2-Bromo-2-methylpropionyl bromide

HCID 88685CAS 20769-85-1
Substructure searchFind similar structures

Basic information

Standard SMILES
CC(C)(Br)C(=O)Br
InChIKey
YOCIJWAHRAJQFT-UHFFFAOYSA-N
Molecular formula
C4H6Br2O
Average molar mass
229.9 g/mol
Monoisotopic mass
227.87853901

Names & identifiers

Preferred name
2-Bromo-2-methylpropionyl bromide
IUPAC
2-bromo-2-methylpropanoyl bromide
English name
2-Bromoisobutyryl Bromide
Molecular formula
C4H6Br2O
Molecular weight
229.9

Names & synonyms

2-Bromo-2-methylpropionyl bromide20769-85-12-Bromoisobutyryl bromide2-Bromo-2-methylpropanoyl bromidePropanoyl bromide, 2-bromo-2-methyl-alpha-Bromoisobutyryl bromidebromoisobutyryl bromide.alpha.-Bromoisobutyryl bromide627F9N9DYA2-bromoisobutyric bromidebromodimethylacetyl bromideEINECS 244-017-3
Show more names
BIBBα-Bromoisobutyryl bromideα-Bromoisobutyryl bromideA-BROMOISOBUTYRYL BROMIDE2-Bromoisobutyric acid bromide2-Bromo-2-methyl2-broMoisobutylyl broMide
2-bromoisobutanoyl bromideAI3-28200DTXSID7045077EC 244-017-3PROPIONYL BROMIDE, 2-BROMO-2-METHYL-2bromoisobutyryl bromideRefChem:466170DTXCID5025077

Database identifiers

CAS
20769-85-1
PubChem CID
88685
DTXSID
DTXSID7045077
UNII
627F9N9DYA
EC Number
244-017-3
Nikkaji
J93.725H

Properties

Computed structural properties

XLogP
2.2
Topological polar surface area
17.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
1
Heavy atoms
7

Experimental & physicochemical properties

Chemical ClassesToxic Gases & Vapors -> Acid Halides
SpringerMaterials PropertiesChemical shift
Physical DescriptionColorless liquid with an acrid odor; [Alfa Aesar MSDS]

Physicochemical properties

Boiling point
162 · 162-164 °C(lit.)
Density
1.86 g/mL · 1.86 g/mL at 20 °C
refractive index
20 · n20/D 1.507(lit.)
Flash point
110 °C · >110°C
storage temp.
30 °C · Store below +30°C.
solubility
Miscible with acetone and carbon disulfide.

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H302 (86.3%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P261, P264, P270, P272, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P333+P317, P362+P364, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 51 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationStatus: Active Update: 20-12-2012 https://echa.europa.eu/registration-dossier/-/registered-dossier/13206
Hazards Summary · 1 item

Causes burns; May cause skin sensitization; Harmful by ingestion; Possible human mutagen; [ECHA REACH Registrations] Corrosive to rabbit skin; 95% sensitization rate in guinea pig maximization study; [EPA - TSCATS] Reacts violently with water; Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; [Alfa Aesar MSDS]

Hazard Classes and CategoriesAcute Tox. 4 (86.3%)

Toxicology

Adverse EffectsDermatotoxin - Skin burns.

Safety data

PPE
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
ridadr
UN 3265 8/PG 2
hs_code
29159080
risk_code
22-34

Chemistry & industry

Uses & manufacturing

UsesUsed to make fine and large scale chemicals; [ECHA REACH Registrations]
General Manufacturing InformationPropanoyl bromide, 2-bromo-2-methyl-: ACTIVE
Applications · 3 items

Description2-Bromoisobutyryl Bromide is a kind of bromide being useful in the chemical industry. It is used as an intermediate for the synthesis of pharmaceuticals, agrochemicals, dyes and other organic chemicals1. It can be used as atom transfer radical polymerization (ATRP) initiator for functionalization of hydroxyl groups present on the surface of graphene oxide; to form an N-protected halodienamide which provided fourand five-membered lactams in the presence of copper (I) and a tertiary amine; in preparation of polycaprolactone macroinitiator via reaction with oligomeric caprolactone dio and mesoporous silica nanoparticles with ATRP initiator anchored on the exterior surface2,3. As a initiator precursor, it can also be used for surface modification of Ethylene-vinyl alcohol (EVOH) copolymer films to grow surface-grafted poly-(acrylamide) chains.

Uses2-Bromoisobutyryl bromide is used to prepare N-protected halodienamide, which provides four- and five-membered lactams in the presence of copper(I) and a tertiary amine. Further, it is used as atom transfer radical polymerization(ATRP) initiator for functionalization of hydroxyl groups present on the surface of graphene oxide. It is also used in preparation of polycaprolactone macroinitiators through reaction with oligomeric caprolactone diol and mesoporous silica nanoparticles with ATRP initiator anchored on the exterior surface.

Usesα-Bromoisobutyryl bromide has been used:as atom transfer radical polymerization (ATRP) initiator for functionalization of hydroxyl groups present on the surface of graphene oxideto form an N-protected halodienamide which provided four- and five-membered lactams in the presence of copper (I) and a tertiary aminein preparation of polycaprolactone macroinitiator via reaction with oligomeric caprolactone diol and mesoporous silica nanoparticles with ATRP initiator anchored on the exterior surface

Upstream & downstream products

Upstream raw materials

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]
爱斯特（成都）生物制药股份有限公司+86-28-85122536 85324413 · [email protected]

Related reactions

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