Chloroform (Slightly), Ethyl Acetate (Sparingly)
[form ]

Liquid
[color ]

Clear colorless to slightly yellow
[Specific Gravity]

1.038
[Water Solubility ]

Miscible with most organic solvents. Immiscible with water.
[BRN ]

1560838
[InChIKey]

GGRHYQCXXYLUTL-UHFFFAOYSA-N
[CAS DataBase Reference]

18997-19-8(CAS DataBase Reference)
[NIST Chemistry Reference]

Propanoic acid, 2,2-dimethyl-, chloromethyl ester(18997-19-8)
[EPA Substance Registry System]

18997-19-8(EPA Substance)
Safety DataBack Directory
[Hazard Codes ]

Xn,Xi
[Risk Statements ]

R10:Flammable.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S16:Keep away from sources of ignition-No smoking .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S41:In case of fire and/or explosion do not breathe fumes .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
[RIDADR ]

UN 3272 3/PG 3
[WGK Germany ]

3
[TSCA ]

Yes
[HazardClass ]

3
[PackingGroup ]

III
[HS Code ]

29159000
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Zinc chloride-->Paraformaldehyde-->Pivaloyl chloride
[Preparation Products]

PIVALOYLOXYMETHYL 6-AMINOPENICILANATE-->Pivaloyloxymethyl6-(phenylacetamido)penicillanate-->(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate-->Adefovir dipivoxil N6-Hydroxymethyl Impurity-->Adefovir dipivoxil-->1-(PIVALOYLOXYMETHYL)-1H-INDOLE-3-CARBOXYLIC ACID-->Azidomethyl pivalate-->2,2-Dimethylpropanoic acid [[[[1-[(2-amino-9H-purin-9-yl)methyl]cyclopropyl]oxy]methyl]phosphinylidene]bis(oxymethylene) ester-->7-Hydroxy-6-methoxy-3-[(pivaloyloxy)methyl]-3,4-dihydroquinazolin-4-one
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

2,2-Dimethylpropanoic acid chloromethyl ester(18997-19-8).msds
Hazard InformationBack Directory
[Chemical Properties]

Clear colorless to slightly yellow liquid
[Uses]

Chloromethyl 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.
[Application]

Chloromethyl pivalate is a pharmaceutical intermediate compound used in the synthesis of active pharmaceutical ingredients. It is also involved in the acylation reaction with 9-(2-phosphonomethoxyethyl)adenine. It is used as a protecting agent for the N-protection of amines. It is also used in the preparation of thivaloyloxymethyl ester of ofloxacin as a prodrug. It is also used in the preparation of sulbactam pivoxil by reaction with the sodium salt of sulbactam. Besides, it is used as a reagent in the synthesis of isoindoline cyclic and continuous flow organic synthesis.
[General Description]

Chloromethyl 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.
[Synthesis]

Chloromethyl pivalate is prepared by the reaction of formaldehyd and pivaloyl chloride. The specific synthesis steps are as follows:
A mixture of pivaloyl chloride (8.56 g, 71 mmol), paraformaldehyde (2.13 g, 71 mmol) and zinc chloride (75 mg, 0.55 mmol) was stirred at 80 °C for 2 h. Purification by vacuum distillation afforded chloromethyl pivalate (41) as a colourless oil (6.29 g, 44.7 mmol, 59%). bp 80 °C/15 mmHg [lit.1 bp 80-81 °C/15 mmHg]; 1H NMR (400 MHz, CDCl3) δ 1.24 (9H, s, tBu), 5.72 (2H, s, CH2).
Chloromethyl pivalate synthesis
Spectrum DetailBack Directory
[Spectrum Detail]

Chloromethyl pivalate(18997-19-8)MS
Chloromethyl pivalate(18997-19-8)1HNMR
Chloromethyl pivalate(18997-19-8)13CNMR
Chloromethyl pivalate(18997-19-8)IR1
Chloromethyl pivalate(18997-19-8)Raman
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

Chloromethyl pivalate, 99+%(18997-19-8)
[Alfa Aesar]

Chloromethyl pivalate, 97%(18997-19-8)
[Sigma Aldrich]

18997-19-8(sigmaaldrich)
[TCI AMERICA]

Chloromethyl Pivalate  [Amino-Protecting Agent],>99.0%(GC)(18997-19-8)
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