Chloromethyl pivalate

Product Name: Chloromethyl pivalate
CAS No.: 18997-19-8
Chemical Name: Chloromethyl pivalate
Synonyms: POM;POM-CL;PIVALOYLOXYMETHYL CHLORIDE;Chloromethyl 2,2-dimethylpropanoate;CMPV;hloromethyl pivalate;Adefovir Impurity 13;chloromethylepivalate;CHLOROMETHYL PIVALATE;CHLOROMETHYL PIVARATE
CBNumber: CB6171175
Molecular Formula: C6H11ClO2
Formula Weight: 150.6
MOL File: 18997-19-8.mol

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Chloromethyl pivalate Property

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.)
Flash point:: 104 °F
storage temp.: Inert atmosphere,2-8°C
solubility: Chloroform (Slightly), Ethyl Acetate (Sparingly)
form: Liquid
Specific Gravity: 1.038
color: Clear colorless to slightly yellow
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: Propanoic acid, 2,2-dimethyl-, chloromethyl ester (18997-19-8)

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Safety

Hazard Codes: Xn,Xi
Risk Statements: 10-20/21/22-36/37/38
Safety Statements: 16-26-36-41-36/37/39
RIDADR: UN 3272 3/PG 3
WGK Germany: 3
TSCA: Yes
HazardClass: 3
PackingGroup: III
HS Code: 29159000

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H226Flammable liquid and vapour

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 141186
Product name: Chloromethyl pivalate
Purity: 97%
Packaging: 25g
Price: $57.1
Updated: 2025/07/31

Sigma-Aldrich

Product number: 141186
Product name: Chloromethyl pivalate
Purity: 97%
Packaging: 100g
Price: $90.1
Updated: 2025/07/31

TCI Chemical

Product number: P1012
Product name: Chloromethyl Pivalate [Amino-Protecting Agent]
Purity: >99.0%(GC)
Packaging: 25g
Price: $26
Updated: 2025/07/31

TCI Chemical

Product number: P1012
Product name: Chloromethyl Pivalate [Amino-Protecting Agent]
Purity: >99.0%(GC)
Packaging: 100g
Price: $66
Updated: 2025/07/31

TCI Chemical

Product number: P1012
Product name: Chloromethyl Pivalate [Amino-Protecting Agent]
Purity: >99.0%(GC)
Packaging: 500g
Price: $205
Updated: 2025/07/31

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Chloromethyl pivalate Chemical Properties,Usage,Production

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).

References

[1] Synthetic Communications, 1995, vol. 25, # 18, p. 2739 - 2749
[2] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 13, p. 3997 - 4011
[3] Patent: WO2013/133726, 2013, A1. Location in patent: Page/Page column 76
[4] Tetrahedron Letters, 1989, vol. 30, # 51, p. 7141 - 7144
[5] Journal of Pharmaceutical Sciences, 1994, vol. 83, # 9, p. 1269 - 1273

Chloromethyl pivalate Preparation Products And Raw materials

Raw materials

Zinc chloride Paraformaldehyde Pivaloyl chloride

Preparation Products

PIVALOYLOXYMETHYL 6-AMINOPENICILANATE Pivaloyloxymethyl6-(phenylacetamido)penicillanate

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Chloromethyl pivalate Suppliers

Americas 1 Belgium 3 Canada 1 China 319 Europe 3 France 2 Germany 6 India 9 Japan 3 Slovakia 1 South Korea 3 Switzerland 4 United Kingdom 9 United States 33 Global 397

Shanghai TongYuan Chemical Co., Ltd.

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View Lastest Price from Chloromethyl pivalate manufacturers

Hebei Chuanghai Biotechnology Co., Ltd

Product: Chloromethyl pivalate 18997-19-8
Price: US $10.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 10 mt
Release date: 2024-12-04

Handan Huajun chemicals Co.,Ltd

Product: Chloromethyl pivalate 18997-19-8
Price: US $13.00/kg
Min. Order: 1kg
Purity: 99.0%
Supply Ability: 500MT
Release date: 2024-01-18

Hebei Chuanghai Biotechnology Co., Ltd

Product: Chloromethyl pivalate 18997-19-8
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 500000kg
Release date: 2024-11-01

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