CAS 13680-35-8 4,4'-Methylenebis[2,6-diethylaniline] (HCID 83656)

Names & identifiers

Preferred name: 4,4'-Methylenebis[2,6-diethylaniline]
IUPAC: 4-[(4-amino-3,5-diethylphenyl)methyl]-2,6-diethylaniline
English name: 4,4'-Methylenebis(2,6-diethylaniline)
Molecular formula: C21H30N2
Molecular weight: 310.48

Names & synonyms

4,4'-Methylenebis(2,6-diethylaniline)Benzenamine, 4,4'-methylenebis[2,6-diethyl-DTXSID4048191EINECS 237-185-44,4'-methylenebis[2,6-diethylaniline]DTXCID5028166Benzenamine, 4,4'-methylenebis(2,6-diethyl-RefChem:96295Benzenamine, 4,4'methylenebis(2,6diethyl237-185-413680-35-84,4-methylenebis(2,6-diethylaniline)

Show more names

JADEWIN MDEALONZACURE(R) M-DEALABOTEST-BB LT000533564,4'-Methandiylbis(2,6-diethylanilin)4,4′-Methylenebis (2,6-diethyIaniline)4,4’-methylenebis[2,6-diethyl-benzenamin4,4'-Methylenebis(2,6-diethylaniline)>

4-[(4-amino-3,5-diethylphenyl)methyl]-2,6-diethylanilineMFCD000715524,4/'-Methylenebis(2,6-diethylaniline)44'-Methylenebis(26-diethylaniline)4-[(4-amino-3,5-diethyl-phenyl)methyl]-2,6-diethyl-aniline4,4'-Diamino-3,3',5,5'-tetraethyldiphenylmethaneBis(4-amino-3,5-diethylphenyl)methane4-[(4-amino-3,5-diethylphenyl)methyl]-2,6-diethylphenylamine

Database identifiers

CAS: 13680-35-8
PubChem CID: 83656
DTXSID: DTXSID4048191
ChEMBL: CHEMBL3183903
EC Number: 237-185-4
Nikkaji: J111.239B

Properties

Computed structural properties

XLogP: 5.7
Topological polar surface area: 52 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 2
Rotatable bonds: 6
Heavy atoms: 23
Formal charge: 0
Complexity: 283

Experimental & physicochemical properties

Physical Description · 2 items

Other Solid

Light brown crystalline solid; [Sigma-Aldrich MSDS]

Collision Cross Section · 1 item

184.4 Å² [M]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID4048191]；196.6 Å² [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID4048191]；196.5 Å² [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID4048191]

Physicochemical properties

Melting point: 88 · 88-90 °C(lit.)
Boiling point: 205 °C · 205 °C / 0.5mmHg
Density: 0.9 · 0.90
vapor pressure: 0 Pa · 0Pa at 25℃
storage temp.: Keep in dark place,Inert atmosphere,Room temperature
solubility: soluble in Toluene
form: powder to crystal
pka: 4.88 · 4.88±0.25(Predicted)
color: White to Almost white
Water Solubility: 440 μg/L · 440μg/L at 20℃
InChI: InChI=1S/C21H30N2/c1-5-16-10-14(11-17(6-2)20(16)22)9-15-12-18(7-3)21(23)19(8-4)13-15/h10-13H,5-9,22-23H2,1-4H3
InChIKey: NWIVYGKSHSJHEF-UHFFFAOYSA-N
SMILES: C(C1=CC(CC)=C(N)C(CC)=C1)C1=CC(CC)=C(N)C(CC)=C1
LogP: 4.29 at · 4.29 at 25℃
CAS DataBase Reference: 13680 · 13680-35-8(CAS DataBase Reference)
EPA Substance Registry System: 4 · Benzenamine, 4,4'-methylenebis[2,6-diethyl- (13680-35-8)
UNSPSC Code: 12162002 · 12162002
NACRES: 23 · NA.23
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 261 · P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
target organs: Respiratory system
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xn
Risk Statements: 22 · 22-36/37/38
Safety Statements: 26 · 26-36
WGK Germany: 3 · 3
TSCA: TSCA listed
HS Code: 29215900 · 29215900
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 4 OralEye · Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 0.7% (2 of 289) of reports.

Warning

H302 (98.6%): Harmful if swallowed [Warning Acute toxicity, oral]；H315 (14.5%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (14.9%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (14.2%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]；H411 (57.4%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 289 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 2 of 289 reports by companies.；There are 9 notifications provided by 287 of 289 reports by companies with hazard statement code(s).；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 Information · 4 items

Chemical: Benzenamine, 4,4'-methylenebis[2,6-diethyl-

Benzenamine, 4,4'-methylenebis[2,6-diethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenamine, 4,4'-methylenebis[2,6-diethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 09-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/21592

Benzenamine, 4,4'-methylenebis[2,6-diethyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Hazards SummaryAn irritant; Harmful by ingestion; [Sigma-Aldrich MSDS] See 4,4'-Methylenebis(2-ethylbenzenamine), 4,4'-Methylenedianiline, and MBOCA.

Hazard Classes and CategoriesAcute Tox. 4 (98.6%)；Skin Irrit. 2 (14.5%)；Eye Irrit. 2 (14.9%)；STOT SE 3 (14.2%)；Aquatic Chronic 2 (57.4%)

Regulatory information

Regulatory Information · 4 items

Chemical: Benzenamine, 4,4'-methylenebis[2,6-diethyl-

Benzenamine, 4,4'-methylenebis[2,6-diethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenamine, 4,4'-methylenebis[2,6-diethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 09-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/21592

Benzenamine, 4,4'-methylenebis[2,6-diethyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
tsca: TSCA listed
hs_code: 29215900
risk_code: 22-36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn
safety_code: 26-36
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H302-H315-H319-H335
REACH Registrations: Active
Hazard Classifications: Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P270-P301+P312-P302+P352-P305+P351+P338

Chemistry & industry

Uses & manufacturing

U.S. Production2023: 55,668 lb；2022: 56,923 lb；2021: 53,343 lb；2020: 22,540 lb

Industry UsesHardener

General Manufacturing Information · 2 items

Paint and Coating Manufacturing

Benzenamine, 4,4'-methylenebis[2,6-diethyl-: ACTIVE

Applications

UsesLONZACURE(R) M-DEA is an excellent chain extender for polyurethanes (PU) and also a curing agent for epoxides (EP). It provides improved mechanical and dynamic properties which cannot be achieved with standard formulations.

Preparation methods · 1 item

Preparation2,6-Diethylaniline (DEA) raw material was dissolved in water, and a certain amount of hydrochloric acid was added to generate 2,6-diethylaniline hydrochloride. Then, a proportional amount of formaldehyde aqueous solution was added dropwise, and the mixture was heated to carry out a condensation reaction. After the reaction was maintained at this temperature, the mixture was neutralized with an alkaline solution to precipitate crude MDEA. This crude MDEA was then decolorized, dehydrated, crystallized, and granulated to obtain 4,4′-methylene-bis-(2,6-diethylaniline).