2-Bromoaniline

HCID 11992CAS 615-36-1

Basic information

Standard SMILES
Nc1ccccc1Br
InChIKey
AOPBDRUWRLBSDB-UHFFFAOYSA-N
Molecular formula
C6H6BrN
Average molar mass
172.02 g/mol
Monoisotopic mass
170.96836129

Names & identifiers

Preferred name
2-Bromoaniline
IUPAC
2-bromoaniline
English name
2-Bromoaniline
Molecular formula
C6H6BrN
Molecular weight
172.02

Names & synonyms

2-BROMOANILINE615-36-1o-BromoanilineBenzenamine, 2-bromo-Aniline, o-bromo-o-AminobromobenzeneVTP98DS78ENSC-7086DTXSID5060645RefChem:85845DTXCID0043054210-421-3
Show more names
2-Bromoanilines1-Amino-2-bromobenzene2-BromoaniLBROMOANILINE(2-)AKOS BBS-000036502-bromo-benzenamin
2-bromobenzenamine2-bromo-aniline2-bromophenylamineMFCD00007632aniline, 2-bromo-2-bromioanilineo-bromo-aniline2-bromaniline

Database identifiers

CAS
615-36-1
PubChem CID
11992
DTXSID
DTXSID5060645
UNII
VTP98DS78E
EC Number
210-421-3
Nikkaji
J94.957D

Properties

Computed structural properties

XLogP
2.1
Topological polar surface area
26 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
8

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Amines, Aromatic
SpringerMaterials Properties15N nuclear magnetic resonance spectrum
Vapor Pressure0.04 [mmHg]
Physical DescriptionBrown solid; mp = 27-32 deg C; [Alfa Aesar MSDS]

Physicochemical properties

Melting point
24 · 24-28 °C (lit.)
Boiling point
229 °C · 229 °C (lit.)
Density
1.52 g/mL · 1.52 g/mL at 25 °C (lit.)
refractive index
1.617 · 1.617-1.619
Flash point
230 °F · >230 °F
storage temp.
2 · 2-8°C

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H302 (96.2%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P262, P264, P270, P273, P280, P301+P317, P302+P352, P316, P319, P321, P330, P361+P364, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 53 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 3 items

Chemical: Benzenamine, 2-bromo-

Status: Active Update: 03-07-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/23361

2-Bromoaniline: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryA skin and strong eye irritant; May induce methemoglobinemia; Harmful by ingestion and inhalation; Toxic by skin absorption; Prolonged or repeated exposure may cause organ injury; [Alfa Aesar MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (96.2%)

Toxicology

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect

Safety data

F
8-23
PPE
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
wgk
3
tsca
TSCA listed
ridadr
UN 2811 6.1/PG 3
hs_code
29214210

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationBenzenamine, 2-bromo-: ACTIVE
Applications · 3 items

DescriptionO-bromoaniline, m-bromoaniline and p-bromoaniline corresponds to the three isomers of bromoaniline. All of them three are toxic with its toxicity being more severe than chloroanilines. It can be all via percutaneous absorption, being hemolytic and able to cause bladder cancer. It is mainly used for dye raw materials, such as azo dyes, quinazoline dyes and so on. Heating together with glycerol, concentrated sulfuric acid and o-bromonitrobenzene can generate 8-bromoquinoline. The preparation of the three isomers is as follows: Take the corresponding nitroaniline as raw material, have it reacted with sodium nitrite in sulfuric acid, leading to the formation of diazonium salt, followed by reaction with hydrobromic acid under the action of cuprous bromide, leading to the formation of nitrobromobenzene, further subjecting to iron powder reaction in the bromic acid to generate the above three isomers. Take benzene as raw material, under the action of iron powder, have it reacted with bromine to generate bromobenzene. It is then reacted with mixed acid (the mixture of sulfuric acid and nitric acid) to generate o-nitrobenzene and p-nitro bromobenzene (orthoaccounts of 35%; paraaccounts of 65%), so that the two are separated, followed by the same process as method one to generate o-bromoaniline and p-bromoaniline. Take bromoacetanilide as raw material, put it into sodium hydroxide solution; apply water vapor reflux to obtain the bromoaniline.

UsesOrganic synthesis intermediates

Uses2-Bromoaniline is used as a corrosion inhibitor, emulsifying and antiseptic agents. It is used in the rubber industry, e.g. diphenylguanidines, phenylenediamines mercaptobenzothiazoles, aniline ketones and etc.

Related reactions

167 records

Linked notes

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