4,4'-Diaminodicyclohexylmethane

HCID 15660

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Basic information

CAS: 1761-71-3
Standard SMILES: NC1CCC(CC2CCC(N)CC2)CC1
InChIKey: DZIHTWJGPDVSGE-UHFFFAOYSA-N
Molecular formula: C13H26N2
Average molar mass: 210.36 g/mol
Monoisotopic mass: 210.20959883

Overview

Yellowish white liquid or brown solid paste. (NTP, 1992)

Names & identifiers

Preferred name: 4,4'-Diaminodicyclohexylmethane
IUPAC: 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine
English name: 4,4'-Diaminodicyclohexyl methane
Molecular formula: C13H26N2
Molecular weight: 210.36

Names & synonyms

1761-71-34,4'-Methylenedicyclohexanamine4,4'-Diaminodicyclohexylmethane4,4'-Methylenebis(cyclohexylamine)Bis(4-aminocyclohexyl)methane4,4'-Diaminodicyclohexyl methaneWandamin HMCyclohexanamine, 4,4'-methylenebis-Bis(p-aminocyclohexyl)methanePACM 20HLR 4219Cyclohexylamine, 4,4'-methylenebis-

Show more names

POLYLINK PACMPACM20DICYKANDIAMINODICYCLOHEXYLMETHANE4,4'-methylenebis(cyclohexan-1-amine)

p,p'-Diaminodicyclohexylmethane4,4'-MethylenedicyclohexylamineDTXSID0024921Methylenebis(4-aminocyclohexane)1,4-Bis(aminocyclohexyl)methane4,4'-MethylenedicyclohexaneamineDI(P-AMINOCYCLOHEXYL)METHANEHLR 4448

Database identifiers

CAS: 1761-71-3、6693-29-4、6693-30-7、6693-31-8
PubChem CID: 15660
DTXSID: DTXSID0024921
ChEMBL: CHEMBL1492978
UNII: AR21XLU05L、B16001JGEW、H8V09V2RM3
EC Number: 217-168-8、229-737-8、229-738-3、229-739-9
Nikkaji: J298.069J、J298.070C、J298.071A、J47.629C

Properties

Computed structural properties

XLogP: 1.9
Topological polar surface area: 52 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 2
Rotatable bonds: 2
Heavy atoms: 15
Formal charge: 0
Complexity: 157

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Amines, Cyclic

Density0.9608 at 77 °F (NTP, 1992) - Less dense than water; will float

SolubilityInsoluble (<1 mg/ml) (NTP, 1992)

Flash Point · 2 items

greater than 200 °F (NTP, 1992)

Flash point > 200 °F

Boiling Point626 to 628 °F at 3 mmHg (NTP, 1992)

Melting Point140-143.6 °F (cis-cis) 147.2-149 °F (trans-trans) (NTP, 1992)

Physicochemical properties

Melting point: 60 · 60-65°C
Boiling point: 330 · 330-331°C
Density: 0.95 g/mL · 0.95 g/mL at 25 °C(lit.)
vapor pressure: 0.1 mm · <0.1 mm Hg ( 38 °C)
refractive index: 1.5032 · 1.5032 (estimate)
Flash point: 230 °F · >230 °F
storage temp.: Keep in dark place,Inert atmosphere,Room temperature
solubility: Chloroform (Slightly), Methanol (Slightly)
form: powder to lump to clear liquid
pka: 10.87 · 10.87±0.70(Predicted)
color: White or Colorless to Almost white or Almost colorless
Odor: Ammonia odor
Water Solubility: Insoluble (<0.1 g/100 mL)
BRN: 2079179 · 2079179
InChI: 1S/C13H26N2/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11/h10-13H,1-9,14-15H2
InChIKey: DZIHTWJGPDVSGE-UHFFFAOYSA-N
SMILES: NC1CCC(CC1)CC2CCC(N)CC2
LogP: 2.03 at · 2.03 at 25℃
CAS DataBase Reference: 1761 · 1761-71-3(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 0 NW77H1O03 · 0NW77H1O03
NIST Chemistry Reference: 4 · Cyclohexanamine, 4,4'-methylenebis-(1761-71-3)
EPA Substance Registry System: 4 · 4,4'-Methylenebis(cyclohexylamine) (1761-71-3)
UNSPSC Code: 12352116 · 12352116
NACRES: 23 · NA.23
Symbol(GHS): 5 · GHS05,GHS07,GHS08,GHS09
Signal word: Danger
Hazard statements: 302 · H302-H314-H317-H373-H411
Precautionary statements: 273 · P273-P280-P305+P351+P338-P310
Hazard Codes: T+,N,C
Risk Statements: 26 · 26-34-51/53-48/22-43-35-22
Safety Statements: 26 · 26-28-36/37/39-45-61-50-14
RIDADR: 2928 · UN 2928 6.1/PG 2
WGK Germany: 2 · 2
RTECS: 1530000 · GX1530000
F: 10 · 10-34
TSCA: TSCA listed
HazardClass: 8 · 8
PackingGroup: III
HS Code: 29213000 · 29213000
Storage Class: 8 A · 8A - Combustible corrosive hazardous materials
Hazard Classifications: 4 OralAquatic · Acute Tox. 4 OralAquatic Chronic 2Skin Corr. 1BSkin Sens. 1STOT RE 2 Oral
Toxicity: 50 inhalation · LC50 inhalation in mouse: 400mg/m3/4H
REACH Registrations: Active
Excepted Quantities: Not Permitted as Excepted Quantity

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 2.3% (29 of 1269) of reports.

Danger

H302 (97.2%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P284, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P320, P321, P330, P333+P317, P362+P364, P363, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1269 reports by companies from 42 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

Hazard information

Regulatory Information · 4 items

Chemical: Cyclohexanamine, 4,4'-methylenebis-

Cyclohexanamine, 4,4'-methylenebis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Cyclohexanamine, 4,4'-methylenebis- 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: 09-02-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14320

Cyclohexanamine, 4,4'-methylenebis-: HSNO Approval: HSR003552 Approved with controls

Other Safety InformationEvaluation - Cyclohexanamine, 4,4'-methylenebis-

DOT LabelCorrosive

Fire HazardsThis chemical is probably combustible. (NTP, 1992)

Health HazardsACUTE/CHRONIC HAZARDS: This compound is corrosive. (NTP, 1992)

Hazards SummaryCorrosive to skin; [Quick CPC] Causes burns; Harmful if swallowed; [MSDSonline]

Safety & protection

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

Personal Protective Equipment (PPE)MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves.

Toxicology

Adverse EffectsDermatotoxin - Skin burns.

Toxicity DataLC50 (mice) = 400 mg/m3/4h

Safety data

F: 10-34
wgk: 2
tsca: TSCA listed
rtecs: GX1530000
ridadr: UN 2928 6.1/PG 2
hs_code: 29213000
Toxicity: LC50 inhalation in mouse: 400mg/m3/4H
risk_code: 26-34-51/53-48/22-43-35-22
Signal word: Danger
Symbol(GHS): GHS05,GHS07,GHS08,GHS09
hazard_code: T+,N,C
safety_code: 26-28-36/37/39-45-61-50-14
hazard_class: 8
Storage Class: 8A - Combustible corrosive hazardous materials
packing_group: III
Hazard statements: H302-H314-H317-H373-H411
Excepted Quantities: Not Permitted as Excepted Quantity
REACH Registrations: Active
Hazard Classifications: Acute Tox. 4 OralAquatic Chronic 2Skin Corr. 1BSkin Sens. 1STOT RE 2 Oral
Precautionary statements: P273-P280-P305+P351+P338-P310

Chemistry & industry

Uses & manufacturing

U.S. Production2023: 25,000,000 - <40,000,000 lb

Consumer UsesNot Known or Reasonably Ascertainable

Industry UsesViscosity modifiers

General Manufacturing Information · 5 items

Wholesale and Retail Trade

Cyclohexanamine, 4,4'-methylenebis-: ACTIVE

Cyclohexanamine, 4,4'-methylenebis-, (trans,trans)-: ACTIVE

Cyclohexanamine, 4,4'-methylenebis-, (cis,trans)-: ACTIVE

Cyclohexanamine, 4,4'-methylenebis-, (cis,cis)-: INACTIVE

Applications · 5 items

Uses4,4'-Methylenebis(cyclohexylamine) is a potential high inhibitive and high temperature resistant shale inhibitor.

Description4,4'-Diaminodicyclohexyl methane is a sodium salt of a cyclic anhydride that is used as a specific treatment for removing dodecanedioic acid from fatty acids. The reaction solution is stable at pH 4-5 and has a viscosity of less than 1000 cps. It has good stability in the presence of amines and can be used in chromatographic science, including chromatography and gas-liquid chromatography. The UV absorption maxima for the acid complex are 195 nm and 240 nm.

Uses4,4'-Diaminodicyclohexyl methane be used as organic intermediates and epoxy curing agents.

Uses4,4'-Diaminodicyclohexylmethane is used as epoxy curing agents. It is a versatile intermediate to produce leather, rubber products, plastics, dyes, and photo sensitive polymers. It is used in manufacturing diisocyanates and polyamides. It is also used as lubricant additive as and corrosion inhibitor.

General DescriptionYellowish white liquid or brown solid paste.