tert-Butyl chloroacetate (HCID 66052)

Names & identifiers

Preferred name: tert-Butyl chloroacetate
IUPAC: tert-butyl 2-chloroacetate
English name: tert-Butyl chloroacetate
Molecular formula: C6H11ClO2
Molecular weight: 150.6

Names & synonyms

tert-Butyl chloroacetate107-59-5Chloroacetic acid tert-butyl estert-Butyl chloroacetateAcetic acid, chloro-, 1,1-dimethylethyl esterAcetic acid, chloro-, tert-butyl esterEINECS 203-506-1NSC 87891AI3-39154NSC-8789105TMW982982-Chloroacetic acid 1,1-dimethylethyl ester

Show more names

153N-6ClCH2C(O)OC(CH3)3tert-ButylChlorate(10E)-3-O-De(αtert-Butyl chloroaceTERT-BUTYL CHLORACETATE3-Formyl Tyrosol αreft-Butyl chloroacetate

TERT-BUTYL CHLOROACETATE [MI]Acetic acid, 2-chloro-, 1,1-dimethylethyl esterRefChem:894636Acetic acid, chloro-, tert-butyl ester (8CI)203-506-1tert-butyl 2-chloroacetateMFCD000009301,1-Dimethylethyl chloroacetate

Database identifiers

CAS: 107-59-5
PubChem CID: 66052
DTXSID: DTXSID7059351
UNII: 05TMW98298
EC Number: 203-506-1
Nikkaji: J5.060A

Properties

Computed structural properties

XLogP: 1.7
Topological polar surface area: 26.3 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 3
Heavy atoms: 9
Formal charge: 0
Complexity: 104

Experimental & physicochemical properties

Kovats Retention Index · 2 items

891

1280

Physicochemical properties

Boiling point: 48 · 48-49 °C/11 mmHg (lit.)
Density: 1.053 g/mL · 1.053 g/mL at 25 °C (lit.)
refractive index: 20 · n20/D 1.423(lit.)
Flash point: 116 °F · 116 °F
storage temp.: Flammables area
form: Liquid
Specific Gravity: 1.053 · 1.053
color: Clear colorless to yellow
Water Solubility: 0.1 g/L · <0.1 g/L (20 ºC)
Merck: 14 · 14,1563
BRN: 1753006 · 1753006
InChI: 1S/C6H11ClO2/c1-6(2,3)9-5(8)4-7/h4H2,1-3H3
InChIKey: KUYMVWXKHQSIAS-UHFFFAOYSA-N
SMILES: CC(C)(C)OC(=O)CCl
LogP: 2.07 · 2.07
CAS DataBase Reference: 107 · 107-59-5(CAS DataBase Reference)
FDA UNII: 5 TMW98298 · 05TMW98298
NIST Chemistry Reference: 1 · Acetic acid, chloro-, 1,1-dimethylethyl ester(107-59-5)
EPA Substance Registry System: 1 · Acetic acid, chloro-, 1,1-dimethylethyl ester (107-59-5)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 2 · GHS02,GHS05,GHS06
Signal word: Danger
Hazard statements: 331 · H331-H302+H312-H314-H226
Precautionary statements: 501 · P501-P270-P240-P261-P210-P233-P243-P241-P242-P271-P264-P280-P370+P378-P362+P364-P303+P361+P353-P301+P330+P331-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P403+P233-P403+P235-P405
PPE: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
Hazard Codes: C,N,Xn,Xi,F
Risk Statements: 20 · 20/21/22-34-50/53-36/37/38-10
Safety Statements: 26 · 26-36/37/39-45-61-60-16-7/9
RIDADR: 2920 · UN 2920 8/PG 2
WGK Germany: 3 · 3
RTECS: 8985500 · AF8985500
F: 19 · 19-21
TSCA: TSCA listed
HazardClass: 3 · 3
PackingGroup: III
HS Code: 29154000 · 29154000
Hazard Classifications: 3 InhalationAcute · Acute Tox. 3 InhalationAcute Tox. 4 DermalAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 3Skin Irrit. 2
Toxicity: 50 · 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.
REACH Registrations: Active
Limited Quantities: 1 L · 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)

Safety & regulation

GHS classification

GHS Classification · 5 items

Danger

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]；H302+H312 (13.1%): Harmful if swallowed or in contact with skin [Warning Acute toxicity, oral; acute toxicity, dermal]；H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]；H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]；H314 (48.8%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]；H315 (51.2%): Causes skin irritation [Warning Skin corrosion/irritation]；H317 (28.6%): May cause an allergic skin reaction [Warning Sensitization, Skin]；H319 (51.2%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H331 (97.6%): Toxic if inhaled [Danger Acute toxicity, inhalation]；H400 (34.5%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]；H410 (34.5%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P363, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 84 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory InformationStatus: Active Update: 23-07-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/20774

Hazard Classes and CategoriesFlam. Liq. 3 (100%)；Acute Tox. 4 (100%)；Acute Tox. 4 (100%)；Skin Corr. 1B (48.8%)；Skin Irrit. 2 (51.2%)；Skin Sens. 1 (28.6%)；Eye Irrit. 2 (51.2%)；Acute Tox. 3 (97.6%)；Aquatic Acute 1 (34.5%)；Aquatic Chronic 1 (34.5%)

Regulatory information

Regulatory InformationStatus: Active Update: 23-07-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/20774

Safety data

F: 19-21
PPE: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk: 3
tsca: TSCA listed
rtecs: AF8985500
ridadr: UN 2920 8/PG 2
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.
risk_code: 20/21/22-34-50/53-36/37/38-10
Signal word: Danger
Symbol(GHS): GHS02,GHS05,GHS06
hazard_code: C,N,Xn,Xi,F
safety_code: 26-36/37/39-45-61-60-16-7/9
hazard_class: 3
packing_group: III
Hazard statements: H331-H302+H312-H314-H226
Limited Quantities: 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
REACH Registrations: Active
Hazard Classifications: Acute Tox. 3 InhalationAcute Tox. 4 DermalAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 3Skin Irrit. 2
Precautionary statements: P501-P270-P240-P261-P210-P233-P243-P241-P242-P271-P264-P280-P370+P378-P362+P364-P303+P361+P353-P301+P330+P331-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P403+P233-P403+P235-P405

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationAcetic acid, 2-chloro-, 1,1-dimethylethyl ester: ACTIVE

Applications

Usestert-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.

UsesIn the glycidic ester condensation.

Preparation methods · 1 item

Preparationtert-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%.