Diisopropylaniline

HCID 32484CAS 24544-04-5
Substructure searchFind similar structures

Basic information

Standard SMILES
CC(C)c1cccc(C(C)C)c1N
InChIKey
WKBALTUBRZPIPZ-UHFFFAOYSA-N
Molecular formula
C12H19N
Average molar mass
177.29 g/mol
Monoisotopic mass
177.15174961

Names & identifiers

Preferred name
Diisopropylaniline
IUPAC
2,6-di(propan-2-yl)aniline
English name
2,6-Diisopropylaniline
Molecular formula
C12H19N
Molecular weight
177.29

Names & synonyms

2,6-DIISOPROPYLANILINE24544-04-5Benzenamine, 2,6-bis(1-methylethyl)-diisopropylaniline2,6-DiisopropylphenylamineAniline, 2,6-diisopropyl-2,6-Diisopropyl aniline2,6-DilsopropylanilineDTXSID5022279BRN 2208763EINECS 246-305-4190BG0089I
Show more names
DIPA2,6-DiisopropylbenzenamineAmitraz E.C.2,6-Di(propan-2-yl)aniline2,6-bis(1-methylethyl)-benzenamin2,6-Di-i-propylaniline2,6-diisopropyl-anilin
DTXCID302279EC 246-305-43-12-00-02764 (Beilstein Handbook Reference)2,6diisopropyl aniline2,6DiisopropylphenylamineAniline, 2,6diisopropylRefChem:587932Benzenamine, 2,6bis(1methylethyl)

Database identifiers

CAS
24544-04-5
PubChem CID
32484
DTXSID
DTXSID5022279
ChEMBL
CHEMBL3183764
UNII
190BG0089I
EC Number
246-305-4
Nikkaji
J33.769B

Properties

Computed structural properties

XLogP
3.2
Topological polar surface area
26 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
2
Heavy atoms
13

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Amines, Aromatic
LogP3.18
Density0.94 @25 °C
Boiling Point257 °C @760 [mm Hg]
Melting Point-45 °C
Vapor Pressure0.00479 [mmHg]

Physicochemical properties

Melting point
-45 °C · -45 °C (lit.)
Boiling point
257 °C · 257 °C (lit.)
Density
0.94 g/mL · 0.94 g/mL at 25 °C (lit.)
vapor pressure
0.01 mm · <0.01 mm Hg ( 20 °C)
refractive index
20 · n20/D 1.532(lit.)
Flash point
255 °F · 255 °F

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 3.4% (2 of 58) of reports.

Warning

H319 (13.8%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P273, P280, P305+P351+P338, P337+P317, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 58 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Chemical: Benzenamine, 2,6-bis(1-methylethyl)-

Status: Active Update: 09-01-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/10001

Hazards SummaryCauses other liver changes and changes in bone marrow and spleen in oral lethal-dose studies of rats; [RTECS] May cause irritation; May induce methemoglobinemia; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesEye Irrit. 2 (13.8%)

Safety & protection

Protective Action Criteria (PAC) · 3 items

9.6 [mg/m3]

110 [mg/m3]

630 [mg/m3]

Toxicology

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

Safety data

PPE
Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
wgk
2
tsca
TSCA listed
rtecs
BX4025000
hs_code
29214980
risk_code
52/53-36/37/38

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationBenzenamine, 2,6-bis(1-methylethyl)-: ACTIVE
Applications · 5 items

Description2,6-Diisopropylaniline is an organic compound with the formula H2NC6H3(CHMe2)2 (Me = CH3). It is a colorless liquid although, like many anilines, samples can appear yellow or brown.

Uses2,6-Diisopropylaniline acts as an intermediate used in the production of carbodiimides stabilizers, synthetic resins, antioxidants and active pharmaceutical ingredients. It is also used in the preparation of multitopic Schiff-base ligand precursors and 4,5-bis(2,6-diisopropylanilino)-2,7-di-tert-butyl-9,9-dimethylthioxanthene. It also undergoes condensation reaction with triacetylmethane to get -[1-(2,6-diisopropylphenylamino)ethylidene]pentane-2,4-dione. Further, it is used to prepare N-heterocyclic carbene complexes for alfa-arylation of acyclic ketones, amination of haloarenes and aqueous Suzuki coupling. In addition to this, it is used in the prepartion of organocatalyst based on naphthalene diimides.

Uses2,6-Diisopropylaniline was used in the preparation of multitopic Schiff-base ligand precursors. It was also used in the preparation of NSN-donor proligand, 4,5-bis(2,6-diisopropylanilino)-2,7-di-tert-butyl-9,9-dimethylthioxanthene.

Uses2,6-Diisopropylaniline is used as intermediate for the manufacture of carbodiimides stabilizers, RIM-PUR, synthetic resins, pesticides, antioxidants, pharmaceuticals and other products. 2,6-Diisopropylaniline may be used in the preparation of multitopic Schiff-base ligand precursors.It may be used in the preparation of NSN-donor proligand, 4,5-bis(2,6-diisopropylanilino)-2,7-di-tert-butyl-9,9-dimethylthioxanthene. It may be used to prepare N-heterocyclic carbene complexes for α-arylation of acyclic ketones, amination of haloarenes, and aqueous Suzuki coupling. 2,6-Diisopropylaniline may be used in the preparation of organocatalyst based on naphthalene diimides (NDIs).

General Description2,6-Diisopropylaniline is an aromatic amine. It reacts with bis(trimethylsilylmethyl)yttrium complexes supported by bulky amidopyridinate (Ap) and amidinate (Amd) ligands to afford yttrium alkyl anilido species. This reaction involves the elimination of TMS (Trimethylsilane).

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]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
玉门市海鼎化工有限公司09376971818 13079324666 · [email protected]

Related reactions

362 records
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