107-59-5

Basic information

• Product Name: tert-Butyl chloroacetate
• Synonyms: Acetic acid, chloro-, tert-butyl ester;aceticacid,chloro-,1,1-dimethylethylester;ClCH2C(O)OC(CH3)3;CHLOROACETIC ACID T-BUTYL ESTER;CHLOROACETIC ACID TERT-BUTYL ESTER;reft-Butyl chloroacetate;T-BUTYL CHLOROACETATE;TERT-BUTYL CHLORACETATE
• CAS NO: 107-59-5
• Molecular Formula: C₆H₁₁ClO₂
• Molecular Weight: 150.6
• EINECS: 203-506-1
• Product Categories: API intermediates;C6 to C7;Carbonyl Compounds;Esters;API Intermediate;Pharmaceutical intermediates
• Mol File: 107-59-5.mol

Chemical Properties

• Boiling Point: 48-49 °C11 mm Hg(lit.)
• Flash Point: 116 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.053 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.75mmHg at 25°C
• Refractive Index: n20/D 1.423(lit.)
• Storage Temp.: Flammables area
• Water Solubility: <0.1 g/L (20℃)
• Merck: 14,1563
• BRN: 1753006
• CAS DataBase Reference: tert-Butyl chloroacetate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyl chloroacetate(107-59-5)
• EPA Substance Registry System: tert-Butyl chloroacetate(107-59-5)

Safety Data

• Hazard Codes: C,N,Xn,Xi,F
• 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
• Hazardous Substances Data: 107-59-5(Hazardous Substances Data)

Usage

Uses

1. Used in the Glycidic Ester Condensation:
Tert-Butyl chloroacetate is used as a reagent in the glycidic ester condensation process, which is a chemical reaction involving the formation of an ester from an epoxide (glycidic ester) and an alcohol or phenol. This process is essential in the synthesis of various organic compounds and polymers.
2. Used in the Synthesis of Imidazol-1-yl-Acetic Acid Hydrochloride:
Tert-Butyl chloroacetate serves as a key intermediate in the synthesis of imidazol-1-yl-acetic acid hydrochloride, a compound with potential applications in the pharmaceutical industry. This synthesis involves the reaction of tert-butyl chloroacetate with imidazole, followed by hydrolysis and deprotection to obtain the desired product.
3. Used in the Synthesis of cis-Disubstituted Aziridine Ester via Aza-Darzens Reaction:
Tert-Butyl chloroacetate is utilized in the aza-Darzens reaction, a type of organic reaction that involves the formation of aziridines from imines and α-haloesters. In this case, the reaction with an appropriate imine leads to the formation of cis-disubstituted aziridines, which are valuable synthetic intermediates and have potential applications in the synthesis of various biologically active compounds.
4. Used in the Synthesis of 1,10-Diaza-18-Crown-6 Based Sensors Bearing a Coumarin Fluorophore:
Tert-Butyl chloroacetate is employed in the synthesis of 1,10-diaza-18-crown-6 based sensors that incorporate a coumarin fluorophore. These sensors are designed for the selective detection of metal ions, which is crucial in various analytical and environmental applications.

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.]

InChI:InChI=1/C6H11ClO2/c1-6(2,3)9-5(8)4-7/h4H2,1-3H3

Synthetic route

chloroacetic acid (79-11-8) + tert-butyl alcohol (75-65-0) → tert-Butyl chloroacetate (107-59-5)

Conditions	Yield
With dmap; bis-2-propyl carbonate; scandium tris(trifluoromethanesulfonate) In dichloromethane at -8 - 20℃; for 2h;	95%
With cerium(IV) trifluoromethanesulfonate In tetrachloromethane at 25℃; for 8h; Esterification;	90%
With Fe3O4/AlFe/Te nanocomposite In neat (no solvent) for 1h; Reflux;

chloroacetyl chloride (79-04-9) + tert-butyl alcohol (75-65-0) → tert-Butyl chloroacetate (107-59-5)

Conditions	Yield
With triethylamine In dichloromethane at 5 - 10℃; for 2h;	92.4%
With aluminum oxide In benzene for 15h; Ambient temperature;	75%
With 2,3-Dimethylaniline	52%

chloroacetic acid (79-11-8) + isobutene (115-11-7) → tert-Butyl chloroacetate (107-59-5)

Conditions	Yield
With sulfuric acid

acetic acid tert-butyl ester (540-88-5) + chloroacetic acid (79-11-8) → tert-Butyl chloroacetate (107-59-5)

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃; for 4h;

2-hydroxycarbazole (86-79-3) + tert-Butyl chloroacetate (107-59-5) → tert-butyl 2-(9H-carbazol-2-yloxy)acetate (210410-32-5)

Conditions	Yield
With potassium carbonate In acetone at 60 - 70℃; for 16h;	100%
Stage #1: 2-hydroxycarbazole With potassium carbonate In acetone at 20℃; for 0.5h; Stage #2: tert-Butyl chloroacetate In acetone at 60 - 70℃; for 12h;	99%

4-Fluorothiophenol (371-42-6) + tert-Butyl chloroacetate (107-59-5) → 2-(4-fluoro-benzenesulfanyl)-acetic acid tert-butyl ester (212770-40-6)

Conditions	Yield
With dmap; potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃;	100%

tert-Butyl chloroacetate (107-59-5) + 2-methoxy-3-methyl-5-nitropyridine (89694-10-0) → tert-butyl 2-(6-methoxy-5-methyl-3-nitropyridin-2-yl)acetate (1188407-19-3)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at -20 - 20℃; for 1h;	100%
With potassium tert-butylate In tetrahydrofuran at -20 - -10℃;	72%
With potassium tert-butylate In tetrahydrofuran Inert atmosphere;	72%
With potassium tert-butylate In tetrahydrofuran at -18 - 25℃; Large scale reaction;

tert-Butyl chloroacetate (107-59-5) + N-Benzylethanolamine (104-63-2) → tert-butyl 2-(benzyl-(2-hydroxyethyl)amino)-acetate (168263-75-0)

Conditions	Yield
With potassium carbonate; sodium iodide In acetonitrile Inert atmosphere; Reflux;	100%

tert-Butyl chloroacetate (107-59-5) + dibenzyl 4-(3-(tert-butoxy)-3-oxopropyl)-1,4,7,10-tetraazacyclododecane-1,7-dicarboxylate → dibenzyl 4-(2-(tert-butoxy)-2-oxoethyl)-10-(3-(tert-butoxy)-3-oxopropyl)-1,4,7,10-tetraazacyclo-dodecane-1,7-dicarboxylate

Conditions	Yield
With potassium carbonate In acetonitrile at 60℃; for 48h;	100%

7-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline (22246-17-9) + tert-Butyl chloroacetate (107-59-5) → tert-butyl 2-(7′-methoxy-3′,4′-dihydro-1H-quinolin-2′-one-1′-yl)acetate

Conditions	Yield
Stage #1: 7-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.25h; Inert atmosphere; Stage #2: tert-Butyl chloroacetate In N,N-dimethyl-formamide; mineral oil for 1.5h; Inert atmosphere;	100%

triisopropyl phosphite (116-17-6) + tert-Butyl chloroacetate (107-59-5) → tert-butyl 2-(diisopropoxyphosphoryl)acetate (103717-28-8)

Conditions	Yield
In dichloromethane for 3h; Heating;	100%

1-methyl-1H-imidazole (616-47-7) + tert-Butyl chloroacetate (107-59-5) → 2-chloro-1-(1-methyl-1H-imidazol-2-yl)ethan-1-one (860772-72-1)

Conditions	Yield
Stage #1: 1-methyl-1H-imidazole With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; Stage #2: tert-Butyl chloroacetate In tetrahydrofuran; hexane at -78℃; for 2.5h;	99%
Stage #1: 1-methyl-1H-imidazole With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 0.666667h; Inert atmosphere; Stage #2: tert-Butyl chloroacetate In tetrahydrofuran; hexane at -78℃; for 2.5h; Inert atmosphere;	80%
Stage #1: 1-methyl-1H-imidazole With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 0.666667h; Inert atmosphere; Stage #2: tert-Butyl chloroacetate In tetrahydrofuran; hexane at -78℃; for 3.16h; Inert atmosphere;	63%

tert-Butyl chloroacetate (107-59-5) → 2-(3-tert-butoxycarbonylmethyloxy-phenyl)-5-(3-tert-butoxycarbonylmethyloxy-phenyl)-1-dehydroabietyl-benzimidazole (727400-72-8)

Conditions	Yield
Stage #1: With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 1h; Stage #2: tert-Butyl chloroacetate at 20℃; for 52h;	99%

tert-Butyl chloroacetate (107-59-5) + salicylaldehyde (90-02-8) → 2-formylphenoxyacetic acid tert-butyl ester (286437-63-6)

Conditions	Yield
With potassium carbonate In N-methyl-acetamide; n-heptane	98.5%

tert-Butyl chloroacetate (107-59-5) + 3(R)-benzyloxycarbonylamino-7-trifluoromethyl-2,3-dihydro-1,5(5H)-benzothiazepine-4-one (98413-36-6) → tert-butyl (R)-3-benzyloxycarbonylamino-4-oxo-7-trifluoromethyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide Ambient temperature;	98%

tert-Butyl chloroacetate (107-59-5) + triphenylphosphine (603-35-0) → (tert-Butoxycarbonylmethylene)triphenylphosphorane (86302-43-4)

Conditions	Yield
In benzene for 48h; Heating;	98%
Stage #1: tert-Butyl chloroacetate; triphenylphosphine In toluene at 80℃; for 48h; Stage #2: With sodium hydroxide In water at 0℃; for 0.25h;	82%
In acetonitrile for 7h; Reflux;	66%
With sodium hydroxide 1.) benzene, reflux, 48 h, 2.) water, 5 deg C, 6 min; Yield given. Multistep reaction;

tert-Butyl chloroacetate (107-59-5) + (2S,3'S)-2-(2'-oxo-2',3',4',5'-tetrahydro-1H-benzo[b]azepin-3'-ylamino)-4-phenylbutyric acid ethyl ester (367909-45-3) → (2S,3'S)-2-(1-tert-butoxycarbonylmethyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylamino)-4-phenylbutyric acid ethyl ester (109010-61-9)

Conditions	Yield
Stage #1: (2S,3'S)-2-(2'-oxo-2',3',4',5'-tetrahydro-1H-benzo[b]azepin-3'-ylamino)-4-phenylbutyric acid ethyl ester With potassium hydroxide; tetrabutylammomium bromide In tetrahydrofuran at 0℃; for 0.5h; Stage #2: tert-Butyl chloroacetate In tetrahydrofuran at 20℃; for 5h;	98%

tert-Butyl chloroacetate (107-59-5) + 6-(hexyloxy)-2H-spiro[1-benzofuran-3,4'-piperidine] hydrochloride (1355087-72-7) → tert-butyl 2-(6-(hexyloxy)-2H-spiro[1-benzofuran-3,4'-piperidin]-1'-yl)acetate (1355087-75-0)

Conditions	Yield
With potassium carbonate In acetonitrile at 55℃;	98%

tert-Butyl chloroacetate (107-59-5) + 4-[bis(ethoxyphenyl)amino]phenol (1421611-75-7) → C28H33NO5 (1421611-81-5)

Conditions	Yield
With caesium carbonate In 1,2-dimethoxyethane at 70℃; for 2h;	98%

potassium (3-acetylphenyl)trifluoroborate + tert-Butyl chloroacetate (107-59-5) → tert-butyl 2-(3-acetylphenyl)acetate (1429507-77-6)

Conditions	Yield
With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); caesium carbonate In tetrahydrofuran; water at 100℃; for 18h; Suzuki-Miyaura Coupling; Inert atmosphere; Sealed tube;	98%

tert-Butyl chloroacetate (107-59-5) + 3-nitro-2-dibenzofurancarboxaldehyde (1246204-39-6) → tert-butyl 3-hydroxy-3-(3-nitrodibenzofuran-2-yl)propanoate

Conditions	Yield
Stage #1: tert-Butyl chloroacetate With zinc In diethyl ether at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: 3-nitro-2-dibenzofurancarboxaldehyde In tetrahydrofuran; diethyl ether at 0℃; for 1h; Reformatsky Reaction; Inert atmosphere;	98%

tert-Butyl chloroacetate (107-59-5) + C21H26N2O2 → C23H28N2O4

Conditions	Yield
Stage #1: C21H26N2O2 With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.333333h; Stage #2: tert-Butyl chloroacetate In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h;	98%

tert-Butyl chloroacetate (107-59-5) + 2-monochlorophenol (95-57-8) → tert-butyl 2-(2-chlorophenoxy)acetate (36304-23-1)

Conditions	Yield
Stage #1: 2-monochlorophenol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: tert-Butyl chloroacetate In N,N-dimethyl-formamide at 80℃; for 2h;	97%
Stage #1: 2-monochlorophenol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: tert-Butyl chloroacetate In N,N-dimethyl-formamide at 80℃; for 1h;
With potassium carbonate In acetone Heating;

tert-Butyl chloroacetate (107-59-5) + potassium ethyl xanthogenate (140-89-6) → O-ethyl S-(tert-butoxycarbonyl)methyl dithiocarbonate (27240-57-9)

Conditions	Yield
In acetone for 18h;	97%
In acetone	97%
In acetone
In acetone at 20℃; for 18h;

tert-Butyl chloroacetate (107-59-5) + benzaldehyde (100-52-7) → tert-butyl 3-phenyloxirane-2-carboxylate (27593-40-4)

Conditions	Yield
With potassium fluoride on basic alumina at 20℃; Darzens condensation;	97%

tert-Butyl chloroacetate (107-59-5) + 3-(2-Chlorophenyl)-6-ethoxycarbonyl-5,7-dimethyl-2,4-(1H,3H)-quinazolinedione (81087-59-4) → 1-tert-Butoxycarbonylmethyl-3-(2-chloro-phenyl)-5,7-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-quinazoline-6-carboxylic acid ethyl ester (81087-77-6)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 80℃; for 1h;	96%

tert-Butyl chloroacetate (107-59-5) + 3(S)-benzyloxycarbonylamino-2,3,4,5-tetrahydro-1,5-benzoxazepine-4-one (99197-92-9) → tert-butyl (S)-3-benzyloxycarbonylamino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate (99197-93-0)

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide Ambient temperature;	96%

tert-Butyl chloroacetate (107-59-5) + 1,5,8,12-tetraazabicyclo[10.2.2]hexadecane-13,14-dione (158498-42-1) → 5,8-Bis(tert-butoxycarbonylmethyl)-1,5,8,12-tetraazabicyclo[10.2.2]hexadecane-13,14-dione (260410-38-6)

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 100℃; Alkylation;	96%

tert-Butyl chloroacetate (107-59-5) + para-nitrophenyl bromide (586-78-7) → tert-butyl 2-(5-bromo-2-nitrophenyl)ethanoate (878672-60-7)

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;	96%
With potassium tert-butylate In N,N-dimethyl-formamide at -20℃; for 0.666667h;	88%
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;	81%
With potassium tert-butylate In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; for 3h;	72%
With potassium tert-butylate In N,N-dimethyl-formamide at 0℃; for 3h;	55%

tert-Butyl chloroacetate (107-59-5) + [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid (53-86-1) → acemetacin tert-butyl ester (75302-98-6)

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; sodium carbonate In toluene at 75℃; for 45h; Large scale;	95.7%

tert-Butyl chloroacetate (107-59-5) + 2-nitronaphthalene (581-89-5) → (2-Nitro-naphthalen-1-yl)-acetic acid tert-butyl ester (120542-07-6)

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at -5℃; for 0.05h;	95%

Bis-(2-methoxyethyl)amine (111-95-5) + tert-Butyl chloroacetate (107-59-5) → N,N'-bis(2-methoxyethyl)-glycine-tert-butyl ester (215101-76-1)

Conditions	Yield
for 72h;	95%
at 20℃; for 72h; Neat (no solvent);	95%

4-nitro-phenol (100-02-7) + tert-Butyl chloroacetate (107-59-5) → (4-nitrophenoxy)acetic acid tert-butyl ester (20768-14-3)

Conditions	Yield
Stage #1: 4-nitro-phenol With potassium carbonate In acetone at 20℃; for 0.5h; Stage #2: tert-Butyl chloroacetate In acetone at 60 - 70℃; for 16h; Further stages.;	95%

Upstream product

• 540-88-5 acetic acid tert-butyl ester 
• 79-11-8 chloroacetic acid 
• 75-65-0 tert-butyl alcohol 
• 115-11-7 isobutene 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 36304-21-9 t-Butyl-(p-tolyloxy)-acetat 
• 36304-24-2 p-methoxyphenoxyacetic acid t-butyl ester 
• 92828-50-7 rac-(tert-butyl) 4-benzyl-4,5-dihydro-5-oxo-2-phenyloxazole-4-acetate 
• 38559-81-8 2-(4-butoxyphenoxy)acetic acid 
• 3406-76-6 (4-bromophenylthio)acetic acid 
• 138563-69-6 tert-butyl 2-(3-nitrophenoxy)acetate 
• 21320-60-5 t-butyl 4-nitro-2-chlorophenoxyacetate 
• 264132-38-9 (1R,2S)-[2-(p-methoxybenzyloxymethoxy)-1-ethenylpropoxy]acetic acid tert-butyl ester 
• 7042-30-0 tert-butyl (Z)-3-phenyl-oxirane-2-carboxylate 
• 789461-69-4 [(S)-4-(2-Amino-acetyl)-3-benzyl-2-oxo-piperazin-1-yl]-acetic acid tert-butyl ester 
• 202653-27-8 (S)-3-Benzyloxycarbonylamino-N-tert-butoxycarbonylmethyl-N-(2,2-dimethoxy-ethyl)-succinamic acid tert-butyl ester 
• 148145-34-0 (S)-4-Benzyloxycarbonylaminoacetyl-1-t-butoxy-carbonylmethyl-2-oxopiperazine-3-propanoic acid methyl ester 

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