tert-Butyl bromoacetate
Basic information
- CAS
5292-43-3- Standard SMILES
CC(C)(C)OC(=O)CBr- InChIKey
BNWCETAHAJSBFG-UHFFFAOYSA-N- Molecular formula
- C6H11BrO2
- Average molar mass
- 195.05 g/mol
- Monoisotopic mass
- 193.99424169
Names & identifiers
- Preferred name
- tert-Butyl bromoacetate
- IUPAC
- tert-butyl 2-bromoacetate
- English name
- tert-Butyl bromoacetate
- Molecular formula
- C6H11BrO2
- Molecular weight
- 195.05
Names & synonyms
tert-Butyl bromoacetate5292-43-3tert-butyl 2-bromoacetatet-Butyl bromoacetateBromoacetic Acid tert-Butyl EsterAcetic acid, bromo-, 1,1-dimethylethyl estertert-Butylbromoacetatet-butyl 2-bromoacetatebromo-acetic acid tert-butyl esterMFCD00000188Acetic acid, bromo-, tert-butyl esterLY42AF89SN
Show more names
tertiary butyl bromoacetate1-Butylbromoacetatetert-Butyl Bromoacetert-Butyl bromoacetate2-Methyl-2-propanyl bromoacetate
BrCH2C(O)OC(CH3)31,1-dimethylethyl 2-bromoacetate1,1-Dimethylethyl monobromoacetateAcetic acid, 2-bromo-, 1,1-dimethylethyl esterBromoacetic acid 1,1-dimethylethyl estertert-ButylBromoacetate-13Ct-butylbromoaceatet-butylbromoacteate
Database identifiers
- CAS
5292-43-3- PubChem CID
- 79177
- DTXSID
DTXSID2063763- UNII
- LY42AF89SN
- EC Number
- 226-133-6
- Nikkaji
- J254.923I
Properties
Computed structural properties
- XLogP
- 1.9
- Topological polar surface area
- 26.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 3
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 104
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Halogenated Esters
SpringerMaterials PropertiesChemical shift
Physical DescriptionColorless liquid with a pungent odor; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 44 · 44-47 °C
- Boiling point
- 50 °C10 · 50 °C10 mm Hg(lit.)
- Density
- 1.338 · 1.338
- vapor pressure
- 1.62 hPa · 1.62hPa at 25℃
- refractive index
- 20 · n20/D 1.445(lit.)
- Flash point
- 121 °F · 121 °F
- storage temp.
- 0 · 0-6°C
- solubility
- Chloroform, Ethyl Acetate (Slightly)
- form
- Liquid
- Specific Gravity
- 1.333 · 1.333 (20/4℃)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P351+P338, P305+P354+P338, P316, P319, P321, P330, P332+P317, P337+P317, P362+P364, P363, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 92 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Status: Active Update: 22-01-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/18866
t-Butyl bromoacetate: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryCauses burns; Harmful by ingestion; [Alfa Aesar MSDS]
Hazard Classes and CategoriesFlam. Liq. 3 (100%)
Toxicology
Adverse EffectsDermatotoxin - Skin burns.
Safety data
- F
- 19
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationAcetic acid, 2-bromo-, 1,1-dimethylethyl ester: ACTIVE
Applications
Usestert-Butyl Bromoacetate is a halogenated t-butyl acetate commonly used as an alkylating agent. tert-Butyl Bromoacetate is used in the synthesis of collagenase inhibitors.
Usestert-Butyl bromoacetate is used as an intermediate in the production of dyes, pharmaceuticals, agrochemicals and in organic compounds. It finds application as an alkylating agent. It plays an important role to prepare (2-oxo-4-vinyl-azetidin-1-yl)-acetic acid tert-butyl ester and in collagenase inhibitors synthesis.
General Descriptiontert-Butyl bromoacetate serves as building blocks during the synthesis of model N-substituted oligoglycines (peptoids) containing an N-linked lactoside side-chain.
Preparation methods
PreparationTert-butyl bromoacetate ester was synthesized using bromoacetic acid and isobutylene as raw materials,Amberlyst 15,a strong acidic cation exchange resin,as catalyst,and tert-butanol as modifier.
Upstream & downstream products
Downstream products
Related reactions
2,343 records
Compound notes
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