tert-Butyl chloroacetate Property

Boiling point:

48-49 °C/11 mmHg (lit.)

Density 

1.053 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.423(lit.)

Flash point:

116 °F

storage temp. 

Flammables area

form 

Liquid

Specific Gravity

1.053

color 

Clear colorless to yellow

Water Solubility 

<0.1 g/L (20 ºC)

Merck 

14,1563

BRN 

1753006

LogP

2.07

CAS DataBase Reference

107-59-5(CAS DataBase Reference)

NIST Chemistry Reference

Acetic acid, chloro-, 1,1-dimethylethyl ester(107-59-5)

EPA Substance Registry System

Acetic acid, chloro-, 1,1-dimethylethyl ester (107-59-5)

Safety

Hazard Codes 

C,N,Xn,Xi,F

Risk Statements 

20/21/22-34-50/53-36/37/38-10

Safety Statements 

26-36/37/39-45-61-60-16-7/9

RIDADR 

UN 2920 8/PG 2

WGK Germany 

3

RTECS 

AF8985500

F 

19-21

TSCA 

Yes

HazardClass 

3

PackingGroup 

III

HS Code 

29154000

Toxicity

rat,LC50,inhalation,4738mg/m3/4H (4738mg/m3),SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTIONLUNGS, THORAX, OR RESPIRATION: DYSPNEABEHAVIORAL: TREMOR,International Journal of Toxicology. Vol. 19, Pg. 333, 2000.

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H226Flammable liquid and vapour

H302Harmful if swallowed

H312Harmful in contact with skin

H314Causes severe skin burns and eye damage

H315Causes skin irritation

H319Causes serious eye irritation

H331Toxic if inhaled

H335May cause respiratory irritation

H400Very toxic to aquatic life

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

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

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P273Avoid release to the environment.

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

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

P309IF exposed or if you feel unwell:

P310Immediately call a POISON CENTER or doctor/physician.

P370+P378In case of fire: Use … for extinction.

P403+P235Store in a well-ventilated place. Keep cool.

P501Dispose of contents/container to..…

tert-Butyl chloroacetate Chemical Properties,Usage,Production

Chemical Properties

clear colorless to yellow liquid. Hydrolysis generates tert-butanol and chloroacetic acid.

Uses

tert-Butyl chloroacetate is used in the synthesis of imidazol-1-yl-acetic acid hydrochloride, cis-disubstituted aziridine ester via aza-Darzens reaction and 1,10-diaza-18-crown-6 based sensors bearing a coumarin fluorophore.

Uses

In the glycidic ester condensation.

Preparation

tert-Butyl chloroacetate synthesis: The tert-butanol was added to the mixture of chloroacetyl chloride and N,N-dimethylaniline, and the temperature was kept below 30°C. The reactant was poured into water, washed and dried, and then fractionated under reduced pressure. The fractions at 48-49°C (1.46kPa) were collected to obtain tert-butyl chloroacetate with a yield of 63%.

Safety Profile

A poison by ingestion. Moderately toxic by inhalation skin contact. S severe sluin and moderate eye irritant. When heated to decomposition it emits toxic vapors of Cl-.

Purification Methods

Check the NMR spectrum; if satisfactory then distil in a vacuum; if not then dissolve in Et2O, wash with H2O, 10% H2SO4 until the acid extract does not become cloudy when made alkaline with NaOH. Wash the organic layer again with H2O, then saturated aqueous NaHCO3, dry over Na2SO4, evaporate and fractionate it through a carborundum-packed column or a 6-inch Widmer column (p 11, see tert-butyl ethyl malonate for precautions to avoid decomposition during disillation). [Johnson et al. J Am Chem Soc 75 4995 1953, Baker Org Synth Coll Vol III 144 1944, Beilstein 2 III 444.]